Peer Groups are more than just Words With Friends

The most powerful business and leadership development opportunity

In 2001, when Bertelsmann closed CDNOW, they offered me the services of an executive outplacement firm. I was skeptical of its benefits given the nature of the tech and startup communities and how jobs are typically found. Having nothing better to do, though, I signed up. It started out as a lot of nonsense (to me, at the time), offering business cards and voicemail, resume editing, self-assessment tools, databases of companies to research… information that was more and more becoming available on the web, and likely wasn’t going to help connect me with that next startup. When I now look back on my six-month experience with the service, two things emerge that make me realize what an amazing opportunity it actually was. First, I got to experience what is was like to work with a few good coaches, including Kay Steinkirchner (Rock) and Richard Marcus, and all the benefits of having such a relationship.


The second benefit was a peer group. The outplacement firm brought the senior executives in their program together into a cohort that met weekly in a coach-facilitated session. We had held different positions in various industries, it was a diverse group of men and women. Over the weeks, relationships were strengthened. We’d support one another, hold each other accountable, and offer insight, connections and assistance, not only during the sessions, but also with ad hoc meetings and by email and phone. I’m not sure I really appreciated it at the time, that it was a mastermind, or accountability group, or personal advisory board. We all eventually found positions and a number of them relocated. To this day, over 15 years later, some of us still keep in touch. That’s pretty remarkable.

Think and Growth Rich

Peer groups are not a new concept. One of the notable first suggestions of the benefits of business peers working together was by Napoleon Hill in Think and Grow Rich (1937). Hill was a mostly failed entrepreneur who became a business writer and eventually made and lost a fortune a couple of times with a series of self-help books (rags to riches, several times over). The turning point of his career was an opportunity to interview (and eventually work with) Andrew Carnegie in 1908. In his huge best seller (some say as many as 20 million copies), he wrote about a “master mind alliance… with one or more persons who will encourage one to follow through with both plan and purpose.” In a later book, Master Key to Riches. Hill writes “every mind needs friendly contact with other minds, for food of expansion and growth.”

Hill worked with many titans of business throughout his career including Ford, Eidson, Bell, Burbank, Rockefeller, Burroughs, Wanamaker, Woolworth. What a master mind alliance that would have made (albeit without much diversity).

I’m not suggesting you go out and read Hill’s books, but just observing that the power of engaging with peers is an old concept in business.

Peer Groups Become Business

I’ve had the chance to explore and work with a number of professional peer groups.

In one company, my CEO was a long time member of Vistage. Founded in 1957, Vistage (formerly TEC, The Executive Committee), turned peer groups in big business with as many 20,000 members in 16 countries, charging as much as $20K per year to belong. A Vistage group is 8-16 executives plus its “Chair” (the person who recruits members and runs the group) and offers the opportunity to get together for support, accountability, and education.

Members spent hours complaining about their bosses and the Chair couldn’t facilitate a positive discussion. It wasn’t apparent that Chairs had any qualifications or training.

Having been prospected as both member and Chair, I had opportunity to work with a few Vistage Chairs and a few groups. My experiences with Vistage could have scared me away from peer groups forever. Some of my observations were: members weren’t always authentic, often chest-pounding of how great things were; in a “Key Group” (members are direct reports of CEOs in other Vistage groups), the members spent hours complaining about their bosses and the Chair couldn’t facilitate a positive discussion; it wasn’t apparent that Chairs had any qualifications or training, that it was something they did in their retirement; educational components were almost always delivered by speakers trying to sell their services. Through my CEO, I could see the impact of his participation in Vistage on our company, and it wasn’t pretty.

I have close colleagues who are dedicated Vistage members and have mostly very positive experiences, as likely does thousands of others. It’s not my intention to vilify the organization, but to observe that “monetizing” something as valuable as a peer group needs to be done so that its benefits are not compromised. Structure, strong coaching, and a healthy culture are necessary.

