The 2 Day Board Meeting: Speed Dating, Texas Hold ‘Em, and Green Pants

Investors in Green Pants
Windsor Circle Investors Rocking the Green Pants

At Windsor Circle, we define team not by who is on the payroll or inside our four walls, but truly by everyone who is working to build the Center of the Retention Automation Universe.

This includes our employees, our service providers (attorneys, accountants, landlords, etc.), interns, and most certainly our investors.

We have worked hard to find investors who share our values, see the same opportunity that we do, and who could add far more than just their dollars to our efforts.

The Two Day Board Meeting…  What the?

Believe it or not, we hold a two-day board meeting every other quarter.  We do this because we want to unlock the collective experience and insights of a talented set of market makers, and feel that you can’t do that with an 3-hour board meeting where all you are doing is giving updates.

We do a financial call two weeks prior to the meeting to get all of the updates done, and to provide 2 weeks of time for the board to think about the data.

The board meeting itself is held onsite, spans two days, and is driven specifically by two main objectives:

  1. Strategic Thinking – We aim to make the board meeting itself a 4 hour conversation.  No board deck, no updates.  We did that in the financial call…  this is about collective thinking, problem solving and “strategery.”
  2. Team Building – We make certain that our entire team is interacting with one another.  Investors, associates, and management team members meet, socialize, share ideas, and solve problems together.

Our March 2015 Agenda

Click here to download our full agenda for this last board meeting.

Here’s a quick summary:

  • Day 1
    • Speed Dating – We needed to help our investors get really deep on the opportunities for both expansion and improvement, and we wanted to expose them to a larger number of our team members, so we created a 3 hour Speed Dating experience.  We had 6 stations, each staffed by 2-3 associates who took them deep on a particular part of the product or the go-to-market strategy around the product.  They had 20 minutes to listen, learn, take notes, and ask questions, and 10 minutes to transition.  In 3 hours, each investor had rotated through all 6 stations in an intimate setting, with the opportunity to directly observe our company and our product for all that was good (and not so good!).
    • Executive Dinner – We made sure that there was time for the investors to build relationships with the management team, and even kept it super healthy (salads and light fare).
    • Texas Hold’em Tournament – That evening, we put away the work stuff and had an all hands poker tournament.  It was a ton of fun to watch a total of ~35-40 engineers and investors, marketers and management, sales and client success all squaring off in a fun game of Texas Hold ‘Em!
  • Day 2
    • Executive Breakfast – This was a second opportunity to deepen executive and board level relationships.  We made it optional, but everyone showed up.  While the dinner the night before was more social, this was a little more structured around strategic conversation and digesting information learned during the Speed Dating sessions.
    • Board Meeting (No Updates…  All Strategy) – This was the big test. We purposefully built no board deck, which felt a little awkward, but it was really freeing.  We had data on hand that we could pop on the screen to answer certain questions, but largely, this was 4 hours of fantastic strategic conversation.  The strength of our investors and advisors really shined through during this session.  We had well connected, deeply educated and experienced people working side by side with us to solve problems and exploit opportunities.  It was quite an experience
    • Investor Panel – After the board meeting and lunch, we held another all hands session, this time in the format of a town hall / panel style interaction.  The investors (now all clad in Windsor Circle Green Pants!) sat up front, with the entire company in the room.  We instructed our company that no question was taboo, and likewise instructed our investors to pull no punches.  Openness and Transparency is a key value for Windsor Circle, so these instructions were well heeded and we had a fantastic and honest conversation as a cohesive team about what the market looked like, what opportunities and threats Windsor Circle has, and what lay ahead for us as we continue our very rapid growth as a company.
    • People Helping People – Opportunity to Pitch to Our Investors – We sought commitment from our investors in advance to spend time with fellow entrepreneurs in our ecosystem here in Durham.  We basically created the opportunity and then got out of the way, so our peers could have direct access to our investors to pitch.  We understand that this was well received by both sides!

One of the Best Board Meetings!

All of our investors reported back that this was one of the best board interactions they’d had in a long time.  Here’s a quick quote from one of our investors.  (Sidenote:  I share this quote not to be pretentious, but rather of evidence that this calculated risk regarding the extended meeting format met with the results we’d hoped for).


Good meetings on Wed & Thurs.  You are the first CEO, in my experience, to successfully pull off a separation of ops and strategy.  Other CEO’s & boards have recognized the value of doing it but most of the time the strategy session devolves into ops anyway, or the strategy is pushed to the end of the meeting and some of the folks have already left.”

If you’d like to download the board agenda for more specific details, click here.