How to transition from a ‘doer’ to a bona fide executive

Look no further than Ontario’s growing tech community as a perfect ecosystem to gather leadership lessons learned. With the proliferation of tech incubators, accelerators, and hubs like DMZ, MaRS, DCS Innovation Lab, and Communitech (and too many more to list), the number of tech-start-ups is growing at a huge rate. With that comes a growing number of founders who are managing the challenges of leading a start-up.

Recently, we interviewed a number of founders of fast-growing tech start-ups in the Toronto-Waterloo corridor: Michael Litt (CEO of Vidyard), Michael Katchen (CEO of Wealthsimple), David Au-Yeung (co-founder of Flipp Corporation), and Kurtis McBride (CEO of Miovision Technologies). A common theme we found across interviews was the challenge of transitioning from being immersed in day-to-day tasks such as product development and marketing, to stepping back and setting a vision for the company as an executive. Imagine making this transition in a matter of months or years. For some of the founders we spoke to, that was their reality.

The challenge with that transition was illustrated nicely by Michael Litt of Vidyard: “If you stay super tactical in your role, you’re going to be like Bambi on ice. Bambi comes running across the snow, hits the ice, and his legs are going in multiple directions. He’s still going across the ice but inevitably will slow down. You have to keep things moving in the same direction, and you as the CEO have to force that path. It’s easy in the growth phase to get caught up in a single function inside the company and to not to think more broadly. But that’s what the [CEO] role is for.”

This is a compelling argument, but can often be easier said than done. Fortunately, the founders we interviewed had a number of pieces of advice for how to transition from a ‘doer’ to a bona fide executive.

Recruit smart people that you trust to do what you used to do. Or as Michael Katchen of Wealthsimple put it, “How do we bring in people that are way smarter and more capable at whatever the role is, compared to me or anyone else on the team?” This sentiment was echoed by David Au-Yeung of Flipp: “When we hire, we make sure that every single developer is better than ourselves.” The take-away here is that not only do you want to hire smart people for the sake of adequately filling a role, but bringing in smart people allows you to let go and trust that they will do the job well – the one that you used to do.

Empower your people. This piece of advice was stressed by Kurtis McBride of Miovision. At Miovision, most decisions are pushed down to the team or individual level as opposed to being driven from the top down. Kurtis noted that “If you fill the company up with people that are empowerable, empower them, and give them a vision of where we are trying to go, you can let them fill the blanks in.” An undercurrent here is that if you have hired people that thrive in an entrepreneurial environment, they will not react well to being micromanaged.

The founder’s role is to set the vision. With the right people in place, the founder must transition into a new type of role – one where they set the strategy for the organization. In the words of Michael Litt, “What the business needs is a global and overarching set of rules and directions that can be communicated to the team and the company. That overarching set of expectations needs to be consistently communicated and iterated upon. When you do that, your executives have a compass and a direction. That allows the teams to direct themselves.”

Staying out of the weeds can be tough. Start-up founders need to make the transition from executing to strategizing even quicker than leaders in larger organizations, where it may take 20 years to rise through the ranks and learn those tough lessons. The transition may be painful but imperative in order to be successful.


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