If everyone needs a coach, how do you pick the right one?

If we’re saying that everyone benefits from a good coach (and we are), how do you pick the right one? There are coaches who specialise in leadership, others in personal performance and some who will super-charge your team coherence. The fit is dependent on you as a person, where you are in your professional trajectory and what stage of development your company is in.

But first, let’s talk about you. For self-diagnosis, this is a great question to ask yourself: “what are my biggest challenges right now?” What are your blocks? Where do you feel you could use some support? Testing the ice and looking for the thin spots will reveal to you, first that you could do with some help, and second, the areas where you might need it.

Selecting a coach

In supporting our own portfolio founders and teams, we connect them to the coaches we’ve come to know and trust. But word of mouth and even a Google search may be the start of your process. Drawing up a shortlist of two or three should get things going. Just meeting for coffee, or an initial meeting with the goal of making sure the fit is right, will make sure you don’t end up with the ‘wrong’ coach. What works for one will not work for another, so ‘try before you buy’ is a more than reasonable approach.

Here are a few questions you could ask your potential coach: “When did you say no to a possible client?”;  “How do you work? What’s your style?”; “How do you think I can make coaching successful?” It’s not so much the specific answers they give here, you’ll learn a lot about them from how they answer as much as what they answer.

How do you know it’s working?

You choose a coach and start meeting regularly. Trust can take a bit of time to build. That’s ok. But if, after a few sessions, the coaching feels like a ‘nice chat’ or a place to just off load, then it’s probably not going to be as effective as it could be. Good coaching can be radically beneficial to you personally and, ultimately, to your company’s bottom line. It’s an investment that should pay off many times over. So if you feel you’re holding back, or you’re coasting, then that can be raised in your session, perhaps leading to a change of coach as a result. And that’s ok.

Remember this is the space where you can try things out, safely. Vulnerability is not just ok, but essential. As our Operating Partner, John Hamm says, “there’s a reason there’s a practice range next to a golf course”. As trust grows, you will get to practice difficult conversations and clarify your motivations. You can see now why the right coach may not need to have ‘been there, done that’ to help you. They will however, have created a space with you where new ideas, old blocks and risky mistakes can be thrown around with complete immunity.

A coach is there to reflect back to you, to be a mirror. They’re also there to root for you and be a cheerleader. Founding and scaling a business is really hard and its pressures can take their toll. If there is a situation where a coach feels you need another level of support, perhaps a counselling space, then they will recommend that. If you pulled a hamstring, a sports coach would send you to the doctor. Part of a coach’s skill is knowing where the boundary between coaching and mental health therapy lies.

Areas to focus on

How will you know where best to drill down? A bit of quick self-diagnosis can help here. Something as simple as this: put seven minutes on the clock; take a piece of paper; on one side head it “what’s my biggest challenge?”; on the other, write, “what’s stopping me solving this?”. And then just write, for seven minutes. You might be surprised at the result. You can do this before you meet your shortlist. You’ll be much more cognizant of what you need from them.


There’s one more thing you can do: talk to coachees. Anyone you know who has a coach will have something of value to pass on. It may be positive and it may be negative. Either way, you’ll learn something. Of course, the positive is going to be more motivating and you may have observed someone really change as a result of their coaching. Seek them out, but remember that hearing the negative won’t do any harm. (Like dating, finding the right coach can involve kissing a few frogs.) A spectacular coach for one person may not spark so well for another. That’s because it is personal work. The relationship, whilst professional and boundaried, is by definition about trust and connection. At Octopus, we’ve put together a bank of coaches covering a spectrum of specialisms and personality types. Whilst we can be sure of quality, when it comes to chemistry, every match is personal.

A few more tips


If you don’t make time for this, it won’t happen. Many people de-prioritise coaching, or never get round to instigating it because of busy schedules. What’s on offer here is change. so the first change you can make is to loosen your grip on the diary.


Commit. Don’t reschedule. Prioritise your coaching sessions. They are not a personal indulgence, but an investment for the whole company. There are no strong companies without strong leaders. Make sure you don’t have to be rushing off to something big straight after the session. Have a bit of cool-down time built in. If you’re clock-watching and less present than you might be, the coaching’s going to be less effective.

Your team

Think about your wider team. We know companies where a coach meets with the whole leadership team once a month, then with individuals in the interim. It works really well.


A coach might concentrate on any of these four areas: communication and decision-making; strategic alignment; execution or culture. Think about where you need the support.


Any time of change (which will be often, if not always, for a rapidly scaling startup), is a good time for coaching support.


Don’t wait for the alarm bells to ring. Get a good coach/coachee relationship going now and you’ll be up and running for when things get tough(er).

Finally, in case you’re carrying any residual doubt, remember how the culture has changed. A few years ago it was, “you have a coach, what’s wrong with you?”. Now it’s, “you don’t have a coach? What’s wrong with you?”





Sign up to our newsletter

Get the latest on the people, businesses and ideas that will change the world.

See more guides