Sneaky and Insightful Questions for the Boardroom, Retreats and for Generative Thinking

Sneaky and Insightful Boardroom Questions

By Carol Weisman, MSW, CSP

            A number of years ago I was facilitating a retreat with the psycho board from hell. They made the Taliban look like wimps. There were only 13 board members and 15 factions. I was called in to make them play nicely I was clueless how to do it. I was sitting at my desk an hour before the retreat with my head in my hands. Our daughter came in and asked what was wrong. I told her I had no idea what I was going to do. She patted me on the head and said that I would figure it out. Great, a 15-year-old had faith in me. I grabbed my brief case and headed out the door.

            Sure enough, she was right. Five blocks before I reached the retreat venue, I figured it out. We started with the question, “If an abused woman came to your agency for help, how should she expect to be treated.” The board spoke eloquently as I filled 12 pages of flip chart paper with words like “with respect, decency, with an eye towards education and as a child of God.” I then asked, “If a person joined your board, how should your new member expect to be treated?” An elderly gentleman with an accent that was a cross between Bugs Bunny and Henny Youngman accent exclaimed, “We’ve been twicked.”

            We then spent 5 hours talking about how the board could model in the board room the behavior they expected from the staff towards a client.

            I am leaving today to work with another troubled board. We will start with note cards. I will be asking them, “List 3 adjectives describing your organization.” I have a feeling the list won’t be pretty. After many hours of interviews, words like, “shaky, suspicious, unprofessional, unkind, malicious” might top the list. I will then ask them to list three adjectives reflecting how they would like their nonprofit to be described. Our discussion will revolve around how to get from point A to point B.

            Other questions to ask in your board room to get discussion going at your next retreat, generative discussion session or strategic planning meeting:

  1. List 5 reasons to put our organization in your will.
  2. List 5 reasons why someone wouldn’t want to be a donor. As a group, brainstorm how to overcome these objections.
  3. If a donor came to us today with $5 million (you pick the number) what would our first priority be? Our second? Our third?
  4.  If you had unlimited resources, what is the one thing you as a board member would like to do for the population we serve?
  5. Ask the staff to present a wish list from under a dollar to over a million.
  6. Ask the staff for a wish list of gifts of time from highly skilled labor ranging from “done in a day” tasks.
  7. What do we do better than any one else in our field?
  8. What program does another agency do better than we do?
  9. What do we do that is the hardest to fund?

10.  If our largest funder went away tomorrow, how would we make up the difference? (If you are getting more than 50% of your funds from one source, put this question at the top of the list)

11.  Have our clients changed in the last 10 years. If so, how have our services changed to meet those changes?

12.  If you can change one law to help our cause, what would it be?

13.  How has the digital age affected the way we do business? What could we do better and how can we get there?

14.  What 3 numbers best tell the story of what we do? i.e. one out of four girls is sexually abused by age 18, one out of 6 boys.

15.  If you are an agency that works to find a cure for disease, how would you like to celebrate a cure?

16.  Why did you join this board?

17.  If Bill Gates were sitting next to you on a plane and you had a chance to explain what we did, how would you pitch our program?

18.  How do you define “our community” when you talk about those we serve?

19.  How do you define “our community” when you talk about those we go to for funding?

20.  If you could swap jobs with a staff member for a day, what would you want to try and why?

21.  Is there anything you have always wanted to do on behalf of our organization and haven’t been asked? (Understand that you might still not be asked. For instance, if you are an opera company and would like to be asked to stand in for the lead, this still might not happen or if you are a hospital and you have no medical background, you still won’t be invited into the operating room to replace a surgeon.)

22.  If the President of the United States called and invited you to Washington to seek your advice on our issue, what would you tell him we must change and why?

23.  If money were no object, how would you spend the rest of your life?

24.  Knowing that we all die someday and that our eulogy will be written, what would you like to be said about your accomplishments as a member of this board?

25.  Is there a question you’ve always wanted to ask in a board meeting that you either thought you should already know the answer to, or was too complicated or too simple, please ask it now. It can pertain to our history, our future, our procedures or some odd combination of letters we use that everyone seems to understand.

26.  Using only one word, how would you describe your first impression of the name of our organization?

27.  Using only one word, how would you describe your first impression of the mission statement of our organization? Do you know the mission statement of our organization? Do you see it as only a legal description or as a marketing and fundraising tool?

28.  Boy’s Town was the subject of a movie many years ago with Bing Crosby. Who would you like to do a movie about your (change to our) organization and who would star it? Cast the board and the staff.

29.  What keeps the board leadership up at night when thinking about this organization?

30.  What keeps the staff up at night when thinking of this organization?

31.  Given that famous people can quickly become infamous people (think Tiger Woods, Martha Stewart and Ken Lay from Enron), who would you have as our spokesperson if you could have anyone?

32.  What’s the first thing that comes to mind when you think of a great evening out? What would you pay for it?

33.  Tell us about a work of art that has touched your life?

34.  What is the most recent compliment you have received that you smile about in private?

35.  What was the last time you wanted to let loose and go screaming into the night?

36.  What childhood dream has come true for you? Who, if anyone, helped make that happen?

37.  What lasting lesson have you learned from working with our organization or in relation to our mission?

38.  What one new thing have you learned in the last week?

39.  Nietzsche said, “That which will not kill you will make you strong.” What have you done that has made you strong and what has made this organization strong? What is the most entrepreneurial thing you’ve ever done? Would you take a similar risk as a board member for this organization? If so, why? If not, why not?

40.  If you were to start this organization all over again, what would you do differently?

41.  You’ve got a call from the Rose Bowl Parade to design a float for the parade to represent the work you do at our nonprofit. What would be the theme and how would you represent it to the millions watching as you pass by? What music would be playing? Who would be on your float?

42.  If there was one question that never really gets asked that you would like an honest answer to with no recriminations, what would it be?

43.  What does “success” mean to you in terms of your work as a board member?

44.  How can you determine if our organization as a whole is successful?

45.  What is the best way to inspire board members? (see last month’s ezine)

46.  What is the best way to inspire staff?

47.   What is one thing you know for sure about our mission?

48.  When would it be appropriate for the staff to call you in the middle of the night?

49.  What scares you most about the future of our organization?

50.  Is there anything that makes you cry when you think of our organization?

51.  Why are you here?

52.  What would you like to accomplish in the next 12 months as a board member/staff members/volunteer of our organization?

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6 Comments »

  1. This is great and will be used at our next retreat. Thanks, Carol!

  2. Susie Minx said

    This is a great list – a little intimidating, but still a great list

  3. Carol said

    GREAT!!!

  4. Patricia Cox said

    Wonderful list that I will use for my upcoming board planning retreat. Thank you!

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