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Writer's picturePaul Hogendoorn

Should You Hire an Entrepreneurial Coach?

Updated: Nov 29

After 42 years of figuring things out as I go, I decided to hire a coach. Four weeks into it, I’m already starting to ‘feel’ a difference, to think differently, to act and execute different.

The only jobs I’ve ever had, other than my first job out of college (which was 45 years ago) and my part time jobs while in school, were working on and for companies I had a hand in starting. All the companies have continued to this day, suggesting we did more things right than we did wrong. So, why should I take on a coach now?


There are a lot of reasons, but first I’ll share why I took so long to make this decision.

I started my entrepreneurship journey ‘organically’-; it was not my specific intention. It started as a hobby, which eventually became a company, and the adrenalin and rush of facing challenges and figuring things out for myself was intoxicating; no other job came close. The money wasn’t great, in fact it was a big step backwards, but that too added to the rush.


Entrepreneurial pursuits are unique and personal journeys, relying largely on your own internal compass, makes it hard to believe that others understand you and your journey well enough to be able to guide or help you, without slowing you down. That’s the first reason.


The second reason is that I considered coaches and consultants to be the same thing, but they’re not. Consultants generally assess situations and conditions and provide advice for the business. Their work is usually based on following or applying known processes and practices, and most entrepreneurs didn’t, or weren’t in the habit of, following known processes or a defined route. Entrepreneurs such as myself, often see consultants as people they have to bring in to solve a problem when an outside influence (say, a bank, or a major investor, or a funding program) insists one is necessary. But coaches are significantly different than consultants.


A coach is someone that focuses on bringing out the best in you, training you, helping you achieve your goal. A coach will focus on maintaining your strengths (the personal things, habits and traits that got you there) as much as your weaknesses (the things that keep you from getting to where you want to be). An Olympic athlete that aspires to win gold knows they can’t get to the podium without having good coaching. Hockey teams with great superstar players get eliminated early in the Stanley Cup playoffs by teams that have superior coaching. Aspiring golfers hire coaches for their conditioning, their swing, their iron play, and their putting. Many top-level athletes now have mental coaching as well. Why? Because they want to be the best they can be. They want to win.


The third reason I didn’t hire an entrepreneurial coach until now was I never encountered one, or perhaps more accurately put, I never encountered one I believed understood ‘me’. Many believed they understood my business, or my journey, or even my objectives, but that would make them good consultants, not good coaches. A coach focuses on the individual athlete or the players, not the sport or game. A coach’s focus is on the person, helping the player be the best they can be.

In the last few years, as I’ve stepped away from the businesses I helped launch and build, I began mentoring young entrepreneurs, and then through happenstance, began coaching fellow entrepreneurs and business leaders that were still in the thick of their careers building their businesses.


Without even realizing it, I had in effect, once again started a new enterprise. But this time though, I was hiring a coach to help. If I learned anything over my 42 plus years of entrepreneurial life, it was that what I’d always done well, I’d likely continue to do well, but what I had always struggled with, I would likely continue to struggle with. I didn’t need a consultant to work on my business, (because I’m figuring out what that is, relying on my trusty inner compass), I wanted a coach to work on myself. My strengths need to be maintained and honed, but my weaknesses need a fresh set of eyes and even a new training regiment, if I truly want to be my best.

Persisting entrepreneurs are a unique breed and quite rare. Exceptional coaches that can help them be the best they can be are just as hard to find. But when you work with one, you know it; baggage gets shed quickly, flexibility and endurance improves, bad habits get identified and new good habits get practiced instead, and most importantly, there’s accountability to someone else – someone you are paying to help make you better at what you do. (One of the first things I learned this time around: "when you pay, you pay more attention").


Was it an easy thing for me (or any career entrepreneur) to do? No. I only wish I had done it sooner. But that too speaks to the nature of the entrepreneur - we eventually figure it out along the way.


Postscript: Its been about a year since I wrote this column, and in that year I've had the privilege of coaching several entrepreneurial founders and CEOs. It has been a fascinating journey. If you are interested in discussing this topic more, reach out to me at paul@tpi-3.ca

Another option is to join a peer-to-peer group for entrepreneurial leaders/founders/CEOs of companies in your area. If you are located in Ontario (Canada), I'd recommend checking out Innovators Alliance (innovators.org).



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