Hiring an Executive Coach? Here Are 9 Questions to Ask

Jennifer Eggers

1 9 Questions to Ask An Executive Coach Are you integrating into a new executive role? Are you an executive looking to bring in an executive coach or advisor to help you get to the next level? An HR business partner who wants to be absolutely sure their next big hire hits the ground running and is a great culture fit?

An executive coach can help you see around corners and demonstrate visible leadership fast whether you’re moving into a new role, trying to change perceptions, or making changes to get promoted.

The catch is that unless you find the right coach you may be flushing money down the drain on a lot of fluff. Coaching MUST be meaningful to be effective. As one recent client, a company President said, “this cannot be a check the box exercise where I keep reflecting and you keep asking questions.” Sadly, with many coaches (even highly certified ones), that’s exactly what it is.

So how can you ensure, from your first meeting, that the coach you chose is the one to get you where you need to go? Here are 9 questions to ask prospective coaches that will give you a good sense of who they are, how they operate, and what YOU can expect.

1. What did you do before you became an executive coach (or what do you do in addition to executive coaching)?

Try to find out what keeps them current and relevant in today’s economy. A great follow-up question is, “What informs your coaching?”. Is it consulting they do when they’re not coaching? Is it experience as a corporate leader? You’re trying to see if they have the expertise you can benefit from AND if they have a means of staying current and relevant if they are only doing coaching.

2. Can you share some of the titles of people you’ve coached most often?

This can give you a sense of what level in the organization they typically work with and what functional areas they may be most familiar with. If these are roles you aspire to or are in today, they will likely be able to add significant value. If they aren’t, it’s not a deal-breaker, but you’ll want to ask what they will need to do to get up to speed.

3. What are some examples of successes your clients have had when they worked with you?

This is your chance to get a feel for the results you can expect and how they will work with you to get there. Pay attention to how much credit they give the client. A coach should be your advocate and while they may be in sales mode, they shouldn’t take all the credit. Asking how challenging it was for the client is a great follow-up.

4. Can you share an example where something just didn’t work out or an engagement didn’t have the success you wanted it to?

This question gets at trust and vulnerability. Most executive coaches have at least one or two clients who didn’t work out. Either they didn’t work on things that matter, didn’t care, or failed to make progress. It’s a good idea to understand how the coach handles these circumstances. Also, pay attention to how the executive coach refers to the client. A great coach should be able to speak objectively even about the worst client. Badmouthing anyone is definitely a red flag. Facts are not.

5. What are some other client challenges you’ve addressed?

You’re looking for experience dealing with challenges that might be similar to yours AND the variety of things they’ve seen because you never know what might come up. I’ve dealt with everything from poor image and dress to every imaginable perception, and quite a few realities, that stood in the way of promotion and worked to fix them. A great coach should have a way of understanding the issue and help you work towards a solution. They also should be honest that 51% of this is the client’s involvement. A coach cannot fix anything by themselves, so they shouldn’t be taking credit for it either.

6. Can you give me a sense of your executive coaching approach and process?

You need to be comfortable that the executive coach or advisor you select has a proven, thoughtful approach and that you know what to expect. You also want to be sure they are flexible and open enough to change that to meet your situation as necessary.

7. How would you propose to help me with [name a challenge]?

This is a great way to get a sense of how they will work with you. You need to be comfortable with that more than their personality.

8. What can I do to get the most out of working with you?

This not only shows you are interested and committed (every executive coach wants to know that), it also will tell you if they’ve thought through their expectations of you and how you can be most effective. In addition, this is a chance to evaluate whether you can (or are willing to) do what it takes to make this work.

9. How are you different from other executive coaches?

This is a great question to inform your decision. I would say something like, “I provide more time than most of my colleagues and I am available as needed between calls any time. I also have more business experience than most coaches, so I tend to blend consulting with coaching. My experience enables me to see around corners, so I can help you avoid pitfalls.” I might also say something like, “If you’re struggling with something I’ve seen 11 times, I’m more likely to roll up my sleeves and help build a plan than ask you to reflect on your feelings.” You want a coach who is brutally honest with this question and isn’t disingenuously tailoring it to you. I know my answer will cost me a few clients and I’m comfortable with that. The ones who stay will get the most benefit out of what I provide.

Taking the time and energy to really vet your coach will ensure you find the best person to help you see results. A coach can help chart the path, but it ultimately comes down to whether you are willing to do the work. Even a rockstar coach cannot guarantee results if you are not ready to get to work.