I’ve always felt confident in my ability to take risks, meet the day’s challenges and manage my
own world. I listen strongly to my inner compass which gives me a feeling of certainty in my

And even armed with this sense of certainty and comfort around my view of the world and my
place in it, I’ve always had coaches and mentors, not only in business but in my personal life as
well. From the time I can remember, I’ve inherently valued the insight and perspective of others
even when it differed from my own. Actually, especially when it differed from my own.
And unlike a large handful of people I’ve met throughout my career, I’ve always understood that
there’s not a chance I know it all. Despite the innate self assurance in my DNA, I’ve always
been clear that I don’t have all the answers.

I recognized a long time ago that “absolute” certainty is not a positive thing. It’s an inflexible way
to think and be. It’s stifling to yourself and others around you. And it’s too extreme. I’m okay with
that. Life is about connection and continuous learning and I live that with every fiber of my

This isn’t to say that I don’t have the courage of my convictions nor trust in my own judgment.
Anyone who knows me will tell you otherwise. But outside perspective and objectivity is
invaluable, and I wouldn’t be where I am today without it.

In today’s world, I applaud companies, organizations and groups that help others build and
succeed in their businesses. I applaud the ones more loudly who make having a coach or
mentor as a prerequisite for the help they provide.

So it isn’t a surprise that when I walked away from the tech world after 20 years, selling the last
of my businesses in 2016, that my time and energy became fully directed and focused toward
being a business coach and mentor.

This was a natural progression based of my belief in the importance of supporting and serving
others and grounded in my belief of the importance of paying it forward – my coaches and
mentors have meant the world to me along my life and career journey. It was and is an
imperative for me to give that back.

Having this context has afforded me a unique point of view in this new chapter – I have
experience as both the client and the coach. I’ve sat on opposite sides of that desk. I know and
see the value from both viewpoints. And I fully agree and embrace the quote by Tim Gallwey,
“Coaching is unlocking a person’s potential to maximize their own performance. It’s helping
them to learn rather than teaching them.”

One of the things I noticed as I set out on this new path was the number of people offering
coaching services. All types of coaches, targeting all types of industries. All offering some sort of
support and guidance to help move others forward in their business.
This got me thinking. With all the options out there, how do you know what makes a good

My gut told me that I knew the answer, but I still wanted to explore further as a means to find
and define my own value proposition, my way to differentiate myself from the surplus of other

And it actually didn’t take long because after very little research, I discovered the most
astounding fact – there was an infinite number of small business coaches out there who had
never owned, ran or built their own business prior to the coaching business they were

Sure they may have worked at high levels in other industries and that no doubt provided them
some understanding and knowledge. Some even had a certificate that called them a coach. But
I wondered how can you provide coaching to small business if you’ve never sat in the chair of
owning a small business? How can you accurately relate to the small business entrepreneur
who has employees to support, overhead to cover, who wants to grow and expand their offering
all while working to ensure that the doors stay open tomorrow, and the day after that? Where
would you get a frame of reference if you’ve never been there yourself? Same thing for
coaching solopreneurs. How can you effectively connect the dots if you’ve only worked with
bigger companies or brands? Getting a paycheck is a very different matter than ensuring you’re
making the right choices to pay yourself. How do you truly understand that pivot?

So back to the original question. What makes a good coach?

The most important rule to follow is this: your coach needs to have walked the walk, someone
who has truly paid their dues and can speak to their real-life experiences.
Ideally, the coach you choose will have failed and succeeded – more than once – and won’t be
afraid to be honest and share the wisdom of those learns because the best coaches are
authentic and radically transparent.

Make sure to take the time to find out what exactly they’ve accomplished. Ask if they have built,
bought or sold a business. Confirm that they’ll understand what keeps you up at night. Reinforce
for yourself that they understand business growth and how to achieve it. Do they understand
change management? Do they understand business development strategy, networking and
business planning?

Truth is any effective coach will listen to your concerns, give you an honest assessment of your
weaknesses, and help you leverage your strengths to maximize opportunities to help you and
your business grow.

But the best kind of coach has context. And by context, I mean they have experience doing
what you do – building, funding, growing and leading business..
Start with that. It’s a great first step.