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308- Brian Gillette Reveals How to Sell IT with Empathy

Dissecting Popular IT Nerds
Dissecting Popular IT Nerds
308- Brian Gillette Reveals How to Sell IT with Empathy
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Brian Gillette

A seasoned sales expert and entrepreneur, Brian Gillette is on a mission to transform sales culture through empathy and vulnerability. As the creator of the “Feel Good Close” methodology, he teaches sales professionals and business leaders how to ethically influence others by genuinely caring about their goals and challenges. Brian draws on his background in enterprise sales and acting to help clients overcome rejection and build authentic relationships.

Brian Gillette Reveals How to Sell IT with Empathy

How can IT leaders effectively “sell” technology initiatives to executives? In this insightful conversation, sales expert Brian Gillette shares his “Feel Good Close” approach, emphasizing empathy, curiosity, and genuine interest in helping others achieve their goals.

Learn practical strategies for overcoming rejection, building trust, and positioning IT as a strategic business partner rather than just a cost center. Empathy and building strong customer relationships are at the core of this approach. By understanding executives’ needs, IT leaders can better demonstrate the business value of IT and influence executives effectively.

Strategic partnerships and focusing on customer service are essential for demonstrating value and aligning technology initiatives with business goals. This method ensures IT is seen as a key player in strategic business decisions.

Disclaimer: The views, thoughts, and opinions expressed by guests on this podcast are solely their own and do not necessarily reflect the views or positions of their employers, affiliates, organizations, or any other entities. The content provided is for informational purposes only and should not be considered professional advice. The podcast hosts and producers are not responsible for any actions taken based on the discussions in the episodes. We encourage listeners to consult with a professional or conduct their own research before making any decisions based on the content of this podcast

3 Key Takeaways

Episode Show Notes

00:00 – Introduction and background

03:45 – MSPs and customer relationships

07:23 – The “Feel Good Close” sales philosophy

13:04 – All jobs promote to sales

18:50 – Using empathy instead of fear in sales

24:50 – Overcoming imposter syndrome

29:40 – Demonstrating business value of IT

34:18 – Dealing with rejection in sales

40:50 – Personal growth and goal-setting

43:48 – Pros and cons of starting an MSP

46:25 – Transitioning to IT consulting

49:53 – Defining your career goals

51:28 – Closing thoughts

Transcript

Speaker 0 | 00:00.800

Everyone out there listening to Dissecting Popular IT Nerds, we are talking with Brian Gillette. This has been a long time coming, like years, years, years coming. Very excited about this, by the way. And I think part of it is because we’re both, I guess it’s fair to say we’re entrepreneurs, whatever that is. I never really thought I would call myself that, but I think I’ve come to terms now with myself that I’m going to call myself an entrepreneur now. odd caster or something. I already got all kinds of things, alerts going off that people are probably hearing and annoying. I really have wanted to, I’ve wanted to have you on this show, but I wanted to make sure we mapped it out right. And it was really beneficial to not only all of the IT directors, CTOs, CIOs, and IT leaders out there that are fighting to get a seat at the executive round table, but also mix in, I beat up on the MSPs a lot. I like to make fun of MSPs, not because I don’t love them. I do love them. It’s just that I decided I didn’t want to work with MSPs anymore years ago, not because I don’t love MSPs because they’re like IT people. They know what an IP address is, right? We can joke around about, like, I don’t know, XP or something. I love it. I love working with them. I love supporting them. Here’s what I didn’t love. I didn’t love their customers. And I am very specific. I learned at one point in my life that I need to only work with people that I like working with. And what that became was, is I loved them. So where do they exist in the world? They exist inside larger companies and their names are IT director, IT manager, VP of IT, CTO, CIO. So I said… Screw it. I’m going to work with them because I love working with them and they love working with their customers and they’re, and they kind of, you know, it’s like it, it all kind of flows through this nice visionary process. I don’t, I don’t know how else to accept that. So I do still work with some MSPs that I like their customers, but you can’t always choose your MSPs customers. I don’t know if there’s any deep thoughts around that. I don’t know if there’s anything you know you’re the guy so and just for everyone out there listening brian is the guy that teaches sales and you can tell me a little bit about your history in the past of being like you know like the sales guy inside enterprise companies and larger companies but brian is the guy that is going to teach us today and i know a lot of people i’ve known um you know you know there’s the the robin robbins in the space of the msps and stuff but i choose only to work with you because i know that you have a polished enterprise sales process and experience and experience. It’s not just a small business thing. It’s enterprise polished sales. And I think that that’s going to be very valuable to IT directors, IT managers that need to sell to executive management that IT is valuable. It’s a business force multiplier. And we deserve always a seat at the executive round table because nothing gets done. in any department, in any company without IT being involved. That was a lot. I’m sorry. Did I just, it was a lot. I’ve had, I’ve drank some coffee today. I’m on some good nootropics. Is it nootropics? Nootropics? I don’t know. Whatever it is, you know, all that stuff that they’re trying to like throw us pills, you know, pills on Instagram and stuff. Anyhow.

Speaker 1 | 03:45.256

Yeah. You’re juiced up. You know, when you were saying you can’t always choose your MSP’s customers and you didn’t like MSP’s customers. What’s funny is that you. What did you say? Is there something deeper there? The thing that’s deeper there is that MSPs don’t like their customers either. And most MSPs don’t actually have-How can they provide customer service?

Speaker 0 | 04:04.695

I don’t even like you.

Speaker 1 | 04:06.476

Well, that’s exactly it. Most MSPs forget that their customer service business and their medium is technology, but they like to think of themselves as technologists, but that’s just not what you really are. A true MSP is actually a customer service business. And technology is the medium with which you provide value. But they like to think I’m going to be a technologist. Everybody’s going to come and sit at my feet and listen to how I do things. And then my customers are going to fall in love with how genius I am. And then when that never happens, they start to build resentment and go, hey, how come nobody cares about how smart I am? Because they forget their job is not to be the hero in their relationships. Their job is to be. the Yoda and then their customer gets to be Luke and gets to go and kill Darth Vader or, you know, go and vanquish the emperor.

Speaker 0 | 04:59.623

It’s pretty deep. It’s pretty deep. And everyone’s going to relate with that. And it’s a theme that comes up on the show a lot is right where we are a, if we’re calling them end users, we say end users, because we know what that means from a technical standpoint. But if we’re calling them end users, we’re, we’re doing it wrong. There are customers.

Speaker 1 | 05:19.877

Yeah, right. A lot of people will, like they hate the word customers, they’ll say partners, or clients or It’s like, if we’re hiding the fact that we’re supporting somebody or selling something to somebody, then that should be a huge red flag. Like, if you’re selling something, stop pretending you aren’t selling. Just be selling.

Speaker 0 | 05:44.521

Okay.

Speaker 1 | 05:45.662

Because if you have this core belief that selling is wrong, bad, self-seeking, then you’re going to start trying to use all this verbiage to hide your job title. In sales, we get titles that are like, head of. customer ecstasy.

Speaker 0 | 06:00.292

Business development. Yeah, right. Just be selling. My first Gmail account, and only Gmail account, I am a salesman at gmail.com. Everyone can send me an email right now.

Speaker 1 | 06:14.801

You’re the one who locked that down when I couldn’t get it. Mine is I am a salesman 87864. I didn’t get there.

Speaker 0 | 06:24.067

I got it from a famous, like, I don’t know. I was a big Zig Ziglar fan when I, when I left Starbucks and he, and he has a, uh, like a famous book, you know, and audio is, you know, secrets of closing the sale. And he reads like some poem that’s like, I’m proud to be a salesman because, and it goes on, everyone can Google it right now. Like Google, like a Zig Ziglar or something. I’m proud to be a salesman because it’s, it’s some anonymous person, but it’s like, because and long story short, the whole theme of the entire, like. pros piece is that nothing gets done until someone makes a sale. A farmer can’t get the beans to the market. Walmart can’t start delivering. I don’t know, whatever it is. Nothing gets done until someone makes a sale. So nothing in your IT stack is going to get upgraded until IT director, you make a sale to executive management. So what’s your philosophy around it? You have this thing that you’ve termed the feel good close. What’s that all about?

Speaker 1 | 07:23.959

Yeah. The feel good clothes is the core belief that selling is an inherently noble profession.

Speaker 0 | 07:30.304

I love you.

Speaker 1 | 07:32.066

And what you’re selling is at its core. I mean, it’s a few things for my personality. What selling means is I personally love introducing people to things that can excite them. Like if I see a movie and I love it. I tell everybody how much I loved it. If I find a new, like this dumb smart mug I’m drinking out of, I’ve sold like six of these because I’m like, oh my gosh, listen, once you go, you’ll never go back. You just got to, but it’s not because I, it’s literally because I found a value and I know other people who could benefit from it and I want them to experience it.

Speaker 0 | 08:12.415

I got it. It’s like Phil’s favorite things. I got Phil’s favorite things.

Speaker 1 | 08:16.057

Right. Because you’re a Phil’s guy.

Speaker 0 | 08:17.898

Darn tough socks. Um, Carhartt pants. What else do we have? Cutco knives. Cutco, man. Cutco. Amazing. Love them. For life. I inherited some Cutco knives from my mother-in-law that are older than me. Saw the Cutco guy. Yeah, no problem. We’ll resharpen them all. Oh, that little tip. Oh, we’ll send you a brand new one. I didn’t even buy them. And they’re replacing them for life.

Speaker 1 | 08:43.435

It’s so awesome.

Speaker 0 | 08:44.776

My mother-in-law’s like, don’t forget who gave those to you. Right.

Speaker 1 | 08:48.558

But you see the point, right? Like selling is inherently noble. And what happens with anything inherently good and noble is that special interests get involved and then we get these splintered variants. And once people started realizing, oh, because I make money when a transaction occurs, I would make more money if I have more transactions. but I have a finite amount of conversations. So let me start transacting with people who shouldn’t buy it. And therein lies, that’s the introduction to the downfall of sales culture. And now we have what I refer to as the adversarial sales complex, which is now rampant. It is this core belief that when you’re selling something, you’re in contest with the person you’re selling to. And in order to achieve the sale, you have to overcome your buyer. And it’s mutual because the buyer says, I have to get what this slimy guy is selling, but I’m not going to put up with any of his crap. And I’m not going to play the game and I won’t take the first price. And I’m assuming he’s lying. So I’m going to come in with all these defense mechanisms and hard outs and excuses so that I can get everything I want out of the sale.

Speaker 0 | 09:57.781

Yeah, but most people would love to just get to that point. Most people would love to get to the slimy battle point. Some people, and I’m sure some of your clients can’t even get there. Some of my guys, they would love to just get to the executive round table to sell the upgrade. But no, no, it’s not in the budget this year. It’s not there, whatever it is. So why don’t we just go to like, why don’t we just start from the very beginning? Like some, I don’t know. I don’t even know where to begin. Maybe you can help us.

Speaker 1 | 10:22.710

Yeah. I mean, I would say that transacting is not selling. Transacting is the by-product. of selling so once you’ve actually done your job of communicating to somebody what they need why they need it and how it’s going to turn them into the person they want to become then the transaction happens on the back end but we think of oh i’m gonna go into i’m gonna go boiler room like chess match negotiation redlining that’s selling that is not selling that is that’s transacting it’s it’s something completely different but uh and i was saying the other day relationships are not transactional No, they, right.

Speaker 0 | 11:01.316

Or relationships are, a relationship is not a transaction.

Speaker 1 | 11:04.478

Right. So especially if you’re like, I have to get, let me say it this way. If you’re an IT director or a CTO, whatever, and you’ve got, there’s a closed door with a bunch of people who write the checks and you’re trying to get this thing done that you’re like, how do they not understand that if they don’t do this, we’re taking massive risk. That’s way more expensive than what I’m asking for.

Speaker 0 | 11:25.489

Let’s use security. Everyone that security might be the hardest thing to sell. because it’s like, I don’t know, maybe selling like insurance or something. I don’t really know what it is, but it is like, well, we haven’t had a breach yet. We haven’t had that. Why do we need this project? Put that one on. Right.

