Why Mastermind Groups Fail…And How To Fix Them

Mastermind Groups Rescue Solo Entrepreneurs

Entrepreneurs spend too much time alone. Mastermind groups to the rescue?

If you don’t know what a mastermind group is, it’s a gathering of 5 to 10 like-minded peers who come together for regular meetings on how to improve in business and in life.  Meetings can take place by phone (lots of people use Instant Teleseminar for mastermind group meetings) or face-to-face.

You can think of a mastermind group as a sort of Board of Directors for your business and your life.  Boards help CEOs brainstorm ideas, clarify vision, and overcome obstacles with their combined resources and knowledge.  Smaller, bootstrapped companies like Instant Teleseminar usually don’t have a Board, so the mastermind group can help fill that void.

At first, joining a mastermind group seems like the perfect outlet for entrepreneurs, since you can’t really talk with non-entrepreneurs about business.  They just don’t give a crap.  One day I was talking with my sister about some of my entrepreneurial customers and the cool things they were working on, when she interrupts,  “You know, entrepreneurs aren’t that great. They’re greedy and all they care about is money!”


Of course, my sister’s idea about what it means to start and run a company simply isn’t true, at least among the business owners I personally know. But she made me realize that entrepreneurs have a fundamental problem: nobody understands us. Our friends and family don’t understand us, our employees don’t understand us, even our spouses don’t understand us. Heck, we often don’t even understand ourselves!

And because of that, we spend way too much time alone, thinking on our own, waiting for a bolt of inspiration that never, or rarely, comes.

Mastermind Groups to the Rescue

So when an entrepreneur friend introduced me to the idea of a “Mastermind Group,” I drank the Kool-Aid in one gulp. Unfortunately, the various groups I’ve been a part of usually die out before fulfilling their promise.  The typical pattern was this: the groups came together with great promise, the first three or four meetings were great, and then they fizzled out as people began to skip meetings or showed up unprepared.

Fortunately, several years back I stumbled across Entrepreneur’s Organization (EO), a global network of more than 5,500 entrepreneurs from 42 countries. The core of the EO experience is called Forum, a monthly face-to-face mastermind group meeting with 6 to 10 business owners. Meetings generally run for 4 or 5 hours, take place in an environment of 100% confidentiality, and are peer-directed, i.e., there is no coach or “guru” in charge of making the magic happen.

5% Conversations

One of the goals of Forum is to encourage what we call “5% conversations.” What’s a 5% conversation? Think of it this way: if 95% of our conversations are fine with friends, family, employees and spouses, “5% conversations” are those things that we would otherwise keep to ourselves. These include the great things that happen to us that we have no outlet for (e.g., it sounds like bragging or is otherwise socially inappropriate to share), and also the really crappy stuff we’re afraid to share for fear of letting down our “never fail” tough guy / gal entrepreneurial shield.

Since the group is committed to confidentiality, its members are able to go into the deep, dark corners of their lives and bare everything, leading to meaningful, life-changing ideas.

No Advice, No Solutions

In addition to 100% confidentiality, another cornerstone of Forum is having a “Gestalt Mindset,” which means:

  1. No giving advice
  2. No problem-solving, and
  3. Sharing only from direct experience.

Sharing only from experience seems obvious enough, but no problem solving or advice-giving? Why wouldn’t the group try to solve each other’s problems? You’d think that’s what it’s all about!

The reason is this: The person presenting an issue ultimately needs to identify his or her own solution. Heck, you’re an entrepreneur: do you do what you’re told? I didn’t think so.

But it runs deeper than that.  By committing to a Gestalt mindset, extraordinary ideas bubble to the surface and give each of us a chance to benefit from the sharing, not just the person presenting the problem. Since experience sharing is real, everyone can put their “bullshit” meters away, at least for a few hours.  The combined experiences of the group come together in unexpected ways that lead to breakthroughs in thinking and approaching life in general. It’s difficult to put into words how all of this works without sounding like magic and fairy dust, but the results of long-time EO members is astounding.

Re-learning How to Listen and Share

Getting this right in a mastermind group takes commitment and patience, which is why most groups end up falling apart unless under the direction of a Coach.  In my experience, EO is the only place a peer-directed approach has actually worked, and I believe it’s because of the rigor and training required of each member. For example, before being admitted to a Forum, each member is required to spend a full day in training to learn how Forum meetings are structured and to practice how to share and give feedback. In other words, members are required to invest in themselves and the group by committing to master these sharing principles.

Unfortunately, EO isn’t for everyone: to apply, an entrepreneur’s business revenues must be a minimum of $1 Million (although there is an EO “Accelerator” program for businesses at $250,000 and above). But any mastermind group can improve its effectiveness by following the principles EO advocates: Have more 5% conversations, have a Gestalt mindset, and take a new approach to listening and sharing.

Are you or have you been a part of a mastermind group?  Share what’s worked (and what hasn’t).