Keep Calm and Dig On

Keep Calm and Dig On

A “fan favorite” module in the leadership programs I teach is called “Expanding Perceptions.” The premise is that challenges arise when we get stuck in our stories: about ourselves, our colleagues, daily situations. To get unstuck, we must be willing to seek new data for the sake of seeing a different perspective. How do we do that? One way is by asking good, skillful questions.

The concept is simple enough to understand. Yet when participants begin the related activity called Question Thinking™, it gets trickier.

The goal of Question Thinking is to develop as many skillful questions as possible about a situation. (The definition of “skillful” is part of the class.) What’s the trick? I ask participants initially only to get curious about the situation, not to solve it.

Without fail, participants list a few questions… and then quickly forget the point of the exercise. During debrief, people sheepishly admit they began to work the problem.

It is endemic. Our ability to stay in the question – even for 5-7 minutes! – is thwarted by the cultural habit to immediately find solutions.

The discussion we then have is: What are we really learning when we jump into problem-solving without first digging a little deeper?

“How many licks does it take to get to the Tootsie roll center of a Tootsie pop?”

Many of you remember this classic 1970 Tootsie Roll ad, which has been randomly playing again recently. The ad highlights a young boy who desperately wants an answer to this question. In the long version of the ad, he asks several animals before approaching the wise owl, who makes a brief attempt to answer the question before succumbing to the technique everyone else uses: just bite it!

(For those of you who don’t know or remember the ad, you can see it here.)

Certainly the point of the ad is not to showcase the owl’s curiosity or patience. The ad makes me curious though. How often do we behave like the owl and dive right into problem-solving when someone brings forth an issue? Do we even know what they’re really asking? As far as the Tootsie pop ad goes, we’ll never know why the young boy was so curious. Further, it seems plausible he could’ve answered the question himself: just start licking, right? Yet he seeks counsel from others to solve it for him.

Most leaders want to empower and develop staff so they might see and do things differently on their own. If this is the case, it’s imperative to get in the habit of getting curious first. Asking questions facilitates people’s own ability to get more clear about issues and to solve things independently.

In other words, developing the ability to ask skillful questions is at the root of the root of any problem.

“We thought we had the answers. It was the questions we had wrong.” – Bono

Many people argue that problem-solving is at the heart of leadership. When we jump right in, however, we’re often only solving the symptom of the issue, which typically returns things to the status quo. If we don’t pause to ask questions, we aren’t really moving forward. We aren't expanding capacity in ourselves, others, or our organizations. And we miss the opportunity to shift perspective.

To be sure, making space to stay in a question requires patience and fortitude, two things that are often in short-supply in hard-charging organizations. One way to begin to practice this is to make it a shared responsibility among teams.

I invite you to bring this topic to your next team meeting. What challenges do you and your team face that might benefit from a strong session rooted in curiosity and good questions? Let me know. I’ll even spring for the bag of Tootsie pops!


Very well articulated argument for one of my favorite topics: asking good questions! To your point, in my own work advising senior executives, I find many times leadership teams run into trouble because, in the rush to define a solution, they don't engage in deep questioning and as a result, end up solving the wrong problem or only address the surface layer of their challenge. One simple trick I taught my teams doing executive advisory work: when doing issue diagnosis, understand the 'why' before the 'what'. When executives raise an issue, the first thing people tend to do say 'Tell me more about issue X: what is the size of this problem? Who does it impact? What have you already done about it?, etc.' But from that lines of questioning, it's very easy to fall into the solutions trap too quickly. Instead, it's much more effective to start with 'why' questions: Why is this issue important to you? If you addressed this issue, what would be the benefits? Why does your boss or CEO care if this problem were solved? How does it connect to the broader strategic goals of the organization? Doing this line of questioning first reveals the broader context for the issues raised...which allows for a much more effective conversation about solutions and quite often, leadership teams realize that the (micro) issue they were focussed on solving doesn't' actually address the larger challenges they were trying to address!

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