Speaker 1 | 11:41.816

And we all know, we all have the stats that over half of the small businesses who get hit by a real event go out of business and how spending goes up 10 or 20 X or whatever after an event. So we all know like, listen, why don’t you just learn from everybody else’s mistakes instead of learning from our own $100 million mistake? Why don’t we learn from their $100 billion mistake? and just frigging buy this, upgrade your firewall, put MFA on these computers. It’s not that complicated.

Speaker 0 | 12:07.849

So let’s just use a couple of examples. I’ve got some that are hypothetical, but maybe not true. Maybe they are, maybe they aren’t. Might have someone out there right now. He might be an IT director and he’s trying to upsell a fiber upgrade on his network and a… And a… maybe fortinet or cisco i don’t know some of these maraqui firewall upgrade along with um backup internet connections he’s trying to do a network upgrade in short yeah and right now everything’s kind of running there’s some latency issues in the network in some locations but they’re they’re working but this new upgrade is going to cost more money and it’s going to be like i don’t know maybe it’s double maybe it’s 50 more maybe he’s going from $2,000 a month to $4,000 a month, but then they’re going to have a firewall upgrade. They’re going to have internet and stuff like that. How does he sell that? How does he even approach that to the executive management?

Speaker 1 | 13:04.564

Right. So for starters, if you’re sitting here thinking, if your mindset is that they’re wrong and I’m right, you’re already going to lose because tie always goes to the leader. in a conversation like this. So if both of you have an argument about why you should and shouldn’t do it, the tie will go to the person who writes the checks. So if you’re thinking, they’re wrong, I’m right, how do I get them to see that I’m right? I have news for you. CEOs don’t read that, don’t work that way. CEOs only like their ideas. And the people who know how to work with a CEO are the ones who know how to implant ideas into their head. You know?

Speaker 0 | 13:48.223

Preach. Teach us. Teach us.

Speaker 1 | 13:50.672

What you do is honestly what I would do, all jobs promote to a sales job. Have you talked about this? If you keep getting promoted, eventually you’re a salesperson.

Speaker 0 | 14:03.360

Yes.

Speaker 1 | 14:04.220

So you’re the top of the IT game and all of a sudden you go, wait a minute. Now, I’m not turning screwdrivers. My job is to convince these people.

Speaker 0 | 14:12.705

Can you say that again? That’s Greg, the Frenchman behind the scenes, my developer that’s… no longer lives in France and is an expat or whatever you call that in Morocco. That’s my developer, Greg, the Frenchman. I should have him on sometimes. He has a great French accent. He’s going to make this quote card. Please say that again. All jobs promote to sale. What is that quote? That’s the quote for this episode. We have to have that.

Speaker 1 | 14:35.616

All jobs eventually promote into a sales job. What can we infer from that? That if you want to get promoted, you have to learn how to sell. And if you’re, and if you are at the top, you need to stop being angry that you’re being expected to sell because that’s why you’re on top. Because you have the ability to make things happen, get things done, which is what selling is.

Speaker 0 | 15:01.919

All of that. Gold. All of that’s gold for me. That just made my day. That made my day. Oh, you hate salespeople? Good luck getting promoted.

Speaker 1 | 15:16.789

You hate your boss.

Speaker 0 | 15:18.790

Oh, so you hate your job, you hate your boss, you hate your life. That’s why you hate salespeople.

Speaker 1 | 15:24.052

Yeah. I don’t know how to help you.

Speaker 0 | 15:28.034

No. Okay. But here, I’m going to throw in this thing because I’ll tell you one person I hate. I’m going to tell you, I hate, I’m going to use the word. All you, all you, uh, whatever people that say you can’t never hate. You can’t ever hate. I’m going to, I’m telling you right now. I hate you can capitalize H A T E Jordan Belfort.

Speaker 1 | 15:44.967

Hey,

Speaker 0 | 15:49.530

tag them, tag them. Yeah. I don’t know. I hate.

Speaker 1 | 15:53.692

Come and get us, Jordan. Huh? Come and get us, Jordan. He’s heard worse.

Speaker 0 | 15:58.214

No, no, but for real. Yeah. Does he do us damage? Or maybe you love him. Like maybe you’re like, no, because to me, he’s like the psychological trickster.

Speaker 1 | 16:07.280

Yeah, right, right.

Speaker 0 | 16:07.940

So he robbed a bunch of old people, burned their money, used it like toilet paper.

Speaker 1 | 16:13.203

And that still books 50 grand a day for speaking engagement.

Speaker 0 | 16:16.405

He’s in my industry. He’ll be people. I’ll be there’ll be like a vendor and the vendor will be like on Channel Partners 2003 or IT Expo or. whatever. We’ve got a special breakout group and you’re invited. And Jordan Belfort is the key. I was like, I just, just so you know, you’ve lost all respect with me. Yeah. I’ll never be. I’m now going to bad mouth you across my platform. And yeah.

Speaker 1 | 16:43.142

Yeah.

Speaker 0 | 16:43.342

I had to, I wanted to have the FBI agent that busted him on my show. He, he politely declined. He politely declined. But that’s what Hollywood’s pushing. They’re pushing, they’re pushing. Yeah. Boiler room. um let’s see what else there’s a few okay so there’s a few that to me represent glenn ross come on guys even the like grant cardones you know like i struggle with him um i don’t know if you know him but i know yeah i mean yeah i mean yeah i know him but i don’t i could care less but keep going but he represents the

Speaker 1 | 17:17.409

same school of thought which is it’s the adversarial complex how do i win and in order for me to win the the customer must lose They wouldn’t have articulated it that way, but that’s what they’re doing. And that’s, that’s Jordan’s whole career was how do I make this person buy something that isn’t real or that they don’t need and that won’t do what I’m telling them it will do. But I’m going to say the right string of words to make them believe that it will.

Speaker 0 | 17:42.081

Hate, hate, literally hate, you know, may the Lord above, you know, I don’t know, guide him and purify his soul or something. I don’t know. Do you know what I mean? It’s the same thing with, it’s the same thing probably like with, with, you know. it’s the same thing with women too like but eventually it’s anybody and i’ve been saying this for a long time and this is why i’m such a huge zigzagler fan anybody can make a sale anybody can climb the corporate corporate ladder anyone can do can cheat steal and and manipulate people on the way to the top but only character and integrity will keep you there you will eventually come crashing down and fall um and i see that a lot in the industry i see a lot of kind of 80 20 like the like It’s just like 80% of the industry is just kind of this like bottom feeder, like, you know, whatever. And then 20% kind of rises up. Then there’s only the top five and top 1%.

Speaker 1 | 18:33.279

Here’s the thing though, Phil, herein lies where I think herein lies the straight and narrow path that created the feel good clothes is we have what I would call an urgency mechanism in sales. You have something that you use to create urgency to drive a sale. Now, most people will use FUD, fear, uncertainty, doubt.

Speaker 0 | 18:50.811

Hate it. Hey,

Speaker 1 | 18:52.528

that’s the whole play that we’re talking about. The play is, I mean, I’ve got big competitors. I’m not going to name any names.

Speaker 0 | 18:57.689

General fear, though. There is I mean, there are some things that you should be afraid of.

Speaker 1 | 19:02.231

Yes, there is a difference. There is a difference between awareness and fear. OK, awareness says, hey, listen, I am I feel I’m under moral obligation to let you know that the way that our firewall is configured, these things are all achievable and it would take me this long to do this bad thing like. or this kind, these are the, these are the very real threats that we’re exposed to versus the twisting of the knife, the, the sort of pseudo, the dark web scans to try to then sell like that’s the MSP.

Speaker 0 | 19:31.145

Yeah. It’s up to you, man. Like if you don’t want to decide it’s on you, it’s not on me. Okay. But I’m just telling you right now, we’re totally vulnerable and here’s blah, blah, blah. Um,

Speaker 1 | 19:37.931

but then here’s the thing, right? So here’s the thing is the average person agrees that you shouldn’t use fear, shock, and awe to sell the average person. All your average listener already feels this way. The thing is that we don’t have an urgency mechanism to replace it. And so we end up being advisory people who don’t get any deals done. And the guys who win are the ones who are scaring the shit out of people. So

Speaker 0 | 20:00.299

Jordan Belfort.

Speaker 1 | 20:02.024

So how do we all agree? Even he knows that it’s wrong, but it works. So how do we replace the urgency mechanism with something that’s more in line with our best practices and the character, the job we want to have? So I argue I’ve invented one and it’s called the empathy mechanism. We can use empathy to make people make decisions because they feel safe, empowered and motivated to make a change.

Speaker 0 | 20:29.552

I’m pulling out my mission statement right now. I’m going to pull out my mission statement because this I think goes, this is why I like you so much. And this is why I only use you. If I am going to refer any MSP to go learn sales, it is only you. And on my IT, I mean the, the, the mission statement for the podcast, I’m going to read this out because I’ve been, I’ve been, you know, you can see, no, no one can see this, but I’ve been like, you know, scratching and changing it for years. You know what I mean? To be the number one. IT leadership podcast and coveted community of IT elite. I’m not taking you in if you’re a scumbag. I’m not. You don’t get on the show. Like you said, I know who you compete with. You’re not getting on the show. Sorry, your competition’s not getting on. You are. I’ve chosen you. You’re of the elite. So congratulations. To put IT leaders first by seeking to understand them and the customers they serve, to be curious. because in IT, you got to be curious. Everyone’s got to be curious. Otherwise, just quit. To lead with, fill in the blank.

Speaker 1 | 21:36.212

Empathy.

Speaker 0 | 21:36.973

You got it. To lead with empathy, excellence. And I added something else before execution. I’ve got it typed out on my new one. This is the scratch pad from yesterday. But yes, empathy. We’re constantly dissecting IT, empowering leaders and driving success. That’s just the mission statement. I haven’t gotten into the mission or the purpose yet. Yeah. Okay. But. Please, make me feel good. Make me believe, Brian. Make me believe.

Speaker 1 | 22:04.495

My mission statement is ennobling sales culture through empathy and vulnerability. Because my 100-year goal is that in 21, 25, somebody is in business and goes, wow, I’m so mixed up. There’s so many directions I could go. I have no clue what to do. I need to go somewhere I can trust. I need a salesperson. That’s my goal.

Speaker 0 | 22:27.951

Yes.

Speaker 1 | 22:30.320

We don’t have time to break down the 100-year strategy, but here’s my point. Listen to how freaking ridiculous that sentence is today. Salespeople are not the place you go when you need somebody you can trust. They’re the place you go when you have to talk to them because you expect the adversarial complex. You expect, listen, this guy’s going to try to pull one over on me. He’s going to give me a phony price with tons of gravy in it. And then he’s going to tell me the thing that they’re pushing rather than the thing that I really need, blah,

Speaker 0 | 22:58.912

So I’m really struggling with this. And I believe some of the other people are struggling with this too. I, uh, it mentioned it’s called, um, imposter syndrome and we have it a lot. The problem is, especially in it and in your business is a lot is it people in general are untrustworthy, are untrusting people. We trust issues. We have a term called zero trust. We have something called dual factor authentication. Yeah. Right? We don’t enter emails into opt-in pages. We do not click on links. Right. Well, we do, but we’re not going to tell you which ones. You know what I mean?

Speaker 1 | 23:46.040

Right, right, right.

Speaker 0 | 23:46.960

You know, so we have that in us to begin with. I’m starting to yell. people tell me i yell a lot i’m a loud talker i was at i was at the embassy the other day trying trying to get a container ship shipped overseas and the lady man here was like sir sir sir could you lower your voice please i’m like i’m just talking normal my kids are liking me they’re like put my kid at a four my kids are putting their their hands over their face they’re like oh they’re like oh we’re cooked we’re cooked we’re not getting whatever we need today this lady just told dad to like you know anyways sorry uh please go 100 your goal i’m gonna be quiet now i’m gonna try not to talk well

Speaker 1 | 24:24.828

I just wanted to throw that out there that I have, I got big plans. I got big plans, but the whole thing is I really fundamentally deeply believe that sales is an inherently noble profession. So one of the, okay, when I start, I’m going to, I haven’t forgotten your question. How do I sell the cybersecurity upgrade? We’re going to get there. But all of this is pretense, pretext of like the way that you’re thinking about it is going to determine whether or not this works in sales.

