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How to Ask Better Questions

Q&A with Tom Puthiyamadam by Karen Christensen

Einstein once said, “If I had an hour to solve a problem and my life depended on the solution, I would spend the first 55 minutes determining the proper question to ask, for once I knew that, I could solve the problem in less than five minutes.” What is involved in determining ‘the proper question’?

The right question to ask is one that will allow you to gain more insight and break through issues that are hidden beneath the surface. In a disruptive business environment, there are four questions we recommend business leaders ask regularly:

  1. What are the big trends that will reshape the business environment?
  2. How will these trends disrupt our industry and business?
  3. What are the highest-impact, most uncertain issues these disruptions bring — and what possible future scenarios do they suggest?
  4. What are the implications of these scenarios?

We’ve found that executives get energized by the insight sharing and debate that takes them through the first three questions, but the real payoff comes in pushing through the fourth question. I advise people to get really specific about implications. By the time the fourth question is answered, you will have developed a forward-looking point of view, and you can then consider what actions are required today so your organization can put the transformation process into motion.

What can leaders do to get better at asking questions?

If you’ve ever spent any amount of time with a four-year-old, you know they love to ask ‘why?’ We can learn a lot from their insatiable curiosity. I advise people to make a habit of questioning their questions. Just as children question all of our answers, question why you are asking the initial question, and try to peel back the layers on what it is that you are seeking to uncover.

If, say, a retail executive’s company is suddenly losing market share, the question to ask isn’t the most obvious one, such as ‘Why is our competitor picking up market share?’ You have to dig deeper and ask things like:

  • Why might today’s customers expect in-store services unrelated to what they’re buying?
  • Why are some competitors adjusting prices in real time?
  • Why do Internet shoppers want alternatives to home delivery?
  • How will technology turn shopping aisles into showrooms? 

The answers to questions like these can offer guidance on how to boost market share, which is what you really want to do.

Talk a bit about the skill of ‘framing’.

Think about what a frame does for a picture: It focuses attention to produce the greatest impact. Generally speaking, you probably know where and why you have a concern, but brainstorming the right ‘framing questions’ can lead to more powerful solutions. As you probe deeper into a problem and decide how to frame it, you may find a new, better solution than what you originally considered.

For example, a home appliances company may try to build a customer bond with its products by launching a smart home app. However, when the business leaders ask probing questions, such as the questions listed earlier, they may re-frame the problem and discover that what customers really want is personalized, on-time service calls. That company could respond by better training service technicians and providing them with digital tools to troubleshoot customers’ problems faster and more effectively.

Talk a bit about the role of diversity in coming up with good questions.

It’s critical to view a problem from more than one angle. Every group of decision-makers should be made up of diverse people who can reach deeper insights together. For example, when we work with clients, we might bring together user experience specialists, designers, financial experts and advertisers, all of whom shed their titles and work shoulder-to-shoulder to create the best solution for the problem at hand. By viewing an issue through multiple lenses, the goal is to drive true transformation, rather than just incremental change.


Tom Puthiyamadam is Digital Global Leader and U.S. Advisory Markets and Competencies Leader at PwC, based in New York City.


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This article appeared in the Fall 2018 issue. Published by the University of Toronto’s Rotman School of Management, Rotman Management explores themes of interest to leaders, innovators and entrepreneurs.

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