When you were (or are) looking for a date, did you just walk into any public place and ask the first person you found to meet your parents? 

Of course not.

So why would you trust what’s possibly the largest investment you’ll make in your professional career to the first coach you meet? 

I often find myself breaking down failed coaching opportunities with both potential clients and other coaches. Inevitably, an overwhelming majority of the time the reason is neither party created intention around the selection process. 

It never ceases to astonish me how often in coaching interviews I have to push my potential clients – those who should be in control of the conversation – to advocate for themselves. 

“Do you want to ask me about my areas of specialty?” 

“Do you want to speak to one or two of my current or past clients?” 

“Are you curious about times where my coaching relationships have failed?” 

Despite the considerable costs of hiring a coach, I still end up being the one to ask these questions in many interviews. It’s a strange contradiction that never ceases to amaze me.

The reality of the situation is that many coaches will not help their clients through the interview in this way, creating poor fits that fail to provide value to either party – and prove a waste of considerable investment for the client. 

At this stage in my career, I’ve interviewed hundreds of potential coaching clients. I want to learn who they are as a person and be sure this is someone who I can pair well with, so that together we realize their full capacity and they can achieve their goals. I’ve written this guide as a very basic structure to help those on the other side of the table to find the right coach for them. 


There is no coach who is everything to everyone, and you should be very afraid of anyone who claims otherwise. All coaches have their areas of expertise, sets of beliefs, styles of coaching, and weaknesses. This is why it’s critical before ever speaking to a potential coach you should first complete an assessment of your current context. 

What do you hope to achieve? 

Individual coaching journeys should have clear objectives. What is this coach going to help you achieve? This is a critical question because it is going to influence who you decide to interview. Remember, coaches have areas they specialize in. 

Are you trying to get healthy? There’s a coach for that, and they’re called wellness coaches. 

Do you need to up your game at work? Then you’ll want to interview performance coaches.  

Do you need to improve your skills at running your team, and in turn fulfill your ambitions of moving up the corporate ladder? You’ll want to start your search with executive coaches.

What type of personality do you need?

Notice I didn’t say “want”. This isn’t about what’s easiest for you, but about what is right for you. Personally, I have a driven personality and challenge all forms of authority. My love language is words of affirmation. Considering these two aspects of myself, the easy path would be to always surround myself with an echo chamber. But this gets me nowhere and I only suffer for it. When it comes to guidance and mentoring, I need someone who is patient but firm, can challenge me on an intellectual and not authoritative level, and knows when to use reassurance to keep me going. 

Before interviewing coaching candidates, do a real assessment with yourself about the types of leaders or mentors you’ve responded well to in the past. 

Here are some questions you can consider asking a potential coach: 

  • Describe to me your greatest coaching success ever. Why do you believe you had such a tremendous impact on this individual? 
  • What types of personalities do you work best with? 
  • What would you describe as your perfect coaching situation, the place a person finds themselves in when you know you can really make an impact?
  • How do you motivate someone who is struggling? 
  • Can you describe to me a coaching situation when you failed? Why do you think this didn’t work out? 


The whole idea of personal values has been reconceptualized time and time again to mean ten different things to ten different people. For this conversation, though, know that values means the frameworks by which you make your decisions. 

For example, as a parent and leader of your household, if you value personal experiences over material things, then you would make the decision to drive the same vehicle until its wheels fall off in order to afford multiple vacations a year for your family. 

When guiding people through a value assessment, I’ll have them list critical decisions they’ve made over the last few years. We’ll then play detective and begin analyzing their decision making process in order to find thematic elements and begin creating a potential outline of their core values.  

What does this mean in terms of finding the right coach? 

Speaking from the coach’s perspective, I’ve found that a clash in values can be very distracting. “Family” is a non-negotiable value for me, and I know for a fact that I could not work well with someone who belittled and devalued their partner and family during our conversations. It would be a trigger for me, and it would negatively impact any work I tried to do with the individual. I also struggle with individuals who are committed to self victimization, and with misogynists and racists. Because I know this, I’ll actively ask questions around these ideas during the interview process. 