Speaker 0 | 24:50.121

Yes. And you know what? And I do want to say there is a good sales movie and I’m just, well, I’m thinking another, right? I’m going to tell you right now, one of the best sales movies ever, one of the best sales movies ever. It is not. The Wolf of Wall Street. It is not Glenn Gary, Glenn Ross. It is not Boiler Room. You know what it is? It’s Tommy Boy. It’s Tommy Boy.

Speaker 1 | 25:09.839

Nice. Right. Because Tommy…

Speaker 0 | 25:13.782

Break parts! Everyone’s… Now everyone’s working! He saved the company!

Speaker 1 | 25:18.025

Right. And you know what’s funny? It’s funny you say that because typically, like, whenever I watch a sales, like, The Office is one of my favorite shows of all time. And one of the things they do to save the American office was… After season one, everybody was like, Michael, we hate Michael. You have to make him more likable. So they had to repitch the show. Greg Daniels had to pitch it again. And he said, we’re going to do two or three things to save him. Number one is we’re going to give him a soft side. They made episodes where he was paternal towards Pam. And number two is we’re going to make him great at sales. So they made an episode called The Client where he saves Dunder Mifflin’s branch because he closes a big deal. Everything they do for sales in that show is absolutely preposterous. You would never really do. It’s like what a writer in Hollywood thinks sales is. But what Tommy Boy did was Tommy Boy was vulnerable and honest. And he just asked for the order. He was like, look, man, we really need this. And I really honestly believe that we’re the best. And the guy went, oh, think about it. And he was like, you can think about it. But why don’t you just trust the brake pad expert here rather than trying to be the brake pad expert with the whole head up the cow’s butt thing? He’s like. He leveraged because he could leverage. You can leverage your reputation when you’re empathetic, but when you’re not empathetic, you can’t leverage your reputation. You have to shove your reputation down their throat and have to say, I’m better than you. And so you have to do whatever I say. But if you, if they feel heard and seen, then you get reputational leverage. You can actually borrow trust because they want to believe you because they feel seen by you. Does that make sense? So anyway,

Speaker 0 | 26:53.304

I think you’re right. You have to be a relationship builder. You have to show that you care. No one cares until you show them how much you care. Right. You have to give more than you take. You have to really be a very good question asker. When you ask really good questions, you learn about them. You can’t try to jump in and say, you know, all these stupid sales things like sell the sizzle and sell the product and whatever, all these terms we see dog and pony show. And, and, uh, single pane of glass was a common one in our industry, you know, sell, you know, you really have to, you really have to learn and get deep and really go deep and understand your people. And if that’s what you call empathy, great. And then really understand what they’re struggling with and help them, I guess, um, prescribe, prescribe like a doctor would a really good doctor as a salesperson, right? Like if you were a sympathetic doctor, like, I feel so bad for you. Yeah. you’ve got cancer and you’re hurting and your your eye is about ready to like fall out of your skull and and all this stuff that would be a really bad doctor but if you’re an empathetic doctor like look i’m this is gonna hurt okay but we’ve we’ve got to shove that um i’m dislocating shoulder back in it’s gonna hurt yeah right if you’re just like oh man just put some ice on it no i

Speaker 1 | 28:08.275

don’t know i don’t know that’s right but so so let’s say that so i have a i have a part two yeah we need a process the thing is is like

Speaker 0 | 28:15.520

we’re just talking right now. We need, let’s give some solid stuff.

Speaker 1 | 28:19.202

And this is what it is. If you’re an IT person, you’re trying to get into the decision-making room and you’re consistently getting, you’re ramming up against, hey, thanks so much, little guy, not in the budget. And you get a noogie and then you walk out and you can’t get taken seriously. Then what you have to do is you have to realize that they have not yet understood how you help them become what they want to become. I’m talking about them personally, because what you’re trying to… what you’re probably trying to do is say what you’re doing is wrong and you have to do it this way and they don’t like that rhetoric and so they don’t have to listen to it but if instead you say hey listen i know i’m the it director i’ve been thinking a lot about this i would love you know we have some decisions we can make in our department over the next one to five years that i think will be paramount to the overall future agility of the organization i would love to have to know what you would like from us in terms of the direction of the business. Where are you taking the business and how can I help? What if we said, how can I help achieve the business’s vision? And they went, what do you mean? Well, listen, can I sit in the room and take notes? And this might inform some of the recommendations that I can make because this could end up saving us hundreds of thousands or even millions over the next decade if I know what our number one priorities are.

Speaker 0 | 29:40.194

Or help us make. hundreds of thousands or millions right hey everyone thinks of it as a cost center so that’s the problem that we have in the show is everyone thinks it is a cost center so they’re going to think what decisions can i make to cut costs and save costs but what kind of decisions can i.t make to actually increase whatever EBITDA, profit margin, gross margin, which is another thing IT directors probably need to know those terms and know how to learn that stuff.

Speaker 1 | 30:08.099

So what if we went in and said, hey, listen, hey, listen, you know, Mrs. Boss, I’d love to know what roadblocks are we seeing on the RevGen side that I might be able to, even if you don’t feel like it’s, even if it doesn’t even feel related to me, it might be more related to me than you think. Is there anything you’re comfortable sharing that I might be able to put my team, we could just put our heads together and come up with some ways. to solve any of our current revenue obstacles? Is there any regions we’re underperforming in?

Speaker 0 | 30:33.709

Greg, we need to, Greg the Frenchman, we need to take these questions. We need to put them in some kind of bullet point and put them in the show, like the top 10, five questions that we need to ask. And with actual technical terminology that doesn’t sound nerdy, that’s more C-level revgen, put revgen in quotes, revgen side. What do we do on the revgen side?

Speaker 1 | 30:54.483

Hey, are there hurdles? Even if you don’t feel like it’s related to IT, Mrs. Boss. But if there’s something that you’re comfortable sharing that I might be able to put my head, like put our heads together on the IT side and see what we can do to help. Because what you need to basically do is introduce, A, that you have a genuine interest in helping them achieve what they want. That is the foundation of selling. You have a genuine interest in them achieving what they want rather than an interest in them buying what you sell. And then you get to say the reversals and things like, I don’t even know if we need a network upgrade right now. It depends what our priorities are. What are we trying to achieve? And of course, you’re trying to push the network upgrade, but you haven’t yet found what we call in the field of clothes, a narrative tunnel, which is a direct line between what you sell and the problem they’re facing. And think of this, like, forgive the dumbness of this example, but you got to build a VPN between these two endpoints. One endpoint is their pain. The other endpoint is your solution. I got to build this tunnel in there so that all… questions will slowly sort of gravitate them closer and closer to what you’re trying to do because we have to have like an anchor point of what are they trying to achieve. So if you’re going in saying, we have to do this thing and they go, not today, buddy, thanks anyway, and that you keep happening over and over again, they’re not the problem. You have to be willing to be the problem here. You need to like look in the mirror and go, I probably am not doing this right. And stop saying my CEO is a schmuck. Nobody gets me. I’m a victim. None of that is going to change the results that you’re getting. All that’s going to do is entrench you further into what’s not working.

Speaker 0 | 32:31.929

Okay. So first of all, I absolutely love it. Absolutely love the VPN tunnel metaphor. I might cry. I might cry. Not going to today. Not that emotional yet.

Speaker 1 | 32:43.615

We’ll get you there. Don’t worry.

Speaker 0 | 32:46.497

We’ll build a VPN tunnel into your soul. Okay. They’re going to get rejected. How should they deal with that? uh yeah when you ask for hey can i have more responsibility and they say no then you say no problem what is it what is the team comfortable with deploying to us that we could help with you said um your secret weapon back in the days when you were an actor in hollywood and uh hopefully you know not homeless on the streets living in a tent um i just have to throw i like to throw um random stereotypes out from time to time because that’s what we do um You said acting is professional rejection. It’s just like sales only rather than rejecting a product. People are rejecting you. And my history of performer forged my internal mechanism for categories, categorizing objections and understanding them without internalizing them. You said I train anyone how to overcome any objection and face any amount of rejection, any amount of rejection while becoming motivated rather than discouraged. And just think about for you guys out there that are, I don’t know, trying to get married or something. Who knows? Like, you know, think about this rejection, embrace it. How do we embrace rejection and run with that? And then let’s continue the VPN metaphor. But I want to throw that in there because some guys are like, yeah, I’ve been doing this all the time. I’ve tried to do that. I’ve tried, I’ve tried, I’ve tried, I’ve tried, I’ve tried, I’ve tried, I’ve tried. And I just get rejected, rejected, rejected.

Speaker 1 | 34:18.049

So we’re discouraged, we’re dejected, we’re jaded now. And then we start to feel bitter or we start to feel resentful. So. what happens is like when you, in the face of rejection, what most sales coaches are going to tell you to do is essentially harden and say, you just have to toughen and callous so that you can get punched more. And I actually think that that is terrible advice. You should not harden yourself to rejection instead. It’s a, because then you can’t like, you can’t be tender and calloused at the same time. You can’t be empathetic and numb at the same time. So if you’re trying to callous yourself, you’re numbing yourself in your interpersonal exchanges. So I’m not saying that you don’t become more resilient, but we become resilient by understanding what this rejection really is. They’re not saying, Phil, you’re not good enough. That’s not what they’re saying. What they’re saying is, I don’t yet understand how you can help me achieve what I’m trying to achieve.

Speaker 0 | 35:19.816

You have not given me enough information or demonstrated enough for me to trust you because trust is two things. It’s both, do I believe this is a… a believably good person? And do I also, number two, believe that they are talented enough and have the skill set to make something happen?

Speaker 1 | 35:36.456

Exactly. And that’s probably why you’re getting rejected is you haven’t built trust with them, but you don’t build trust by doing, I’ll say it this way. You don’t just build trust by doing the bare minimum and staying in your lane. You can build trust by slowly, incrementally asking for more responsibility.

Speaker 0 | 35:54.211

And demonstrating that you actually know what EBITDA means now.

Speaker 1 | 35:57.954

Yeah, you know what it means.

Speaker 0 | 35:58.734

Or that you’ve sat down with the CFO or the CFO said in a meeting, hey, you know what? The new IT, I actually sat down with me and asked me the other day, what’s the, you know, what is our gross margin on, you know, blah, blah, blah. I don’t know why he was asking me, but I think he had something to do with, you know, the machines in the shop and production or something. I don’t know.

Speaker 1 | 36:15.381

Exactly. So like, hey, I’m making some IT recommendations, things that are going to potentially categorize or catapult us into the new AI arms race. I’ve got some questions.

Speaker 0 | 36:25.986

I want to make this as how we block all the people trying to sell me AI on LinkedIn. That’s the first thing that we’re deploying. Anyways, right.

Speaker 1 | 36:33.188

But if you, it’s exactly what you’re saying. If you can demonstrate to them that you are interested in what they’re interested in, that’s like, I mean, dude, that’s Carnegie 101 becoming more likable. You know, how to win friends and influence people is some great advice. It’s also 90 years old. So, you know, repeating their name and making excessive eye contact. doesn’t really translate the same way as it did in the 60s, 70s, 80s, even the 90s. So like, likability has evolved as culture has evolved. But there’s some basic like you can build as the kids say, you can get the Riz, you can get more charisma by simply demonstrating to people that you want them to achieve to look better. And hey, if I do my job, you get everything you want and you look fantastic. Can I ask you three or four questions? They’re gonna go hell yeah, ask me about myself. I love talking about myself. And those sorts of things can build trust. But if you’re getting rejected, it simply means that you’re either you’re maybe you’re asking too soon. Maybe you’re misreading the room. Maybe they’ve got stuff going on their end.

Speaker 0 | 37:33.865

Maybe you’re just a bad person and you don’t give a crap about anyone else. You ever thought that? You ever thought that maybe you’re just a selfish, self-centered, arrogant a-hole? Maybe. That could be a factor. That could be a factor.

Speaker 1 | 37:50.362

I’ve got news. If you can’t find the a-hole in the room, it’s you. And this is it, man. If we want to have empathy-Oh,

Speaker 0 | 38:00.550

gosh. I just had flashbacks of numerous groups and rooms, and I was like, oh, no, I was the one there. Oh, I should have been a little bit nicer.

