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New directors, building a questioning toolkit, should start with vision, test assumptions, examine risks, probe impact and reflect regularly on how the board adds value.
The best questions signal engagement, not ego. They invite dialogue, not defensiveness.
A director’s legacy may not be the answers they gave, but the conversations they sparked.
Effective directors are defined less by the answers they give and more by the questions they ask. A carefully framed question can surface hidden risks, test long-held assumptions or reveal a strategic opportunity.
“There’s definitely an art in asking quality questions, with the right timing,” says Scarlett McDermott, Managing Director of Longitude Advisory and a board member at the Australian Information Security Association and Akin Agency.
“Having been in plenty of board meetings prior to my first as a director, I was surprised at how the dynamic changes when you’re on the other side of the table.”
Tony Faure, Chair of oOh!media and Year13, agrees. “When you move from an executive role into a board position, it’s a big shift. As a CEO, you’re focused on momentum. In the boardroom, you’re thinking about shareholder expectations, regulatory exposure and reputational risk. The perspective is broader and the accountability feels heavier.”
The first board meeting: Theory meets reality
At her very first board meeting Stephanie Bown GAICD, author of Curious Connected & Calm and a board member at NFP LeaderLife, was struck by how formal the meeting was.
“It lacked flow,” she says. “Here’s the balance sheet, here’s the CEO report. It felt like trying to read tea leaves. I felt like I had to catch up and was missing the big picture.”
After the meeting, she requested a conversation with the CEO. Her question was simple: “Do we have a strategy document or a vision statement?”
“That question kicked off a new visioning process as a board,” she says. “Understanding the direction we’re trying to go, what possibilities there are. The chair was very open.”
From that point, LeaderLife began building a stronger shared understanding of purpose, she says. “Gaining a sense of what we’re collectively trying to do and how we add value as directors changed the nature of our conversations”.
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Questions first-time directors should ask
For first-time directors, Bown says there are two key questions they need to ask:
What is our vision for this organisation, and how do we create real value for our stakeholders?
How do we know if we are being successful? What are our key measures of impact?
At LeaderLife, KPIs such as program participation existed, but weren’t regularly shared with the board.
“Understanding those metrics created a strong sense of impact,” says Bown.
It also revealed a gap. “No-one on the board had strong fundraising capability to support the CEO. The board is now actively recruiting to fill that strategic need.”
For an SME board, McDermott suggests asking:
What are the external trends shaping our strategic planning?
Where and how are we investing in maturing or changing our capabilities as an organisation?
“These questions will help to orient you with the future direction of the organisation and to understand key risks and investments,” she says.
For an ASX-listed company board, Faure suggests asking:
How effectively are we communicating our competitive edge to customers, partners and the market?
What specific gap in the market do we fit into and why are we uniquely positioned to fill it?
“Good boardrooms don’t add noise,” says Faure. “At the end of the day, the goal is to bring clarity to executive teams that are moving fast and carrying out those day-to-day operations.”
Questions directors should avoid
It’s easy to get into the weeds.
“You don’t need to be asking about micro-level things like individual hires, campaign tactics or the day-to-day running of the business,” says Faure. “The board’s role is oversight and direction. Management’s role is execution. You need to trust the team to make those day-to-day decisions and focus your energy elsewhere.”
Adds McDermott, “I try to avoid overly retrospective questions that focus on assigning responsibility for past decisions. It’s important to understand context, but boards add most value when they are forward-looking.
“A question framed as ‘Why did we do this?’ can feel accusatory. Reframing it as ‘What assumptions were we operating under and have they changed?’ keeps the focus on learning rather than on blame.”
Strategic oversight focuses on the what and why at the organisational level, rather than the who and how of day-to-day operations.
The director’s questioning toolkit
The best questions signal engagement, not ego. They invite dialogue, not defensiveness.
For new directors, building a questioning toolkit is an investment in effectiveness. Start with vision. Test assumptions. Examine risk. Probe impact. Reflect regularly on how the board itself adds value. Because in the end, a director’s legacy may not be the answers they gave, but the conversations they sparked.
Asking great questions starts with preparation before the meeting. Taking time to understand the context, what’s already been discussed and what you hope to learn will lead to questions that go beyond the surface level.
The other critical ingredient is curiosity. Curiosity will steer you towards questions challenging assumptions, surfacing opportunities and making the most of the collective thinking of the board.
If you have both of those things covered, you’re on track to ask impactful questions that will move the organisation forward.
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