Today’s Focus: Why Questions Are a Superpower in Leadership

Perhaps you recently took in some Will Ferrell as Buddy the Elf and heard that quote: it’s a question that he had embedded into his life, and I think we can learn a lot from that.

It was something he valued and it was something that he used to form connection.

I often think about networking and connecting with others, and initial questions and follow-on questions can be a fundamental superpower: how often have you heard something and said to yourself, “THAT is a great question?” I always love when I have those moments. What are some of your favourite questions to ask yourself? What about others? 

Some good ones that I’ve seen recently:

• Before speaking, ask yourself, “Why am I saying this?” – Marshall Goldsmith
• Entrepreneur Simon Squibb opens with everyone asking, “What’s your dream?”
• Steve Jobs recruited John Sculley from Pepsi by asking, ”Do you want to sell sugar water for the rest of your life, or do you want to change the world?”

Are great questions merely a bug, not a feature? Are they just a “verbal tick”? Is “that’s a great question” a filler? Stephen J. Dubner on the Freakonomics podcast, explored that question in a podcast episode in early 2023. My friend, Katelyn Bourgoin (The Buyer Psychologist) recently shared the following:

I agree: if you want better outcomes, you need to ask better questions. Well said, Katelyn!

What about “Dumb Questions”?

Dumb questions can also be really powerful: a great example of that is Under Armour CEO Stephanie Linnartz, who moved over from Marriott. While she left just over a year after taking the job, she laid out some great wisdom with LinkedIn News shortly after she had taken the job:

Before she moved into the executive seat at Under Armour, she toured stores and casually asked salespeople about, well everything: “Why do you do this? What’s selling? Why is this over here?”

We always have presuppositions about why things are the way that they are, but, if we come into an industry, as Linnartz did, getting that fundamental knowledge of “why?” is important.

I’ve found that in my career as well – I love to ask dumb questions. Any time when I’ve worked with clients on research projects, whether they’re trying to establish new markets abroad, whether they’re trying to innovate in a certain area, or even as they try to navigate regulations and approvals, asking “why is it like this? Why do you do that?” can be highly illuminating.

Often, industries tend to have baked in assumptions: recently, UnitedHealth Group CEO Andrew Witty related about the healthcare industry,

“We know the health system does not work as well as it should, and we understand people’s frustrations with it. No one would design a system like the one we have. And no one did. It’s a patchwork built over decades,” Witty wrote. “Our mission is to help make it work better.”

That “patchwork” comment resonated with me: if you don’t ask the questions to understand the patchwork, you’ll likely miss the fundamental suppositions that industry insiders have, which often, you can use to exploit opportunity.

Patchwork in industry creates opportunity to do things in a better way. What I didn’t relate in my last piece on the healthcare industry was that I believe that entities like CostPlusDrugs.com are a template for disrupting a market that is begging for it: through transparency, the company has grown to millions of clients, and I expect that will continue. Mark Cuban and his team are asking questions about a market that has a lot of baked in assumptions: further (and interesting in today’s climate), he’s already disclosed he wants to tackle insurance. I expect he will have a hospital solution, too: all in good time, especially as he vows to F*&K up the healthcare industry.

Another sector with a lot of patchwork? Financial services. The more I learn about it, the more I have questions: there is a lot of “patchwork” baked in (like the fact that COBOL is still so prevalent, even though there are fewer and fewer who can code in the language: don’t worry, AI is coming to help) and as technology advances, change is challenging and shifting some of that patchwork: and that’s not unique in industry.

Why can’t I fix my tractor? Why can’t I fix my Iphone? These are “dumb” questions that begin to approach something fundamental, which is the systems level understanding of “what is” today: it can also help us probe at future possibilities and opportunities as well.

Questions are useful for people across organizations: whether you’re a C-suite leader, whether you’re running a team, or whether you’re just trying to get a grip on your own actions, they can be illuminating: but, only if you’re willing to ask them.

Some closing thoughts:

• Questions can reveal great data sets if you formalize and standardize them. Claire Hughes Johnson (former COO of Stripe) speaks to this in the context of hiring here.
• Questions can be illuminating. I’m looking at you, coaches and managers! Understand why people do what they do, and what motivates them.
• Good questions take practice. You’re going to fall on your face for a while: this is a muscle.
• Good questions take an understanding of the world and of different verticals. There’s a reason why so many innovations these days are being driven by the concept of biomimicry, for instance.
• Be patient with questioners: they might not truly know what you know, and it might open new ways of thinking of existing paradigms and problems, even for you (back to those “dumb questions”: the most expensive words in business are “because we’ve always done it that way.”

How are you thinking about questions in your life? What questions are top of mind for you? What are you going to do with the answers?

By the way: don’t miss out on tools like Marshall Goldsmith’s bot and Tim Ferriss’s bot: trained on different data sets from both people, respectively, they might just help you get the questions AND answers you need.

Take care and talk soon.
– Jonathan