I’m very protective of my time and don’t want it wasted on a doomed relationship. Neither should you

To clarify, I’m not telling you to seek out coaches that share the same values as you. That wouldn’t necessarily be a positive. Sometimes you want a clash of values, so long as you are always conscious and intentional about the conversations. But there are some areas that can be damaging when it comes to conflicting values, and you should be very proactive in navigating these waters. 

Here are some potential questions you can consider: 

  • When was the last time you had to make a major life decision? How did you determine your path forward? 
  • Have you ever had a client bring a situation to you that seemed unethical? How did you handle that situation? 
  • What do you consider to be the 3 most critical personality characteristics a leader should possess? 
  • Who is the most impactful mentor you’ve ever possessed in your life? Why?
  • What is one major regret you’ve had in your professional career? What did you learn from it? 
  • What is the one personality trait others can possess that really triggers you? Why so? 


Now that you’ve outlined some information about yourself, you’ll want to create an ideal coaching profile. Here are some key areas to focus on. 

Areas of Specialty: Covered above. Be clear in what you’re trying to achieve, and then determine what areas of speciality your ideal coach will possess. 

Personality & Coaching Style: Noted above. Personal development journeys are full of periods of challenges and discomfort – what type of person do you need to lead you through these times? 

Other Characteristics: Some people work better with a specific gender, and this is fine. I don’t do well with socializers who make lots of small talk, and I need a Type-A to counterbalance my own self. Be creative, but remain open minded. 

Potential Values & Core Beliefs: Covered above. 

Specific Areas of Experience: Sometimes it can be refreshing to have a set of eyes from another industry to come in and help you gain a deeper understanding of your context, due to lack of bias. Other times, the lack of context can be a hindrance, such as an educational administrator hoping to find executive coaching support and working with someone who simply can’t relate to the complexities of that bureaucratic world. 

Weaknesses: Very few people like to talk about their weaknesses. Nonetheless, I’ll bring this topic up if my potential clients don’t. I want them to know that I’m passionate about some topics to a fault, and can unintentionally steer conversations at times because of this. That I’m not great at managing my calendar, and I’ll mess it up if my assistant is out that week or working on other projects. Ask your potential coach about their own areas of weakness and/or growth. The last thing you want on a coaching journey are weekly surprises. 


The personal and coaching profiles will serve as guiding documents through the next stages, since once you begin interacting with people things will get messy. It’s inevitable. 

What do I mean by this? 

Take “good neighbor” syndrome, for example. Many organizations do not have hiring protocols in place to guide the process, and instead rely on a couple of interviews. The leader will get their resume a short time before the interview, sit down with them and ask some questions, and then make the decision on whether to hire them. If they think something along the lines of, “This person would be a good neighbor, I could see myself liking working with them” then the person gets hired. 

This is nuts. 

But this is also the process by which most people decide on a personal/professional coach. 

Get your profiles in place. It’s a non-negotiable. Once done you can begin researching potential coaches and getting a list of candidates together. Use Google and LinkedIn to drive your early efforts, and searching keywords concerning the areas of specialty you require is a great starting point. When you find someone, dig deeper into their online presence and find articles they’ve written and look over their social media posts. Before you ever speak a word to them, you could already have a considerable amount of information on your candidates with some targeted questions ready to go. 

When you have a handful of potential coaches, create a set of 3-5 interview questions and email them. Based on responses or the lack thereof, you’ll be able to whittle your list down by at least half. And from there you’ll be able to set up one on one interviews. 

Online Coaching

When I first began my practice, I was very hesitant to coach in an online or phone-based format. In fact, I didn’t pick up my first long distance client for close to a year. Now, a majority of my business occurs in the virtual world. 

Personally, I’ve found online coaching to be much more focused than in person sessions. I would never think of making that a definitive statement for all persons, and I’m only speaking to my experience. My greatest fear in picking up long distance clients was based on the belief that I’d lose effectiveness by not being able to pick up on physical reads I can make in-person. Yet, this hasn’t proven the case at all. 

If you find yourself in a similar place and fearing the online coaching format, I’d consider challenging yourself by interviewing 1-2 potential coaches online and see what you think. 


Great Coaching Match = Personality + Values + Specialties 

Before you ever speak to a potential coach, you should already have an ideal candidate profile in place. Interviewing is inevitably emotional, and you want profiles that can anchor you throughout the process.

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