Tool F
Conversation Guide
This is mutual diligence. You are testing whether they can govern, and they are testing whether this is worth their name. A prospect who asks you nothing is telling you something.
Testing for engagement
- Tell me about a commitment you made in the last two years that turned out to be harder than expected. What did you do?
- What else are you giving time to right now, and honestly, where would this sit in that order?
- When you have served on a board or committee before, what did you actually do between meetings?
Testing for governance understanding
- In your own words, where is the line between governing this organization and managing it?
- Describe a time you disagreed with an executive you also liked. How did that go?
- What would you want to see in a board packet to feel prepared to vote?
Testing for capacity: time, energy, capital
- Roughly how many hours a month feels sustainable for you, in a busy season and not just a good one?
- Board members here make a personally meaningful annual gift and help secure resources. How does that land with you?
- Which is easier for you, giving money, opening doors, or doing work? There is no wrong answer, and I would rather know now.
Testing for independence
- If the board needed to evaluate me honestly, could you participate in that conversation without discomfort changing your answer?
- What is your relationship to the other people already involved here?
- How do you handle a conflict of interest when the conflict is social rather than financial?
Testing for community standing and reach
- Who in this issue area would take your call this week?
- What is your own experience with the community or issue we serve?
- Where do you think the ecosystem around this issue is getting it wrong?
Questions they should be asking you
Offer these out loud if the prospect does not raise them. A board member who joins without asking these will not challenge you later either.
- What is the business model, and how does this get paid for in three years?
- What does the board actually decide here, and what does staff decide?
- What is the hardest thing about this organization right now?
- What happened with the last board member who left, and why?
- How will you use me, specifically, and what would make this a waste of my time?
- What is your relationship with the current board like when you disagree?
Draft for your judgment. Use these as prompts, not a script. The best recruiting conversations sound like two experienced people thinking out loud about an organization they both care about.