Sessions I like

Breaks!

I basically never schedule enough breaks. Retreats can be intense, people might be jetlagged. Breaks can help people rest to be ready for sessions. And they can also give people time to chat with colleagues, strengthening relationships and throwing up important discussions that you didn’t think to schedule.

First session: Founding story, vision, and mission (~30m-1h)

You can’t do this enough!

Primarily the CEO, but also other co-founders / long-term staff.

Some possible things to cover:

• What’s your founding story, what’s the breathless history of your organization?
• How did you notice the gap? Why did you do what you did?
• Why does your organization exist?
• What’s the overall goal for the org, in detail? If you succeed, what will be different about the world?

When you’re preparing for this, I think it’s really important to slow down, reflect, try to listen to your emotions and your body, and find answers to these questions that you resonate with emotionally. If you really feel why this matters, you’ll do a much better job of getting others to feel it matters.

If you have a bit more time, I think that it can be great to also prompt everyone on the team to reflect for a few minutes on why they decided to join the org, and what motivates them to stay, and share that back.

Feedback session (1.5h)

How?

• Before the session, ask everyone to do a brief (~1 page) self review (strengths, weaknesses, development focuses). This can be very rough — bulletpoints — and can be copied from previous performance / self reviews / 360s.
• At the start, explain how the session will work. Emphasize particularly that this is going to be a quick-fire session, and that people should cut hedging and caveats. Everything is being shared with a spirit of “I don’t know, but maybe…X”
• 3 minute timer, where everyone writes: What feedback do you want? Any particular focus areas?
• Set a 5 minute timer. Each person goes to one other person’s self review and begins to comment on and add to it.
• Focus on things you haven’t said before, don’t hedge too much. All of this is with a spirit of “I don’t know, but maybe…X”
• Do this in suggest edits so you can see who said what
• Repeat the above 5-7x times, with people gradually working down the list of people that they work most closely with
• 3 minute timer for everyone to reflect on the prompt: Why didn’t you share this feedback earlier?
• Ok, you didn’t think of it, you didn’t have time. But how could we get to a point where, as soon as it could possibly have been shared, it was?
• ~15 minutes for people to read and reflect on their own feedback.
• Read your feedback
• What strengths do you want to lean into?
• What do you want to change?
• Everyone presents back: 1-2 takeaways

After: schedule a cosy / positive team bonding activity (e.g. dinner) to reinforce positives!

Ask [Org] Anything (~1.5h)

Anyone can ask anyone anything.

This is useful for:

• Clearing up confusions and concerns that people have
• It’s easy to underestimate all the things that you (as manager/CEO) have context on but others don’t understand!
• Build trust with the team by holding leadership to account.
• In particular, there’s something powerful about staff members knowing that they can ask anything, and that it will get addressed in front of the whole team.

How?

1. Before the session, have a form with option for anonymous submissions. Ideally share this a day or two before the session, and also set aside 30m-1h for people to write up questions.
2. Ask a non-leadership person read and collate the questions into groups (but without editing anything).
1. If you / other leadership team members want to see the Qs beforehand to prepare that’s fine. But don’t cut / dodge any questions.
3. Have (the same) non-leadership person read the questions out loud. The CEO will decide who should answer the question — often it’ll be the CEO, but sometimes whoever owns the relevant area.
1. You can say “I’m afraid I can’t say more about that because …” or simply “I’m afraid I can’t answer that” or similar if there are good reasons not to answer. People will understand! But make sure there’s actually a good reason, and you don’t overuse this.
4. Keep going until you run out of either time or questions.
5. If you run out of time, try to (briefly) address the remaining questions later, either in writing or in an optional follow-on call (can be after the retreat). By answering all the questions you make clear that you’re not dodging any.