The Key Question for Every CEO and Chairperson?

A discussion article. Part of The Thinking Upgrade.

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Imagine being asked to explain your organisation to someone who will inherit the world it is helping to create.

They have seen your financial results. They know your job title. They understand that leading an organisation involves difficult choices, competing expectations and responsibilities that do not disappear when the working day ends.

But they want to ask you something more fundamental.

“What is the future you want to help create – globally,nationally and locally – through your organisation?”

What would you say?

Would you describe the organisation you want to build, or the world you want that organisation to help build? Could you explain how the two connect? And would someone examining your investments, products, employment practices, incentives and everyday decisions recognise the future you described?

Every organisation participates in shaping the conditions in which other people live. It influences what gets made, what gets valued, how people spend their time, which behaviours are rewarded and which possibilities receive support. Its choices reach beyond its own walls, sometimes far beyond the people who have chosen to buy from it or work for it.

That makes leadership a profound responsibility. You are directing resources towards one version of the future, while other versions remain unrealised.

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How consciously have you chosen that future?

An organisation cannot solve every problem. Its leaders cannot control every consequence. But they can decide what they are trying to contribute, what they are prepared to question and what they will no longer excuse.

That begins with a question which can sound almost unreasonable in an established boardroom: why does this organisation need to exist?

Its longevity is part of its history. Its size describes its scale. Its profitability tells us something important about its financial performance. Yet the deeper question remains: what does its existence make better, for whom, and at what cost?

Imagine that it disappeared. What would people genuinely miss? What essential service, useful capability, enjoyment, connection, security or opportunity would be lost? What harm might diminish? Could the valuable contribution be provided in a better way?

An organisation does not have to save the world to deserve a place in it. Feeding people well, repairing what is broken, creating beautiful things, enabling play, providing dependable services and helping people enjoy their lives are worthwhile contributions. The question is whether we understand the value we create clearly enough to distinguish it from the activity we have become accustomed to maintaining.

Every organisation draws on precious resources: human, man-made and natural.

People commit portions of their finite lives to it. Buildings, machinery, infrastructure, energy, materials, land and capital support its operations. Knowledge developed by earlier generations helps make its work possible. Other people and other possibilities compete for many of those same resources.

When someone gives your organisation ten years of their working life, what have those years helped create? What have they gained, and what have they had to give up? When natural resources are consumed, what enduring benefit has justified their use?

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What makes your organisation worthy of the resources it uses – and how would you know if that answer had changed?

This deserves more than a purpose statement. It requires an honest examination of benefits and harms across the organisation’s activities and relationships.

Who benefits from what you do? Who carries the costs? Which costs appear in your accounts, and which are absorbed by employees, families, suppliers, communities, public services, other species or future generations?

A benefit to one group does not make harm to another disappear. Some trade-offs are unavoidable; others survive because the people experiencing their consequences have little influence over the decision.

Could your account of organisational success withstand a conversation with those people? Would they recognise their experience in it?

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Then consider what your organisation encourages people to do.

Every product, service, incentive and working practice makescertain behaviours easier, more attractive or more necessary. An organisationcan help people learn, repair, cooperate, save, create, care and make informedchoices. It can also encourage waste, dependency, overconsumption, dishonesty,exhaustion or the pursuit of short-term rewards at someone else’s expense.

What behaviours must your customers repeat for your organisation to thrive? What must employees do to get ahead? What do suppliers learn they must tolerate to keep your business?

If your stated values reward care but your targets reward disregard, which will shape people’s actions?

And if the behaviours on which your success depends became normal everywhere, what kind of world would result?

This is where the conversation becomes uncomfortable. An organisation may provide real benefits while also sustaining patterns its leaders would not wish for their own children. It may help solve one problem while deepening another. It may improve its own performance by moving difficulty elsewhere.

Good intentions are a starting point. They need to be tested against what actually happens.

What consequences have surprised you? What do you suspect but have not investigated? Which harms are repeatedly described as isolated incidents, even though the same incentives remain in place?

No leadership team can anticipate everything. But once an unintended consequence becomes visible, the next decision is made with that knowledge. What will you change because you now know?

There is another question that deserves a place in this discussion: what positive progress might your organisation be slowing down or blocking?

Perhaps a better solution threatens an established source of revenue. Perhaps an internal project is protected because influential people built their reputations around it. Perhaps customers cannot easily leave, suppliers cannot challenge terms, or employees cannot introduce improvements without navigating layers of permission.

Perhaps resources remain committed to preserving something familiar when they could support something much more valuable.

Resistance can be deliberate. It can also emerge through ordinary routines: a budget carried forward, a risk assessment that considers only the dangers of change, a performance target that makes experimentation unattractive.

Would you welcome a development that substantially improved people’s lives if it weakened your current business model? Would you help your organisation adapt, even if doing so reduced your own status or reward?

What, exactly, are you committed to preserving: the contribution, the institution, the current model, or your position within it?

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These questions lead directly to the people at the top.

