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Choose Your Questions Wisely

ask great questions Oct 15, 2023

If you’re a regular reader of The Savvy Director blog, then you know how much emphasis DirectorPrep places on the value of questions. Questions are directly related to a board’s ability to learn and understand, to think things through and make good decisions. In many ways, a board’s value lies in how well the directors question management, advisors, and each other.

As a director, asking questions helps you fulfill your fiduciary duty by satisfying yourself about what’s in your organization’s best interests. But asking questions to obtain information is just the tip of the iceberg. There are so many other reasons for you to ask questions - to increase understanding, reduce ambiguity, encourage dialogue, launch discussions, challenge assumptions, and uncover biases.

Whether you’re an experienced director or you’re new to the role, if you want to make a point and you suspect it could be contentious, framing it as a question is almost always a safe way to do it.

In fact, when you’re careful about when and how you pose questions, you can build trust and resolve conflicts even though you’re asking the hard questions that others are afraid to. Savvy directors have the courage to ask tough questions, but they frame them in a clear and respectful way, using framing, tone, and body language to put tough issues on the table without triggering defensiveness.

Choosing a question wisely, then asking it in the right way at the right time, is a valuable skill. It starts with being clear about the reason you want to ask it in the first place. Before you ask a question, ask yourself, “What’s the purpose?”


Be clear about your purpose.

When you’re reviewing material for an upcoming board or committee meeting, chances are you’re making note of any questions that come to mind. Regardless of whether you’re jotting them down on paper or using the Note function in your board portal, coming up with questions comes naturally to most directors. To my mind, your meeting PREP isn’t complete until you’ve reviewed your questions to choose the one or two that will really add value to your board, and that others probably won’t ask.

Choosing wisely involves thinking about your purpose in asking the question in the first place. Being clear about your purpose helps you decide on the type of question, and the words, timing, and tone of voice to achieve the outcome you’re hoping for.

The reason to ask a question seems obvious - to get an answer. But in the boardroom, there are many other reasons. For directors, questions are excellent, multi-purpose tools, useful for a range of situations that include establishing facts, developing understanding, clarifying, assessing, challenging, scrutinizing, prompting discussion, reframing issues, stimulating new perspectives, aiding decision making, identifying risk, and motivating behavior change. And they have the added advantage of being a safe way to make a point.

Let’s explore some of the most common purposes for boardroom questions.

To establish facts. As a director, you’re faced with huge amounts of information you need to absorb and understand. The right questions enable you to cut through the surplus detail to get at what the board needs to know.

Ask yourself if the board really needs the information you’re about to ask for. If it’s vital, you might ask the question even though you personally know the answer, because you suspect some board members don’t know it and you want to ensure everyone has the same information. If it’s not vital – let’s say it’s just a matter of satisfying your curiosity - you might decide to skip the question in the interests of time.

To clarify information. Ask clarifying questions when something is unclear, and you want to avoid confusion or misunderstanding. If you’re new to the board, you might want to take these questions offline. But if not, and there’s something you don’t understand, chances are others are in the same boat. That makes it worthwhile to ask at a board meeting.

Asking a clarifying question has the added benefit of showing that you’re interested in what someone has to say – interested enough to make an effort to fully understand. With this type of question, you can avoid defensiveness and minimize resistance.

To deepen understanding. Important, complex topics deserve consideration and scrutiny at the board table. As a director, you have a right and a duty to probe deeply before the board makes a decision - discussing critical strategic issues, considering options, and assessing risks.

Open questions that engage directors’ critical thinking skills are needed to deepen the board’s understanding of complex problems in our VUCA world.

To challenge assumptions. We all take certain things for granted. What seems self-evident to one person may not be obvious to another. Asking questions that bring tacit assumptions to the surface helps the board to resolve differences.

Assumptions are what we believe to be true without requiring any supporting evidence, often without being aware of them. All that’s needed to make an assumption is incomplete information about a situation and an unwillingness to ask questions to fill in the blanks. The blanks get filled in with individual interpretations that have us jumping to conclusions. The best way to help your board move away from assumptions and toward facts and data, without generating defensiveness, is by asking questions.

To reframe an issue. Because directors come with different perspectives, they can ask questions that reframe an issue and provide a way forward. Reframing is a powerful tool for problem solving because it enables us to look at the big picture and think of an issue from multiple perspectives. The way you frame a problem determines the potential solutions that get identified, so reframing it helps to generate more options.

