This guide will help you make the most out of working with a coach. As someone who’s worked with over a hundred startup founders by now, I’ve seen what helps my clients use our relationship (and their money!) effectively, and what gets in the way.
This guide is not about choosing a coach, except for a few thoughts about how to approach the very first meeting with a coach you’re considering hiring. There are excellent guides on how to choose a coach, for example
A complete guide to finding the right coach for you by Richard Hughes-Jones
An entrepreneur’s guide to finding a coach by Steve Schafman
Instead, in this guide I’ll assume you know what coaching is, what you’re looking to get out of it and are either talking to some prospective coaches or already working with one.
There are specific ways you can maximise what you get out of coaching. Your return on your investment (ROI) depends not only on what you invest, but also on the skills of the coach, the chemistry between you two and how you approach coaching (your engagement effectiveness). This guide is all about what you can do to maximise the coaching ROI.
If you take only one thing out of this guide, let it be this: hiring a coach and not engaging effectively is like buying an iPhone and only using it for phone calls. This is a shame, considering that coaches are expensive, and your time is even more valuable.
Don’t expect advice
George Warren, a coach and a coach supervisor, said it well in his newsletter. Coaching is not about hacks, advice, tips and tricks, or shortcuts.
This applies even in situations when the coach might be well qualified to have an important opinion thanks to their experience. Giving advice is almost always a disservice to the client because it implicitly reinforces the idea that the coach has the answers and the client isn’t capable of finding their own way forward.
You may ask, Why choose a coach who’s been in your shoes, e.g. a founder a CEO, if they aren’t going to give you advice? If your coach has relevant experience, it will be easier for them to really understand what you’re doing through. When my clients say something like “I can’t stomach a 3x pref on this deal, but the anti-dilution protection on a down round would be even worse”, I know what they mean, and my clients know that I know what it’s like to negotiate VC investment. This informs what questions I might ask, not what advice I might give.
Having said that, it’s absolutely not a prerequisite for a coach to have the same professional experience. There are brilliant coaches for CEOs, for examples, who have never been a CEO themselves. Likewise, just because a coach has relevant work experience, doesn’t mean they’ll be the right coach for you.
Do: Expect your coach to help you find your own answers.
Don’t: Expect your coach to tell you what to do.
Approach it as a relationship, not as a transaction
Coaching is a special kind of a relationship between a client and a coach that’s designed to help the client grow personally and professionally.
You’ll get more out of your coach if you focus on building a deep relationship with them in a way that will help you grow, as opposed to simply seeing each coaching session as a transaction that will help you address specific issues, even though you’ll generally focus on something specific in each coaching session.
“You're the average of the five people you spend the most time with”
—attributed to Jim Rohn
A coach may not be someone you spend most time with, but the relationship you’ll have with them will impact you and your growth. The quality of this relationship — trust, challenge, respect, mutual expectations — matters just as much as specific issues you discuss in your coaching calls, if not more.
One way to see this relationship is a commitment to each other: both the coach and the client commit to each other to do what they can to help the client make the most out of coaching. The stronger the commitment on both sides, the more you’ll get out of coaching.
This also means that choosing the right coach for you might involve more than just a one-off coaching session. Talk to a few coaches. Listen to their podcast interviews. Read what they share online. Get a sense of who they are as people and if they’re someone who you’d like to build a relationship with. Talk to their clients. Take your time.
Do: See coaching as a relationship in the context of which you grow.
Don’t: Approach coaching as a series of transactional conversations.
Don’t hold back
I wouldn’t expect anyone, including myself, to share their deepest secrets and fears in my first conversation with a potential coach (or therapist, or anyone). It takes time to build trust and get to know each other. Having said that, the more you give yourself permission to open up about how you’re really feeling, what challenges you’re really facing and what your dreams really are, the more progress you’ll make in coaching.
Coaching works with the whole person, meaning that even if you both agree on helping you be a better CEO, the rest of your life will still be relevant to this agenda. This might include your childhood memories, your relationship with your family, your health concerns and that one thing that you never told anyone about, but which still sends shivers down your spine.
