Here's the top-line:
1. What is one “tough” conversation that you’ve been avoiding with a colleague, friend, teammate, leader, and/or community member?
Why? What’s holding you back from having this necessary chat? Or are you just avoiding conflict while everyone pays for the avoidance? Most leaders know — all too well — the cost of not having tough conversations sooner.
2. What is one anxiety or insecurity that you need to share that you’ve kept to yourself?
Who needs to know what you know? What is holding you back from staying mentally fit and healthy? What data is missing (if any) that will help you get more comfortable with sharing?
3. What are you not proud of right now inside your team, your project, your community and/or the culture that you’ve intentionally designed and built?
What needs to change? The beautiful thing about this question is that everyone immediately has a thought (or two) but very few people ever share these thoughts publicly!
4. What documentation (e.g. culture docs, community processes, operational workflows, etc.) needs to be updated?
Remember, a strong team, organization, and community has a strong culture around documentation and keeping it updated!
5. What cultural debt have you accrued in the last week that needs to be addressed?
Another way of asking this: What cultural belief and/or community behavior needs to be addressed, refined, and/or changed? An even more specific way of asking this question: Is there any belief (or value) that we preach but do not actually practice? Address this immediately.