I hate asking for help.

After years of running board meetings and leading corporate innovation workshops, I learned how valuable it was to have a roomful of people thinking about your problems.

And for some reason, that sort of structure felt like a more comfortable environment to ask for help.

My college friends were scattered across the country due to the way that work and life takes you all over the place. We had been getting together once a year.

Sometimes it was for a music festival. Sometimes it was to visit a friend’s new city. It was fun. Mostly, we got drunk.

After a few years of that, the idea of a “Personal Board of Directors” popped in my head:

Warning, crazy idea:

I've been fascinated with the idea of having a "personal board of directors" where you have an "annual meeting". What we do is meet somewhere and we spend an hour on each of us. A person gives a 10-15 min presentation (Slide deck, or just rattle off updates) on your life. You hit a variety of topics depending on what is most important/interesting to you: professional life, significant other, hobbies, passions, financial situation whatever--whatever you feel comfortable sharing. For the next 45 minutes, we are the "board of directors" for that "company". We put our brains to work on thinking about how we can improve that person's life. Maybe it's just advice. Maybe it's just sharing some sympathy. Maybe it's just having a laugh. But for this hour we collectively devote our energies to that guy's personal development.

We tested it for the first time in Nashville in 2014. One guy’s relationship was in crisis. Another had an insufferable boss. Another was worried that he’d become the kind of person he used to make fun of.

Seven years later, we’re still going strong and it’s not a stretch to say it has been life-changing. Each one of us is in a materially better place thanks to this practice.

I’ve since run this with other group of friends. I’ve had a number of other people ask for the playbook on to run one of these. So here it is.

Bourbon Boardroom* Playbook:

  • Typical size: 4-8 people. 5 is ideal.
  • Each person gets a session in the “hot seat”
  • Each person’s session should run 30 minutes total. We recommend 5-10 minutes of letting the person speak on whatever and then discussion for the remainder. The discussion is the important part, not whatever thoughts the person offers to kick it off
  • If most of you are arriving from out of town, aim for a 3-day weekend
  • Run the Boardroom as early as is convenient. If people arrive on Thursday evening, start the sessions at noon on Friday. The big reason to do this is that it gives maximum time for “hallway conversations”. These smaller conversations carry a different tone and timbre than the more public sessions.
  • Pick a boring locale. Los Angeles, NYC, etc. have too many temptations. Party some other weekend; the goal here is to gain from and further solidify strong social bonds.
  • Does the order matter? If it’s your group’s first ever boardroom weekend, then yes. The first person to kick it off should be either a) the person who proposes the boardroom or b) someone who can set the tone of openness and vulnerability.

* Initially, we called it “Bourbon Boardroom” because I thought that in order to get men to open up and be vulnerable it was important to drape things in the language of alcohol and business. After introducing this concept to lots of other guys, I still think this is true.

After you run these weekends for a year or two, awesomely weird traditions will arise. In our case, it’s t-shirts sporting designs of our faces, hot sauce challenges, and even clothing swaps.

The benefits sustain well beyond the actual weekend. The once-a-year in-person gathering has significantly increased the quality of our ongoing text thread and solidifies it as a place you can ask and receive help on almost anything.

Consider trying it with your group of friends. Ever since we started it, this weekend is one of the highlights of my year.

Waterproof goal sheets
Slide decks optional but help you organize your thoughts

Experiments and modules attempted:

  • Subtraction session: much of the boardroom experience involves discussing things that we will add to our lives and new activities we intend to perform. This module involves considering what options should we let go. What should we get rid of for the sake of sanity, clarity, and focus?
  • Pre-board meeting survey of satisfaction a relationship, career, mental health, physical health, social life, organization systems.