Better Questions Make for Better Decisions

While anyone can ask questions, effective questioning requires skill and strategic thinking, especially for senior leaders whose role it is to guide their teams through uncharted territories. To foster innovation and effective decision-making, leaders must cultivate an inquisitive mindset and prioritise strategic questions over merely operational ones.

The former British Prime Minister Tony Blair wrote a marvellous autobiography, A Journey, which repays the reading as it contains a host of vignettes into the challenges faced by leaders. In the chapter 'We Govern in Prose', Blair offers some insightful thoughts about another British Prime Minister, Neville Chamberlain.

For those who are unfamiliar with this period of history, Chamberlain is perhaps most widely known, and often mocked, for his attempts to appease Hitler prior to the outbreak of the Second World War. In hindsight the course of action Chamberlain chose seems singularly clueless, but as Blair insightfully observes:

Chamberlain was a good man, driven by good motives. So what was the error? The mistake was in not recognising the fundamental question. And here is the difficulty of leadership: first you have to be able to identify that fundamental question. That sounds daft - surely it is obvious; but analyse the situation for a moment and it isn't.

For decision makers in organisations, the stakes are considerably lower than the likelihood of another world war. Yet, the principle involved, remains the same—have they identified the fundamental question?

This issue becomes greatly magnified when the flow of questions is coming thick and fast. In such situations, key insights and concerns are often pushed to one side as positional authority and authoritarian styles dominate the decision-making process in an attempt to maintain control and not lose momentum.

This intractable problem has no easy fix as a comprehensive solution involves reasoned deliberation, authoritative leadership, and capabilities which account for a complex range of strategic challenges. However, one key to the solution can be implemented by everyone within an organisation—regardless of seniority—and that is asking better questions.

Questions Are Cheap, Questioning is Expensive

If you have spent any time around children, or even vaguely remember what it was like to be a child, you will know that questions abound:

Parent: "It's time to go to bed now."
Child: "Why?"
Parent: "Because it's late and you need to sleep."
Child: "Why?"
Parent: "So you can be well-rested for school tomorrow."
Child: "Why?"
Parent: "Because getting enough sleep helps you learn and grow."
Child: "Why?"
Parent: "Because your brain and body need rest to function properly."
Child: "Why?"
Parent: "So you can have energy and feel good during the day."

Because questions come so readily as part of the human condition, we can be lulled into thinking that asking questions is a simple process—yet this is far from true. This is because there is a difference between asking questions and the process of questioning. The former can be discharged by simply asking "why?" and has become a widely used approach in organisations thanks to the 'Five Whys' technique. While this is not without some merit, it suffers from several criticisms—most notably that the volume of 'whys' creates a false sense of plumbing to the root cause of a situation. In consequence simply asking "why?" differs from a series of strategically positioned questions designed to take the participants on a journey of discovery.

This is a critical concept because in the world of business, the average manager has no more experience in asking questions than does the average employee. In many ways, questions are analogous to opinions (everyone has one), while the act of questioning is analogous to reasoned deliberation—only seasoned experts can do it well.

Unlike in other professions—psychologists, philosophers, lawyers, historians, or medical doctors—managers are not formally trained in the art of questioning. This is not only problematic, but highly costly for organisations.

AI is only adding momentum to this problem, as services such as ChatGPT or Copilot drive the shift from managers as subject matter experts (SME), who lead the team due to their expertise, to managers as questioners in chief. This shift in management approach was summed up by Jane Fraser, CEO of Citigroup, in an interview for Fortune magazine: 'innovation isn't happening because there's a genius at the top of the company that's coming up with the answers for everything.'

The role of managers—particularly senior ones—is to help other managers and employees explore ideas they didn't realise needed exploring.

Yet to explore the unexplored involves not just improving questioning technique, it necessitates effective time management. In a time bound meeting, every question asked is one less question that can now be asked. For this reason, managers need to be awake to when a line of questioning is giving diminishing returns, when staff are becoming encamped in a fixed mindset about a topic, or when a subject is considered sensitive and is being avoided. 'Don't mention the restructure' is a classic in this genre.