Becoming a CEO or chairperson can demand enormous commitment, capability and resilience. There is much to respect in accepting the responsibility. Yet appointment cannot settle, for the duration of a tenure, whether someone remains the right person for the work ahead.

“To what degree am I the best possible person for this role – and to what degree am I actually being the best possible leader I can be?”

Those are different questions.

The first concerns the fit between your capabilities and the organisation’s needs. The second concerns what you do with those capabilities today.

A highly capable leader can be distracted, defensive, exhausted or poorly supported. Experience can inform judgement and also make familiar answers too comfortable. Someone can understand the importance of listening while creating an atmosphere in which few people feel able to disagree.

Being the best possible is a continuing practice, shaped by real human limits. It requires self-knowledge, honest feedback, disciplined learning and support. It also requires the humility to recognise when the organisation needs capabilities you do not possess.

How well do you understand your own motives, biases and emotional reactions? What happens to your thinking when your authority is challenged? Who can tell you that you are wrong without having to calculate the personal consequences first?

When did constructive feedback last change an important decision – or the way you behave?

A CEO should be able to examine how their leadership affects the organisation’s direction, culture, execution and capacity to learn. A chairperson should be able to examine whether the board brings independent judgement, meaningful challenge and effective scrutiny – including scrutiny of the chairperson.

Mutual confidence matters. So does the ability to ask difficult questions without turning them into a contest of loyalty.

The same examination belongs with the whole board and executive team. Do we have the best possible combination of people for the challenges and opportunities ahead? And are we enabling those people to contribute at their best?

Impressive individual credentials cannot compensate for a team that avoids disagreement, misses crucial perspectives or struggles to think together. Who notices what the rest overlook? Who understands the numbers well enough to challenge the assumptions beneath them? Who asks about the human consequences? Who connects immediate decisions with longer-term possibilities?

What evidence demonstrates the quality of our collective thinking? What have we changed after discovering that our confidence exceeded our understanding?

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Consider, too, the use of your own time.

As a thought experiment, imagine that much of the analysis,drafting, coordination and reporting you currently undertake could be performedwell by capable colleagues and carefully used AI. What would remain that most required your personal attention, judgement, authority or relationships?

Which decisions genuinely need you? Which conversations can you uniquely unlock? Where does your involvement create exceptional value? Where does it delay others or prevent them from developing?

Some responsibilities cannot simply be handed over. Accountability remains even when work is delegated. Yet personal accountability does not require personal involvement in every task.

What percentage of your time goes towards the highest-value contribution you can make – and what evidence supports your answer?

Open your calendar. Does it reflect the future you say matters? Is there time to think, listen, learn, examine consequences and develop others? How much is absorbed by habitual meetings, duplicated oversight, avoidable approvals or activity whose value nobody has recently questioned?

Reflection, rest and informal conversations can be essential to good leadership. A crowded diary can conceal wasted time just as easily as an empty hour can create space for a vital insight. The question is what your use of time makes possible.

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Finally, there is remuneration.

How do you justify what you receive?

Scarcity of capability, substantial responsibility and sustained contribution can support a strong case for significant reward. But comparison with other highly paid leaders does not, by itself, explain your own value.

What part of the organisation’s progress reflects your contribution? What reflects the efforts of colleagues, inherited strengths, public infrastructure or favourable circumstances? Have you built capabilities that will endure after you leave? Have rewards risen while other people have absorbed the risks or costs?

Could you explain your remuneration plainly to someone whose work enables the organisation to function, and whose annual income may be a small fraction of yours? Could you do so with evidence, respect and an acknowledgement of collective effort?

An honest answer deserves to be heard. An uncomfortable answer deserves to be examined.

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The value of this discussion lies in what follows it.

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A leadership team might begin by describing the future it wants to help create, examining where present decisions support or undermine that future, and inviting challenge from people who experience the consequences. It could then choose what to strengthen, what to redesign, what to stop and how to judge whether the changes are working.

Some conclusions will be difficult. A cherished product may need to change. A profitable practice may need to end. Investment may need to move. The board may need different capabilities. A leader may need to make room for someone else.

There is also enormous possibility here. An organisation can become a place where human ingenuity, resources and collective effort produce more lasting value; where commercial strength supports a worthwhile contribution; where people can take pride in both what they achieve and how they achieve it.

A leader’s influence extends to what other people come toregard as normal. Serious self-examination at the top can give others permission to question, learn and improve. Avoidance at the top can teach them to remain silent.

One day, your tenure will end. The title will pass tosomeone else. The consequences of your decisions may continue in people’s lives, in the capabilities you developed, in the opportunities you enabled and in the damage you prevented – or left behind.

Imagine returning to the person who will inherit that world.

They ask again:

“What is the future you want to help create – globally,nationally and locally – through your organisation?”

Then they ask the question that gives your answer its weight:

“What are you prepared to change to help create it – including in yourself?”

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Thanks for reading.

Best,

Rob

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