Naturally, it takes time to build trust. It keeps deepening over months and years. Yet, if you feel you can’t be completely open with your coach, share it with them. Any good coach will respect your boundaries and not push further, and at the same time they might help you become more aware of why it feels so difficult to be more vulnerable.
Sometimes we don’t have words for what is it that we want to share. A coach can help you make sense out of it and find a way to sit with an uncomfortable feeling until right words emerge.
If you feel you can’t tell your coach that you can’t be vulnerable with them, it’s probably a sign that the two of you don’t have a good fit.
Do: Be open with your coach about everything relevant to the topic.
Don’t: Expect to make progress without sharing what’s really going on.
Take action between coaching sessions
Coaching work is mostly about two things: what’s going on and what are you going to do about it. While coaching sessions are great to deepen your understanding of what’s happening, experiencing new ways of relating to yourself or planning next steps, it is you, and not your coach, who’ll need to apply what you learned in coaching sessions in your life.
If you don’t try different things in between coaching sessions, a coach will pick up on this pattern and help you reflect on it, but ultimately, only you can take action.
This point is so obvious that it’s difficult to stress it, but it needs stressing, because time and time again I come across clients who are very happy to talk about their goals, their challenges, their feelings only to fall back to their old ways in between coaching calls. Progress can be painfully slow.
You hired a coach to make progress. Not taking action will all but guarantee lack of progress.
Do: Work with your coach to translate your insights into next steps and make them.
Don’t: See coaching as something that only happens when you’re talking to the coach.
Have high expectations
You should have high expectations for coaching. Coaching costs money, and it also takes a lot of time and attention, which is the most precious resource of any founder. Working with a coach has an opportunity cost: if you’re working with this coach, you are not working with someone else. For all these reasons you should expect a lot from coaching, and if you don’t feel like it’s really, meaningfully, making a difference, discuss it with your coach.
Maybe they’re not the right coach for you. Maybe something in your approach needs to be different. Maybe it’s something else. But if you aren’t really excited about the difference coaching makes in your life, something needs to change.
This is also the reason why I think you should pay slightly more than you’re comfortable with to your coach. I do. Even though intellectually I understand that my time and attention are more valuable than my money, paying my own coach an amount of money that’s meaningful to me helps me to remember that I didn’t hire him to have a nice conversation twice a month. It reminds me to have high expectations. It reminds me to make an effort, show up and make sure I don’t waste his and my time.
At the same time, it’s important to be patient. We need to have high expectations for our coaches and also remember that real, profound change takes time.
It can be hard to tell the difference between the need to be patient and the need to start working with another coach. This can be a great question to bring into the coaching space.
Do: Expect coaching to make a big difference and don’t settle for less.
Don’t: Get a coach unless you’re serious about some big, meaningful change.
Strive to set big goals
This is slightly different from having high expectations. It’s ok not to have clarity on what your big goals are. It’s perfectly reasonable to start working with a coach to clarify what exactly your goals are. However, if you come with high expectations for coaching, but don’t translate those expectations into specific goals, it’ll be less likely that you’ll achieve it.
When I first started coaching, I let one client down. She reached out “to be a better CEO”, but struggled to articulate what it meant to her. I made the mistake of ignoring this and instead went with the flow of helping her work through this or that problem that happened to be on her plate that week. When we wrapped up our work a few months later, neither of us was sure if she became a “better CEO”.
That was a lesson for me: if a client doesn’t have big, clear, audacious goals that look a bit intimidating, it’s far less likely that they will achieve them. Many, maybe most, clients don’t have enough clarity on what their big goals are. It’s ok. Clarifying them can take several coaching conversations. They also evolve over time. And yet, how can they be achieved if they aren’t clear?
Do: Strive to set big goals and work with you coach to clarify them.
Don’t: Simply focus on what’s in front of you without a sense of direction.