Yet, if history demonstrates one thing clearly, it is that leaders are more likely to get into trouble for the questions they do not ask than for the questions they do. In business this reality is writ large when senior managers and directors are held accountable in situations in which they had failed to ask appropriate questions and instead relied heavily on the advice of staff or contractors. In extreme cases, managers and board members can go to jail for not asking the right questions.

In 2014 a failure of investigation led a team at the French rail operator SNCF to neglect an essential piece of data during its €15 billion purchase of 1,860 regional trains. No one thought to ask whether the platform measurements were universal. They weren't. The trains proved too wide for 1,300 older stations—a mistake that cost €50 million to fix.

Strategic Vs Planning Questions

In Strategic Direction Versus Initiative Planning I outlined the key difference between planning and strategy:

Planning is a deductive process used by managers to achieve orderly outcomes. The purpose is to provide clarity regarding what to do about events that will take place.
Strategy tends to be inductive in nature and revolves around looking for relationships and patterns. These relationships and patterns help the strategist to draw conclusions from which they can make choices about events that may take place.

In the realm of questioning, there are planning questions and strategic questions. Just as the strategic direction must be set before teams can start planning for the initiatives, strategic questions need asking before teams can get into the nitty gritty of planning questions. The challenge is keeping stakeholders in the right zone. In much the same way as when you try and talk about outcomes with most stakeholders they dive straight into solutions, so too with strategic questioning people will tend to instead ask a host of technical planning questions—or give planning answers to strategic questions.

In the realm of strategic questioning, excellent research was conducted by Arnaud Chevallier, Frédéric Dalsace, and Jean-Louis Barsoux at the IMD Business school. Their work grouped strategic questions into five domains:

Investigative (What's Known?): seeks to understand what is known to help dig deeper into the viability of possible solutions. Examples include:
- How feasible is each option?
- What are the causes of the problem?
Speculative (What If?): seeks to reframe understanding based on possibilities to find a more creative solution. Examples include:
- What potential solutions have we not considered?
- What can we simplify/modify/eliminate?
Productive (Now What?): seeks to understand capabilities and availabilities such as availability of talent, time, budget. Examples include:
- Do we have the resources to begin work?
- Are we ready to decide?
Interpretive (So What?): seeks to understand the nature of the problem, not just the surface issue. Examples include:
- How does this fit with our strategy?
- What did we learn from the new information?
Subjective (What's Unsaid?): seeks to understand the emotion of decision making such as personal reservations or hidden agendas. Examples include:
- How do you feel about this decision?
- Are stakeholders genuinely aligned to the strategy?

Breaking the Question Cycle

At the start of this column, I noted that a manager's experience and expertise can blind them to the situation at hand as they press for what they know to be true rather than challenging their existing assumptions. The same is true of questioning.

Because of this, it is important to begin by questioning your questioning style. This can be done by thinking about a series of questions for two or three projects, giving it a few days in between thinking about each project, and see if any consistent trends or blind spots surface. Perhaps you are very strong on investigative and productive questions, but weak or avoidant of speculative or subjective questions. Such bias is important to understand as it helps to unlock your primary modality in questioning, or rather the way in which you listen to the answers. Are you questioning/listening to fix or to learn?

There is a time and place for both and knowing when to use which is essential in the process of asking questions to make better decisions. Asking to fix tends to be of more value in the planning phase of the work—once the strategic decision has been made. This is because we have decided the what and now need to implement which is a how driven process. But before planning comes strategy, and for strategic questions we need to remain of an inquisitive neutral mindset. Something which is all about listening to learn.

The latter capability of listening to learn is vital for anyone seeking to move up the career ladder because with seniority comes increased risk and the opportunity to take bigger steps and deploy more resources. In such an environment, a manager will come across an increasing number of situations of which they have no experience or expertise. In such a setting, the only deeply established skillset which is effective is the ability to question and learn from those questions.

High performers do this ably and quickly, seeming to rapidly master a new domain in a very short time span and provide value to the project. IQ and EQ help greatly with this, but in the end it all comes down to asking the right questions. For which engaging with the key domains of strategic questioning will act as an inestimable base, no matter your industry.

Good night, and good luck.