To generate ideas. When we’re looking for ideas, asking questions helps to open up discussion and allow multiple perspectives and opportunities to emerge. The right questions can prompt innovative, creative thinking within an environment where people feel comfortable putting forward their ideas.

To make decisions. When it comes to decision-making, questions can be used every step of the way to identify selection criteria, weigh the pros and cons of different options, and make an informed choice.

Many factors can get in the way of good decision-making, causing the process to go off the rails. One thing a director can do to get the process back on track is to ask questions like, “What else do we need to know?”, “What are our blind spots?”, “Have we heard all the voices?”, and my personal favorite, “How does this link to our strategy?”

To envision the future. Great questions are an important foundation for strategic thinking. They provoke deep insight, forcing us to step back, see things from a new perspective, and explore possibilities. Catalytic questions are a great tool for strategic planning because they invite creativity and exploration, encourage reflection and insights, and help us think more deeply about the future.

To build trust. Asking questions engages your colleagues, demonstrates respect, diffuses tension, obtains buy-in, and make people feel valued. Through your use of the right question, asked at the right time in the right way, you can express interest, build rapport, persuade others, and resolve disagreements. All of this adds up to building trust with management and your fellow board members.

 Ask the right question.

There is rarely a right answer to a wrong question. Knowing what to ask boils down to being clear about your purpose for asking it. What are you looking for? Facts, expert advice, a well-reasoned judgement, or something else entirely?

Here are a few examples of the types of questions you can use effectively in the boardroom.

  • Closed questions. These can be answered with a simple yes or no, or a few words. They’re useful for establishing facts, clarifying information, or confirming understanding, but they need to be used carefully. Your tone and manner can direct a specific response that you’re looking for. Also, make sure not to ask too many closed questions in a row – it can seem like an inquisition.
  • Open questions. Open questions can’t be answered with a simple yes or no. They’re a good way to encourage discussion, develop understanding, prompt reflection, and stimulate new ideas. You can switch closed questions to open ones. Factual questions like what, where, when, how, and who become open when you use language such as “What if … ?”, “How might we … ?”, “What makes you say that?”, or “Why do you think that?”
  • Fact-finding questions. These are used to gather specific information or data, and for the most part they’re straightforward and impartial. Make sure to differentiate facts from interpretation. Open questions work better for interpreting information, but if you’re just looking for facts and figures, go ahead and use closed questions.
  • Clarifying questions. These help you better understand information that’s been presented. They can be open or closed, depending on the situation. Open clarifying questions invite someone to elaborate on their message or expand on their ideas, whereas closed ones simply ask them to confirm or deny that what you heard was what they were trying to say.
  • Probing questions. These are used to delve deeper into a particular issue, uncover more information, share feelings, think critically, or challenge assumptions. Probing questions can be tough to ask without triggering defensiveness. It’s important to frame them in a clear, respectful way, using non-threatening words, tone, and body language.
  • Hypothetical questions. These explore potential outcomes or scenarios. Asking, “What would happen if … ?” is a great way to delve into both strategy and risk.
  • Holistic questions. These questions are used to form a comprehensive understanding of a subject, taking into account multiple perspectives and encouraging a broader viewpoint. Examples include “How does this fit into the bigger picture?” and “What are all the factors that contribute to … ?”
  • Conflict resolution questions. These questions are designed to help people understand each other’s perspectives and find common ground. For example, “What do we all agree on?” or “What do we all want to achieve?”


Questions and The Savvy Director

Given that asking great questions is one of The Six Habits of the Savvy Director, it’s a topic that I write about frequently. For the full range of articles about questions, click on Ask Great Questions under Filter by Topic on The Savvy Director blog page. You’ll find it either on the right hand side or the bottom of the page, depending on the device you’re using.

Here are a few of my favorites:


Your takeaways:

  • If you want to make a point, and you suspect it could be contentious, framing it as a question is almost always a safe way to do it.
  • Before you pose a question, ask yourself, “What’s the purpose?” It will help you choose the right words, timing, and tone of voice.
  • Valid reasons for asking questions in the boardroom include establishing facts, clarifying information, deepening understanding, challenging assumptions, reframing issues, generating ideas, making decisions, envisioning the future, and building trust.
  • Knowing what kind of question to ask boils down to being clear about your purpose for asking it. Whatever your purpose, choose your questions wisely.
  • Click on Ask Great Questions under Filter by Topic on The Savvy Director blog page for ideas on how to use questions to have an impact on your board.




Thank you.


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


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