Getting Value from Board Discussions: A Few Hard-Earned Learnings and Observations

Lately, a few coaching clients have come into sessions feeling frustrated with how their board meetings are going. These are experienced, thoughtful CEOs—but they’re running into a recurring challenge: their boards often seem a step behind the management team in how they’re thinking about the business.

Despite everyone’s best intentions, board members are frequently surprised by information the CEO assumed was already well understood. Too much valuable meeting time ends up being spent re-explaining context. I’ve heard some version of, “We’ve talked about this before, but the board is reacting like it’s brand new,” more than a few times recently.

To be clear, these aren’t disengaged boards. They’re composed of capable, well-prepared people who care deeply about the organization’s success. They are fully committed to supporting the CEO and adding value. And yet, frustration builds.

I’ve been on both sides of this dynamic—as a CEO and as a board member—and I shudder to think what grade my past colleagues would give me in either role. So I offer these thoughts not as an expert, but as a fellow “sinner”—someone who’s had the good fortune to work with many organizations over the years, and now, as a coach, gets to observe a wide range of talented leaders in action.

Here are a few things I’ve seen that seem to make a real difference:

Good Board Discussions Start with Good Management Team Discussions

CEOs who work most effectively with their boards almost always begin by establishing a strong strategic rhythm with their management teams. They create regular space for conversations that go beyond day-to-day execution and into what’s next.

Some practical elements of that process include:

• A quarterly review of progress against strategic objectives, anchored by three distinct conversations:

  • The “On the balcony” conversation - Where are we seeing progress? What’s harder than we thought? What are we learning?

  • The “Let’s look ahead” conversation - What issues or opportunities might emerge in the next 6–12–18 months?

  • The “Does this need to come to the board?” conversation - If yes, when? In what form? What do we want to get from engaging the board on this? Will it require a decision, or is it something they can help us think through?

This kind of regular “strategy cadence” helps teams anticipate issues, sequence board communication more effectively, and stay clear on the purpose of each board discussion.

A Few Tools to Tee Up Better Board Conversations

In addition to internal management rhythm, I’ve seen a few simple tools—used consistently and with intention—that really help.

Board Calendar

When I was in management, I didn’t fully appreciate the value of a board calendar. But once I became a board chair, I saw how useful it can be.

A good calendar process:

• Covers the board’s regular business (budget, audit, reviews, etc.), giving management a clear runway to prepare.

• Acts as a working tool—especially when tied to quarterly strategy reviews—to schedule strategic discussions and flag in advance the materials and context needed.

Board Dashboard

A one- or two-page snapshot of key business data, shared consistently, strengthens the connection between management and the board.

A good dashboard:

• Includes leading indicators, not just lagging ones.

• Can be shared more frequently (e.g., monthly), giving board members a sense of real-time trends.

• Helps surface questions or blind spots that might otherwise be missed.

“Top-of-Mind” CEO Discussion

This doesn’t need to be formal—in fact, the best versions often aren’t. Just carve out a few minutes at each meeting for the CEO to share:

• What you’re wrestling with

• What might become important

• What’s keeping you up at night

In my experience, the most effective CEOs bring their boards into their thinking earlier—especially when things aren’t fully baked. It’s remarkable how often a group of seasoned leaders can help accelerate clarity simply by listening and asking the right questions.

That’s it- a few things I’ve observed, and a few I wish I’d done better when I was in the seat myself. If you’ve seen other ways boards and CEOs can work more effectively together, I’d love to hear about them.

When done well, coaching gives executive leaders a place to unpack challenges like these—with space to explore alternatives and a trusted partner to test ideas. If you think you’re at a point where coaching might be valuable—whether you’re new to your role or preparing to take the next step—let’s talk.

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