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Jonathan Bennett

I help progressive leaders get clear on what they want and how to make it happen


About Jonathan

My Story:

I’d quit an executive role at a large hospital to strike out on my own, founding a management consulting firm.

And, for 10 years, things were pretty great. The company grew. We became a B Corp and served hundreds of organizations across Canada.

Except I’d become…unfulfilled.

For years I’d been delivering consulting projects that clients loved, but I wasn’t happy anymore. Nothing had really changed about the work, so I thought it was me. I thought that I just needed to dig deeper, work harder. Though nothing I tried seemed to relieve this feeling: that I was supposed to be doing something else. But what?

Then one Monday, looking at the week ahead on my phone’s calendar and desperately trying to find some motivation, three things sparked hope. They were all coaching sessions.

You see, I had, over the past few years, been taking on leaders to coach. I’d started reluctantly—I didn’t think I wanted to coach. After all, I was a management consultant! But, one by one, leaders accumulated on my coaching roster, and unexpectedly, I found enormous joy in it.

Why? Because coaching meant going deep. Making lasting, personal change with interesting, powerful people. Working one-on-one had such an impact. Not better, just different. I was serving leaders, not their organizations. This was the different for which I’d been searching.

That Monday, I immediately knew what I had to do.

With a succession plan in place, I stepped away from consulting for good. I went ‘all in’ on executive coaching—starting a new company.

Since I made that decision, it’s been transformational for me. It’s what I’m supposed to be doing with my life.

My mission now is to help purpose-driven leaders—to go from overwhelmed and stuck, to thriving, quickly.

It’s lonely being a leader. There’s often no one you can really talk to. I’ve been there.

So, wherever you’re at, I’ll bring 25 years of creativity and leadership success to your situation. You’ll experience humour and empathy, and see firsthand why I am known for my deep-listening and breakthrough questions that create insights and new strategies.

  • Canada
  • Chartered Director (C.Dir.)
Who I Help
  • B Corps
  • Boards
  • CEOs
  • C Suite
  • Directors
  • Entrepreneurs
  • ESG
  • Executive Directors
  • Founders
  • Vice Presidents