Don't be a passenger

Sam¹ had a successful YC batch and a fresh seed round behind him. He also carried the weight of being a first-time CEO and a clear feeling that what came next would hinge on how he handled it. His peers recommended a coach. $25k for six months felt steep, but if that was the cost of becoming like the founders he looked up to, so be it.

By the end of it, Sam discovered that the entire engagement was a "waste of time" when one of his angel investors, a former operator, grilled him for just 20 minutes. That painful conversation exposed his poor grasp of even the most fundamental drivers of his business. He was frustrated to admit that a couple of phone calls did more than six months and $25,000.

What went wrong for Sam was that nobody had named, out loud, what he was actually there for. The $25k lesson was that he needed business-fundamentals accountability — a kick in the ass on the metrics he didn't know that he didn't know. Instead, he got a personality assessment and self-help content that "sounds good but isn't helpful day to day."

About a quarter of the founders I interviewed had at least one engagement that didn't work. The thread across them wasn't about the quality. Instead, it came down to choices the founder didn't know they were making about what they were buying, who they were hiring, what they were agreeing to, and how they were showing up.

What you're here for

Allan's experience was the opposite of Sam's. He'd interviewed several coaches and settled on one with a tactical business focus. Then his cofounder relationship started to fall apart. The coach wasn't helpful with that and Allan navigated the separation on his own, wondering afterward if he could have done it better, or reached key decisions sooner. What he actually needed, it turned out, was someone more personal and psychological. He found that person on his second try. "Significant upgrades in between sessions," he told me, once someone was finally working with him on his fears and limiting beliefs rather than his business plan.

And it's not just a question of which coach. There's a wide adjacent neighborhood: therapy, mentors and advisors, peer groups, and even your second uncle Gary who once worked for IBM in the 80's. Adrian explored most of it. A mentor, he found, is "someone who's done what you're doing before and can give you advice." Therapy "unlocks issues that hold you back." His real challenge was getting clarity on what was next in a career transition, to which his therapist surprised him with: "you don't need therapy, you need a coach."

Adrian took that advice to a friend who recommended the coach he ended up choosing. Among the founders I spoke with, almost all the coaches were sourced through their network. As Ed Batista says, "if you're a tech CEO in San Francisco, this should take about 10 minutes."

It's fine to not know exactly what you want yet. A conversation with a good coach is a great way to discover it. In fact, I think a coach worth hiring will press you to name it, and articulate clearly whether they see a potential fit. If they don't, that's useful information too.

The tryout

What else should you be looking for in that first conversation? Three things showed up consistently in my interviews: trust, challenge and chemistry.

Trust. Without it, nothing else works. Trust grows over time, but you should feel its presence right away. Cristina said it well: "My coach is so kind, calm, and approachable that I felt safe to go into those rough spots — and not sugar-coat or minimize." A coaching relationship may be unlike any other you've had. A place to bring the thing you've been hiding from everyone else. What you get out of it is a direct result of how much you allow yourself to be seen, and how much you loosen your attachment to being right and let something new in. 27 of 29 founders named trust as a top selection criterion.

Challenge. The ability to push you into the things you'd rather avoid. To ask you questions you'd rather not answer, to help you sit with feelings you'd rather not feel. To keep you accountable to your stated vision of yourself and your future. Joe put it dryly: "If it's comfortable, that's probably a sign it's not working." Validation feels good. It also keeps you stuck. Being willing to tolerate discomfort opens the door to growth. Don't pay a coach to be your friend.

Chemistry. Vibes. Hard to articulate, easy to feel. Helps you relax, trust and get curious. "Right coach for me is not right coach for you," said Dimitri, who interviewed five to ten coaches with unicorn-CEO resumes before hiring a first-time coach with no credentials, because the chemistry was right. Two years later he was clear it was the right call. Only 2 of 29 founders said certifications mattered. Pedigree is a weaker signal than your gut.

It might take one conversation or several. My advice: try to experience how they coach. Bring a current issue that matters. See how they hold it. Don't expect an epiphany, but do expect to feel what working with them is like. Are you left with a sense of possibility? Is this someone you want to talk to again?

The warm up

Once you've decided to move forward with an engagement, your coach will offer a structure that supports it. The written contract will cover a lot of this and it's important to fully understand and discuss your mutual agreements. Cadence. Between-session access. Intensity. Assignments. Confidentiality.

