This weekend we held Founders annual offsite. When planning for it, different people made me realise that we had probably underplanned it. "Sounds great", they said as they were telling me about offsites that turn out to be a little more than a long long meeting in a location far from the office. But I started to have my doubts.
In our busy business life there is a clear bias for efficiency. We want everything to run smoothly, we want to be doers and we want to use every single minute in the most optimised way. Going the opposite direction feels sloppy and it is difficult to kick away that guilty feeling. Then, as the first day unfolds, you start to see the magic happening. People that would normally barely have time for a quick "good morning" getting together and engaging in deep conversations, lots of side discussions getting to the bottom of past situations not properly closed, plans being made, ambitions being shared.
I think now that feeling comfortable with unplanned time takes courage and experience. Falling back to filling every moment with an agenda item is the easy thing. Controlling for efficiency can guarantee a safe outcome, but it will never be like optimising for serendipity. It's like engaging in a long dialogue and feeling comfortable with keeping silent. Try it.