The Best Questions Boards Can Ask Their CEOs

Across hundreds of conversations on Enter the Boardroom, one theme repeatedly emerges when Chairs and CEOs reflect on effective boards.

The boards that add the most value do not do so by giving answers. They do so by asking better questions - questions that cut through noise, surface assumptions, slow down decisions and sharpen judgment.

What follows is a set of questions our guests consistently pointed to as raising the quality of boardroom conversation and improving CEO decision-making.

What this article reveals at a glance

1. The quality of board challenge is determined by the quality of its questions.
The most effective boards avoid performative challenge and instead ask questions that force clarity, trade-offs and honest reflection.

2. Great questions surface assumptions early.
Many failures stem not from bad intent, but from unspoken assumptions. The best boards make those assumptions explicit and test them collectively.

3. Boards often add value by slowing decisions down rather than speeding them up.
Several guests emphasised the importance of knowing what must be decided now, and what benefits from further thought.

4. The most powerful questions reconnect strategy to reality.
Whether through customers, operations or people, effective boards continually test whether what they are hearing matches what is actually happening.

Taken together, these questions reveal a shift away from boards as reviewers of information, and towards boards as shapers of thinking.

The Best Questions Boards Can Ask Their CEOs

What is our north-star metric?

“What are the most important things we need to know? Let’s focus on those and find the right way of measuring them. With Moonpig, we knew that repeat rate was the single biggest predictor of long-term success. If customers came back after trying the product, we knew we were getting everything else right.” Nick Jenkins, Founder and former CEO of Moonpig, former Dragon on Dragon’s Den, Chair of Virtualstock, NED at Green Energy Options and Trustee at Operation Fistula

Are we being honest about capability?

“Could the company invest sufficiently to succeed, or do we need to partner with somebody else?”
Sir Donald Brydon, Former / Chair of Tide Holdings, Adarga, PrimaryBid, Sage and London Stock Exchange Group 

What would we be talking about if we didn’t have this board paper?

“I like to read all the board pack, then put it aside and say, ‘what would we be talking about? What should we be talking about if we didn't have these board papers?’” Susannah Nicklin, CFA, Chair of Schroder BSC Social Impact Trust plc, NED at Ecofin Global Utilities & Infrastructure Trust plc and North American Income Trust plc

Can you see it if you close your eyes?

“I understand the strategic objective, but I can’t see it if I close my eyes. What does it actually look like when we’re doing this well?” Owen Eastwood, Author of Belonging and Performance Coach at HoKo 

Are we choosing partners or just taking cash?

“Closing a round isn’t closing a deal. It’s getting married to a group of humans you’ll be tied to for years.” Marta Krupinska, CEO & Co-Founder of CUR8, Chair of YBI and NED at ACUA Ocean 

Where are we allocating assets and why?

“Strategy is really about asset allocation — time, money, people — and changing your mind halfway through creates chaos.” Roger Parry CBE, Former Chair of Oxford Metrics, Director at the Donmar Warehouse, Partner at Stoneglade Capital 

Are we still genuinely customer-led?

“I’ve been on boards where the customer is never mentioned, and they’re always worse for it.”  Dame Jayne-Anne Gadhia, Lead Non-Executive Director at HMRC, Senior Independent Director at Tate, Chair of Moneyfarm and an Advisor to The Vanquis Banking Group, UniCredit and the Fintech Growth Fund

Who are the most critical people in this organisation?

“You have to ask who actually makes this company work, and then make sure you look after them.”
Martin Gilbert, Co-founder and former CEO of Aberdeen Asset Management, Executive Chairman of River Global PLC, Chairman of Revolut and Toscafund

What would have to be true for this to work?

“What would have to be true for A to be a great idea? For B? For C? … Of all the things that would have to be true, which ones are you least comfortable with?” Roger Martin, Professor Emeritus at Rotman School of Management, University of Toronto, best-selling author of over five management books, including Playing to Win

What things are you doing which you don’t need to be doing?

“I ask them to tell me what are the things they’re really focused on — green. Amber, what are the things you don’t really need to do, but you do? Red are the things you really could delegate.” Lord Charles Allen, Baron Allen of Kensington, CBE, Chair of Moelis & Co, Balfour Beatty Plc, Global Media & Entertainment Group, and The Invictus Games.

Who makes which decisions?

“One of the most crippling things for an organisation is not having clarity about who makes decisions. Boards need to be really clear about how decisions get made, who owns them, and how accountability works.”  Sara Weller CBE, Chair of the Money and Pension Service and former/NED at BT, Virgin Money and Lloyds Banking Group and UK Department for Work and Pensions 

Are we having a high-quality conversation?

