The Board Question Most CEOs Can't Answer on the Spot

The message usually lands late at night a few days before the board meeting. "Can you pull together something that more clearly shows how our work is tying back to the strategic plan?"

If you lead communications at a foundation, you know that message. You know the chaotic days that follow it, too: numbers requested from five departments and delivered in five formats, a deck assembled after hours, stories chosen to stand in for the data nobody can find. You do gymnastics to make disconnected activities sound like they all roll up to the strategy.

But let's be real about what that scramble really is. You are being asked to create, practically overnight, a narrative that connects the strategy to the organization’s day-to-day operations when that connection has never existed.

You're not the only one. When we interviewed senior communications and marketing leaders at community foundations across the country this spring, we asked whether their organizations could show, on demand, how the year's work was advancing the plan. The honest answer was almost always “no.” Not in any centralized, ready-to-go way. They could tell beautiful stories, but the connecting tissue of a cohesive narrative and relevant data to support it would take days, several people, and advance warning that the question was coming.

Now consider the person that scramble ultimately serves. Somewhere above you, a CEO is carrying a question into the boardroom: "How is this year's work advancing our plan?" Board chairs ask it in plain words, at unplanned moments, as they should. 

When the question comes, it isn't the communications director on the spot. It's the CEO, with the whole table watching. That's where this discomfort actually lives — at the top. The scramble before the meeting is just a symptom of the problem the CEO owns.

This is not a memory problem, a competence problem, or a courage problem at any level. It’s an operational problem. Boards can’t have meaningful strategic discussions when the organization hasn’t created a coherent, accessible way to demonstrate strategic progress.

In most organizations, the board’s strategy-update agenda item defaults to conversations around financials and outputs: not because they matter most, but because that’s the only information available on demand. Try to dig deeper, and the picture becomes hazy. The measures live in five systems, tended by five departments, and the dashboard is perpetually "in progress."  

One board chair, we were told, wanted to see the needle moving, not to hear that internal capacity was being built. And one leader asked the salient question: "Where did we land the plane?" Strategic planning in our field takes off with great ceremony. It rarely lands anywhere in particular.

The chair's question about how the work is advancing the plan comes in plain English, and the answer will only survive scrutiny if it’s specific: Which measurable objectives moved this quarter, and by how much? 

You can't assemble an answer like that the night before. It has to be designed into the year itself: choosing a handful of priorities, which means explicitly stopping some work; every department knowing which objective its work serves; and developing a rhythm where the question gets asked — and answered — internally each quarter, so the boardroom is never the first place it's asked out loud.

It's worth building that connection between activities and strategic priorities. A CEO who can easily explain how the day-to-day work is advancing the plan changes the posture of the whole organization: Staff see the line between their Tuesday work and the organization’s mission, and the chair walks out an advocate. When the challenging year comes, as it always does, that answer is what tells everyone what to strike and what to protect.

And the last-minute scramble ends. 

If you're not the one who answers to the board, you know who is. And you know the next late-night text is already on its way. Imagine the difference it would make — for you, for your team, for your organization — if you collaborate with that person to start the conversation about connecting the work to the strategy before the scramble does it for you.