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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A week or so before I was due to meet Charles Handy, the most horrendous thing happened: his wife Elizabeth – the life partner thanked in all his many books for giving him the courage to change the course of his life – was killed in a road accident. The interview was of course postponed; I doubted it would ever take place; I doubted, too, whether he would make the long trip to Australia to address the Australian HR Institute’s national convention.

But a little over a month after the tragedy, I receive confirmation not just that Handy will be fulfilling his speaking commitment, but also that he is willing to do the interview. Indeed, he says generously that it will help him form his thoughts ahead of his speech. To carry on working is essential, he explains. Faced with such inexplicable loss, one can either give up or fight on. He has chosen to fight.

We meet at his apartment in south-west London, in the grey, somewhat forbidding building he and his wife occupied for more than 50 years. Inside, the flat is light, airy, peaceful.

Born in Ireland, his father was a Protestant vicar, and Handy once thought about becoming a priest himself, despite not believing in God. A colleague joked that he would make a very good bishop but a very bad curate, and the remark is spot on: with his balding head, stately manner and patient wisdom, I have never met anyone more episcopal.

When we are settled, he hands me a piece of paper headed ‘Letters to My Grandchildren’. This, he says, is where his talk in Melbourne will begin. It is the working title for his next book, which will outline the sort of world his grandchildren – now aged 11 and 12 – can look forward to. If looking forward is the right phrase, because he says there will be many challenges and uncertainties.

Ever since his 1989 book The Age of Unreason, which foresaw the great disruption that would overtake working and social structures (the two in his view are inseparable), this is the theme he has returned to constantly. “When I was young I thought everything was fixed,” he tells me. He couldn’t have been more wrong.

Defining moments

Handy joined Shell as an executive straight from Oxford in the mid-1950s and thought that would be it: relentless progress up the corporate ladder before retiring on a fat pension to play golf and grow hydrangeas. Organisations were highly structured and apparently durable; career paths carefully plotted. But after 10 years, with Elizabeth egging him on to change direction, he chucked in his executive career to become one of the UK’s first professors of management.

Similarly, the world he began deciphering in the 1970s, initially in his influential textbook Understanding Organizations, was also undergoing a revolution, with big companies starting to outsource in search of flexibility and some behemoths falling by the wayside because of their failure to adapt. The truth, he found, was that nothing was fixed.

Books such as Gods of Management and The Future of Work concentrated on business theory. But the death of his father and a spell running a centre that looked at the ethical questions facing society changed his thinking. He became what he calls a “social philosopher”, asking not how organisations were structured, but what was their purpose.

He became interested in questions of identity – his own and that of companies, treating the latter like people who could have breakdowns, lose their self-belief, respond to psychological help.

“A company in law is an individual person,” he says, “and, if you think of it as a person, that’s actually quite revealing. They should have an identity, a persona, an outward image; they should have a purpose in life; they should be able to get by; and they shouldn’t sell themselves cheap.”

Looking forward

His message in Melbourne will be that, though we don’t know exactly what the future holds, there are some straws in the wind, that “the future is here somewhere if you can glimpse it”.

“I think we are going to see the progressive dissolution of institutions,” he argues. “The things that hold society together are going to fragment and dissolve. It may not look like it from outside because they will still say ‘We are Unilever’ or whatever, but inside they will be a fluctuating group of smaller networks which will come and go and not be wholly owned by anybody.”

This new working world will comprise the three Cs – “creatives, carers and custodians”. The creatives will be fine in our entertainment-obsessed age; the carers will have their clearly demarcated place in an ageing society; but spare a thought for the third group – the managers trying to hold this fragmenting, highly individualised society together.

“There’ll be no kind of safety in an institution. Companies can no longer afford to buy all of an individual’s time and then have the terrible bore of telling them what to do with it. They will buy an employee’s product or output instead, and work will be reshaped around that,” he says.

Change fascinates Handy. How do people and businesses survive it, even turn it to their advantage? His most recent book, The Second Curve, argues that people, businesses and societies should seek to introduce radical change when they are strong and before the first curve charting their success starts to dip.

That is difficult: why change a winning team, a winning formula? But that’s exactly when you have to introduce change: inside every successful person or company is a complacent failure waiting to express itself unless it embarks on its second curve. Every big company, like every empire in history, believes its hegemony will continue forever; the sun will never set. But ask Kodak (or indeed the Romans): the sun can set, the shutter can close, very quickly.