Next Generation Peer Groups

Being an entrepreneur and problem solver, I decided I could do better. I studied other established professional peer group businesses, including Entrepreneurs Organization (EO), Young Professionals Organization (YPO), and The Alternative Board (TAB). I assessed peer group SaaS platforms, facilitated by technology, not coaches. I looked at what was being done with peer cohorts in startup accelerators. With the backing of my business incubator, Novotorium, I had the opportunity to build a peer group system and in 2011 created the first “Acceleration Group.”

The Acceleration Group was a cohort of about a dozen entrepreneurs of mostly young businesses (given we were an incubator). We met two days each month, in the style of a “retreat,” with a formal agenda and the facilitation of at least two coaches (usually myself and Chuck Hall). It was a combination of accountability, education, peer support, and coaching. Each day we’d have a couple of advisors (partners) scheduled to visit - to present, educate, and offer 1:1 coaching in an area of their expertise. We’d also have team building opportunities and tools that they could use to grow their businesses. And food.


Each member of the peer group grew tremendously as leaders and business people. Sometimes their companies thrived, and sometimes they pivoted, restarted or folded, as a result of the outside-in and unemotional perspectives that their group and the education offered. It was often raw. There were tears - of frustration, sadness, or happiness. Even in the cases where a member might have closed their business, they usually stayed in the program and helped others grow theirs. Several members thought that two days a month wasn’t enough, so they took the initiative to start a weekly video call to be together more frequently. That’s how peer support was supposed to feel and work.

A resulting benefit of the program was a tremendous growth of everyone’s networks. Members of the program shared networks with each other, and got the benefits of our networks and those of our partners. The education and advisory partners we enlisted each committed a couple of hours every few months to support us. They did so in part because of the value of the experience, and the exposure they received - but mostly because it allowed them to grow their network. They became part of an exclusive group of providers who also helped one another and for who we (the incubator) would always be looking to make connections.

Though the program was costly to operate, yet we offered it free to incubation prospects. Their active participation was required - everyone had to take it seriously. Free or paid, a peer group only works when its members are all in. Ultimately, after I left Novotorium about a year later, they pivoted and the program was sadly ended.

About the same time, I brought the Bootstrappers Breakfast program from Silicon Valley to Philadelphia. It’s an informal mastermind with 12-20 entrepreneurs coming together for breakfast once per month to help one another. It worked so well, to provide peer support for those that didn’t otherwise have access, that I opened another in Baltimore and later Chuck did so in Atlanta. There are now 18 chapters of the program. It’s been over five years and we’ve learned a lot about entrepreneur and CEO peer groups.

Benefits of a Peer Group

I wasn’t yet done reinventing peer groups. There were another iterations that I tried as I was starting to understand the most important benefits that members were realizing. These are the benefits on which I began to focus:

  • An outside-in perspective of a member’s business and leadership. It is a safe environment to share and discuss even the most sensitive issues. Each leader gets a sounding board for feedback and diverse perspectives. You are surrounded by many experiences that can be leveraged, and different ways to think.
  • A strong sense of accountability. Peers become familiar with one another’s businesses and hold each other accountable for efforts and goals each one is working towards. There is increased satisfaction in mutual accountability and accomplishments. A coach provides structure and reinforcement for this to work consistently - it requires diligence.
  • Multiple networks join together to create a greater collective network. Each member in a peer group brings connections. Knowing that more opportunity comes through second level contacts (weak ties as described by Mark Granovetter and Malcolm Gladwell), by participating in group, leaders get the benefit of such greater access.
  • It’s lonely at the top. Even good leaders need support and motivation to combat the emotional drain of the challenges and pressures that are faced nearly daily. By participating in a peer group, each leader is able to give and receive empathy. Even the most supportive spouses, friends, and advisors can’t relate the way a peer group can.

Doing Peer Groups Right

Given these benefits, I’m now more clear about what elements are required to be able to deliver an effective and enjoyable peer group experience.

