12 questions to ask before any executive retreat.

A retreat fails or succeeds before anyone books a flight. Answer these twelve questions first, and you'll have done the hardest part: defining the function the retreat exists to serve. The format — location, activities, agenda — should be designed around your answers, never the reverse.

Use this as a working checklist before you brief any facilitator (including us). Bring it to your leadership team and answer it honestly together — the conversation itself is worth the hour.

Outcomes

1. 1If you could accomplish only one thing, what would make the whole retreat worthwhile?
2. 2What should people be feeling, thinking, and saying to one another differently afterward?
3. 3Why can't you achieve this in the normal course of business — what's actually in the way?

The team & the organization

1. 4What is the biggest challenge — or opportunity — facing the team right now?
2. 5What are the team's real strengths, and where does it quietly struggle?
3. 6Are there specific dynamics or relationships we should handle with care?

Preferences & constraints

1. 7How comfortable is the group stepping outside its comfort zone — and where's the line?
2. 8Any hard constraints — physical limits, dietary needs, places or activities that are off the table?
3. 9What does this team find genuinely engaging — and what makes them check out?

Follow-up & measurement

1. 10How will the learning be carried back into the day-to-day — by whom, starting when?
2. 11How will you measure whether it worked — and when will you check?
3. 12What kind of reinforcement or support would help the change actually hold?