Executive Coaching Can Be Your Secret Weapon

Executive coaching is a great tool for growth, if it’s done well.

Sean Byrnes

May 9, 2023

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Executive coaching is a great tool to improve your abilities as a leader. By providing honest feedback, outside perspective, and decades of experience a great coach can help you grow just as your company grows around you.

Unfortunately, great coaches are hard to find. The most qualified people often don’t have the time or interest in being coaches, and many unqualified or ineffective coaches have flooded the market. As a result, hiring a coach can be a difficult process. Even if you do find a great coach, most people don’t get the most from the experience.

I’ve spent time as an executive coach over the past nine months and learned a lot about effective coaching, how to find a coach and how to get the most of the experience. Here is a playbook based on that experience that you can follow to make it work for you.

What is an Executive Coach?

The job of a coach is not to make decisions for you but instead provide you with frameworks, advice and perspective to help you make great decisions. Every leader has their own style, and the goal is to help you refine and improve your personal style, even if it’s different from your coach’s. Success is when you feel confident in yourself when making critical decisions for your company.

Coaches help in a variety of different areas, and here are some common ones that I help my clients with:

Designing the structure of your teams and organization, solving organizational problems and preparing your company for growth.
Help you resolve conflicts and disputes both among your team and between you and your team members.
Planning for a fundraising process and helping you craft your fundraising pitch.
Building strategies for your product, marketing, and sales teams to improve your go-to-market engine.
Managing your relationships with investors.

Coaching does have its limits, and there are some things that a coach won’t or shouldn’t do for you:

Introduce you to potential investors or customers.
Recruit potential employees for you.
Directly manage your team or mediate conflicts among your team.
Coach your team.

These limits are important because your coach works for you. They should always be on your side and looking out for your best interests, and any of these situations can change that dynamic.

It’s also important to note that coaching is not therapy. Therapy can help you process life as an individual, and can be an important part of mental health. Coaching is designed to improve your professional performance as a leader. These things can be closely related, but coaches are neither trained or equipped to help you with mental health challenges. Beware of coaches that blur that line.

How do you find a great coach?

Even with a clear definition in mind, finding a great coach requires patience and commitment. The best coaches I know rarely have openings in their client lists, so I know it can be frustrating.

To get started, talk to your peers and network to see which coaches they use. Most coaches, especially when they are getting started, find most of their clients through referrals. If you have raised money from investors, they can be a fantastic source of coach connections. The most important thing is that everyone in your network knows you are looking for a coach, so they can be on the lookout for you.

One of the great changes in the past decade is that coaching has gone from a negative signal to an expected practice. That means there is no stigma associated with posting on social media and telling everyone you are looking for a coach. In fact, since it’s expected, this is a common way you find coaches these days!

Finally, there are services like Practice that specialize in connecting people with great coaches. While I haven’t used them myself I have heard great things about them.

When you do meet with a prospective coach, you want to understand if they are a good fit for you as there are no coaches that are perfect for everyone. The best way to find out is to do a free, introductory coaching session. Most coaches offer these free sessions so that both sides can decide if working together is a good idea. It does mean you will invest a few hours on test sessions before finding your coach, but that time investment is much better than making a mistake in engaging with the wrong coach.

Before engaging a coach, you should speak with their references. Even coaches that are just getting started will have references that can tell you about what it is like working with them over time. This can provide context you cannot get in a single session, and give you the confidence you’re making the right decision.

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How do you get the most from your coach?

To make the most of coaching requires effort on your part. You will need to prepare for coaching sessions, and follow up to turn feedback into action. Ahead of each session you should:

Provide a 2 minute update on the state of the business, so the coach has context to help you evaluate your problems.
Prepare a list of issues or problems you want to cover and provide background on all of them. These should be sent by email ahead of time so that your coach can prepare as well.
Provide updates on the problems discussed in previous sessions so you can track the impact of your coaching.

That might sound like a lot of work, and if it does you should adjust to fit your needs. Coaching should not feel like work and increase your stress, you don’t need yet another task item every week. Coaching should be refreshing, and help relieve a small part of the burden you are carrying as a leader.

When done well, coaching helps accelerate your natural learning process by giving you structure, feedback and reference. You decide how fast and what you will learn, and your coach helps you on that journey.

Coaching is not for everyone as it requires humility and introspection. There is also no coach that is good for everyone, it’s your personal judgment about who will be a good coach for you. Even if you have a good fit today, that doesn’t mean you’ll have the right fit in a year. You should constantly re-evaluate if coaching is productive and worth your time, to ensure you are always getting the most out of it.

Finally, here are some answers to questions I am sure are on your mind:

No, sorry, I can’t be your coach. I’m not a full time coach and my client list is full at the moment. I’m sure you can find a great coach!
No, unfortunately I can’t recommend a coach for you. However, I recommend trying Practice, a service for connecting people with great coaches.
Yes, I would love to hear from you if you disagree with this or have a different experience! I’m always interested in learning.
Absolutely, there are a ton of other resources to learn about coaching and how to get the most from it. The Homebrew Guide to Executive Coaching is fantastic, as is Ed Batisa’s How To Find a Coach.

The leadership journey is really hard, which is why we all follow it together. Coaching can help make the journey a bit easier, and is worth a try.

Thanks to Andy Sparks for reviewing this piece, he writes a great newsletter on being a founder called Hoo Boy which I recommend.

For more on becoming a better leader, see:

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