Weekly/Monthly Exec Team Dinners

In the most recent episode of Acquired, Ben Gilbert and David Rosenthal interview Howard Schultz, the founder of Starbucks. It’s an excellent, wide-ranging show with many incredible takeaways. One anecdote that stood out occurs at the 57-minute mark when Ben and David ask Howard about his two key leaders. Howard shares that every single Monday night for ten straight years, the three of them had dinner together. 

There’s so much power in the value of long conversations about what’s going on, what’s working well, and what’s not. This allows for alignment, the ability to disagree and commit, and a general mind meld among founders. Much of this happens organically, especially in the earliest days when everyone is in the same office together, checking in daily through stand-ups and regular meetings. However, as the business grows, it becomes harder and harder due to more requests for your time, more travel, more issues, and more team members. These increased demands on the founding team make it even more valuable to have a regular, unscripted, long chunk of time to get together without the distractions of the office and day-to-day tasks.

At Pardot, we did this for many years as our monthly strategy dinner. On the first Wednesday of every month, the leadership team would get together for a 3+ hour dinner. During dinner, we would go over anything and everything, focusing primarily on the harder, more strategic topics that needed more time to flesh out. Regular tactical items were addressed in our daily and weekly meetings. Anytime we had an issue that was too large or strategic but not urgent, we would put it in a Google Doc and then address whatever was in the Google Doc at the monthly strategy dinner.

At SalesLoft, a few years in, as the business was scaling, we did the same thing—a monthly strategy dinner with the executive team where we hashed out the most important topics. I vividly remember sitting at Maggiano’s, debating substantial pricing and packaging changes to the software, and dealing with so much complexity, edge cases, and customer anecdotes. Having these intense conversations helped everyone be heard, but more importantly, it helped us arrive at the best decision. We were much better off as a company and organization with these monthly strategic dinners.

My recommendation to entrepreneurs is to establish a regular dinner or offsite with the exec team where parking lot items and big topics are debated. This isn’t an exercise in consensus building; it is an exercise in laying everything out, making sure everyone’s heard, and having a leader make a decision.