January 27, 2023

How to Have a Difficult Conversation with Your Board Chair

Working with a nonprofit board chair can be an excellent, growth-filled partnership—or not.

Even great board chair and CEO relationships have pinch points. Not-so-great nonprofit board chairs and CEO relationships have more. Pinch points are opportunities to explore trust and get laser clear on the relationship.

Running a nonprofit is a complex undertaking. Board chairs and executive directors need to discuss tricky issues. These difficult conversations between CEOs and board chairs can be launchpads for greater trust and impact.

However, for the nonprofit CEO, difficult conversations with board chairs always carry risks. The board is your boss, and the board chair leads the board.

How can you master difficult conversations with your nonprofit board chair? This video guides you.


Chapters of How to Have a Difficult Conversation with Your Board Chair


Pinch Points and the Board Chair Problem

Working with your board chair can be a wonderful, enriching partnership. But even in the best of relationships and, maybe especially in the best of relationships, there are pinch points. There are places where it’s awkward, and you have conversations that you need to have that you’d probably rather not have.

But to grow the relationship, to make things right with you, there are words you need to say. But with your board chair, it’s especially awkward. Why is it so tricky? Because the board is your boss. And the board chair leads the board. Therefore it’s always higher risk to endeavor to have real heart-to-heart truth-telling conversations. How can you do this? And how can you do it well in a way that enhances that relationship?



Why Getting this Right Matters

Let’s approach it with five different steps. Why does this matter? Because a thoughtful approach will lead you to be able to measure what you do and to look at how you can build this skill. Because you’re going to have difficult conversations (I’m sorry) for the rest of your working life, if not your whole life.



What You Want

Number 1 is to decide what it is you want. Hear this. You’re not getting what you want. What is what you want? Is what you want. What does success look like? Does it mean shorter meetings? Does it mean less like putting me in the hot seat? Does it mean less solution-giving? Whatever that is, you want to be able to articulate exactly what success looks like. And where you hope and want to go with your conversation. What you want should be measurable, reasonable, and clear. Anyone else on the outside world could say, “Yeah, I get it. I see what you want.”



The Stories We Tell

The second step of preparing for tricky conversations is to get your head clear. This is the most emotionally complex because we tell ourselves stories, and we need to have those stories stop or at least be identifying that our story, our interpretation of reality. So, Byron Katie has four wonderful questions that she asks, and I have used in my work and my highlight and find them really helpful to get my head clear about what’s really going on, at least for me emotionally.

The first question: Is it true? You say yes or no.

The second question says, is it really –absolutely sure it’s true? And really, we cannot know why someone did something or their intent.

The third question is, what happens when you believe this story or the thought that you’ve been telling yourself? I feel fearful. I worry about my job. I get anxious. I get angry, or whatever those things are, those are the reactions you have to the thinking you’re doing.

Finally, who would you be, and even better, what would happen in your organization without that thought? What would free up? What would change, and what if the opposite was even true?




Get Ready

It’s time to actually do some planning for the conversation. The first piece of this planning portion you want to do is to get the facts out. What was it that happened? On this date, you said this. I said that. This is what I want to talk about. I looked at my whiteout. I saved this whiteout just to cancel and reschedule our meetings, and I’ve used it all up. These are factual, observable behaviors –like a videotape was watching it. And your emotion is out of it, but you’re going to talk about what actually happened. Just the facts, ma’am.

Secondly, the part of this is to think about what’s in it for your board chair. This could be very basic, like—“Hey, we’ll get it done. We’ll get it done first thing in the week, and it’ll be over with and I will not bother you again unless there’s an emergency. Or number 2, “You know when we’re having this conversation, you know I get kind of quiet? I’m sure you’re wondering what the heck’s going on with me. And you’re like; I have to be so careful with this person. She’s on eggshells whenever I give solutions. We can do better than that. I can make that feeling go away.”

The plan, then, is what actually happened because you’re going to share that and then why it might be in their interest to come along and change the behavior in the direction you want.



Let’s Do This

The next step is actually having the conversation. It’s getting it on the agenda. It’s starting with the facts because that was happened to both of you, and you can agree on that. Sometimes at that point, it’s helpful, depends on your relationship, to state the risk. “I am concerned about bringing this to you because I know that the board is my boss, and therefore, I’m afraid of that… that this will be a problem for me .”

Whether you decide to talk about the risk or just share the experiences and some of your reactions, why you might have been unhappy or upset about that, the next step is always to listen.

What happened for them. How do they experience that?

Then it’s time to look for solutions. What are the options? How can we go forward and do better in the future? How can we avoid this? This might be a time for a new ground rule that you set. I will always let you know within 48 hours if I hear from you or don’t hear from you, then I’m making a decision. Whatever it is, you should be able to find some common ground in a way that you can move forward together.



Yes, It’s Over. Not Done

The final step is to evaluate how it went. Both in terms of the content the conversation as well as how the process worked for you. What steps were really useful? What did you do really well? How can you build on that?

Doing some evaluation will allow you to focus and center in and reinforce what you did well so that you can repeat it and strengthen other relationships that are important to you.



Pinch Point Conversation Skills

I’m Karen Eber Davis, and if you would like some help building this skill or other work with your board, please don’t hesitate to reach out to me. I’d love to see you get what you need and want for you and your nonprofit.


Music Credit: Bensound.com/free-music-for-videos

Karen Eber Davis

Karen Eber Davis provides customized advising and coaching around nonprofit strategy and board development. People leaders hire her to bring clarity to sticky situations, break through barriers that seem insurmountable, and align people for better futures. She is the author of 7 Nonprofit Income Streams and Let's Raise Nonprofit Millions Together.


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