Notes on Corporate Retreats for Startups

Earlier this month I had the opportunity to attend a corporate retreat for a large startup that’s now fully remote. As part of spending a couple hours at the multi-day event, I asked general questions about the retreat to a variety of team members from the frontlines to senior executives. Primarily, my questions where ones like what did you like, what didn’t you like, and what would you change.

Now, this was a big event with several hundred employees. The format was roughly two days of speakers ranging from company leadership to hired experts on topics like personal productivity. After the main event for all employees, some departments and teams stayed an extra day for more specific workshops and working sessions. Counting the time to fly in ahead of the first day and fly out after the third day, it was a full four day commitment for a huge number of people.

Here are some of the notes I took after talking to several people:

• Multiple, interesting venues – The two main days were held at different locations with one being a stadium and one being a local theater. Employees enjoyed having different venues and getting a feel for two of the most iconic places in town. Without question, the theater was considered the better venue for acoustics as a large stadium usually isn’t ideal for sound quality.
• Mix of corporate topics and “fun” topics – Team members liked how the company invested in great outside speakers and mixed them in with presentations on the roadmap, fireside chats, and general corporate topics. Quality speakers cost extra, but are well worth it if financially feasible.
• Becoming an event planner / travel agent – Senior execs I talked to were emphatic that it took way more time and energy to plan and coordinate the event. One likened it to the effort to organize and run a giant wedding. From travel to hotel to food to venues to speakers, it was the equivalent work of multiple full-time people for the months prior to make it all happen.
• Face-to-face is incredibly valuable – Without prompting, the first response from everyone was how great it was to see co-workers in person and build deeper relationships. Of course, there were some comments about how it’s natural to build up a more complete image of someone where you’ve only seen their head on a screen only to find out people were taller or shorter than expected, different mannerisms, and other characteristics you wouldn’t know without human interaction.
• Ad-hoc questions and side-bar conversations – The last item I heard was around the value of ad-hoc questions and side-bar conversations. So often, typical meetings, chat rooms, and email exchanges have a specific focus or agenda. Hanging out at a multi-day event inevitably has downtime that leads to talking about so much more than the standard topics. There’s tremendous value here that’s hard to quantify.

With huge numbers of startups now remote or hybrid, the growth in corporate retreats is exceptional. Look for many more best practices and resources to emerge as this area of the startup world grows.

What else? What are your favorite best practices for corporate retreats?