Six Questions to Help You Hire a Great Exec Coach

It’s seems like the startup world has finally started to catch on to the power of executive coaches. Similarly, it seems like a lot of people are becoming coaches. While I was at Techstars Boulder, I developed a coaching program that matched dozens of great executive coaches with startup founders, and I saw first-hand what an amazing match can do for a founder and for a company. Finding the right executive coach is part science and part art. I have suggestions for startup founders going about the process of finding the right coach for them. I always tell founders to meet at least three coaches to compare. It’s important to have the right chemistry match as much as the details of a coach’s style needs to align. When it’s right, you’ll both feel it.

Image by mohamed Hassan

But before you start meeting coaches, take some time to reflect on what you are looking for in a coach, and here are some questions to get you started:

Questions To Ask Yourself Before You Start the Search:

1) Are you looking for wellness and support or are you looking for candor and holding your feet to the fire? If you want behavior change, you want the later. Some coaches might push back on this, but in my experience, every coach better at either the “care personally” or the “challenge directly” part of coaching to use Kim Scott’s Radical Candor framework. It’s not just true for coaches, most people if you ask them are better at one and have work at the other. I suggest that you understand if you’re looking mostly for support, encouragement, wellness, etc. or if you really want the tough love approach. They both have value, and picking a coach that has a natural strength in the style you need most is one of the most important factors for a great match. Also note that if you need your feedback to be gentle, find a coach that can do that for you regardless of whether they are having a good day or not. When I’m coaching, I know I have a very direct style, and it works great when it’s a fit, but it’s awful when it’s not. Similarly, I know founders who really want it direct and end up working with a coach that’s “too fluffy”. Know thyself before you pick a coach. If you’re having trouble knowing which you respond best to, think about the people in your life that have given you feedback that you’ve responded well to. What do they have in common?

2) What are your objectives? What does success look like? How will you know along the way, track progress or regularly check-in on if it’s “working” for you? This set of questions will help you know what it is you are really seeking so a potential coach can tell you if they can help you. Get clear if you want help with business issues, life issues or both. Some coaches deal with a very wide set of issues, some are more narrow. I once asked a founder what his objectives were for coaching and he answered, “To quit smoking.” I knew then we weren’t a match. It feels awful to spend time and money with a coach and yet feel like you’re not getting anywhere. It doesn’t feel great on their end either. If you’re thinking about hiring a coach, why do you think you need one? All my founder friends have one is not a good answer! Of course your objectives can and should evolve with the relationship, but having something juicy to work on to start with, an area of life that you really want help with, will make coaching far more fulfilling for everyone involved. Once you’ve identified this area or areas, consider how you might know if you’re making progress or meeting your objectives. If you’re stuck, this is a great question to ask a prospective coach. The right match will have answers that feel right to you. If not, try someone else.

3) How much time do you expect to spend with a coach? Do you want to meet every week? Every other week? A different cadence? I’ve seen lots of time scales work here, but I advise against anything longer than regularly meeting every two to three weeks at the maximum. Startups move quickly, a lot happens in just a week, and you don’t want to spent the whole time together just updating on what’s happened since your last sync. It can also flex as needed. It might be more often at the start as you’re getting to know each other and then add more space as the relationship matures. You can propose meeting more often if something challenging comes up and you need more. These are things to think through on your own. Does your need for coaching ebb and flow or do you hold pretty steady?

4) How available do you want a coach to be for you? Do you expect to be able to call them or text them and get a response or will it be limited to your regular sessions? Some coaches will be a fit for the “always on” needs and some will not. If you are looking to a coach as someone to call in a crux, be clear with yourself and with them about it upfront.

5) What is your budget? Think about it as a flow rather than an absolute cost. What can you afford on a monthly basis? Coaches have a wide range in terms of cost, sometimes it equates with experience and quality, but not always. Good coaches charge anywhere from a couple hundred to a couple thousand per session. Many will ask for a retainer or a monthly commitment upfront. Know what your comfortable level is. If you meet a coach that you like but isn’t in your price range, ask for referrals to other coaches they recommend. Coaches know other coaches and generally want you to find the right fit.

6) Do you prefer to work with or hear the truth from men or from women or are you in different? I worry this question is too binary or may evoke a reaction for some people, but it’s my experience working with many founders that some have a strong preference to be coached by a woman or by a man, and just as many have no preference at all. It’s important to check in with yourself on whether you have a preference, own it, and look for a coach that matches. Coaches sometimes have to deliver hard truths, and I encourage you to think about who might be the best messenger for you to receive those truths from.

