The Complete Guide to Peer Coaching

Some of the most impactful therapy sessions of my life haven’t come from a therapy session. They didn’t involve exchanging money, or billing insurance. In fact, they didn’t even involve a therapist at all. 

Instead, they were part of a peer coaching practice that I’ve been doing for 2.5 years with my friend (and co-author of this piece), Casey Rosengren

We’ve explored everything from tactical business issues, to major career decisions, to romantic relationships. I’ve felt almost every emotion imaginable in our sessions, and made major changes in my life and my business because of the work we’ve done together. He has too.

We invented this peer coaching format together by accident, and it has been extraordinarily useful to both of us. We think it could be helpful to a lot of other people, especially otherwise high-functioning, ambitious people who want to experiment with creating more support for themselves to work through issues in their work and their lives.

This article is a guide to the peer coaching practice we’ve been doing together. We’ll take you step by step through how it works, and how to do it. But first, let’s talk about why we think it actually works.

Why Peer Coaching

There’s a strong norm in therapy, rooted in the historical development of talk therapy, that you shouldn’t know much about your therapist—and you definitely shouldn’t be personal friends with them.

This comes primarily from its theory of change: therapists are supposed to be a blank canvas of positive regard, and it’s set up this way so that you can transfer the way you relate to other people in your life onto your relationship with your therapist. This allows you to understand your own patterns and have corrective learning experiences that might help you change.

There is a science and an art to therapy. There is a reason therapists are licensed professionals that need to go to school for many years to practice. For many problems and people, seeing an actual therapist is crucially important and not at all replaceable by peer support or coaching. Casey and I both see actual therapists in addition to doing peer coaching with each other. 

But still, for certain kinds of problems and certain kinds of people, the definition of what “therapy” is and who can perform it is a little narrow. Most meta-analyses find that your connection with your therapist (the so-called therapeutic alliance) is the number one predictor of successful outcomes.

Given that the alliance is so crucial, we believe that with a certain type of friend and a simple set of practices aimed at building and maintaining a safe connection, it is very possible to create a healthy space to feel supported and create growth for yourself–both personally and professionally–without payment and without a formal therapy relationship.

We believe this because we’ve done it. 

Moreover, we think making this kind of experience more common is crucially important because therapy and coaching is so valuable for so many people, but it tends to be expensive, and finding someone you like is really hard.  

If you’re dealing with clinically significant issues in your life, peer coaching is probably not your best route to get help. But if you’re a founder, operator, or investor looking to better navigate the challenges you’re facing at work, and would like to develop a closer bond with someone else who’s looking for the same thing—peer coaching can be a massive upgrade to your week.

So what is peer coaching and how can you implement it in your own life? Let us explain.

What is peer coaching

Peer coaching is a structured way to learn, grow, and share with a close friend. It’s a deep commitment to creating a supportive environment where you and a friend can develop as individuals.

The bare bones structure of it is to meet weekly for an hour, with one person as the “coach” and the other as the “focus person,” and to alternate each week who is in each role. The focus person shares whatever questions or challenges they’re sitting with, and the coach’s job is to listen, and at times, reflect or share their own experience.

While Casey and I both have a deep interest in psychology and some training in active listening skills, we believe that the structure we’ve created is simple enough that it can be utilized by almost anyone, so long as they’re willing to learn and follow a few guidelines for creating a safe container.

What you can get out of it

You can expect to get a bundle of three things from peer coaching:

  • Accountability
  • Tactical and strategic advice
  • A place to process what's on your mind, and to feel seen, listened to, and understood

Most founders and operators come to coaching or therapy looking for tactics and accountability. They want to know how to deal with a specific co-worker, or growth problem, or fundraising situation. 

You can definitely get this out of peer coaching at a much lower cost than the $2,500 / hour you might spend on an executive coach. You’re likely to be a step or two ahead of your peer coach in one domain or set of problems, and a step or two behind in another. In these situations tactics and advice are incredibly helpful.

But we think the main function of peer coaching is actually to provide the third thing: a place to process what’s on your mind and a feeling of being seen and listened to. We have found that only when that feeling is present is it possible for the coach to give advice or create accountability in a way that feels good.

The reason for that goes back to something we mentioned up top: therapy is effective to the extent that there is a strong therapeutic alliance. The task of a peer coach is first and foremost to create and maintain that alliance. 

Advice-giving and accountability—as well intentioned as they might be—can create ruptures if the person being coached isn’t ready to receive them, or doesn’t feel like they’ve been fully heard.

There’s a term in the therapy world, popularized by Carl Rogers, called unconditional positive regard—which basically means it’s the therapist’s job to be understanding and be accepting of their client, to listen carefully to them, and also to be the bearer of hope that they can work through their problems and learn to change.

This, we think, is the bedrock of peer coaching. The tactical advice and accountability is kind of the cherry on top.

There are so many anecdotes about how lonely it is to be a founder, but there are not many suggestions for how to alleviate this loneliness. It might be obvious, but in our experience the best way to address loneliness is to connect with others who have gone through similar circumstances. Peer coaching is a great way to do this.

How to do peer coaching

Finding your partner


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