Say it if you’re thinking of wrapping it up
If you’re considering wrapping up a relationship with a coach, share your thinking with your coach sooner rather than later. No good coach will put any pressure on you to stay in a coaching relationship. However, if you’re not sure it’s serving you and you’re not saying it to the coach, it’ll become a self-fulfilling prophecy: without addressing what’s not working, it won’t get better, you’ll feel uncomfortable that you’re not being completely open, which will only reinforce the sense that something is wrong.
Often, you’ll have great reasons to wrap up a coaching relationship. Discussing it with your coach will either improve the coaching relationship and remove our doubts or give you clarity of what to look for when you start working with a new coach.
A coach has the same ethical obligation to you. The Code of Ethics of the International Coaching Federation states that the coach should
Remain alert to indications that there might be a shift in the value received from the coaching relationship. If so, [the coach should] make a change in the relationship or encourage the Client(s)/Sponsor(s) to seek another coach, seek another professional or use a different resource.
Do: Be open if you start thinking about wrapping up a coaching relationship.
Don’t: Abruptly terminate a coaching relationship unless something is really wrong.
Choose time, space and tech that works for you
It’s hard to have a coaching conversation if you happen to be in a busy café, when your coaching call is sandwiched in between a meeting with an investor and an interview with a potential CTO, after you had your fourth coffee of the day.
A good, meaningful, impactful coaching conversation needs space and attention. Discuss with your coach what time and day of the week work best for you. Get a quiet, private room where you won’t be disturbed or seen, where you have the privacy to cry or shout “I fucking hate them” if you need to, without worrying if anyone will notice.
Leave some time before the call to take a deep breath, reflect on how are you, think about what you want to bring up and what you want to get out of it. Leave some time after the call to reflect on the lessons and next steps, and let any emotions calm down. This alone will make a big difference to how much you get out of coaching.
The tech you’re using for remote coaching calls makes a big difference. If the coach can’t clearly see your face because you’re sitting against a window or they can’t clearly hear you because of poor quality wireless headphones or poor internet connection, the quality of the coaching session will be impaired. The tech matters.
I know there are exceptions and sometimes we’re on the move and we really need to have a coaching call from a café or an airport. There are exceptions to every rule.
Do: Consider when and where you’ll be taking coaching calls.
Don’t: Leave the choice of time and space to the last minute.
Choose to face discomfort
There’s a lot of nuance in this phrase. Coaching isn’t meant to help through applying more pressure on the client. Coaching is not about applying pressure. All of us already have enough internal and external pressure in our lives. We don’t need more. However, growth of any kind is sometimes uncomfortable, in a way that working out in a gym can be uncomfortable (although it shouldn’t be painful). A good coach will help you navigate your growth with just the right level of discomfort for you.
It’s important that as a client you choose your level of discomfort and negotiate it with the coach. Like in a gym, if you push yourself too hard, it won’t be sustainable. If you don’t challenge yourself to explore new ways of showing up, even when they are uncomfortable, this might limit your growth. In coaching, you’re in the driving seat, choosing how you want to approach it.
Trying to change how you think, feel or act, especially if you’ve got big goals and high expectations, will be uncomfortable at times. That’s why it’s important to choose to face discomfort.
Some questions a coach might ask might be uncomfortable. They aren’t doing it to hurt you and they will know how to ask these questions skillfully. Yet, it’s their job to ask questions that you wouldn’t ask yourself and have courage to say things that no one else in your life will dare to tell you. This can be uncomfortable.
And yet, all of this is done in service of growth, just like my personal trainer, Antonio, tells me to pick up a bigger weight not because he enjoys seeing me struggle, but because he knows I can lift it before I have the courage to try it myself.
Do: Trust your ability to tolerate discomfort you choose to face in coaching.
Don’t: Expect growth and change to always be easy.
Prepare for the first session with a coach
The best way to figure out whether a particular coach is the right one for you is to have a coaching conversation with them. Not having a conversation about coaching, but actually being coached. Every good coach I know will offer a free, no strings attached, coaching session to get to know each other. In fact, if someone tries to charge you before they know you’re the right client for them, it’s a big red flag.
So the very first time you meet a potential coach, bring a real problem, a real goal, a real challenge, the biggest reason you decided to reach out to a coach in the first place. And then resolve to make as much progress as you can in that first call. The more you give, the more you’ll get out of this process.
