Matching Coaching Clients with Coaches: Questions to ask

Olga Skipper
7 min readJun 28, 2021
Photo by Nicholas Barbaros on Unsplash

I get this question quite often: “How do I find a coach?” And I get the complexity behind it: different coaching schools, different approaches, different styles, and so much “low quality” coaching.

The same happened to my friend's circles. My excitement about my own journey as a client and my devotion to my profession led my friends to a very natural question — how can I get the same outcome? How can I find a good coaching match for myself? So I started matching my coaching colleagues with my friends. By now, almost everyone who came to me with this question works with a coach that I matched them with, and from it being “a gut feeling,” I learned what actually works, and I want to share this checklist with you.

Enjoy the read, and if you want me to recommend you a coach, don’t hesitate to leave a comment.

You want to find a coach, and you have never worked with one, you might google for coaches, search their profiles on LinkedIn or Instagram, ask for a recommendation on your Facebook feed. Now you sit in front of a list of names and their profiles. Yet, it is still hard to tell who is good, who is not, and who would match your coaching topic.

Here where I would start.

Prep

First, ask yourself the following questions; later in this post, you will see how to match these answers to a coach:

  • What is my desired outcome? Spend some time imagining the best possible outcome without any limitations. As if you have a magic wand and everything is possible. Please write it down.
  • What do I know about myself? My personality type, my limitations, my strength, and weaknesses? How do I commit? Where I resist change etc.? Please write it down.
  • What is missing for me to move forward and gain the desired outcome by myself? What hinders the change? Lack of motivation? Lack of a cheerleader? Lack of self-belief? Skill? Mindset? Certain Experience? Please write it down.

First Screening

As the second step, check a coach’s website first and search for the information in the following categories:

Coaching certification:

  • Do they have a coaching certification? They should have at least one. Personally, there is no difference for me, whether it is an academic one (like Columbia University, Georgetown, etc.) from an Independent educational Institution (Co-active Coaching, New Ventures West, etc.) or an industry one (ICF/ECA). Proper certification shows their commitment to their profession.
  • How long was the coaching course that they took? You want to look for someone whose core coaching education was at least 9 months long. This is a great indication of whether they learned coaching as a skill (courses 3 months long and less) or put time and effort into integrating the knowledge, learning the profession, and discovering their own self.
  • Do they continue their education? When was the last time they took a coaching-related course? It can be anything, from a mindfulness course to a facilitation course, etc. It shows you that a coach invests into their personal growth, is committed to the profession, and what skills they needed to acquire to serve their existing clients better. Every coach is different, and their education path can highlight what interests them and what they focus on. 1 or 2 courses per year is a good amount, depending on their duration.

About the coach:

  • Do they coach a topic or a person? There is a difference between coaching, for example, for sales skills and coaching startup entrepreneurs. One focuses on skills, the other on the person across the table. Both are valid approaches; the question here is what do you feel is missing in your case to move forward: a skill or a mindset? Do you want to be trained in something or walk your own path?
  • Any prior experience that might be helpful in your coaching process/topic? For example, HR and management experience, startup and entrepreneurship experience, transition experience. It is not a must, yet it might help you find someone working within your coaching topic.
  • Geography and demographics: Do you need someone thinking cross-border and cross-culturally, or is your topic within the same cultural background as you are in? Or maybe some other cultural background that you are missing? For example, I coach in German, but I will never be the best “German coach.” I know coaches that are so much better in coaching someone within the german context than I am, aka Germans coaching Germans. I am always in between cultures and geographies, as are my clients, which my clients can benefit from and relate to.
  • How different is the coach from you? The “difference” should be there. It should be intriguing, not alien. For example, you know that you are a very left-brain pragmatic person. Working with someone right brain spiritual might be a great way to expand your repertoire and look at the topic from a different perspective. Yet, you both should have some common ground still that will ensure that you trust the coach. At the same time, with someone who seems like a copy of you, you will have a great time and quick connection, but you might be missing some new ways of interpreting and dealing with your situation.

About clients:

  • How do they describe their target group? Can you relate? It takes a coach some time to distill who do they want to work with. “Want” is usually a combination of a coach’s expertise and effectiveness in working with a particular target group. Aka, they’ve seen success in working with the topics of that target group, and they can relate to who the clients are. You can find an example on my website.
  • What is the usual duration of their coaching engagements? What you are looking for — is the coach's approach and their point of view. If we are speaking about someone who coaches a person (not a topic), then I would look for someone who understands that no one size fits all and that change needs time. If someone offers you a “standard program that fits all for a guaranteed long-term mindset change,” then they have no clue what they are talking about. With “skills” coaching, it might be different.

If the initial screening ticks all boxes, move to the third step and get on the phone/zoom with 2–3 coaches that you shortlisted. The first “chemistry session” is free. Its purpose is to discover whether there is a match between you and a coach, ask additional questions, and help you formulate the coaching topic sharper.

Chemistry Call

If their website doesn’t give you the information I mentioned in the initial screening, don’t hesitate to ask a coach about their certification, background, and a typical coaching client. On top of that, you might want to dig deeper into the following aspects.

What to ask during the Chemistry Call:

  • How much does it cost and why? Pricing that coaches set depends on many factors: their expertise, geography, business model, target clients, the typical duration of the coaching engagement, etc. Don’t hesitate to have this conversation with a coach; you might learn a lot about their approach.
  • What was their motivation to become a coach and stay in the profession? There is no right or wrong way to answer the question. What you are screening for is a healthy balance between “serving oneself” and “serving others”. You don’t want extremes: someone who is purely ego-driven or chose this profession to devote themselves fully to “saving others”.
  • What self-care and support system the coach has in place? Coaching is a demanding profession and, if done right, requires a coach to be serious about their own self-care and their own support system. I strongly believe that a coach needs to go to a therapist to maintain their mental health and have a supervisor or a supervision group that they seek support from. Some coaches have a mindfulness practice. Don’t hesitate to ask.

Your impression after the Chemistry Call:

  • Do you believe you can trust this person to hold a safe space for you and for your topic? Or will you hide something from them? Trust is critical here.
  • Do you trust they have your best interest in mind? And are you comfortable pushing back? Does the coach accept your pushback? Coaches are human beings and they might be (and will be at some point) wrong in their judgment or their approach to your topic. Coaching should be a relationship of two equal partners that talk to each other on the same level. No gurus, No magic pills here.
  • Are they curious about you and your topic or are they judging you? Do they put an effort in really understanding who you are, or they give you a “diagnosis” or a ready made solution without understanding your context?
  • Can you really afford it? It is your responsibility to weight out whether the coaching will support you or be a burden in some way. Coaching pricing needs to be a bit uncomfortable in order for you to show commitment and be motivated to work towards the desired outcome, yet not too uncomfortable that you start hating the journey. For comparison, therapy pricing should be very comfortable for you in order for you to stay longer in therapy and have lower entry barrier.
  • Do you see something in their personality/style that inspires you and you would like to learn (to be)? For example, calmness, resilience, determination, work-life balance. Anything really. Coaches and clients “rub off each other” during the coaching engagement and you definitely want something good to rub off you:)

I hope this checklist helps you to find your perfect match.

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Olga Skipper

Executive coach and Advisor for Tech Founders and Entrepreneurs. Asking uncomfortable questions. http://olgaskipper.com