[02:15] Tell me how you got started in IT.

I grew up in Jamaica and I’ve been in IT since I was a kid. I was President of the Computer Science Club and taught myself coding. My yearbook said I was most likely to be the next Bill Gates. I started building my own computers out of old PCs. When everyone else went to university, I went to flight school. I combined my love for aviation and computers at first, but I remembered how much I hated coding, so I transitioned to regular IT.

[08:15] When you were growing up in IT, what was your biggest gap in knowledge around the business of IT?

I always thought I was going to be a coder that made money. Things are a lot different now. Formal education is overrated and there is less hands-on experience. The reality is that college is more about the connections you make.

[10:15] How did you learn the language of the IT business? Did you learn at college?

Absolutely not. There were a few things I learned, like basic accounting and finance classes. In my position that side of things was never really part of my job but I learned from people above me or on my team. There’s always a lot to learn.

[12:35] Do you think it’s an important gap to fill?

Absolutely. Technology is the easy part to learn. Learning the impact on the business is the hard part to learn. The last 2 years have shed a light on this for IT leaders.

[13:50] What would your biggest question be for you regarding the business side of IT?

What is their biggest problem? If I can understand what keeps them up at night, I can formulate an idea to tackle the issue.

[15:35] What’s your philosophy surrounding end-users and coaching a team to communicate with them?

I’m very big on customer experience. I always try to have an open-door policy for the team to improve things. Sometimes team members will identify someone as a problem child and I try to get them to see things from that client’s perspective.

[17:30] How do you deal with a supposed problem child?

For example, now people are working at home and setups have changed. IT teams have to realize that for people not used to technology or IT that these changes can interrupt the workflow with something as simple as a USB adapter or monitor resolution.

[21:10] Who guides the digital roadmap and who should guide it in organizations?

I feel very strongly about this. It should be a combination of the IT department and executive management.

[23:24] Where do the big problems lie in implementing that strategy?

Communication is very important.

[25:15] How should IT be implementing those conversations?

The conversations should be happening at the executive level and keeping us informed. Things shouldn’t be a surprise. If the company doesn’t value your opinion, it may be time to move on for your own growth.

[28:20] What should you say in a job interview to ensure you’re at the right place?

I list what’s important to me, my core values, and deal-breakers and match those to the conversations.

[33:05] What advice do you have for people looking to get into IT?

The internet has almost leveled the playing field to a certain extent. There’s so much learning you can do for free. Options are available; take advantage of free resources. Start with that and explore.

[36:40] How many hours do you think someone needs to put in before getting a job?

Everyone’s’ situation is different and it really depends on what you can do on your path. A tech sales job can be a good starting point, or an internship, or coding boot camp. There are many options.

[41:45] What’s your final message to IT leaders out there?

You have to learn what is important to your organization and the executives. You also have to learn the marketing side of things. It’s all part of your job. The politics will always be there. You have to learn how to appeal to people and build relationships. You almost have to play the politics game.