How to Choose a Coach


Years ago, I sat down with a famous coach in New York. I wanted to ask him some questions about his practice, the work and about the business behind it. It was early days for Plucky and I had an instinct that coaching could be a direction I’d like to go in.

We met in a public coffee shop, where he proceeded to have a conversation that left me gutted. A networking coffee turned into some weird life crisis. When he left to go back to his office, I felt dazed and bruised, though I was effusively thankful to him because somehow I thought the crying meant that he, the wise coach, saw problems in me that I didn’t. It was only days later that I realized: 

This guy does not use his powers for good.

In the space of 45 minutes, this man used his savvy people skills to poke holes in my optimism and dreams about starting my own business. It took me weeks to come back from that low place, months to replace the self-doubt he planted in me. Looking back, it makes me very angry.

Today, as an experienced coach myself, I want you to hear this vital message: you should always feel safe with a coach.

You should trust that your vulnerability is an honor for someone to witness… and no matter how many podcasts and books and speaking tours a coach has marketed, do not hire them if they don’t make you feel safe.

So how do you find someone trustworthy? That’s what I’m going to talk about today. Much like therapists, consultants and great plumbers, the best way to find a safe coach is by word of mouth. 

Step 1: Poll your people.

Shoot a note to those in your tightest circles. These could be current colleagues, former colleagues, Slack communities you’re involved with or local connections. Be specific about what you’re looking for: “I’m looking to work with a career coach” or “Does anyone have a recommendation for a coach who focuses on workplace issues?” could be good lines.

If those conversations aren’t fruitful, move to larger social networks like Twitter or LinkedIn. Give a little more clarity in these larger spheres – “I’m looking to work with a career coach in Denver/remotely” or “Does anyone know of a leadership coach who works with senior managers?” Since the folks seeing your messages may not know you, these extra details can help narrow down the search pool.

If you’re really having a hard time finding a short list based on these methods, go ahead and google. But be warned: coaches describe their services in so many ways that the results will be messy. Some coaches have certificates, others don’t. Some specify the clients they are looking to work with and others are broad. This is why word of mouth helps so much; it’s not like doctors, where your search for “podiatrist” at least gets you in the ballpark of feet!

Step 2: Test Drive.

Set up initial calls with a few coaches. Most coaches offer a free initial conversation so that you can learn more about their practice and they can get to know you. You need to feel solid about this match because effective coaching doesn’t work if you can’t say real shit!

Important questions to consider:

  • Do you trust this coach? (Deep in your gut. Listen to it.)
  • Are you intimidated by this coach? (Do you feel like your answers should be Really Polished? This won’t help you.)
  • How do this coach’s experiences and interests match up with what you need? (Do they usually focus on accountants but you’re a CTO?)
  • Are you ready to invest in this kind of resource? 

As a coach, here’s what I’m listening for:

  • Is this person ready for coaching?
  • Does this person understand the change their seeking? (Basically, are they just in need of venting or can they glimpse actions that they feel ready to take?)
  • Does this person value things that are very different than me? (Do you want to make ALL THE CASH at any cost to the humans around you? If so, Plucky is probably not your jam.)

Step 3: Marinate.

Sit on it, even for a day. (Feel free to disregard this advice if you’re super-convinced… that happens sometimes!)

Pausing on this decision for a short period of time can help you reflect on the experience and investment you’re about to make. Are you really ready to change things up? Is this the time?!

If you’re feeling ready, email that coach back and say COACH, I CHOOSE YOU! 

If you’re not feeling ready, that’s important to communicate, too. Props to self-aware people who know how to say no when something isn’t the right option.

Step 4: Begin.

The first 1-2 sessions may involve backstories and catching your coach up, but don’t let it become a game of Let Me Tell You About My Whole Life. A good coach is going to be able to meet you where you’re at and ask clarifying questions, as needed. 

Step 5: CHANGE!

Coaching can be a game-changer when it comes to defining your career and the direction you’re headed. Hell, sometimes it just helps to have another person hear your words and recite them back to you! Humans are funny like that.

In your coaching relationship, challenge yourself to take risks, process decisions and step out of the worn path that got you here. Good coaching leads you to new, confident places… and with some thoughtful discerning, you’ll find the right person to take you there.

Check out more Plucky blog posts about coaching or shoot a note if you want to talk about coaching. We’re taking on new clients in 2020!