10 Tough Questions Every Board Member Should Ask

by Joan Garry

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Our Board Treasurer and Director of Finance were presenting our $5mm budget and back then (late 90s) there was always a conversation about the cost/benefit of direct mail.

Fair enough. After all, snail mail can cost a lot to send and the direct return is not often that great.

But then a board member brought up that “piercingly strategic” question. Yes, that’s sarcasm.

“So what is the cost of a first class stamp?”

We have a $5mm budget and this board member’s primary concern is the cost of a first class stamp? Talk about tripping over pennies on your way to dollars.

Two big takeaways from this story…

  1. Board members should ask questions.
  2. Board members should not ask every question.

So I thought I’d offer ten suggestions about the kinds of questions they should ask.


In this list, there is not a single softball question. And some of these questions may get the Executive Director’s hackles up.

Whatever hackles are.


You might believe your board members don’t understand the work as well as you do. And you may be correct.

But there’s a negative consequence to this belief. You approach board meetings like it’s “show and tell”. No time for questions. Or you discount their questions because you feel they’re not well informed.

That’s a mistake. Why?

A board that asks challenging and provocative questions…

  • is well informed.
  • is engaged.
  • raises your level of play.
  • sees things you miss.
  • sees around corners and helps you avoid trouble.

Plus, their questions can lead to a discussion of what is possible rather than simply what “is”.

I believe that a thriving nonprofit is like a twin engine jet. A high performing board should see themselves in the list of roles above.


1. How are we measuring our success?

Monitoring the success of programs against the mission is a key responsibility and boards don’t push enough on this. Many Executive Directors talk about how hard it is and will default to lots of anecdotes.

Program evaluation doesn’t have to be hard. Sometimes it can be as simple as pre and post surveys. But E.D’s don’t prioritize this enough and boards have a definite role in introducing more accountability.

2. What is the plan for revenue diversification and how can we be a part of the solution?

Too many nonprofits live or die by special events, and it’s time for board members to start weaning organizations off of gala/ticketed event revenue.

And remember, pushing the org will demand that board members stretch too. Board members love to sell tickets to events while asking for direct gifts is more of a challenge. Maybe invest in board members as ambassadors and storytellers or invest in a part-time grant writer. Everyone will have to move a bit out of their comfort zones but a diverse revenue stream is key to a thriving nonprofit.

3. If we got a huge bequest, what would we do with it?

It’s long overdue for nonprofits to think about what is possible – to come from a place of abundance rather than scarcity. I want board members to challenge staff leaders to think big and I want staff leaders to be receptive to this kind of conversation – to embrace it. An Executive Director may be frustrated that your board is not engaged but please be open to the possibility that the conversation may in fact ignite your board in a new way.

4. When is your next vacation planned?

The reason this is a tough question is that Executive Directors have a hard time letting go – and so it can be tough to get a staff leader to commit to a break. I believe board members have to challenge and push E.D’s to take real time (more than a week) and to really detach. It’s important for the E.D. and for the board to see what we call “bench strength” – who will step in and keep things moving.

5. Can you prepare a detailed succession plan?

Ask your E.D. to take this seriously and craft a full on succession plan. Not just “what do we do in the short term if the E.D. is hit by a bus?” Have the E.D. document items like 1) internal candidates (yes or no and why?), 2) search firms and why 3) what to look for in a replacement 4) external folks who should in fact be considered and 5) a communications plan that can be executed quickly. This is just for starters.

6. Tell us about your staff – your rock stars, the challenges, and the emerging leaders.

Board members should understand the E.D. as a manager, how they read their staff members and what the bench strength looks like. Board members who run companies and manage staff will have so much to offer – insights, possibly pro bono professional development. Some E.Ds might push back that this is their purview but the work takes a team and the board (the owners?) absolutely need to know about the strength of the team.

7. What other organizations do our donors support?

Several reasons this is important – Board members need to understand the other organizations in the sector “orchestra” and how your organization distinguishes itself. Also, board members really need to understand the sector and a deeper knowledge of other organizations offers that perspective.

8. What do you see as the biggest challenge the org faces? What keeps you up at night?

As I mentioned earlier, staff leaders often take a “show and tell” approach with their boards – and try to only share the good news. They must be pushed to speak to the big threats so that you all can problem solve together. The board must frame this question with a spirit that reminds the E.D. that the board must and will be part of the solution but can only do so if they understand the threat.

9. How is staff morale? Do they feel overworked?

Boards often focus only on the E.D. rather than asking different kinds of questions to understand how intense the work is for the full staff. A thoughtful conversation about this can preempt attrition. The group (staff and board) can develop creative retention strategies. If the E.D. can avoid being defensive, there are great ideas that can come from such critical conversations.

10. What is your career trajectory? How long will you be with us?

I ask board chairs how long their E.D. plans to stay. Usually I get a shrug. “I haven’t asked.”

Are they worried that asking the question will incentivize their E.D. to leave sooner?

The organization needs strong leadership and solid transitions. Sometimes I think boards avoid the conversations in the hopes that the E.D. will not ever leave. That is not how it works.


OK, so I’ve given you 10 good questions to ask. Grown up questions that prompt important conversations. Questions that tie to the important responsibilities that board members have. Questions that are in the best interest of the long term sustainability of the organization.

Executive directors: listen up and be receptive to these questions and what they are really about.

Board members: You have an important job. These questions tie to the important responsibilities that you have.

Try some of these questions on and let me know in the comments below how it goes. And I’m very happy to entertain ideas for other questions to add to the list.

Please share!

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