Speaker 1 | 38:08.357

When you leave and you go, I just realized I was not very likable in that.

Speaker 0 | 38:12.320

Yeah, I was the guy. I was the guy there.

Speaker 1 | 38:14.402

Wow. I just talked about myself.

Speaker 0 | 38:16.343

Yeah, I’m very good at being harsh on myself. that that’s like the number one piece of feedback people have told me forever. Phil, you’re too hard on yourself. No, I immediately thought like, Oh gosh. Yep. Nope.

Speaker 1 | 38:27.018

But there’s also a difference between there’s a difference in self-loathing and self self-assessment, right? Like, cause sometimes we say, well, it’s like we’re too we’re too fragile to ever really look inwards and evolve. And so then what we do is we like, it’s like there’s this hydrophobic bubble around our ego. And then it kind of, it, any feedback goes one of two ways. It either goes the other way and goes, no, it’s that person. That person’s the problem. Or it goes straight to self-loathing and we go, oh yeah, man, you stupid idiot moron. But that’s not self-assessment. That is actually cowardice because you’re not willing. You’re not willing to say,

Speaker 0 | 39:05.014

I believe.

Speaker 1 | 39:06.495

I’m not a, yeah, I did something bad and I, but I can change.

Speaker 0 | 39:11.156

Yes.

Speaker 1 | 39:11.796

I can change that habit. I can, I can listen more and talk less. Next time I’m. rambling and talking until I’m blue in the face in the elevator with somebody who I don’t know, why don’t I shut up, take two deep breaths, and then ask them a question? And then just try my hardest to listen for 30 seconds.

Speaker 0 | 39:30.081

Change is hard. So change is hard. So change is hard. What is the answer? Mechanism. What’s the mechanism? What is the mechanism for that change? Because it’s like, I remember I was given the, gifted the book. I think Mark Lindstrom, he was the VP of Starbucks at the time, gifted me the book, First Break All the Rules. And, you know, that whole series, that whole Marcus Buckingham series or whatever, like the first one’s First Break All the Rules, the next one’s now. I think discover your strengths. And then the third one is put your strengths to work. You know, like kind of like the premise of that whole thing is that like, you’ll never fix someone’s weaknesses. You don’t, you shouldn’t try to make someone’s weaknesses into strengths and you should always focus on people’s strengths, but you do need to make your weaknesses, not like self imploding, you know, self-destructive issues. Right. So how do we form, you know, it’s a, I guess, atomic habits. It’s been on, it’s number one on the New York times best. selling this forever. We’ll just plug him one more time for free, whatever. Atomic habits, it’s great.

Speaker 1 | 40:34.529

It’s atomic habits. It’s, you know, everybody gets analysis paralysis when they look internal and they go, oh man, like, I don’t even know where to start. The way you start is one foot at one step at a time. Like I say, the best sales training I ever got was three years of therapy.

Speaker 0 | 40:50.794

Mine was, I really liked Franklin Covey’s seven habits of highly effective people. I know it’s been around for a long time, but that was like life altering for me. That was, that was life altering for me. The bucket, the whole bucket list thing. I’ve done the bucket list multiple times. The first time I did that list, I was, I was broke. I mean, I was making $26,000 a year and married and had one kid and a pregnant wife and lived in a low income housing. And, you know, I think it was, you know, the paycheck came in bi-weekly at 600 bucks, like after taxes, like how ridiculous is that? I don’t even, you know, and I remember I made that bucket list because they, back then Starbucks made. tons of money and they were like sending us management to all kinds of classes they sent us to that class and i wrote that bucket list down when i looked at it the other day because i was doing this training for my staff again and it was like everything on that list was checked off and there was things i remember when i wrote the list i thought this is never gonna happen i’m never gonna have a a house in a foreign country and go surfing you know and like i recently but you know i mean you know may the lord love blessed and protected by it. I recently bought a villa in Morocco and was surfing in Agadir and I never thought I’d be in Morocco and surfing in Agadir and think that this was like amazing. But again, I never, it was like anything that I ever say, I never won’t do, you know, but, and I’m looking at the bucket list and I’m like, oh my Lord, we, we did all of this. Anyways, go ahead.

Speaker 1 | 42:13.517

So if you have to the IT director, I mean, maybe, maybe this is a decent segue. Um, cause we still have never really gotten through all the tactics. but the decent segue eventually into like, what do you, what do you want? I mean, my, my favorite, my like life question is why are you alive? You know, what, why are we doing this?

Speaker 0 | 42:31.427

Exactly.

Speaker 1 | 42:32.568

But essentially figure out what you want and why you want it. And then learn through curiosity, empathy, and humility. That’s you just ask, what’s the mechanism. That’s it. Be curious about other people care about them and then be humble. If you can do those three things. you will make, you will have a linear growth in every area of your life.

Speaker 0 | 42:53.747

Let’s get to you and what you do, because there are MSPs and there are MSPs and we’re going to, that we’ll listen to this and we’ll edit this and put some, like some, if you listen to all the way to the end of the episode, you’ll get to this. Um, you know what I mean? But, um, it, it applies to every, obviously your, your feel good clothes applies to everything. And we could do a part two of this episode and we could, you know, however we want to do this. Um, I ask people on the show a lot, what’s your end game? So you’re a VP of technology, you’re a CTO, and I ask them what the end game is. And I would say 95% of the time is, I don’t know. And some of these guys have side gigs and it might be like, well, I’m going to invest some money into real estate or I’m going to do this and this and everything. Why should they or why should they not possibly start their own MSP? What are the benefits of it?

Speaker 1 | 43:48.712

The benefit of an MSP is that you can, you have to start an MSP because you really like the work. It’s like, it’s like owning a restaurant. Like you don’t go into a restaurant unless you love service and hospitality. You don’t go into MSP unless you love fixing puzzles at scale and solving problems. If you just want to like make more money in IT, you should just consult, you know, you could make good money. If you just consult MSPs, because most of them suck. But you can start an MSP. And what’s great, especially if you’ve got a Rolodex already, and you know businesses who would hire you, and you want to… One of the benefits of being an MSP is that you get to sort of like… You get more perspective. And with it comes more… It’s like you get more at-bats to execute projects. So if you like doing stuff, if you like getting stuff done, MSP is amazing because… you don’t do one network refresh every 10 years.

Speaker 0 | 44:46.662

You do one every month because I love that.

Speaker 1 | 44:50.187

If you like doing that stuff, it’s amazing, right? You also get to be cutting on the cutting edge, if you will, if you so choose to be on what’s happening in the channel, the MSP channel, which is like, Actually pretty cool. I also want to say that if you want to be in a business that will be different every five years, well, you guys, you’re already in tech. Like, you know, tech changes fast. But enterprise tech changes the slowest, right? Because it’s the biggest gears. So you’re making longer term CapEx investments. You’re working and you’re getting full life cycle out of all of your engagements, blah, blah, blah. You’ve got more hardware infrastructure, right? Versus like a little, you’re not a digitally nomadic little business like me, a bunch of millennials on laptops and all over the world. Yep. Who don’t, I’ll never need an MSP ever, no matter how much money I’ll never need one. You know,

Speaker 0 | 45:44.164

um, I’ll be careful what you say.

Speaker 1 | 45:46.165

Uh, well, maybe I will, but not in their current form. I actually think the future of MSP is like no code, low code, to be honest. But, um,

Speaker 0 | 45:54.532

Are you going to help talking with Greg? You would love seeing what we’re doing. you would lose your mind. In fact, I’ll tell, I’ll show you after the show, show you. Okay.

Speaker 1 | 46:02.137

So if you want to start an MSP, it’s like, if that’s my point is if you love that, if you love the trade, you love the craft and you want to stay sharp and you want to build relationships. But if you’re an it guy who doesn’t want a boss and that’s it, don’t start an MSP. In fact, what’s that?

Speaker 0 | 46:21.345

Well, you said consulting. How do they do that? Okay. Well, how about that?

Speaker 1 | 46:25.387

Yeah. Get get really choose one thing that you’re the most excited about in technology and then become the best at it how do they start selling that how do they start selling that that’s a good question uh do they join the feel good clothes program yeah you could always go you could you know pay somebody like me to give you the fundamental how does the fundamentally like principles of how to sell something to anybody somebody like me could help you with that easily the question becomes ultimately it’s always going to come back to but what do you want you Why are we selling this? Who are we selling it to? What is, what’s it going to do to their life? And why are we doing it? What are you trying to achieve? So I think the thing to start with is start with make the big, beautiful plan for your life. That’s how you know, if you should start an MSP is like, what do you want? When do you want to be done working? What do you want work to look like over the next decade? Because managed services is not an easy business. And it’s also not one where there’s, there’s not a lot of passive owners, unless you’re doing it at scale with like a roll-up platform and a private equity backed. Maybe, but then that’s a totally different conversation. That’s not the same skills. You’re not even in technology anymore. You’re an M&A person at that point.

Speaker 0 | 47:34.008

Let’s pick two. Let’s pick two. So MSP, you love more at bats. You love forklifting projects and you love building your own similar help desk team and guys like that. And you’re going to manage these customers. You’re going to help them take technology and grow their business and bring it into the future and embrace technology as a business force multiplier. Okay. And then you’re going to be empathetic and you’re going to be laser focused and you’re going to do it better than anybody else. And then we’re going to talk about how you don’t get undercut by small businesses and all that stuff if they join your program. Okay. Now, however, let’s just say there, you know what? I’m just the guy that somehow is really good at mapping out ERP implementations or SAP, blah, you know, or doing these different things. And yeah, you want to take this like very ninja consulting route, then your program would be good for them as well.

Speaker 1 | 48:28.483

I could, yeah, I could definitely help them. I mean, my community is super geared towards MSPs, but I’ve had guys join who are like, I’m not an MSP, but I get it. I really want to be in the community. They’re excited. I had a cyber consultant and he does like 60 to a hundred thousand dollar engagements with F500 businesses. That’s what he does. And he does like cyber audit. cyber assessment scores. And then he gets them.

Speaker 0 | 48:50.453

I’m going to do the assessment, the audit. I’ll put the roadmap together and then I’ll tell you exactly how to execute it with your team.

Speaker 1 | 48:56.415

Yeah. And this is a guy I don’t have to hire.

Speaker 0 | 48:58.176

And then you don’t have to hire a CISO and you can just, uh, you know, I can work side by side with your it director. I want to know who that guy is, by the way. I want to know that guy. He probably, yeah. Please introduce me to him. He should be,

Speaker 1 | 49:10.061

I will. His first name is Brandon lives in South Carolina. He makes 450 K a year in his pocket. He does projects in a smelly t-shirt in his house.

Speaker 0 | 49:19.665

He probably doesn’t. We’ll probably delete that part of the show unless he’s totally okay with that. Then that’s cool.

Speaker 1 | 49:24.668

He kills it. There’s a lot of Brandons in South Carolina. Here’s what we’re going to do.

Speaker 0 | 49:28.990

We’re going to put a non-smelly shirt on you, Brandon. We’re going to like, you know, we’re going to like shine you up a little bit and then you’re going to do a million a year. Yeah.

Speaker 1 | 49:38.194

But the point is that when I asked him, hey, what are your goals? He’s like. I just want to add more. He basically said, I want redundancy and resilience to the career I built for myself. I’m like, do you want to make more money? He’s like, not at all. I don’t want to work.

Speaker 0 | 49:51.328

I want time. He wants time.

Speaker 1 | 49:53.491

He wants time. And 450 in South Carolina is a pretty good freaking living, man. He’s doing great.

Speaker 0 | 50:02.417

That’s awesome. So that’s me, man. That’s what I want. That’s what I want.

