Most people have heard a version of the saying ‘good leaders ask good questions’. It’s less common, however, to think about asking a good mix of different types of questions.

“When you read about this in management literature, you get insights like, ‘Good questions are follow-up questions or open-questions, but [leaders need] a little more guidance than that,”  says Arnaud Chevallier, strategy professor at IMD Business School in Switzerland.

Particularly for first-time leaders, the tendency to jump into solution mode before letting curiosity play out can put many organisational elements at risk, such as innovation (if we don’t ask questions to surface everyone’s ideas), psychological safety (if people don’t feel they can push back on an idea) and wasting time or resources (if we put all our energy into solving the wrong challenge).

That’s why Chevallier has spent years determining five types of questions that he and his co-researchers believe will help leaders and organisations to operate on a deeper, more strategic level.

“I think all executives and professionals should develop a mindful set of questions that they’re constantly updating to serve them better in the decisions they’re making,” says Chevallier.

5 types of questions

Over three years, Chevallier and his co-authors Frédéric Dalsace and Jean-Louis Barsoux, also professors at IMD, conducted interviews with hundreds of top-performing executives to learn about their favourite types of questions.

“Then we refined them using the Delphi method and organised the questions into general buckets.”

They also conducted a robust literature review.

“Management executives aren’t trained to ask questions, but other professions are – physicians, psychologists, journalists, lawyers. We wanted to learn as much as we could from those other fields [whose workforces] have thought long and hard about the meaning of questions.”

From this research, they first determined four types of question, which are as follows:

1. Investigative questions

These types of questions follow a similar line of thinking to Toyota’s ‘five whys’, says Chevallier.

“This is epitomised by the ‘what’s known?’ type of question. Investigative questions help you probe the root causes of the problem, and help you to go deeper into the decision you need to make.”

Examples:

• What is and isn’t working?
• What are the causes of the problem?
• How feasible and desirable is each option?
• What evidence supports our proposed plan?

2. Speculative questions

Going deep with investigative questions is important, but not sufficient, says Chevallier. 

It’s also useful to go broader with your line of questioning. This is where speculative questioning comes into play.

“We epitomised speculative questions within ‘what if?’ For example, ‘What if we didn’t care about costs?’ or ‘What if we could relax these other constraints?’

“[These questions] foster innovation by challenging the implicit or the explicit assumptions we come to in our decisions.

“For HR professionals, who are addressing the human component of [work], you really need to develop your subjective question mix so you’re always asking yourself ‘what’s the actual meaning that’s going on behind the words?’”

Examples:

• What other scenarios might exist?
• Could we approach this differently?
• What else might we propose?
• What can we simplify, modify, combine or eliminate?
• What potential solutions have we not considered?

“All executives and professionals should develop a mindful set of questions that they’re constantly updating to serve them better in the decisions they’re making.” – Arnaud Chevallier, strategy professor, IMD Business School

3. Productive questions

It’s also important to have a set of questions that are designed to move processes along, says Chevallier. He refers to these as the ‘Now what?’ questions.

“They’re here to help us adjust the pace of the decision making – sometimes accelerating it because the deadline is coming, or sometimes slowing down because we’ve come to a decision with a preconceived mindset or there might be cognitive biases that are crowding our judgement.”

Examples:

• What do we need to achieve before we advance to the next stage?
• Do we know enough to move forward?
• Do we have the resources to move forward?
• Are we ready to make a decision?
  

4. Interpretative questions

Interpretative, or sense-making, questions help us take what we’ve learned from our investigative, speculative and productive questions and turn them into insights.

“[These questions] are epitomised by the ‘So what?’ Okay, we’ve figured out this one thing, what is that telling us about our overarching goal?'”

Examples:

• What did we learn from this new information?
• What could this mean for our present and future actions?
• How does this fit in with our overarching goal?
• What are we trying to achieve?

Chevallier and his colleagues were originally happy with these four types of questions, but after analysing the insights gleaned from their discovery sessions with the executives, they realised something was missing. 

They needed a question type that surfaced the many things that are often left unsaid, which led to the addition of a fifth type of question.

5. Subjective questions

“We’re not dealing with robots. We’re dealing with people. In every conversation, there are hidden emotional or possibly political sets of insights. [In these cases], it’s [important] to figure out the meaning behind the words,” says Chevallier.

For people managers, this is where you might uncover people’s frustrations, tensions or hidden agendas. People’s answers to these types of questions can often lead you down a completely unexpected (and often critical) pathway.

From an organisational perspective, subjective questions can protect a business from risks such as wasted budgets, reputational damage and causing dissent or disengagement to brew in teams.

Examples:

• How do you feel about this decision?
• What aspect of this most concerns you?
• Are there any differences between what was said, what was heard and what was meant?
• Are all stakeholders genuinely aligned?
• Have we consulted all the right people?

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Curious cultures

While Chevallier and his colleague’s research didn’t go into detail about the cultural environments that are required to allow for these types of questions, his opinion is that trust and psychological safety are key to making these types of questions effective.

In an article for Harvard Business Review, they wrote: “Team members may be reluctant to explore emotional issues unless the leader provides encouragement and a safe space for discussion. 

“They may fail to share misgivings simply because no one else is doing so – a social dynamic known as pluralistic ignorance. Leaders must invite dissenting views and encourage doubters to share their concerns.”

You also need to choose your timing wisely when asking certain questions, says Chevallier.

“If you come into a new position and start asking a bunch of speculative questions, it might be too early. You might first need to establish those relationships with people.”

Read HRM’s article about how to build social capital in the workplace.

Auditing your question default

Chevallier and his colleagues have created an interactive tool – which will launch later this year – to help leaders assess which type of questions they default to. For example, you might complete the assessment and discover you have very few points allocated to speculative questions.

“[In that case], you could make a list of 10 speculative questions and, ahead of a meeting, highlight a couple that you’d like to ask,” he says.

There’s no specific mix of questions to ask, he adds. The research isn’t suggesting every situation calls for one of each type of question.

“You might ask five different investigative questions. It depends on the specific situation. 

“The five types of questions, hopefully, help people realise that there are various ways to look at a problem or a decision. Before we follow our muscle memory into one direction or another, we should periodically step back and ask, ‘Are we still going in a productive direction?’

“The world of today is not like the world of yesterday. We absolutely need to update the way we make sense of it or we’re at risk of not being able to decipher it.”

Example questions listed in this article sourced from Dalsace, Barsoux and Chevallier’s article on their research in Harvard Business Review print edition (May-June 2024). You can read the online version here.

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