A wrong way to approach a first coaching call is to show up without really having an intention to be coached, just to talk. If you don’t want to be coached, why speak to a coach?
If you meet a potential coach for a one off coaching session without an intention to be coached, you won’t get much out of it. You’ll leave the session wondering what was the point and why would anyone pay money for this. It’s worth being prepared.
Do: Bring your biggest dream, your biggest challenge, your biggest question or your deepest feelings to your first coaching session with a potential coach.
Don’t: Just show up without an intention to be coached.
Prepare for every session, not just the first one
Actually, it makes a big difference to be prepared for every session, not just the first one. Take some time the day before or earlier on the day of the coaching session to spend 10-20 minutes reflecting what is going on in your life and what you’d like to focus on in the coaching conversation.
After the coaching session, maybe the next day after you had a chance to sleep on it, set a reminder to reflect on the takeaways from the call and action steps. Schedule when you’ll put them into practice. Reflect again on what you learned about yourself and about your situation.
“Taking a bit of focused time before and after sessions is something my clients often say they wish they’d done more”
Cat Totty, Founder and CEO coach
Do: Prepare for all coaching sessions and set aside time to reflect on them.
Don’t: Simply show up unprepared and then forget about the coaching call when the session ends.
Don’t assume it’s “hell yes” on both sides
Coaches coach because they love helping people grow, change, learn new things and achieve more than they thought was possible. A coaching engagement should start with a “hell yes” feeling on both sides. If both the coach and the client feel like “maybe it could work, maybe not”, what are the chances the client will achieve transformational results?
You want to work with a coach who’s carefully choosing their clients. They’re doing it not out of arrogance (hopefully!), but out of a desire to make a big difference. If there’s a “hell yes” feeling on both sides, the chances that the coaching engagement will be successful are so much higher.
Do: Ask a potential coach how they choose clients and how they feel about working together.
Don’t: Assume any coach will be happy to work with you just because you’re paying.
Give feedback
Like anyone else you’re working with, your coach will benefit from feedback. Tell them what’s working and what’s not working for you. The more your share with them, the stronger your coaching relationship will become. The stronger your coaching relationship, the more you’ll get out of it.
Give feedback in any form and at any time. Mid-way through the session. By email after the meeting. Right at the start of a coaching call. As long as the feedback is not given at the end of the coaching engagement when it’s too late to make changes, it can be used to improve the coaching relationship.
Do: Tell your coach what’s working and what’s not.
Don’t: Expect your coach to read your mind.
Use an AI coach
Finally, since it’s 2023, you can use an AI coach together with a human coach. I wrote about how I do it in this essay.
An AI coach isn’t a replacement for a real coach, but it’s a powerful complement. If you incorporate regular reflections with an AI coach into your routine, it will super-charge your progress with your real coach.
There’s no best practice for combining an AI coach with human coaching. The entire field of AI coaching is nascent. So experiment with it, find out what works for you, discard what doesn’t and keep looking for ways to deepen your self-awareness and find new ways to show up in this world. After all, that’s why we choose to be coached.
Do: Experiment with new technologies.
Don’t: Expect AI coaching to be completely useless or a perfect replacement for the real thing.
Conclusion
The return on investment in coaching is a simple formula:
The more skilled the coach, the more they’ll be able to help.
The better the fit between you two (“hell yes” on both sides), the easier it’ll be to work.
The higher your engagement effectiveness (everything in this essay), the more you’ll get out of coaching.
The top three variables have a far bigger influence on the overall ROI than the financial cost. Nail the numerator (three things above the line) and the denominator (financial and opportunity cost) will hardly matter. Ignore any part of the numerator and you will likely be disappointed.
My hope in writing this guide is that it’ll help anyone working with a coach (or considering it) make the most out of it. Being coached is a big commitment, so it only makes sense to take it seriously.
Thank you Joel Chippindale and Cat Totty for suggestions and for reading this draft.
Excellent piece, and I appreciate the shout out.