Speaker 1 | 50:06.060

But the other route to your point, if you want to do ERP map, you want to map out ERP implementations, what you do is like starting a business and mapping ERPs. Those are two completely different things. And you probably don’t want to actually start or run a business. If you probably want freedom, but the truth is, if you knew what it took to start and run a business and grow it, you probably don’t want it. especially if you don’t want to sell. So what you do is you find the people who are doing what you do, or you think of yourself as an arrow in a sharpshooter’s quiver. You become a really specific solution for something Phil can sell to other IT directors, something that MSPs can add to their suite to roll them out and make them more holistic. You go to an MSP roll-up platform and say, hey, how are you guys doing ERPs? Do you guys want to integrate all your acquisitions into a singular homogenized? thing. I want to be that for you. And then what you do is sell how you being great at what you do helps them achieve what they want to achieve. It’s the same damn strategy as when you’re trying to sell these projects and implementations to your, to your uppers, but now you’re selling it. You’re repackaging it, but all sales comes down to, you want to get what you want. I want to be the guide that gets you there. And when you’re done with, when we’re done together, you have more of what you want and less of what you hate that sales.

Speaker 0 | 51:28.080

Ryan Gillette, everyone, the feel good clothes. You can reach out to him on LinkedIn. I will have all of the links in the descriptions on the show page and everything. Thank you so much. This has been a long time coming and it was outstanding. I really appreciate it.

Speaker 1 | 51:42.459

Thanks, man. So glad to be here. Hope this was helpful.

Speaker 0 | 51:44.983

It was great.

308- Brian Gillette Reveals How to Sell IT with Empathy

Speaker 0 | 00:00.800

Everyone out there listening to Dissecting Popular IT Nerds, we are talking with Brian Gillette. This has been a long time coming, like years, years, years coming. Very excited about this, by the way. And I think part of it is because we’re both, I guess it’s fair to say we’re entrepreneurs, whatever that is. I never really thought I would call myself that, but I think I’ve come to terms now with myself that I’m going to call myself an entrepreneur now. odd caster or something. I already got all kinds of things, alerts going off that people are probably hearing and annoying. I really have wanted to, I’ve wanted to have you on this show, but I wanted to make sure we mapped it out right. And it was really beneficial to not only all of the IT directors, CTOs, CIOs, and IT leaders out there that are fighting to get a seat at the executive round table, but also mix in, I beat up on the MSPs a lot. I like to make fun of MSPs, not because I don’t love them. I do love them. It’s just that I decided I didn’t want to work with MSPs anymore years ago, not because I don’t love MSPs because they’re like IT people. They know what an IP address is, right? We can joke around about, like, I don’t know, XP or something. I love it. I love working with them. I love supporting them. Here’s what I didn’t love. I didn’t love their customers. And I am very specific. I learned at one point in my life that I need to only work with people that I like working with. And what that became was, is I loved them. So where do they exist in the world? They exist inside larger companies and their names are IT director, IT manager, VP of IT, CTO, CIO. So I said… Screw it. I’m going to work with them because I love working with them and they love working with their customers and they’re, and they kind of, you know, it’s like it, it all kind of flows through this nice visionary process. I don’t, I don’t know how else to accept that. So I do still work with some MSPs that I like their customers, but you can’t always choose your MSPs customers. I don’t know if there’s any deep thoughts around that. I don’t know if there’s anything you know you’re the guy so and just for everyone out there listening brian is the guy that teaches sales and you can tell me a little bit about your history in the past of being like you know like the sales guy inside enterprise companies and larger companies but brian is the guy that is going to teach us today and i know a lot of people i’ve known um you know you know there’s the the robin robbins in the space of the msps and stuff but i choose only to work with you because i know that you have a polished enterprise sales process and experience and experience. It’s not just a small business thing. It’s enterprise polished sales. And I think that that’s going to be very valuable to IT directors, IT managers that need to sell to executive management that IT is valuable. It’s a business force multiplier. And we deserve always a seat at the executive round table because nothing gets done. in any department, in any company without IT being involved. That was a lot. I’m sorry. Did I just, it was a lot. I’ve had, I’ve drank some coffee today. I’m on some good nootropics. Is it nootropics? Nootropics? I don’t know. Whatever it is, you know, all that stuff that they’re trying to like throw us pills, you know, pills on Instagram and stuff. Anyhow.

Speaker 1 | 03:45.256

Yeah. You’re juiced up. You know, when you were saying you can’t always choose your MSP’s customers and you didn’t like MSP’s customers. What’s funny is that you. What did you say? Is there something deeper there? The thing that’s deeper there is that MSPs don’t like their customers either. And most MSPs don’t actually have-How can they provide customer service?

Speaker 0 | 04:04.695

I don’t even like you.

Speaker 1 | 04:06.476

Well, that’s exactly it. Most MSPs forget that their customer service business and their medium is technology, but they like to think of themselves as technologists, but that’s just not what you really are. A true MSP is actually a customer service business. And technology is the medium with which you provide value. But they like to think I’m going to be a technologist. Everybody’s going to come and sit at my feet and listen to how I do things. And then my customers are going to fall in love with how genius I am. And then when that never happens, they start to build resentment and go, hey, how come nobody cares about how smart I am? Because they forget their job is not to be the hero in their relationships. Their job is to be. the Yoda and then their customer gets to be Luke and gets to go and kill Darth Vader or, you know, go and vanquish the emperor.

Speaker 0 | 04:59.623

It’s pretty deep. It’s pretty deep. And everyone’s going to relate with that. And it’s a theme that comes up on the show a lot is right where we are a, if we’re calling them end users, we say end users, because we know what that means from a technical standpoint. But if we’re calling them end users, we’re, we’re doing it wrong. There are customers.

Speaker 1 | 05:19.877

Yeah, right. A lot of people will, like they hate the word customers, they’ll say partners, or clients or It’s like, if we’re hiding the fact that we’re supporting somebody or selling something to somebody, then that should be a huge red flag. Like, if you’re selling something, stop pretending you aren’t selling. Just be selling.

Speaker 0 | 05:44.521

Okay.

Speaker 1 | 05:45.662

Because if you have this core belief that selling is wrong, bad, self-seeking, then you’re going to start trying to use all this verbiage to hide your job title. In sales, we get titles that are like, head of. customer ecstasy.

Speaker 0 | 06:00.292

Business development. Yeah, right. Just be selling. My first Gmail account, and only Gmail account, I am a salesman at gmail.com. Everyone can send me an email right now.

Speaker 1 | 06:14.801

You’re the one who locked that down when I couldn’t get it. Mine is I am a salesman 87864. I didn’t get there.

Speaker 0 | 06:24.067

I got it from a famous, like, I don’t know. I was a big Zig Ziglar fan when I, when I left Starbucks and he, and he has a, uh, like a famous book, you know, and audio is, you know, secrets of closing the sale. And he reads like some poem that’s like, I’m proud to be a salesman because, and it goes on, everyone can Google it right now. Like Google, like a Zig Ziglar or something. I’m proud to be a salesman because it’s, it’s some anonymous person, but it’s like, because and long story short, the whole theme of the entire, like. pros piece is that nothing gets done until someone makes a sale. A farmer can’t get the beans to the market. Walmart can’t start delivering. I don’t know, whatever it is. Nothing gets done until someone makes a sale. So nothing in your IT stack is going to get upgraded until IT director, you make a sale to executive management. So what’s your philosophy around it? You have this thing that you’ve termed the feel good close. What’s that all about?

Speaker 1 | 07:23.959

Yeah. The feel good clothes is the core belief that selling is an inherently noble profession.

Speaker 0 | 07:30.304

I love you.

Speaker 1 | 07:32.066

And what you’re selling is at its core. I mean, it’s a few things for my personality. What selling means is I personally love introducing people to things that can excite them. Like if I see a movie and I love it. I tell everybody how much I loved it. If I find a new, like this dumb smart mug I’m drinking out of, I’ve sold like six of these because I’m like, oh my gosh, listen, once you go, you’ll never go back. You just got to, but it’s not because I, it’s literally because I found a value and I know other people who could benefit from it and I want them to experience it.

Speaker 0 | 08:12.415

I got it. It’s like Phil’s favorite things. I got Phil’s favorite things.

Speaker 1 | 08:16.057

Right. Because you’re a Phil’s guy.

Speaker 0 | 08:17.898

Darn tough socks. Um, Carhartt pants. What else do we have? Cutco knives. Cutco, man. Cutco. Amazing. Love them. For life. I inherited some Cutco knives from my mother-in-law that are older than me. Saw the Cutco guy. Yeah, no problem. We’ll resharpen them all. Oh, that little tip. Oh, we’ll send you a brand new one. I didn’t even buy them. And they’re replacing them for life.

Speaker 1 | 08:43.435

It’s so awesome.

Speaker 0 | 08:44.776

My mother-in-law’s like, don’t forget who gave those to you. Right.

Speaker 1 | 08:48.558

But you see the point, right? Like selling is inherently noble. And what happens with anything inherently good and noble is that special interests get involved and then we get these splintered variants. And once people started realizing, oh, because I make money when a transaction occurs, I would make more money if I have more transactions. but I have a finite amount of conversations. So let me start transacting with people who shouldn’t buy it. And therein lies, that’s the introduction to the downfall of sales culture. And now we have what I refer to as the adversarial sales complex, which is now rampant. It is this core belief that when you’re selling something, you’re in contest with the person you’re selling to. And in order to achieve the sale, you have to overcome your buyer. And it’s mutual because the buyer says, I have to get what this slimy guy is selling, but I’m not going to put up with any of his crap. And I’m not going to play the game and I won’t take the first price. And I’m assuming he’s lying. So I’m going to come in with all these defense mechanisms and hard outs and excuses so that I can get everything I want out of the sale.

Speaker 0 | 09:57.781

Yeah, but most people would love to just get to that point. Most people would love to get to the slimy battle point. Some people, and I’m sure some of your clients can’t even get there. Some of my guys, they would love to just get to the executive round table to sell the upgrade. But no, no, it’s not in the budget this year. It’s not there, whatever it is. So why don’t we just go to like, why don’t we just start from the very beginning? Like some, I don’t know. I don’t even know where to begin. Maybe you can help us.

Speaker 1 | 10:22.710

Yeah. I mean, I would say that transacting is not selling. Transacting is the by-product. of selling so once you’ve actually done your job of communicating to somebody what they need why they need it and how it’s going to turn them into the person they want to become then the transaction happens on the back end but we think of oh i’m gonna go into i’m gonna go boiler room like chess match negotiation redlining that’s selling that is not selling that is that’s transacting it’s it’s something completely different but uh and i was saying the other day relationships are not transactional No, they, right.

Speaker 0 | 11:01.316

Or relationships are, a relationship is not a transaction.

Speaker 1 | 11:04.478

Right. So especially if you’re like, I have to get, let me say it this way. If you’re an IT director or a CTO, whatever, and you’ve got, there’s a closed door with a bunch of people who write the checks and you’re trying to get this thing done that you’re like, how do they not understand that if they don’t do this, we’re taking massive risk. That’s way more expensive than what I’m asking for.

Speaker 0 | 11:25.489

Let’s use security. Everyone that security might be the hardest thing to sell. because it’s like, I don’t know, maybe selling like insurance or something. I don’t really know what it is, but it is like, well, we haven’t had a breach yet. We haven’t had that. Why do we need this project? Put that one on. Right.

Speaker 1 | 11:41.816

And we all know, we all have the stats that over half of the small businesses who get hit by a real event go out of business and how spending goes up 10 or 20 X or whatever after an event. So we all know like, listen, why don’t you just learn from everybody else’s mistakes instead of learning from our own $100 million mistake? Why don’t we learn from their $100 billion mistake? and just frigging buy this, upgrade your firewall, put MFA on these computers. It’s not that complicated.

Speaker 0 | 12:07.849

So let’s just use a couple of examples. I’ve got some that are hypothetical, but maybe not true. Maybe they are, maybe they aren’t. Might have someone out there right now. He might be an IT director and he’s trying to upsell a fiber upgrade on his network and a… And a… maybe fortinet or cisco i don’t know some of these maraqui firewall upgrade along with um backup internet connections he’s trying to do a network upgrade in short yeah and right now everything’s kind of running there’s some latency issues in the network in some locations but they’re they’re working but this new upgrade is going to cost more money and it’s going to be like i don’t know maybe it’s double maybe it’s 50 more maybe he’s going from $2,000 a month to $4,000 a month, but then they’re going to have a firewall upgrade. They’re going to have internet and stuff like that. How does he sell that? How does he even approach that to the executive management?

