The power of asking the right questions—especially in board meetings—is often underestimated. Yet, mastering this skill can dramatically enhance your board’s effectiveness.

Too often, questions are misused as tools for blame or as thinly veiled statements. For example, “Why is this behind schedule?” really means “This is behind schedule, and it’s your fault.” Or, “Why can’t your team get this right?” translates to “Your team isn’t capable.”

But the true purpose of a question is to spark curiosity, encourage exploration, and open the door to possibilities. The best questions inspire “What if?” and “How else?”—driving deeper insights and better decision-making.

Start asking these critical questions and see the difference in your board’s effectiveness.

The first and most important set of questions to ask are: What’s going well? What’s not? And what actions do we need to take to improve?  

A well-crafted question can unlock valuable insights, spark creativity, and foster a strategic culture in the boardroom. One of the most effective questions you can ask follows a simple three-part structure. Each part serves a distinct purpose.

The first question, “What’s working here?”, encourages participants to recognize and articulate what is going well with a particular issue or project. This positive framing sets the stage for a constructive discussion.

The second question, “What’s not working?”, shifts the focus to areas that need improvement—but with curiosity rather than blame. By inviting input from all board members and staff, it ensures a more comprehensive analysis rather than relying on a single perspective.

The final question, “What do we need to do about it?”, encourages diverse viewpoints on possible solutions. Instead of narrowing the discussion to one predetermined fix, this approach invites creativity and opens the door to multiple strategic options.

Another important question a board should ask—especially after a complex discussion or major decision—is, “What are we missing?”

This simple yet powerful question can reveal hidden opportunities, potential risks, or critical perspectives that could shape the organization’s strategy and decision-making.

This question serves two key purposes:

It allows the group to reaffirm their choices, ensuring that nothing critical has been overlooked.

It creates space for new insights—inviting participants to identify any gaps in the discussion that may have gone unnoticed.

This question is particularly effective at the end of a strategic planning retreat or strategic plan review, where reflection can strengthen alignment and reinforce a shared sense of purpose.

The key is to ask it with genuine curiosity, not as a way to imply that others have missed something only you can see. When approached with openness rather than criticism, this question fosters deeper thinking, strengthens group confidence, and ensures that decisions are as robust as possible.

The next important question to ask is “How does this help deliver against our vision, and how can we align it more closely?”

This question is one of the most powerful strategic filters a board can use. Your organization's vision statement isn’t just words on a page—it defines the impact you aim to have on the communities you serve. Every board discussion and decision should be evaluated through this lens.

This question serves a dual purpose. It encourages broad discussion while keeping the focus on what truly matters; ensuring that every choice, initiative, or strategy actively contributes to the organization's overarching vision. By continuously assessing alignment, your board can refine options, make more purposeful decisions, and drive meaningful impact.

When you're feeling unsure about what to ask, a simple yet powerful approach is to pose the question, “What questions should we be asking?” This not only helps refocus the conversation but also brings clarity to key issues and encourages meaningful discussions.

Similarly, when a discussion becomes confused, unclear, or loses direction, this question serves as an effective tool to regain focus, ensuring that the conversation stays productive and purposeful.

This simple yet powerful question serves as a reset button, helping directors break through confusion, refocus, and approach the discussion from a fresh perspective. It’s particularly useful when no one is quite sure what to ask next.

Variations of this question can further refine its impact:

“What questions should we be asking to view this differently?”

“What questions should we be asking to bring more clarity?”

By shifting the focus back to inquiry rather than assumption, this approach helps reframe the discussion, steering it away from personal agendas, hidden biases, or unproductive debate. Instead, it opens the door to deeper insights, better decision-making, and a more constructive dialogue.

To unlock fresh perspectives, ask: If we couldn’t do it this way, how else might we do it?

One of the biggest barriers to innovation and strategic thinking is the belief that something is already working perfectly. Just as assuming something is wrong can limit perspective, assuming something is right can create blind spots; preventing new opportunities from being explored. 

To shift your perspective and explore new possibilities, also try asking: “If we couldn’t do it this way, how else might we do it?”

This question encourages fresh thinking at both the board and staff levels. It opens the door to innovative solutions, alternative approaches, and even new revenue streams that may have been overlooked. By challenging the status quo, organizations can uncover creative possibilities and stay ahead in an ever-changing landscape.

What are the Yes Buts?

In any discussion, especially when exploring new ideas or considering alternative options, there’s often an unspoken hesitation—the “Yes, but…” that lingers in the back of people’s minds.

This internal resistance usually stems from concerns about feasibility, risks, past experiences, or simply a reluctance to step outside of familiar territory.

These statements can quickly shut down conversation and stall innovation. Common examples include:

“Yes, but it’s not in our budget.”

“Yes, but we don’t have enough staff.”

“Yes, but it will take too long.”

When left unchallenged, these objections can lead to unproductive debates about who is right or wrong, based solely on the original “Yes, but…” premise. However, instead of treating them as roadblocks, we can transform them into powerful questions that drive creative problem-solving.

For example:

“Yes, but it’s not in the budget.”  

Invite inquiry by asking - “Whose budget is it in? What if it didn’t need to be in our budget? Could we fund it differently?”

“Yes, but we don’t have enough staff.”

Invite discussion by asking the question  - “Who else could do it? Could we automate or outsource part of it?”

“Yes, but it will take too long.”

Encourage exploration by asking  - “What could speed up the process? What if we phased it in?”

By reframing objections as questions, we encourage new perspectives and uncover possibilities we might have otherwise dismissed. In board discussions, inviting people to openly express their “Yes, buts…”—without accepting them as immovable truths—creates an environment where real innovation can happen.

Instead of letting “Yes, but…” limit your thinking, use it as a tool to unlock fresh opportunities.

In Closing 

A director’s impact lies not in statements but in the questions they ask, driving deeper discussions, strategic thinking, and better decisions.

To support this, some boards include key questions in board papers to help directors refine their inquiry skills. Others go further, requiring that proposals include at least two viable options and two strategic questions, ensuring discussions explore alternatives rather than defaulting to a single choice. 

By prioritizing inquiry over assumption, boards foster sharper insights, more informed decisions, and greater overall impact.