“A high-quality conversation has three attributes: people are either contributing or genuinely listening, there’s a healthy balance between advocacy and inquiry, and you have a sense that you’re getting somewhere. If you’re not learning and moving closer to a good decision, that’s a signal something is wrong.” Amy Edmondson, Professor of Leadership & Management at Harvard Business School, ranked #1 management thinker in the world by Thinkers50 in 2023

How do we know when we need to stop something?

“Where are the risks in that? What if it doesn’t work? How do you know you’re successful, and when do you call a halt if it’s not delivering? Those are the questions boards should be asking.” Tamara Box, Partner at Reed Smith LLP, Chair at Interpath Advisory & The Eve Appeal, NED at Hanover Capital, and Trustee at the Chartered Management Institute

“How soon will we be able to tell if this isn’t working? “It cuts through the optimism bias and makes it okay for us to check.” Professor Doyin Atewologun, former Dean of the Rhodes Scholarship at the University of Oxford and is currently the Founder and CEO of Delta, Advisor to the board of the Tearfund and Trustee at the Old Fire Station

What assumptions are we making, and are they shared?

“You will never have all the information, so you need assumptions. The problem is that assumptions are often made individually and not articulated. Good boards make assumptions explicit and agree them collectively.” Professor Stanislav Shekshnia, Professor at INSEAD, where he directs board development programs, and Chair of TechnoEnergy AG 

What trade-offs would you actually make if you had to?

“It’s not enough to talk about must-haves and nice-to-haves. If you had to force rank and make trade-offs, where would you make them and why? The value is in the discussion that triggers.” Angela Seymour-Jackson, Chair of PageGroup, Deputy Chair of Pikl, SID at Trustpilot Group, and NED at Future and Janus Henderson Group

What is the right thing to do for the business, regardless of the markets?

“There was never a conversation about doing the wrong thing because it would be more acceptable to the market. It was always: if this is the right thing for the business, then that’s what we should do.”  Kate Swann, Chair of Moonpig, Beijer Ref, Parques Reunidos, and IVC Evidensia and former CEO of WH Smith

Have you lined up your successor?

“‘As soon as my team is ready, I will move to the side. I’m not gonna wait a minute longer.’ Guess what? CEOs like that never have a team that’s ready, right, because they never have a board that’s ready to challenge them.” Elena Botelho, Co-author, The CEO Next Door, Partner at ghSMART

How much of this decision do we need to make today?

“One of the questions I frequently ask in board meetings has always been, how much of this decision do we have to make today? Instead of thinking, actually, maybe we need to deal with one piece of this and then spend a little bit more time thinking about what comes next.” Margaret Heffernan, Author of seven books, including Wilful Blindness, Uncharted and Embracing Uncertainty, former CEO of InfoMation Corp, ZineZone Corp, and iCast Corp, Thinkers50 Hall of Fame Member 

“Often the way around these things is not to drive to a conclusion in the moment. It’s often better to take time, to pause, to reflect, to get more information, and to bring something back…” Professor Malcolm Press CBE is Vice-Chancellor of Manchester Metropolitan University and President of Universities UK

Where can we have a credible impact on ESG issues?

“Where do we have legitimacy and leverage? Where can we actually drive change with our business model, rather than making big picture commitments we can’t realistically deliver on? … Those geopolitical questions belong squarely at the board table.” Professor Alison Taylor, Clinical Associate Professor at NYU Stern School of Business and author of Higher Ground: How Business Can Do the Right Thing in a Turbulent World 

How strongly do you believe what you’re saying?

“If you were to go down route A, you would need to believe the following. How strongly do you believe it: absolutely, kind of, or not at all?” Douglas Flint CBE, Chair of Aberdeen, IP Group and the Royal Marsden NHS Trust and former chair of HSBC Group Holdings and NED at BP

What is the cost of doing nothing?

“What is the cost of doing nothing? The cost of inertia is usually never factored in.” Amanda Mackenzie OBE is NED at British Land and at Lloyds Banking Group, where she chairs the Responsible Business Committee

What exactly have we decided?

“You can spend three hours discussing strategy, but unless you are crystal clear about what has been approved, what has stopped, and what has changed, the conversation hasn’t done its job.” Sir Ian Cheshire, Chair of Land Securities Group and Spire Healthcare Group. Former Group Chief Executive of Kingfisher plc and Chair of Channel 4, Barclays Bank UK and Debenhams