Speaker 1 | 13:04.564

Right. So for starters, if you’re sitting here thinking, if your mindset is that they’re wrong and I’m right, you’re already going to lose because tie always goes to the leader. in a conversation like this. So if both of you have an argument about why you should and shouldn’t do it, the tie will go to the person who writes the checks. So if you’re thinking, they’re wrong, I’m right, how do I get them to see that I’m right? I have news for you. CEOs don’t read that, don’t work that way. CEOs only like their ideas. And the people who know how to work with a CEO are the ones who know how to implant ideas into their head. You know?

Speaker 0 | 13:48.223

Preach. Teach us. Teach us.

Speaker 1 | 13:50.672

What you do is honestly what I would do, all jobs promote to a sales job. Have you talked about this? If you keep getting promoted, eventually you’re a salesperson.

Speaker 0 | 14:03.360

Yes.

Speaker 1 | 14:04.220

So you’re the top of the IT game and all of a sudden you go, wait a minute. Now, I’m not turning screwdrivers. My job is to convince these people.

Speaker 0 | 14:12.705

Can you say that again? That’s Greg, the Frenchman behind the scenes, my developer that’s… no longer lives in France and is an expat or whatever you call that in Morocco. That’s my developer, Greg, the Frenchman. I should have him on sometimes. He has a great French accent. He’s going to make this quote card. Please say that again. All jobs promote to sale. What is that quote? That’s the quote for this episode. We have to have that.

Speaker 1 | 14:35.616

All jobs eventually promote into a sales job. What can we infer from that? That if you want to get promoted, you have to learn how to sell. And if you’re, and if you are at the top, you need to stop being angry that you’re being expected to sell because that’s why you’re on top. Because you have the ability to make things happen, get things done, which is what selling is.

Speaker 0 | 15:01.919

All of that. Gold. All of that’s gold for me. That just made my day. That made my day. Oh, you hate salespeople? Good luck getting promoted.

Speaker 1 | 15:16.789

You hate your boss.

Speaker 0 | 15:18.790

Oh, so you hate your job, you hate your boss, you hate your life. That’s why you hate salespeople.

Speaker 1 | 15:24.052

Yeah. I don’t know how to help you.

Speaker 0 | 15:28.034

No. Okay. But here, I’m going to throw in this thing because I’ll tell you one person I hate. I’m going to tell you, I hate, I’m going to use the word. All you, all you, uh, whatever people that say you can’t never hate. You can’t ever hate. I’m going to, I’m telling you right now. I hate you can capitalize H A T E Jordan Belfort.

Speaker 1 | 15:44.967

Hey,

Speaker 0 | 15:49.530

tag them, tag them. Yeah. I don’t know. I hate.

Speaker 1 | 15:53.692

Come and get us, Jordan. Huh? Come and get us, Jordan. He’s heard worse.

Speaker 0 | 15:58.214

No, no, but for real. Yeah. Does he do us damage? Or maybe you love him. Like maybe you’re like, no, because to me, he’s like the psychological trickster.

Speaker 1 | 16:07.280

Yeah, right, right.

Speaker 0 | 16:07.940

So he robbed a bunch of old people, burned their money, used it like toilet paper.

Speaker 1 | 16:13.203

And that still books 50 grand a day for speaking engagement.

Speaker 0 | 16:16.405

He’s in my industry. He’ll be people. I’ll be there’ll be like a vendor and the vendor will be like on Channel Partners 2003 or IT Expo or. whatever. We’ve got a special breakout group and you’re invited. And Jordan Belfort is the key. I was like, I just, just so you know, you’ve lost all respect with me. Yeah. I’ll never be. I’m now going to bad mouth you across my platform. And yeah.

Speaker 1 | 16:43.142

Yeah.

Speaker 0 | 16:43.342

I had to, I wanted to have the FBI agent that busted him on my show. He, he politely declined. He politely declined. But that’s what Hollywood’s pushing. They’re pushing, they’re pushing. Yeah. Boiler room. um let’s see what else there’s a few okay so there’s a few that to me represent glenn ross come on guys even the like grant cardones you know like i struggle with him um i don’t know if you know him but i know yeah i mean yeah i mean yeah i know him but i don’t i could care less but keep going but he represents the

Speaker 1 | 17:17.409

same school of thought which is it’s the adversarial complex how do i win and in order for me to win the the customer must lose They wouldn’t have articulated it that way, but that’s what they’re doing. And that’s, that’s Jordan’s whole career was how do I make this person buy something that isn’t real or that they don’t need and that won’t do what I’m telling them it will do. But I’m going to say the right string of words to make them believe that it will.

Speaker 0 | 17:42.081

Hate, hate, literally hate, you know, may the Lord above, you know, I don’t know, guide him and purify his soul or something. I don’t know. Do you know what I mean? It’s the same thing with, it’s the same thing probably like with, with, you know. it’s the same thing with women too like but eventually it’s anybody and i’ve been saying this for a long time and this is why i’m such a huge zigzagler fan anybody can make a sale anybody can climb the corporate corporate ladder anyone can do can cheat steal and and manipulate people on the way to the top but only character and integrity will keep you there you will eventually come crashing down and fall um and i see that a lot in the industry i see a lot of kind of 80 20 like the like It’s just like 80% of the industry is just kind of this like bottom feeder, like, you know, whatever. And then 20% kind of rises up. Then there’s only the top five and top 1%.

Speaker 1 | 18:33.279

Here’s the thing though, Phil, herein lies where I think herein lies the straight and narrow path that created the feel good clothes is we have what I would call an urgency mechanism in sales. You have something that you use to create urgency to drive a sale. Now, most people will use FUD, fear, uncertainty, doubt.

Speaker 0 | 18:50.811

Hate it. Hey,

Speaker 1 | 18:52.528

that’s the whole play that we’re talking about. The play is, I mean, I’ve got big competitors. I’m not going to name any names.

Speaker 0 | 18:57.689

General fear, though. There is I mean, there are some things that you should be afraid of.

Speaker 1 | 19:02.231

Yes, there is a difference. There is a difference between awareness and fear. OK, awareness says, hey, listen, I am I feel I’m under moral obligation to let you know that the way that our firewall is configured, these things are all achievable and it would take me this long to do this bad thing like. or this kind, these are the, these are the very real threats that we’re exposed to versus the twisting of the knife, the, the sort of pseudo, the dark web scans to try to then sell like that’s the MSP.

Speaker 0 | 19:31.145

Yeah. It’s up to you, man. Like if you don’t want to decide it’s on you, it’s not on me. Okay. But I’m just telling you right now, we’re totally vulnerable and here’s blah, blah, blah. Um,

Speaker 1 | 19:37.931

but then here’s the thing, right? So here’s the thing is the average person agrees that you shouldn’t use fear, shock, and awe to sell the average person. All your average listener already feels this way. The thing is that we don’t have an urgency mechanism to replace it. And so we end up being advisory people who don’t get any deals done. And the guys who win are the ones who are scaring the shit out of people. So

Speaker 0 | 20:00.299

Jordan Belfort.

Speaker 1 | 20:02.024

So how do we all agree? Even he knows that it’s wrong, but it works. So how do we replace the urgency mechanism with something that’s more in line with our best practices and the character, the job we want to have? So I argue I’ve invented one and it’s called the empathy mechanism. We can use empathy to make people make decisions because they feel safe, empowered and motivated to make a change.

Speaker 0 | 20:29.552

I’m pulling out my mission statement right now. I’m going to pull out my mission statement because this I think goes, this is why I like you so much. And this is why I only use you. If I am going to refer any MSP to go learn sales, it is only you. And on my IT, I mean the, the, the mission statement for the podcast, I’m going to read this out because I’ve been, I’ve been, you know, you can see, no, no one can see this, but I’ve been like, you know, scratching and changing it for years. You know what I mean? To be the number one. IT leadership podcast and coveted community of IT elite. I’m not taking you in if you’re a scumbag. I’m not. You don’t get on the show. Like you said, I know who you compete with. You’re not getting on the show. Sorry, your competition’s not getting on. You are. I’ve chosen you. You’re of the elite. So congratulations. To put IT leaders first by seeking to understand them and the customers they serve, to be curious. because in IT, you got to be curious. Everyone’s got to be curious. Otherwise, just quit. To lead with, fill in the blank.

Speaker 1 | 21:36.212

Empathy.

Speaker 0 | 21:36.973

You got it. To lead with empathy, excellence. And I added something else before execution. I’ve got it typed out on my new one. This is the scratch pad from yesterday. But yes, empathy. We’re constantly dissecting IT, empowering leaders and driving success. That’s just the mission statement. I haven’t gotten into the mission or the purpose yet. Yeah. Okay. But. Please, make me feel good. Make me believe, Brian. Make me believe.

Speaker 1 | 22:04.495

My mission statement is ennobling sales culture through empathy and vulnerability. Because my 100-year goal is that in 21, 25, somebody is in business and goes, wow, I’m so mixed up. There’s so many directions I could go. I have no clue what to do. I need to go somewhere I can trust. I need a salesperson. That’s my goal.

Speaker 0 | 22:27.951

Yes.

Speaker 1 | 22:30.320

We don’t have time to break down the 100-year strategy, but here’s my point. Listen to how freaking ridiculous that sentence is today. Salespeople are not the place you go when you need somebody you can trust. They’re the place you go when you have to talk to them because you expect the adversarial complex. You expect, listen, this guy’s going to try to pull one over on me. He’s going to give me a phony price with tons of gravy in it. And then he’s going to tell me the thing that they’re pushing rather than the thing that I really need, blah,

Speaker 0 | 22:58.912

So I’m really struggling with this. And I believe some of the other people are struggling with this too. I, uh, it mentioned it’s called, um, imposter syndrome and we have it a lot. The problem is, especially in it and in your business is a lot is it people in general are untrustworthy, are untrusting people. We trust issues. We have a term called zero trust. We have something called dual factor authentication. Yeah. Right? We don’t enter emails into opt-in pages. We do not click on links. Right. Well, we do, but we’re not going to tell you which ones. You know what I mean?

Speaker 1 | 23:46.040

Right, right, right.

Speaker 0 | 23:46.960

You know, so we have that in us to begin with. I’m starting to yell. people tell me i yell a lot i’m a loud talker i was at i was at the embassy the other day trying trying to get a container ship shipped overseas and the lady man here was like sir sir sir could you lower your voice please i’m like i’m just talking normal my kids are liking me they’re like put my kid at a four my kids are putting their their hands over their face they’re like oh they’re like oh we’re cooked we’re cooked we’re not getting whatever we need today this lady just told dad to like you know anyways sorry uh please go 100 your goal i’m gonna be quiet now i’m gonna try not to talk well

Speaker 1 | 24:24.828

I just wanted to throw that out there that I have, I got big plans. I got big plans, but the whole thing is I really fundamentally deeply believe that sales is an inherently noble profession. So one of the, okay, when I start, I’m going to, I haven’t forgotten your question. How do I sell the cybersecurity upgrade? We’re going to get there. But all of this is pretense, pretext of like the way that you’re thinking about it is going to determine whether or not this works in sales.

Speaker 0 | 24:50.121

Yes. And you know what? And I do want to say there is a good sales movie and I’m just, well, I’m thinking another, right? I’m going to tell you right now, one of the best sales movies ever, one of the best sales movies ever. It is not. The Wolf of Wall Street. It is not Glenn Gary, Glenn Ross. It is not Boiler Room. You know what it is? It’s Tommy Boy. It’s Tommy Boy.

Speaker 1 | 25:09.839

Nice. Right. Because Tommy…

Speaker 0 | 25:13.782

Break parts! Everyone’s… Now everyone’s working! He saved the company!

