Finding Your Coach: Fit Is Everything

Steve Schlafman
4 min readJan 25, 2020
Photo: Irina Nalbandian via Unsplash

Over the last two months, I’ve had dozens of conversations with potential coaching partners (I prefer this term over ‘clients’). I enjoy these conversations because I learn so much about a person — their history, company, vision, aspirations, blockers and more. I’m also able to glean who they want to become and what they hope to achieve in the coaching relationship.

When I kick off the first discussion, I explain that one of our objectives in the ‘dating’ process should be to determine mutual fit. In fact, I go so far to say that I don’t view these conversations as a sales process but rather a fit process. Fit is incredibly critical because it has a direct impact on the strength of the alliance and quality of outcomes.

Working with a coach is a big investment in time, money and energy. Both sides should feel amped to co-create a partnership, embark on a life-changing journey and grow together over time. If there’s one ounce of hesitation or a lack of genuine excitement, that’s a good indicator that the relationship is likely not a fit.

Here’s the truth: there are thousands of coaches with different life experiences, philosophies and approaches. That’s why I always recommend that prospective partners should talk to at least three to four other coaches. That way, they can see with a variety of options, understand what’s out there and make an informed decision.

Just a few weeks ago, I gave a talk about coaching and angel investing to a large group entrepreneurs in NYC. One of the founders in the audience asked me how she should think about determining fit with a prospective coach. I explained to her that finding and selecting a coach is a very personal decision but there are a number of attributes she could use to evaluate potential fit.

Some of these include:

  • Context: does the coach have some familiarity with my situation?
  • Experience: does the coach have relevant and ample experience?
  • Philosophy: do the coach’s philosophy and values resonate with me?
  • Specialty: does the coach have specific training based on my needs?
  • Connection: do I feel energetically connected to the coach?
  • Proximity: do I want to work face-to-face or am I ok with virtual sessions?
  • Trust: do I trust this person and feel safe when I talk with them?
  • Cost: does the price fit within my budget?
  • Gender: do I prefer to work with a man or woman?

That list is by no means exhaustive but should hopefully provide some insight into how you might be able to determine fit. Again, this is a highly personal decision. A coach who is a good fit for you might not be a good fit for me. Everyone has different experiences, needs and desires. That’s why it’s so critical to get referrals and talk with a variety of coaches.

Here’s a relevant story to illustrate fit. Last month, I was talking with a founder who recently closed a seed round. He interviewed more than six coaches over two months and eventually narrowed the field down to two. I was one of the finalists. This founder ultimately chose the other coach because they had very specific industry and domain expertise. For this CEO, experience and context were really important and highly valued. When he told me about his decision, I was genuinely happy for him. He had found a coach that was a great fit. I seriously wish that for everyone.

Fit is a two way street. Not only does the partner have to be stoked but so do I. I’m very open about this when I kick off a dialogue with a prospective partner. I only have eight coaching slots so everyone counts. That’s why I view this as a fit process rather than a sales process.

So what attributes do I look for in a prospective partner? I’ve honed these over the last few years:

  • Ambition: Is this person highly ambitious and motivated?
  • Impact: Does this person want to have a big impact?
  • Awareness: Is this person self aware intellectually and emotionally?
  • Integrity: Is this person honest and generally a good human?
  • Growth: Is this person committed to personal growth and learning?
  • Belief: Is this someone I deeply believe in and want to see thrive?

These heuristics may evolve but so far they have been incredibly effective. Not all coaches value the same attributes in their partners / clients. One coach I know requires their clients to be in tune with their body / somatic states. That’s another reason why it’s important to ask and have the fit conversation early in the process.

As you might be able to sense, finding and achieving fit is more of an art than a science. It’s very subjective. I’ll venture to say it’s not too dissimilar to finding a mentor or even a life partner.

Here’s the good news. The world is filled with thousands of amazing coaches with incredible experience and a deep desire to serve. Your ideal coach is out there waiting to help you bring your vision to life. Don’t forget to take your time and enjoy the process. Fit is everything. Good luck!



Steve Schlafman

Founder & Transition Guide at Downshift, the world's first decelerator for high performers in transition.