One question I get when talking about weekly tactical meetings is how we deal with the fact we don’t discuss items that will take longer than 15 minutes. The weekly tactical is designed to review our weekly KPIs and talk through any items that come from the ad hoc agenda. When a more strategic topic comes up, and requires additional time for discussion, it gets put on the parking lot (a Google Sheet) for the monthly strategy session.
Monthly strategy sessions can be anywhere from one to four hours. Once Pardot hit super high growth mode, we’d have a nice dinner once a month that was our monthly strategic meeting. Format wise, we’d keep it simple and semi-structured:
- Exercise for team members to get to know each other better (e.g. where were you born, how many siblings do you have, what’s one memory from your childhood, etc.)
- For each department, what’s working well and what’s not working well
- Parking lot items
- What are the three most important things we need to do as a company in the next 30-90 days
Monthly strategy sessions are a key part of high growth organizations for aligning the executive team and debating critical topics. Entrepreneurs would do well to incorporate monthly strategy sessions into their rhythm.
What else? What are some other thoughts on monthly strategy sessions?
David Cummings on Startups 
Hi David,
I don’t have a comment on this particular topic at the moment, but I just wanted to say thank you for all of your great insight. You are awesome.
I find my partner and I often talking about many of these topics, only to have you send out a post at night bringing clarity to the very same topics, and in greater detail.
Please continue to write, you are helping entrepreneurs everywhere.