Level Up Your Boardroom Questions

One of the most powerful tools in your director’s toolbox is the art of asking great questions. It’s so important that it’s one of The Six Key Habits of the Savvy Director. Regardless of your sector, your governance model, or the length of your tenure, your ability to ask insightful, timely, and courageous questions helps you create a lasting impact and elevates your board’s performance.

As a director, chances are you have lots of experience asking questions in high-stakes situations. Meaning you already have questioning skills.

But as with any skill, you can always improve.

In the boardroom, questioning is your superpower. So, leveling up your questioning skills is worth the time and effort.

Questions in the Boardroom

Boardroom questioning isn’t about interrogation – it’s about illumination. Questioning drives strategic thinking, risk awareness, and accountability. Good questions uncover blind spots, clarify assumptions, challenge Groupthink, stimulate dialogue, and strengthen transparency. The result is better board decisions.

At the board level, the best questions are:

• Strategic. They test alignment with your mission and vision using a future-oriented focus.
• Risk-focused. They surface potential threats, uncertainties, and opportunities.
• Financial. They probe your organization’s fiscal health and sustainability.
• Performance-related. They assess organizational effectiveness with a focus on metrics, KPIs, and benchmarking.
• Integrity. They help ensure ethical conduct, regulatory compliance, and good governance practices.
• Stakeholder-focused. They consider external impact with a focus on engagement and reputation.

Effective Questioning

While most directors understand the importance of good boardroom questions, many struggle with mastering the art of doing so effectively. Leveling up your questioning skills starts with recognizing barriers and committing to overcoming them. In the boardroom, the barriers include fear of appearing uninformed, reluctance to challenge dominant voices, and a board culture where questions are seen as adversarial.

To overcome these barriers and improve your questioning technique, it helps to keep these principles in mind:

• Purpose. Make sure your questions align with a valid purpose such as strategy or governance responsibilities
• Clarity. Frame precise, unambiguous questions.
• Respect. Tone and timing matter. Questions should invite constructive dialogue, not defensiveness.
• Open-ended: To encourage discussion, avoid yes or no questions. Instead, aim for questions that explore, not just confirm.
• Balance: Mix probing follow-up questions with supportive questions to build trust and insight.

Avoid Triggering Defensiveness

Sometimes, even though the content of your question is valid, the intent, tone, or timing can trigger defensiveness. Here are some tips to keep in mind.

• Set your intention. Know why you’re asking the question. Is it to clarify, challenge assumptions, explore risks, or drive strategic thinking?
• Be clear about what you’re asking. Remember to W.A.I.T. (Why Am I Talking?) Don’t start talking until you have your question framed.
• Choose the right time. Ask questions when the agenda reaches the relevant item. To avoid an ambush, give the board chair advance notice if you’re going to ask about sensitive issues.
• Use neutral language. “Why” can sound accusatory. Try “What” or “How” questions instead. Avoid emotionally loaded words like “wrong,” “failure,” or “mistake.”
• Maintain a collaborative tone. Use inclusive language like “we” and “our” rather than “you” and “your” to foster trust and signal partnership.
• Focus on the issue, not the person. Keep the conversation objective and non-personal. Separate the decision from the decision-maker.
• Use context to build understanding. Context helps people see you’re looking for insight, not assigning blame. Pre-frame your question with wording such as “Given our strategic goal to expand internationally, I’d like to better understand …”
• Listen actively to the response. Show engagement with eye contact and nodding. Avoid interrupting. Summarize what you heard before asking a follow-up question.
• Follow-up constructively. Build on what’s already been said to demonstrate you’re listening and seeking deeper understanding.

Frame Questions with Curiosity, Not Critique

Curiosity opens doors; critique can close them.

One of the most effective ways to improve your questioning skills is to focus on how you’re framing your questions. Pay attention to how your question is worded, making sure to use neutral, inclusive language that focuses on solutions, not blame.

By way of illustration, here are examples that show how questions based on the four lenses of The Director’s Focus – strategy, risk, people, and finance – can be reframed.

Strategy Lens. Instead of “Why haven’t we expanded into new markets yet?” ask “What factors are influencing the timing of our expansion into new markets? How does this align with our long-term strategy?” The first focuses on what hasn’t been done and doesn’t invite constructive discussion. The second has a more neutral tone, requesting context and tying the answer to strategic goals.

Risk Lens. Instead of “Why did you ignore the possibility of supply chain disruptions?” ask “What contingency plans do we have in place to address potential supply chain disruptions?” The original question implies negligence and puts the respondent on the defensive. Rewording it keeps the focus on proactive planning and finding solutions.

People Lens. Instead of “Don’t you think our leadership team is too inexperienced for this project?” ask “What skills and experience do we need in our leadership team to ensure the success of this project, and how will we address any gaps?” The original question sounds personal and judgmental and will likely cause defensiveness. The reworded question focuses on capability needs and solutions rather than criticizing individuals.

Finance Lens. Instead of “Why are we spending so much money on this initiative?” ask “What is the expected return on investment and how does the spending compare with similar projects?” The first sounds like criticism without context and doesn’t invite a detailed breakdown. The second invites explanation and benchmarking, keeping the tone neutral and fact-based.