  • When a peer group is facilitated, ideally by a professional coach, it is more resilient. A software platform or peer “pressure” aren’t sufficient. Experience, judgment, and strong organizational development skills keep the members on track.
  • All members must have some skin in the game. A monetary fee is the easiest way to achieve this. It takes a good coach to screen prospective members and form a group whose members will be fully engaged. An ongoing obligation keeps them invested.
  • The schedule and format for the group must be structured. Meeting times and places should be regular and predictable. Each meeting has an agenda. Accountability and actions items are tracked. Members and any presenters are always prepared.
  • Groups are better with diversity in its members. It is said that when ten people in a business group always agree, nine of them are unnecessary. The more different personalities, experiences, and perspectives are at the table, the higher the value of the conversation.
  • The group must be willing to openly share contacts and networks. Online tools may facilitate this, but it’s more than just becoming connected on LinkedIn. There has to be a desire and willingness to create a greater collective network.
  • The group must be a safe space, so it needs to be non-commercial. There is no up-sell, soliciting amongst members, or advertising or promotion by speakers or guests. The peer group isn’t a gateway into something bigger, it’s a destination.
When ten people in a business group always agree, nine of them are unnecessary.
— Adapted from William Wrigley

It’s not easy to build and maintain groups that meet all of these requirements. You’ll find lots of compromises, like peer groups that were created to generate leads for consultants or investors, or ones that exist to try to upsell other services, and many where everyone is just too alike. Those are not terrible, they do provide some of the benefits, but they’re not optimal.

Trajectify Leadership Groups

In 2014, shortly after I created Trajectify, we started our first paid peer group, called TAG (Trajectify Acceleration Group). At its peak, the group had eight CEOs from various industries at different stages. SaaS, engineering, benefits, service company, fitness studio - from about $250K to $2.5M in annual revenues. They were young companies and mostly first time CEOs. We met once a month for four hours, usually the same place, day and time. Our agenda was reporting out (accountability), hot seat (mastermind), and education. I had “curated”  the group and always led the session. We often had a guest facilitate the education component. We used a Google group to communicate between sessions.

Most of the CEO’s bonded quickly and became supportive. There was trust and honesty. The program was being effective. As we were doing an annual planning session at the end of 2015, I realized that six of the companies (75%) had doubled revenues that year.

In 2016, it appeared that the companies and their leaders had grown in different directions. Member’s attendance became less regular. We saw the group start to lose its effectiveness and decided to cancel it. The two years together was great and we, as coaches, were interested to learn and try again. While my focus went back to mostly private business and leadership coaching for the next year, we continued to assimilate our learning about peer groups, studied more models and put together a plan.

What were some of the things we had learned? Diversity in the beginning is good, but if it’s too diverse, the entrepreneurs might grow too far apart. The education component also became challenging as the members grew at a different pace. We didn’t necessarily have members with similar levels of “grit,” and the intensity levels some put into the group (and into their businesses) were too different. We also felt that eight wasn’t enough (sorry Tom Braden). The group should have been bigger, and we should have built multiple groups to be able to share resources and network, and create opportunities for fluidity in a peer group ecosystem.

Our Next Generation

I wanted to evolve peer groups once again, so after starting planning late last Spring, we’re ready to launch the next generation. I think peer groups should each have some element of narrowness (focus), so four groups are being created - for early stage entrepreneurs, CEOs of later stage businesses, those building professionals services companies, and for entrepreneurs in the food and hospitality industry. With such division, the program structure and content can be tailored to the unique issues facing those leaders, yet each group is sufficiently broad to allow for a beneficial diversity. Early stage entrepreneurs have a lot they need to learn, so more education is helpful. Those in professional services probably need more frequent support. Food entrepreneurs often work unusual hours and need flexibility in meeting times.

We’ve developed new processes and technologies to support the groups and assist with accountability. And all will be coach led. Having four groups starting simultaneously creates a larger community and makes more resources and a larger network available to all members. We can also share content across groups, access more impressive guests and presenters, and do multi-group events and retreats.

We’re trying to check off the boxes - what it takes to do a peer group the right way and to deliver the benefits the members need. I invite you to reach out if you’d like more insight into all that I’ve learned about peer groups. Trajectify has private coaching clients who are also members of other peer groups, like TAB and EO, so our perspective is not only limited to our own groups. As always, I really just like to help!

Being part of a good peer group is one of the strongest business and leadership development opportunities.

Learn more about the new Trajectify Leadership Groups that are forming now. Members that are accepted in 2017 will receive a charter discount of $100 per month.