My Mentors

This will be a very ‘me’-centric article – but please bear with me, and I will get back to regularly scheduled programming soon. Truth be told, the reason I wanted to write the article last week on mentoring was so that I could write this week’s article spotlighting some of the key individuals that have had an outsized impact on my career. I always tell my son that the path to success involves a combination of natural skill, hard work, and a whole lot of dumb luck. Getting the opportunity to cross paths with the people featured in this article means I have had more dumb luck than I deserve for this lifetime.

Simon South

In seventh grade, I stood in the lunch line at school and overheard a ninth-grader in the line ahead of me talking about a computer program he had written. I announced that I was a programmer too – having just completed a marvel of modern engineering myself1. But instead of laughing at me, ignoring me or giving me an atomic wedgie, Simon took me under his wing. He introduced me to Pascal, the concepts of readability, and gave me the confidence to write and distribute my shareware on the local BBS system. Simon helped mould the foundations of the software engineer I am today.

Simon helped me through another critical transition in life when he invited me to share an apartment with him during my first year of univeristy. I was probably not the best flatmate – but he suffered through my foibles and we parted as friends.

Craig Voisin

I first met Craig in a 4’x4’ windowless interview room in Needles Hall at the University of Waterloo. He and a fellow employee were interviewing me for an internship at Quack.com. I must have done okay because halfway through the interview, he told me he was going to hire me (much to the shock of the other interviewer, who tried to pull him aside and remind him that they still had other candidates to see). I turned down an offer at Microsoft to go work for Craig2 – and had the experience of a lifetime (first at Quack and then later at iSemantic – a startup we founded).

Craig showed me the importance of dreaming big and following those dreams. At iSemantic, we were not just writing a new piece of software – we were going to disrupt the entire data analytics and BI establishment. Working with Craig, I learned the importance of connecting the business and technology. I learned that you could have the most elegant technical solution to a problem, but it would not go anywhere unless it solved a business challenge. These early lessons have been foundational to my career and serve me to this day.

Dan Drew

If you have been reading along, you will have seen Dan’s name come up in a previous article. Dan was one of the most prolific engineers I have had the honour to work with. He is responsible for a large portion of the SCCM client and server framework – a system that has stood the test of time and is still used to manage hundreds of millions of clients nearly twenty years after its inception. When Dan found something that wasn’t right, he would fix it (usually on the Friday to Monday shift). He lived to hear that a problem was ‘impossible’ so that he could dig in deep and find a solution.??

But Dan’s influence didn’t stop at the code – and he was able and willing to jump in and help drive requirements, customer escalations, and management issues3. On multiple occasions (1, 2, 3), Dan spotted talent in the organization and encouraged and sponsored engineers to follow their dreams. In my case, Dan made a spot for me on his team and put me in a position where I could thrive.??

David James

Last, but most certainly not least, is Mr. James. Dave was my manager for fifteen years at Microsoft and has had an outsized impact on my career and life. Many, if not most of the Flegg’s Follies articles are my vein attempt to share the lessons he has taught me. Dave guided me through the transition from individual contributor to architect and taught me how to lead a team. He was the Machiavellian manager who first set me up with a team to lead and allowed me to fail safe. Later, he created a tech lead position, sponsored me for the role, and provided the mentorship I needed to succeed.

Dave and I didn’t always agree – but even though he was my boss he supported me and encouraged thoughtful dissent.? Usually, we would find a middle ground and the results speak for themselves.? Intune Mobile Deice Management, SCCM Current Branch, co-management, Endpoint Analytics, and CMPivot were all projects that started late at night with a discussion on our whiteboard.?

Dave taught me that to run a team at scale you need to find, foster, and empower talented engineers to make the right choices.? That by helping people grow and by doing what is right for the customer you can build billion-dollar businesses. I am forever in his debt.

As you can see, I have been extremely fortunate to have crossed paths with some incredible people that have shaped my career. Without the help and influence of Simon, Craig, Dan, and Dave, I would have likely taken a very different path in life?. It reminds me how important mentorship can be and why I am so passionate about paying it forward. Who were your mentors? Have you thanked them lately?

Be Happy!

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Footnotes:

1. Okay, technically, the American flag program was many years before, and I was writing much cooler stuff by then – but it was still all in BASIC.
2. Funny story. When I initially applied for an internship at Microsoft, they didn’t give me an interview. Later that week, I was drinking my sorrows away at the?Weavers Arms?pub when I saw some Microsoft folks setting up for a recruitment event. With a little bit of liquid courage, I approached one of the managers and asked why they hadn’t given me an interview. I happened to have a resume in my backpack – and when I handed it over, the manager said he could pencil me in for an interview the next day after I sobered up. I interviewed. Microsoft offered me a job. But I turned them down and went to go work for Craig instead.
3. Dan’s interventions didn’t always go smoothly. Buy me a drink sometime, and I will tell you some stories of vicious arguments that I bore witness to when Dan made attempts to fix things that were probably a bit too far out of his scope of influence.
4. When I first moved to Seattle, I wanted to buy a live-aboard sailboat, pay it off and set sail around the world. Which means this could be me. Maybe I am not so thankful after all.

Please note that the opinions stated here are my own, not those of my company.