Reframe on the Spot

Despite your best intentions, you can slip up and unintentionally cause others to feel defensive with one of your questions. Be on the alert for:

• Non-verbal cues. Body language such as crossed arms, leaning back, or jaw tightening; facial expressions like frowning , narrowed eyes, or pursed lips; and avoidance of eye contact.
• Sharp tone. Short, clipped answers , a raised voice, or overly formal language instead of a normal conversational style.
• Deflection. Changing the subject, answering a different question, or referring vaguely to process or policy.
• Justification. Using phrases like “We had to…” or “There was no choice…” early in the response.
• Hesitation. Pausing for a long time before answering or visibly searching for the “right” answer.

If you pick up on any of these signs of defensiveness, you can still recover by reframing your question on the spot so it lands more constructively.

• Restate your intent. “I’m asking to understand the factors involved, not to question the work you’ve done.”
• Soften the language. Switch from “Why” to “What” or “How.” “What led to that decision?”  instead of “Why did you do that?”
• Acknowledge their effort. “You’ve clearly put a lot of thought into this. Can you walk us through the reasoning?”
• Use inclusive words. “How can we ensure we’re aligned on this approach?” “We” signals partnership rather than interrogation.

More Ways to Level Up

Here are a few more techniques you can choose from to sharpen your boardroom questioning skills. Use what works for you.

Prepare for meetings with a questioning lens. Review your board material critically, highlighting unclear points, inconsistencies, or assumptions. Ask yourself What’s missing? What assumptions are being made? What outcomes are implied but not stated? Formulate a few questions in advance.

Use layered questioning. A layered approach is a deliberate progression from broad exploration to focused probing. It helps uncover deeper insights, prevents premature closure of discussion, and encourages people to think beyond immediate answers. Here’s an example:

• Layer 1 – Strategic. Sets the stage and invites a wide perspective. “What’s our long-term plan for expanding into new markets?”
• Layer 2 – Tactical. Moves toward specifics that support the strategic vision. “What resources are we allocating to achieve that expansion?”
• Layer 3 – Analytical. Identifies potential obstacles and ensures mitigation plans. “What risks could derail this initiative, and how are we addressing them?”
• Layer 4 – Outcomes. Encourages thinking about impact, sustainability, and long-term benefit. “If we succeed, how will this change our competitive position?”

Use a structured thinking framework. Structured frameworks help you anchor your questions in a clear context, so they’re strategic, relevant, and actionable. The Director’s Focus is one such framework. Try using its four lenses – strategy, risk, people, and finance – to help you craft questions that are balanced, comprehensive, and aligned with your oversight responsibilities.

Practice active listening. Great questions often emerge from what’s said – or not said – in the room. Active listening is more than hearing words – it’s about interpreting meaning, identifying gaps, and probing deeper. It builds trust, ensures questions are grounded in what’s been said, and allows you to uncover hidden issues.

Watch for These Mistakes

Many directors underestimate how much the quality of their questions impacts their board’s effectiveness. Watch for common mistakes like:

• Overloaded questions. Multi-part, overly complex questions cause people to answer only part of the question or miss the core issue altogether.
• Unprepared questions. With inadequate preparation, your questions will waste time and undermine your credibility.
• Leading questions. Phrasing questions in a way that suggests a preferred answer discourages open discussion.
• Not listening to the answer. Planning your next question instead of listening to the response means you’ll miss the opportunity for follow-up.
• Accepting vague or incomplete answers. If you don’t follow up with a probing question, your board might miss the critical information it needs to make a decision.

Commit to Improving Your Questions

As a board director, you’re expected to probe, explore, and challenge with skill and integrity. When you improve your questioning skills, you create a lasting impact and elevate your board’s capacity to govern well.

Practice makes perfect. Asking questions helps improve your ability to ask even better questions in the future. Why not commit to asking one high-impact question at each board meeting? Try out some of the tools and techniques we’ve explored in this edition of The Savvy Director.

Your Takeaways

Here’s a simple checklist to use before asking a boardroom question.

• Have I clarified my purpose?
• Is my language neutral and non-judgmental?
• Am I focusing on the issue, not the person?
• Is now the right time to ask?
• Does my question align with one of the four Director’s Focus lenses?
• Am I ready to listen fully to the answer?

Resources

• The Art of Asking Questions in the Boardroom. Lyn McDonell. The Accountability Group. 2025
• How to ask the right questions. Daniel Taylor. Corporate Governance Institute. June 2021.
• The Art of Asking Questions: A Key Competency for Board and Advisory Directors. William “Bill” Jones. Medium. February 2024.
• The Boardroom Question That Changes Everything. Heidi Prowse OAM. LinkedIn. September 2025.
• Essential Boardroom Questions For Non-Executive Directors. Actuate. June 2025.

Thank you.

Scott

Scott Baldwin is a certified corporate director (ICD.D) and co-founder of DirectorPrep.com – an online membership with practical tools for board directors who choose a learning and growth mindset.

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