A further danger for companies, in Handy’s view, is to allow the shareholders to call all the shots. He sees shareholders not as the owners of a business, but as the suppliers of capital being rented by an organisation. The people who really matter are the managers, the workforce and the customers – they are the true “stakeholders”. He sees the privileging of shareholders from the 1970s on as a disaster, turning companies into machines whose sole purpose was to make money for shareholders, leading to the financial crash of 2007-8 and bringing capitalism itself into disrepute.

In The Second Curve, he talks about “citizen organisations”, which are based on trust rather than control and allow “tenured workers” to vote on the direction of the company to offset the power of shareholders. It is a seductive concept.

Handy believes that as the world of work changes, and structures and hierarchies fall apart, governments will face huge challenges. Who will pay taxes, for one thing, and how will they be collected? If fewer of us are employees, and we have portfolio careers and come in and out of employment, the tried-and-trusted methods of tax collection start to break down. Throw in an ageing society and greater wealth inequality, and the world’s debt crisis can only be intensified.

He has no accounting answer to that conundrum, but instead offers one of his lateral jumps to reframe the problem.

The right questions

“The old thinking assumes everything can be given a monetary value, which is basically untrue. Air, water, smog can’t be given a monetary value. It also assumes everyone is a rational, calculating individual who believes that what matters most is money. But as Brexit shows, people make choices not just about what’s in their economic interests, but also what accords with their ideology or even what’s more fun. None of this is taken into account by traditional economics.”

Handy is fond of reframing problems in this way. He also likes to ask open rather than closed questions. Schools, he suggests, get this all wrong. Thus for him the question, as he says in his chapter on education in The Second Curve, should not be “How far is it to Birmingham?” but “Why should we go to Birmingham?”

That realisation no doubt explains why he gave up writing textbooks and embarked on writing provocative ethical treatises. Stock answers hold no interest for him, which is why he dislikes being called a “management guru”. Gurus claim to have all the answers and are seeking to attract followers. He has only questions, he says, and the ones that galvanise him these days concern who we are, what we are for and where we are going. He never quite escaped the moral imperatives of the vicarage in which he grew up, and, though he doesn’t believe in God, he is still seeking the god he believes is in all of us if we can unlock it.

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Tell us about your role at Boohoo.

I manage a small team, including the HR manager and coordinators across our head office and distribution sites as we provide resourcing and learning and development.

We look after all our people and work to support the business with the right people, who have the right skills and are in the right place at the right time.

Our main focus is employee engagement
– it’s important to us that people are happy at work and want to stay with us. We have a fantastic culture and pride ourselves on being ‘different’, so it’s something we strive to maintain through our people values.

My role involves a lot of contact with the main board to make sure we have the right HR strategy and plans in place.

What impact has Boohoo’s rapid expansion had on the organisation’s recruitment program?

It’s had a real impact. We now have two people dedicated solely to recruitment. We also have an ATS (applicant-tracking system) that sits behind our careers page.

This is really important to us as the growth of our brand means that we now attract a lot more direct applicants, which is great.

We are also looking for people with international experience, and as we expand language skills will become ever more important.

It’s essential we keep up to pace with the changing demands of the business, and that our selection process helps us identify people who can ‘do’ the job and are also a good match for our values.

Tell us about any challenges this growth has presented, and how you’ve overcome them.

The growth brings with it a demand for great people, and so we have maintained a focus on quality and adapted our recruitment processes to deliver this.

Communication is also increasingly important, and while I would love to say that we have all the answers, it’s really a work in progress.

Now we are a much bigger team, we are constantly working to identify the best methods of ensuring we are all on the same page. We have focus groups to address this and are also exploring new technologies to support this.

What inspired the move from the hospitality industry to fashion?

After many years in
the hospitality industry I was ready for a change, and having always loved fashion
I thought Boohoo would be a great opportunity.

I was also attracted by the fact that Boohoo didn’t have an HR function when I joined and so the opportunity to work with a blank canvas was exciting.

How has your CIPD membership assisted your career development?

As an HR team we use the CIPD in a number of different ways – the factsheets, research and other resources can be very useful as a starting point, as can being able to interact via social media.

For me, completing my CIPD qualifications was a great way to re-focus the underpinning theory and open my mind to new and different ways of thinking that can be adapted into your workplace and thought processes.

Working in HR is a constant learning process and understanding different approaches is something my CIPD membership and qualification has been really useful for. Making sure theories are properly applied in a way that is right for our specific business can then be the challenge.

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