Jacob's startup exited to a larger company and he took a senior role. Some challenges soon arose with his new boss and he agreed to executive coaching offered by the company. However, a few months later, "my boss told me the things I'd shared in confidence with the coach." With trust destroyed, Jacob ended up leaving the company. A rare case, but one that underscores the importance of getting clear on your agreements - especially if someone else is paying the bill.

This isn't just a website TOS you sign without reading. How you hold your agreements in this relationship will expose how you hold agreements in the rest of your life. Do you agree to things when you don't mean to? Do you fail to keep your agreements without saying anything? Do you name it explicitly when existing agreements no longer serve? Do you hold expectations of others without their knowing and blame them when they don't deliver? This is a really rich territory for coaching in itself and this step is your first rep.

Jacob didn't give up, but took his lessons and hired a different coach at his next company. With a more explicit container, he went on to have a transformative engagement over the next two years.

Don't be a passenger

The structure is also the foundation for helping you take full responsibility for what you get out of coaching. While it may be another Zoom call, it's definitely not a passive webinar. Just like in the athletic origins of coaching - if you want to be a high performing athlete, you need to show up prepared to do your work and be a full partner in creating and developing towards your goals.

Edgar and his two co-founders were several years into their company when they hired a coach to help resolve some new disagreements. From the start, he was reluctant to do it and thought it was too expensive compared to using their existing network informally. But his co-founders insisted. Edgar wanted out after 6 months because he didn't feel challenged: "No epiphanies. A lot of validation. Was looking for conversations beyond 'no shit.'". Instead, he stuck with it for another 12 months, grumbling about the rigid framework the coach was trying to impose on him, but paying anyway. "I should have been a better partner to the process. I took more of a passenger approach," said Edgar in retrospect.

I was Edgar in my first coaching experience. And I still notice myself being Edgar in other areas of my life even today. But that noticing is the call to return.

I'm not saying you should do all the work. It's a partnership. You can expect your coach to lead. And, you should lead too. And that means showing up like you have skin in the game, because you do.

If you want more guidance, just ask your coach how to get the most out of their coaching. They'll tell you. It's not rocket science - make the commitment to get the most out of it and the rest will follow. Show up prepared, tell the truth and voice your feedback. The conflict avoiders and people pleasers inside us may hold you back, saying to trust the coach, surely they know what they're doing, but they also take you away from the exact thing you're paying for.

A client came to me with years of withholds kept from his co-founder. Both colluded to keep the peace over growing their relationship, and the company with it. It took four months to build the capacity to have that deep conversation, but the real work was outside the room. Taking the risk of revealing himself to others, grounded in confidence of who he is as a leader - imperfect, but caring deeply and willing to be with his and others' discomfort.

What you practice in coaching may well be the very muscle you need to develop elsewhere in life. How you show up here will reflect and help you confront whatever's in the way of resolving your challenges or achieving your stated goals. And you'll know it's working when the muscle you're developing starts to show up elsewhere. Asking for what you want. Facing and naming when something isn't working. Getting into the driver's seat of your life and dropping the blame.

A coach can hold up the mirror. It's on you to make the commitment to face it and be willing to change if you don't like what you see. That's both the limit of what coaching can do and what makes it powerful.

Best time to plant a tree

Four pieces ago² I started by saying coaching probably isn't for you. I still mean it. Most founders won't get a coach, won't need one, and will be just fine. The skepticism is also real and often correct.

But the founders I interviewed who did get support, whether through coaching, therapy or groups, described what they got as one of the most consequential decisions they made. Not because it made their company succeed, but because they recovered the qualities of leadership that let them lead better while suffering less. And if business is an infinite game, that seems like a good deal.

That's why I continue to work with a coach. I don't need one. But I want one. I want someone who believes in me on the days I don't. Someone who spots, names and doesn't buy into my disempowering beliefs. Someone who'll keep holding me accountable to the bigger version of what I said I want. Someone who'll ask me the tough questions I'm avoiding asking myself. Someone who can teach by modeling a different way of being, remind me who I really am when I forget.

Not everyone wants that, and I respect that. Now may not be the right time for you. But if something resonates in here, I hope these four posts have helped you ask better questions — of yourself, and of whoever you end up choosing to walk with you.³

Coaching is just one place to grow. The rest of your life is the rest.

1. All names have been changed to protect privacy.

2. This is the fourth and final piece in a series. The earlier posts: Why Coaching Probably Isn't For You, Suffering Alone Isn't a Strategy, and The Most Expensive Person in Your Company.

3. If you're ready to explore what support could look like for you, let's have a chat.