Speaker 1 | 25:18.025

Right. And you know what’s funny? It’s funny you say that because typically, like, whenever I watch a sales, like, The Office is one of my favorite shows of all time. And one of the things they do to save the American office was… After season one, everybody was like, Michael, we hate Michael. You have to make him more likable. So they had to repitch the show. Greg Daniels had to pitch it again. And he said, we’re going to do two or three things to save him. Number one is we’re going to give him a soft side. They made episodes where he was paternal towards Pam. And number two is we’re going to make him great at sales. So they made an episode called The Client where he saves Dunder Mifflin’s branch because he closes a big deal. Everything they do for sales in that show is absolutely preposterous. You would never really do. It’s like what a writer in Hollywood thinks sales is. But what Tommy Boy did was Tommy Boy was vulnerable and honest. And he just asked for the order. He was like, look, man, we really need this. And I really honestly believe that we’re the best. And the guy went, oh, think about it. And he was like, you can think about it. But why don’t you just trust the brake pad expert here rather than trying to be the brake pad expert with the whole head up the cow’s butt thing? He’s like. He leveraged because he could leverage. You can leverage your reputation when you’re empathetic, but when you’re not empathetic, you can’t leverage your reputation. You have to shove your reputation down their throat and have to say, I’m better than you. And so you have to do whatever I say. But if you, if they feel heard and seen, then you get reputational leverage. You can actually borrow trust because they want to believe you because they feel seen by you. Does that make sense? So anyway,

Speaker 0 | 26:53.304

I think you’re right. You have to be a relationship builder. You have to show that you care. No one cares until you show them how much you care. Right. You have to give more than you take. You have to really be a very good question asker. When you ask really good questions, you learn about them. You can’t try to jump in and say, you know, all these stupid sales things like sell the sizzle and sell the product and whatever, all these terms we see dog and pony show. And, and, uh, single pane of glass was a common one in our industry, you know, sell, you know, you really have to, you really have to learn and get deep and really go deep and understand your people. And if that’s what you call empathy, great. And then really understand what they’re struggling with and help them, I guess, um, prescribe, prescribe like a doctor would a really good doctor as a salesperson, right? Like if you were a sympathetic doctor, like, I feel so bad for you. Yeah. you’ve got cancer and you’re hurting and your your eye is about ready to like fall out of your skull and and all this stuff that would be a really bad doctor but if you’re an empathetic doctor like look i’m this is gonna hurt okay but we’ve we’ve got to shove that um i’m dislocating shoulder back in it’s gonna hurt yeah right if you’re just like oh man just put some ice on it no i

Speaker 1 | 28:08.275

don’t know i don’t know that’s right but so so let’s say that so i have a i have a part two yeah we need a process the thing is is like

Speaker 0 | 28:15.520

we’re just talking right now. We need, let’s give some solid stuff.

Speaker 1 | 28:19.202

And this is what it is. If you’re an IT person, you’re trying to get into the decision-making room and you’re consistently getting, you’re ramming up against, hey, thanks so much, little guy, not in the budget. And you get a noogie and then you walk out and you can’t get taken seriously. Then what you have to do is you have to realize that they have not yet understood how you help them become what they want to become. I’m talking about them personally, because what you’re trying to… what you’re probably trying to do is say what you’re doing is wrong and you have to do it this way and they don’t like that rhetoric and so they don’t have to listen to it but if instead you say hey listen i know i’m the it director i’ve been thinking a lot about this i would love you know we have some decisions we can make in our department over the next one to five years that i think will be paramount to the overall future agility of the organization i would love to have to know what you would like from us in terms of the direction of the business. Where are you taking the business and how can I help? What if we said, how can I help achieve the business’s vision? And they went, what do you mean? Well, listen, can I sit in the room and take notes? And this might inform some of the recommendations that I can make because this could end up saving us hundreds of thousands or even millions over the next decade if I know what our number one priorities are.

Speaker 0 | 29:40.194

Or help us make. hundreds of thousands or millions right hey everyone thinks of it as a cost center so that’s the problem that we have in the show is everyone thinks it is a cost center so they’re going to think what decisions can i make to cut costs and save costs but what kind of decisions can i.t make to actually increase whatever EBITDA, profit margin, gross margin, which is another thing IT directors probably need to know those terms and know how to learn that stuff.

Speaker 1 | 30:08.099

So what if we went in and said, hey, listen, hey, listen, you know, Mrs. Boss, I’d love to know what roadblocks are we seeing on the RevGen side that I might be able to, even if you don’t feel like it’s, even if it doesn’t even feel related to me, it might be more related to me than you think. Is there anything you’re comfortable sharing that I might be able to put my team, we could just put our heads together and come up with some ways. to solve any of our current revenue obstacles? Is there any regions we’re underperforming in?

Speaker 0 | 30:33.709

Greg, we need to, Greg the Frenchman, we need to take these questions. We need to put them in some kind of bullet point and put them in the show, like the top 10, five questions that we need to ask. And with actual technical terminology that doesn’t sound nerdy, that’s more C-level revgen, put revgen in quotes, revgen side. What do we do on the revgen side?

Speaker 1 | 30:54.483

Hey, are there hurdles? Even if you don’t feel like it’s related to IT, Mrs. Boss. But if there’s something that you’re comfortable sharing that I might be able to put my head, like put our heads together on the IT side and see what we can do to help. Because what you need to basically do is introduce, A, that you have a genuine interest in helping them achieve what they want. That is the foundation of selling. You have a genuine interest in them achieving what they want rather than an interest in them buying what you sell. And then you get to say the reversals and things like, I don’t even know if we need a network upgrade right now. It depends what our priorities are. What are we trying to achieve? And of course, you’re trying to push the network upgrade, but you haven’t yet found what we call in the field of clothes, a narrative tunnel, which is a direct line between what you sell and the problem they’re facing. And think of this, like, forgive the dumbness of this example, but you got to build a VPN between these two endpoints. One endpoint is their pain. The other endpoint is your solution. I got to build this tunnel in there so that all… questions will slowly sort of gravitate them closer and closer to what you’re trying to do because we have to have like an anchor point of what are they trying to achieve. So if you’re going in saying, we have to do this thing and they go, not today, buddy, thanks anyway, and that you keep happening over and over again, they’re not the problem. You have to be willing to be the problem here. You need to like look in the mirror and go, I probably am not doing this right. And stop saying my CEO is a schmuck. Nobody gets me. I’m a victim. None of that is going to change the results that you’re getting. All that’s going to do is entrench you further into what’s not working.

Speaker 0 | 32:31.929

Okay. So first of all, I absolutely love it. Absolutely love the VPN tunnel metaphor. I might cry. I might cry. Not going to today. Not that emotional yet.

Speaker 1 | 32:43.615

We’ll get you there. Don’t worry.

Speaker 0 | 32:46.497

We’ll build a VPN tunnel into your soul. Okay. They’re going to get rejected. How should they deal with that? uh yeah when you ask for hey can i have more responsibility and they say no then you say no problem what is it what is the team comfortable with deploying to us that we could help with you said um your secret weapon back in the days when you were an actor in hollywood and uh hopefully you know not homeless on the streets living in a tent um i just have to throw i like to throw um random stereotypes out from time to time because that’s what we do um You said acting is professional rejection. It’s just like sales only rather than rejecting a product. People are rejecting you. And my history of performer forged my internal mechanism for categories, categorizing objections and understanding them without internalizing them. You said I train anyone how to overcome any objection and face any amount of rejection, any amount of rejection while becoming motivated rather than discouraged. And just think about for you guys out there that are, I don’t know, trying to get married or something. Who knows? Like, you know, think about this rejection, embrace it. How do we embrace rejection and run with that? And then let’s continue the VPN metaphor. But I want to throw that in there because some guys are like, yeah, I’ve been doing this all the time. I’ve tried to do that. I’ve tried, I’ve tried, I’ve tried, I’ve tried, I’ve tried, I’ve tried, I’ve tried. And I just get rejected, rejected, rejected.

Speaker 1 | 34:18.049

So we’re discouraged, we’re dejected, we’re jaded now. And then we start to feel bitter or we start to feel resentful. So. what happens is like when you, in the face of rejection, what most sales coaches are going to tell you to do is essentially harden and say, you just have to toughen and callous so that you can get punched more. And I actually think that that is terrible advice. You should not harden yourself to rejection instead. It’s a, because then you can’t like, you can’t be tender and calloused at the same time. You can’t be empathetic and numb at the same time. So if you’re trying to callous yourself, you’re numbing yourself in your interpersonal exchanges. So I’m not saying that you don’t become more resilient, but we become resilient by understanding what this rejection really is. They’re not saying, Phil, you’re not good enough. That’s not what they’re saying. What they’re saying is, I don’t yet understand how you can help me achieve what I’m trying to achieve.

Speaker 0 | 35:19.816

You have not given me enough information or demonstrated enough for me to trust you because trust is two things. It’s both, do I believe this is a… a believably good person? And do I also, number two, believe that they are talented enough and have the skill set to make something happen?

Speaker 1 | 35:36.456

Exactly. And that’s probably why you’re getting rejected is you haven’t built trust with them, but you don’t build trust by doing, I’ll say it this way. You don’t just build trust by doing the bare minimum and staying in your lane. You can build trust by slowly, incrementally asking for more responsibility.

Speaker 0 | 35:54.211

And demonstrating that you actually know what EBITDA means now.

Speaker 1 | 35:57.954

Yeah, you know what it means.

Speaker 0 | 35:58.734

Or that you’ve sat down with the CFO or the CFO said in a meeting, hey, you know what? The new IT, I actually sat down with me and asked me the other day, what’s the, you know, what is our gross margin on, you know, blah, blah, blah. I don’t know why he was asking me, but I think he had something to do with, you know, the machines in the shop and production or something. I don’t know.

Speaker 1 | 36:15.381

Exactly. So like, hey, I’m making some IT recommendations, things that are going to potentially categorize or catapult us into the new AI arms race. I’ve got some questions.

Speaker 0 | 36:25.986

I want to make this as how we block all the people trying to sell me AI on LinkedIn. That’s the first thing that we’re deploying. Anyways, right.

Speaker 1 | 36:33.188

But if you, it’s exactly what you’re saying. If you can demonstrate to them that you are interested in what they’re interested in, that’s like, I mean, dude, that’s Carnegie 101 becoming more likable. You know, how to win friends and influence people is some great advice. It’s also 90 years old. So, you know, repeating their name and making excessive eye contact. doesn’t really translate the same way as it did in the 60s, 70s, 80s, even the 90s. So like, likability has evolved as culture has evolved. But there’s some basic like you can build as the kids say, you can get the Riz, you can get more charisma by simply demonstrating to people that you want them to achieve to look better. And hey, if I do my job, you get everything you want and you look fantastic. Can I ask you three or four questions? They’re gonna go hell yeah, ask me about myself. I love talking about myself. And those sorts of things can build trust. But if you’re getting rejected, it simply means that you’re either you’re maybe you’re asking too soon. Maybe you’re misreading the room. Maybe they’ve got stuff going on their end.

Speaker 0 | 37:33.865

Maybe you’re just a bad person and you don’t give a crap about anyone else. You ever thought that? You ever thought that maybe you’re just a selfish, self-centered, arrogant a-hole? Maybe. That could be a factor. That could be a factor.

Speaker 1 | 37:50.362

I’ve got news. If you can’t find the a-hole in the room, it’s you. And this is it, man. If we want to have empathy-Oh,

Speaker 0 | 38:00.550

gosh. I just had flashbacks of numerous groups and rooms, and I was like, oh, no, I was the one there. Oh, I should have been a little bit nicer.

Speaker 1 | 38:08.357

When you leave and you go, I just realized I was not very likable in that.

Speaker 0 | 38:12.320

Yeah, I was the guy. I was the guy there.

Speaker 1 | 38:14.402

Wow. I just talked about myself.

Speaker 0 | 38:16.343

Yeah, I’m very good at being harsh on myself. that that’s like the number one piece of feedback people have told me forever. Phil, you’re too hard on yourself. No, I immediately thought like, Oh gosh. Yep. Nope.

Speaker 1 | 38:27.018

But there’s also a difference between there’s a difference in self-loathing and self self-assessment, right? Like, cause sometimes we say, well, it’s like we’re too we’re too fragile to ever really look inwards and evolve. And so then what we do is we like, it’s like there’s this hydrophobic bubble around our ego. And then it kind of, it, any feedback goes one of two ways. It either goes the other way and goes, no, it’s that person. That person’s the problem. Or it goes straight to self-loathing and we go, oh yeah, man, you stupid idiot moron. But that’s not self-assessment. That is actually cowardice because you’re not willing. You’re not willing to say,

Speaker 0 | 39:05.014

I believe.