The above questions assume you are paying for the coach or are being reimbursed. It’s different when a company hires a coach to work with an executive in order to address a specific issue or set of issues. If you are hiring a coach to work with another leader in the company, make sure you are clear about the objectives and what behavior change you need to see over what timeframe. Any mismatches here can be devastating. Coaches have a tendency to be client-directed, which is great when the client is paying. Expect any good coach to keep confidentiality with their client, but also have a process for checking in on how you think things are going and whether you are seeing the kinds of behavior change you’d hoped for when hiring a coach.

Image by Soul of Startups

Once you are clear on your needs and preferences for a coach, you’ll want to have some questions at the ready to ask as your interviewing possible fits. Ask whatever questions feel most alive for you and help you understand someone’s style, make sure your preferences match how they operate and evaluate chemistry. Here are a few I can recommend:

Questions to ask a potential coach:

1) What is your process for onboarding new clients? Some coaches do a pre-interview, some do a 360 evaluation, some approach new relationships ad hoc, and some just dive in. Ask about what it looks and feel like to build a relationship with this coach.

2) Do you consider yourself more caring or more challenging? I’m sure they do both, but ask them to choose a strength. My experience is that everyone is better at one or the other. If they protest, get curious or move on. I’m not a fan of people who say they do both equally well. It’s like asking someone in a job interview, “What’s your biggest weakness?” and having them reply, “I work too hard.” It strikes me as inauthentic, and that’s a terrible way to start a relationship with a coach. If they want your business so bad they are afraid of offending you or saying the wrong answer, they also aren’t a good match for you. And if they honestly don’t know for themselves which is their greater strength, run far, far away.

3) What can you expect from them? What will they expect from you? Many coaches will ask you to build new habits or make behavior changes that will be helpful to your growth. One coach I know requires clients to have a meditation practice. Another requires they journal once a week. Some clients want an agenda before a coaching session. What are expectations are for each other are much better clarified up front. If the coach has a requirement, are you willing to meet it?

4) What training and experience do you have coaching? There are a myriad of different certifications a coach could come with, or none at all. It’s a completely unregulated space, which is great for people with more business experience to work with executives and their careers, but it means you need to do your homework and understand what you’re paying for. Most coaches have some mix of business and psychology expertise. They will have a different perspective given the training they have had. Ask about their approach and what makes them different from other coaches. Ask what kinds of executives they’ve coached, and if you weren’t already referred to this coach, ask for a referral.

5) In what formats do you like to coach? Are we in-person, virtual, or a hybrid as needed? If in-person, will there be walk-and-talks, a sit down affair, or local coffee shop they frequent? If you’re paying on the low end, expect to go to them, and vice versa, but everyone is different. Many coaches are now much more adept at virtual coaching and have opened their doors to remote clients, a good thing for all of those far-flung founders.

6) What and how do you charge? Get clear on the rate, what it covers and what it doesn’t. Does the coach need to be paid a retainer, monthly installments, in advance or as you go? Is there a minimum engagement or time period involved? You don’t want to be surprised here, and no that coaches are usually working for themselves, so asking them to wait 30 days for payment and delivering invoices is a real pain for them. A stipend or a retainer can really ease the burden on their side.

Lastly, there is the job of finding some coaches to evaluate. Ideally, you would ask someone who both knows you, at least a little, and who knows a number of coaches. The more coaches someone knows, the more likely they are to help you get a list of people that are a better fit for you. I’ve done this for countless founder and leaders, and I always think deeply about who might be good matches stylistically. This is the art of finding a great coach, it’s just a sense for who would work well with whom. If you have a maven like that in your life, lucky you. The next best method is to ask other leaders or founders if they know any coaches or have worked with any coaches that they would recommend. This is likely to yield just one name, so you’ll have to ask a few different people to get at least a few to interview. If possible, inquire what the experience was like and why they would recommend or not recommend that coach. Pay special attention to style matches and mismatches as well as what objectives the coach was hired for and how similar that scenario is to your own.

A final note. If you have a history of mental illness, I strongly advise you to find a coach with mental health credentials. There are many in the coaching world. Our minds are our most precious assets, and while I believe that many people from a variety of backgrounds can make great executive coaches, not everyone has the training needed to appropriately handle your mental health in the coaching context.

In the end, it’s all about fit. If you’re looking for a coach, I hope you find one that suits you and that you’re able to build a meaningful, trust-based relationship that helps you do your best work and live your best life.

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