Asking the right questions: what great thinkers teach leaders about inquiry
Voltaire once wrote, “Judge a man by his questions rather than by his answers.” That single line turns a lot of conventional leadership wisdom on its head. We are used to celebrating the leader with the confident answer, the bold solution, the decisive verdict. But if Voltaire is right, the real test of leadership is not how quickly you can respond – it is how carefully you can inquire.
In a world of dashboards, metrics and AI‑generated insights, answers are abundant and cheap. Questions are scarce and expensive. They demand attention, humility and the willingness to admit that you may not yet be looking at the problem in the right way. The leaders who stand out today are not the ones who claim to “have all the answers”, but the ones who take responsibility for framing the right questions.
In this article, I explore what various thinkers, scientists and practitioners have said about the significance of asking the right questions – and what their insights mean in practice for leadership, risk and resilience.
Questions as a window into judgment
Voltaire’s challenge – “judge a man by his questions” – suggests that questions reveal something deeper than our rehearsed answers ever will. Answers can be memorised, scripted or outsourced to experts. Questions, by contrast, expose what we notice and ignore, whose views we value, and how we understand our own responsibilities.
In a boardroom, for instance, two directors may listen to the same operational report but ask very different questions. One dives straight into short‑term numbers: “What’s this going to do to our quarterly results?” Another starts with stakeholders: “Who will be most affected by this change, and how do they experience it?” Both questions are legitimate, but they reveal very different priorities. Over time, a pattern of questions becomes a portrait of leadership judgment.
This is why many experienced consultants and coaches pay close attention to the first questions leaders ask. Before any solution is proposed, those questions signal how a leader frames value, risk, time horizon and accountability. If the questions are narrow, defensive or purely technical, the resulting solutions will be as well.
For leaders working in risk and continuity, this is not an abstract point. The questions you ask (or fail to ask) in the early stages of strategy, change and incident response will shape the entire trajectory of the work. If you start with, “How quickly can we get this signed off?”, you will get speed. If you start with, “What would ‘safe enough’ look like here, and for whom?”, you invite a very different kind of conversation.
Defining the problem: Einstein’s 55 minutes
A quote often attributed to Albert Einstein goes like this: “If I had an hour to solve a problem, I would spend 55 minutes thinking about the problem and 5 minutes thinking about solutions.” Whether or not he actually phrased it this way, the principle has echoed through management thinking for decades: the way you define the problem largely determines the quality of the solution.
This is not a plea for analysis paralysis. It is a reminder that premature answers are one of the most common ways organisations waste time and money. We launch projects before clarifying what success really looks like. We deploy technology before articulating the human problem it is meant to solve. We change structures and processes while quietly preserving the assumptions that created the issues in the first place.
Quality pioneer W. Edwards Deming made a similar point from a different angle: “If you do not know how to ask the right question, you discover nothing.” He spent his life helping organisations improve quality and reduce variation, yet he insisted that the starting point was not a tool or a method, but a disciplined form of questioning. What is the system? Where does variation come from? What is the evidence?
The relevance to today’s risk and resilience agenda is obvious. Before asking, “How likely is this scenario?”, it is often more powerful to ask, “What would have to be true for this scenario to matter to us?” Before asking, “What incident response plan do we need?”, you might first ask, “What fragile dependencies are we taking for granted?” The right questions surface hidden assumptions, fragile links and blind spots – the raw material of real resilience.
From this perspective, “asking the right questions” is not a soft skill. It is an essential part of operational due diligence.
Wrong questions, wrong answers
Several writers have warned that there is no clever way to salvage a bad question. Ursula K. Le Guin once observed that “there are no right answers to wrong questions”, and various speakers in business and personal development have echoed the same idea in different words: you cannot get right answers if you are asking the wrong questions.
We have all experienced this in everyday life. Ask “Who is to blame?” and you will get blame. Ask “What can we learn?” and you will get learning. Ask “How do we make people comply?” and you will get a compliance mindset. Ask “How do we make it easier to do the right thing?” and you will get ideas about design, incentives and support. The answers dutifully follow the path laid down by the question.
