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  • Jason R. Waller

Should I Join a CEO Peer Group?

The benefits and drawbacks of joining a professional mastermind.


Peer groups and mastermind groups seem to be popping up everywhere. A few months ago, I was talking to a Series B founder CEO who told me he had been “reached out to three times [that] week” about joining a peer group. I’ve put together and facilitated a few such groups, and was actually talking to him about joining my own CEO peer group (which is full and on a waitlist as of now, no pitch here!). A few years ago, it seemed nobody had heard of a peer group. Today, I notice that most people I talk to have either joined or thought about joining something similar.


Similar communities are being tailored for content creators, influencers, and side-hustlers alike. So what’s the big deal? Why is it becoming a more common part of professional development (and a more popular business model for service providers)? How does it help and where does it fall short?


A peer group is just what it sounds like

First, some definitions and a lay of the land. A peer group or mastermind (they might be slightly different but I’ll use the terms interchangeably) is a community of similar individuals who get together regularly to support each other. Sometimes, it’s a big, broad group; sometimes, it’s a tight-knit, tightly defined group.


There are oodles of masterminds that are put together by the peers themselves, but professional peer groups are often externally facilitated and, to some extent, deliberately curated to have the right balance of individuals. The target market is almost always the CEO or executive-level leader of an established company, although there are plenty of other models here.


There are several “flavors” of peer groups

The quintessential peer group model takes a dozen CEOs in a given geography and brings them together every month, often with some kind of speaker or program to kick off a facilitated group session. Members bring topics to problem solve with the group and the group acts as a “coach” of sorts, supporting the members and keeping them accountable to their goals and actions. The most well-known player here is Vistage.


Other peer groups have popped up. Growth10 focuses on a virtual model with companies at similar or smaller sizes to Vistage, while groups like Startups.com have bolted on curated cohorts to their platform, focusing on early stage founders. Many other well-respected organizations, such as the Young Presidents’ Organization, the Women Presidents Organization, and the Entrepreneurs’ Organization, are broader communities that have smaller sub-communities and mastermind groups that operate similarly.


Still others have driven toward a more hybrid model, offering more than just peer groups. My own CEO peer group included, among other things, 360 assessments, executive coaching, and fractional talent support. Women-focused executive community Chief offers an exclusive network first and peer groups second. Each program is different and, unsurprisingly, the pricing models are all over the place — ranging from one hundred to several thousand dollars per month.


Should you join one? It depends

There are a lot of good reasons to join a paid mastermind, and about as many to not. Rather than tell you my opinion, I’ll share what I’ve seen and heard from others.


Pro: Invest in your personal growth

Most of us, especially CEOs, don’t take a lot of extra time to reflect inward and focus on growth. These mastermind programs encourage that. They encourage separation from the day-to-day and from the detail in favor of reflection and introspection. It’s an opportunity to check in on not just “what you’re doing” but also “who you’re being.”


Con: It costs money and takes times

Some of these programs are a full day long. Almost all are at least a few hours every month. Add to that the travel to the location, if it’s not virtual, and the cost of accommodation added to the program itself, and the result is significant. It’s an investment.


Pro: Get unique input on tough problems

The value of the peer group is that it is your own personal board of advisors. There are no misaligned incentives and everyone is rooting for you. As such, the advice is genuine. And often, the advice is coming from a totally new place that you hadn’t thought of before, from people in different industries, geographies, etc.


Con: It might be too homogenous (or too diverse)

I wish peer groups did a better job of gender and ethnic diversity, but the fact is few do. There are masterminds specific to all sorts of underrepresented groups, however. On the other hand, groups are often diverse in terms of things like industry, geography, and age. This is usually a good thing, but not if you only want to join a B2B SaaS group.


Pro: Feel supported and connected

As you integrate into the group, you’ll find that it’s a valuable family of people who have been on the same journey that you have. For my founder CEOs in particular, it’s refreshing to “be yourself.” It’s a lonely journey, and having people rallied to support you is special.


Con: You don’t always need a professional facilitator

There’s value in an external moderator — to a point. We help to bring out the best conversations, keep the focus impartial, and monitor “share of voice.” But for more informal groups, it might be easier to get a half-dozen people together on Zoom and experiment with what works best on your own.


Pro: Build meaningful new relationships

Regardless, you’ll be meeting new and interesting people. I’ve seen connections with investors, board members, employees, and everything in between come out of peer groups. But it’s not just networking, it’s more meaningful. It’s friendship and partnership.


Like most things, you get out what you put in

There’s no one-size-fits-all solution, and I’ve seen many people not be a good fit for their peer group. Sometimes it’s the dynamic, but more often than not I can tell early on that they don’t go into it hoping to get anything out of it. If you do choose to try out a peer group, I challenge you to: show up, show up, show up.


Show up physically and make the time to be there with your group. Show up mentally and be present, contributing to the conversation and asking questions of others. And show up emotionally. Take part in building trust with the group by being vulnerable and taking off your mask.


Good luck on your journey.

Originally published in Mind Cafe