Speaker 1 | 39:06.495

I’m not a, yeah, I did something bad and I, but I can change.

Speaker 0 | 39:11.156

Yes.

Speaker 1 | 39:11.796

I can change that habit. I can, I can listen more and talk less. Next time I’m. rambling and talking until I’m blue in the face in the elevator with somebody who I don’t know, why don’t I shut up, take two deep breaths, and then ask them a question? And then just try my hardest to listen for 30 seconds.

Speaker 0 | 39:30.081

Change is hard. So change is hard. So change is hard. What is the answer? Mechanism. What’s the mechanism? What is the mechanism for that change? Because it’s like, I remember I was given the, gifted the book. I think Mark Lindstrom, he was the VP of Starbucks at the time, gifted me the book, First Break All the Rules. And, you know, that whole series, that whole Marcus Buckingham series or whatever, like the first one’s First Break All the Rules, the next one’s now. I think discover your strengths. And then the third one is put your strengths to work. You know, like kind of like the premise of that whole thing is that like, you’ll never fix someone’s weaknesses. You don’t, you shouldn’t try to make someone’s weaknesses into strengths and you should always focus on people’s strengths, but you do need to make your weaknesses, not like self imploding, you know, self-destructive issues. Right. So how do we form, you know, it’s a, I guess, atomic habits. It’s been on, it’s number one on the New York times best. selling this forever. We’ll just plug him one more time for free, whatever. Atomic habits, it’s great.

Speaker 1 | 40:34.529

It’s atomic habits. It’s, you know, everybody gets analysis paralysis when they look internal and they go, oh man, like, I don’t even know where to start. The way you start is one foot at one step at a time. Like I say, the best sales training I ever got was three years of therapy.

Speaker 0 | 40:50.794

Mine was, I really liked Franklin Covey’s seven habits of highly effective people. I know it’s been around for a long time, but that was like life altering for me. That was, that was life altering for me. The bucket, the whole bucket list thing. I’ve done the bucket list multiple times. The first time I did that list, I was, I was broke. I mean, I was making $26,000 a year and married and had one kid and a pregnant wife and lived in a low income housing. And, you know, I think it was, you know, the paycheck came in bi-weekly at 600 bucks, like after taxes, like how ridiculous is that? I don’t even, you know, and I remember I made that bucket list because they, back then Starbucks made. tons of money and they were like sending us management to all kinds of classes they sent us to that class and i wrote that bucket list down when i looked at it the other day because i was doing this training for my staff again and it was like everything on that list was checked off and there was things i remember when i wrote the list i thought this is never gonna happen i’m never gonna have a a house in a foreign country and go surfing you know and like i recently but you know i mean you know may the lord love blessed and protected by it. I recently bought a villa in Morocco and was surfing in Agadir and I never thought I’d be in Morocco and surfing in Agadir and think that this was like amazing. But again, I never, it was like anything that I ever say, I never won’t do, you know, but, and I’m looking at the bucket list and I’m like, oh my Lord, we, we did all of this. Anyways, go ahead.

Speaker 1 | 42:13.517

So if you have to the IT director, I mean, maybe, maybe this is a decent segue. Um, cause we still have never really gotten through all the tactics. but the decent segue eventually into like, what do you, what do you want? I mean, my, my favorite, my like life question is why are you alive? You know, what, why are we doing this?

Speaker 0 | 42:31.427

Exactly.

Speaker 1 | 42:32.568

But essentially figure out what you want and why you want it. And then learn through curiosity, empathy, and humility. That’s you just ask, what’s the mechanism. That’s it. Be curious about other people care about them and then be humble. If you can do those three things. you will make, you will have a linear growth in every area of your life.

Speaker 0 | 42:53.747

Let’s get to you and what you do, because there are MSPs and there are MSPs and we’re going to, that we’ll listen to this and we’ll edit this and put some, like some, if you listen to all the way to the end of the episode, you’ll get to this. Um, you know what I mean? But, um, it, it applies to every, obviously your, your feel good clothes applies to everything. And we could do a part two of this episode and we could, you know, however we want to do this. Um, I ask people on the show a lot, what’s your end game? So you’re a VP of technology, you’re a CTO, and I ask them what the end game is. And I would say 95% of the time is, I don’t know. And some of these guys have side gigs and it might be like, well, I’m going to invest some money into real estate or I’m going to do this and this and everything. Why should they or why should they not possibly start their own MSP? What are the benefits of it?

Speaker 1 | 43:48.712

The benefit of an MSP is that you can, you have to start an MSP because you really like the work. It’s like, it’s like owning a restaurant. Like you don’t go into a restaurant unless you love service and hospitality. You don’t go into MSP unless you love fixing puzzles at scale and solving problems. If you just want to like make more money in IT, you should just consult, you know, you could make good money. If you just consult MSPs, because most of them suck. But you can start an MSP. And what’s great, especially if you’ve got a Rolodex already, and you know businesses who would hire you, and you want to… One of the benefits of being an MSP is that you get to sort of like… You get more perspective. And with it comes more… It’s like you get more at-bats to execute projects. So if you like doing stuff, if you like getting stuff done, MSP is amazing because… you don’t do one network refresh every 10 years.

Speaker 0 | 44:46.662

You do one every month because I love that.

Speaker 1 | 44:50.187

If you like doing that stuff, it’s amazing, right? You also get to be cutting on the cutting edge, if you will, if you so choose to be on what’s happening in the channel, the MSP channel, which is like, Actually pretty cool. I also want to say that if you want to be in a business that will be different every five years, well, you guys, you’re already in tech. Like, you know, tech changes fast. But enterprise tech changes the slowest, right? Because it’s the biggest gears. So you’re making longer term CapEx investments. You’re working and you’re getting full life cycle out of all of your engagements, blah, blah, blah. You’ve got more hardware infrastructure, right? Versus like a little, you’re not a digitally nomadic little business like me, a bunch of millennials on laptops and all over the world. Yep. Who don’t, I’ll never need an MSP ever, no matter how much money I’ll never need one. You know,

Speaker 0 | 45:44.164

um, I’ll be careful what you say.

Speaker 1 | 45:46.165

Uh, well, maybe I will, but not in their current form. I actually think the future of MSP is like no code, low code, to be honest. But, um,

Speaker 0 | 45:54.532

Are you going to help talking with Greg? You would love seeing what we’re doing. you would lose your mind. In fact, I’ll tell, I’ll show you after the show, show you. Okay.

Speaker 1 | 46:02.137

So if you want to start an MSP, it’s like, if that’s my point is if you love that, if you love the trade, you love the craft and you want to stay sharp and you want to build relationships. But if you’re an it guy who doesn’t want a boss and that’s it, don’t start an MSP. In fact, what’s that?

Speaker 0 | 46:21.345

Well, you said consulting. How do they do that? Okay. Well, how about that?

Speaker 1 | 46:25.387

Yeah. Get get really choose one thing that you’re the most excited about in technology and then become the best at it how do they start selling that how do they start selling that that’s a good question uh do they join the feel good clothes program yeah you could always go you could you know pay somebody like me to give you the fundamental how does the fundamentally like principles of how to sell something to anybody somebody like me could help you with that easily the question becomes ultimately it’s always going to come back to but what do you want you Why are we selling this? Who are we selling it to? What is, what’s it going to do to their life? And why are we doing it? What are you trying to achieve? So I think the thing to start with is start with make the big, beautiful plan for your life. That’s how you know, if you should start an MSP is like, what do you want? When do you want to be done working? What do you want work to look like over the next decade? Because managed services is not an easy business. And it’s also not one where there’s, there’s not a lot of passive owners, unless you’re doing it at scale with like a roll-up platform and a private equity backed. Maybe, but then that’s a totally different conversation. That’s not the same skills. You’re not even in technology anymore. You’re an M&A person at that point.

Speaker 0 | 47:34.008

Let’s pick two. Let’s pick two. So MSP, you love more at bats. You love forklifting projects and you love building your own similar help desk team and guys like that. And you’re going to manage these customers. You’re going to help them take technology and grow their business and bring it into the future and embrace technology as a business force multiplier. Okay. And then you’re going to be empathetic and you’re going to be laser focused and you’re going to do it better than anybody else. And then we’re going to talk about how you don’t get undercut by small businesses and all that stuff if they join your program. Okay. Now, however, let’s just say there, you know what? I’m just the guy that somehow is really good at mapping out ERP implementations or SAP, blah, you know, or doing these different things. And yeah, you want to take this like very ninja consulting route, then your program would be good for them as well.

Speaker 1 | 48:28.483

I could, yeah, I could definitely help them. I mean, my community is super geared towards MSPs, but I’ve had guys join who are like, I’m not an MSP, but I get it. I really want to be in the community. They’re excited. I had a cyber consultant and he does like 60 to a hundred thousand dollar engagements with F500 businesses. That’s what he does. And he does like cyber audit. cyber assessment scores. And then he gets them.

Speaker 0 | 48:50.453

I’m going to do the assessment, the audit. I’ll put the roadmap together and then I’ll tell you exactly how to execute it with your team.

Speaker 1 | 48:56.415

Yeah. And this is a guy I don’t have to hire.

Speaker 0 | 48:58.176

And then you don’t have to hire a CISO and you can just, uh, you know, I can work side by side with your it director. I want to know who that guy is, by the way. I want to know that guy. He probably, yeah. Please introduce me to him. He should be,

Speaker 1 | 49:10.061

I will. His first name is Brandon lives in South Carolina. He makes 450 K a year in his pocket. He does projects in a smelly t-shirt in his house.

Speaker 0 | 49:19.665

He probably doesn’t. We’ll probably delete that part of the show unless he’s totally okay with that. Then that’s cool.

Speaker 1 | 49:24.668

He kills it. There’s a lot of Brandons in South Carolina. Here’s what we’re going to do.

Speaker 0 | 49:28.990

We’re going to put a non-smelly shirt on you, Brandon. We’re going to like, you know, we’re going to like shine you up a little bit and then you’re going to do a million a year. Yeah.

Speaker 1 | 49:38.194

But the point is that when I asked him, hey, what are your goals? He’s like. I just want to add more. He basically said, I want redundancy and resilience to the career I built for myself. I’m like, do you want to make more money? He’s like, not at all. I don’t want to work.

Speaker 0 | 49:51.328

I want time. He wants time.

Speaker 1 | 49:53.491

He wants time. And 450 in South Carolina is a pretty good freaking living, man. He’s doing great.

Speaker 0 | 50:02.417

That’s awesome. So that’s me, man. That’s what I want. That’s what I want.

Speaker 1 | 50:06.060

But the other route to your point, if you want to do ERP map, you want to map out ERP implementations, what you do is like starting a business and mapping ERPs. Those are two completely different things. And you probably don’t want to actually start or run a business. If you probably want freedom, but the truth is, if you knew what it took to start and run a business and grow it, you probably don’t want it. especially if you don’t want to sell. So what you do is you find the people who are doing what you do, or you think of yourself as an arrow in a sharpshooter’s quiver. You become a really specific solution for something Phil can sell to other IT directors, something that MSPs can add to their suite to roll them out and make them more holistic. You go to an MSP roll-up platform and say, hey, how are you guys doing ERPs? Do you guys want to integrate all your acquisitions into a singular homogenized? thing. I want to be that for you. And then what you do is sell how you being great at what you do helps them achieve what they want to achieve. It’s the same damn strategy as when you’re trying to sell these projects and implementations to your, to your uppers, but now you’re selling it. You’re repackaging it, but all sales comes down to, you want to get what you want. I want to be the guide that gets you there. And when you’re done with, when we’re done together, you have more of what you want and less of what you hate that sales.

Speaker 0 | 51:28.080

Ryan Gillette, everyone, the feel good clothes. You can reach out to him on LinkedIn. I will have all of the links in the descriptions on the show page and everything. Thank you so much. This has been a long time coming and it was outstanding. I really appreciate it.

Speaker 1 | 51:42.459

Thanks, man. So glad to be here. Hope this was helpful.

Speaker 0 | 51:44.983

It was great.

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