For leaders, this means that one of the most powerful interventions you can make in a meeting is to gently challenge the question itself. When the conversation narrows to “Which option should we choose, A or B?”, you can pause and ask, “What’s the question we’re trying to answer here – and are A and B the only ways to answer it?” That move alone can reopen possibility, re‑centre purpose and avert a lot of unnecessary conflict.
It also changes how we think about expertise. Experts often feel pressured to respond quickly and definitively. But sometimes the most expert move is to say, “Before I answer that, can we step back and ask a different question?” The courage to reframe is a hallmark of mature leadership. It is also a powerful modelling behaviour for teams: you are giving people permission to interrogate the question, not just the answer.
Questions as a leadership practice
Management writer Peter Drucker once remarked, “My greatest strength as a consultant is to be ignorant and ask a few questions.” At first glance, this may sound like false modesty. Yet there is a serious point behind it: in complex systems, the pretence of omniscience is more dangerous than admitted ignorance.
The best leaders use questions in at least three ways.
First, they use questions to create clarity. They ask, “What problem are we really trying to solve?” “Who is our customer here?” “How will we know if this has worked?” These questions turn vague intentions into concrete commitments.
Second, they use questions to create ownership. Instead of issuing instructions, they ask, “What options do you see?” “What would you recommend?” “What would make this easier for your team?” Questions like these delegate thinking, not just tasks, and invite people to step into responsibility.
Third, they use questions to create safety. Questions such as “What are we missing?” or “What feels risky or uncomfortable about this plan?” signal that dissent and doubt are not only allowed but welcome. Over time, this builds a culture where raising concerns is seen as an act of care, not disloyalty.
Leadership thinkers such as Michael Marquardt have gone so far as to talk about “questioning cultures” – organisations that place a deliberate emphasis on inquiry, reflection and constructive challenge. In those environments, questions are not an admission of weakness. They are how the organisation stays alive to reality.
If we take this seriously, then “asking the right questions” is not simply a personal trait of the heroic leader. It becomes a distributed capability. Leaders model it, but they also design forums, rituals and processes that make questioning routine: after‑action reviews, pre‑mortems, risk workshops, learning circles, customer listening sessions.
From quotation to habit: making questioning practical
It is one thing to enjoy these quotations and nod in agreement; it is another to turn them into daily practice. The shift from answers to questions can feel risky for leaders who have built their identity around being the expert problem‑solver. Yet it does not require you to abandon expertise. It asks you to redeploy it.
A practical starting point is to adopt a small handful of “anchor questions” you use consistently in different contexts. For example:
- At the start of a project: “What problem are we really trying to solve, and for whom?”
- In risk and resilience conversations: “What assumptions does this plan quietly rely on?”
- When evaluating an incident or failure: “If we assume good intent, what system conditions made this outcome more likely?”
- In strategy discussions: “What would have to be true for this to succeed – and how can we test those conditions early?”
- At the end of a meeting: “What question should we be asking next time that we did not ask today?”
Over time, these questions become part of your leadership signature. People begin to anticipate them, which is exactly the point. When your organisation starts asking them before you arrive in the room, you know that inquiry has become cultural, not personal.
You can also pay attention to your own “first question reflex”. After a presentation or report, notice what you instinctively ask first. Is it about numbers, people, purpose, risk, reputation, learning? That first question shapes the conversation that follows. By consciously adjusting it – for example, by starting with, “What perspective has not been heard yet?” – you can steer discussions in more thoughtful directions without adding more meetings or more content.
Finally, remember that asking better questions is not about cleverness. It is about care. We ask better questions when we care more deeply about consequences, stakeholders and truth than about being seen as decisive. The leaders we remember are rarely the ones who dazzled us with instant answers. They are the ones who helped us see problems more clearly, possibilities more broadly and responsibilities more honestly.
If the voices quoted here have a common message, it is this: in complex times, the quality of our questions may be the most important leadership asset we have. The good news is that it is a skill we can all practise – one conversation, one meeting, one carefully chosen question at a time.
The trap isn’t “no answers”; it is “great answers to the wrong question”. If you change the question from “Who’s to blame?” to “What can we learn?”, you change the behaviour and the culture that follow.
A simple experiment: in your next meeting, don’t try to sound smarter with better answers. Try to be braver with better questions – especially the first one you ask.
John Salter Consulting Services 