The Questioning Leader: Rethinking How We Learn, Listen, and Lead

In Question to Learn, Joe Lalley invites leaders to rediscover an often-overlooked skill—asking questions not to prove what they know, but to explore what they don’t. In my recent conversation on The Business of Government Hour, Lalley lays out how leaders can reclaim curiosity as a catalyst for learning, empathy, and innovation. Through rich stories drawn from his career and personal life, he argued that “the true power of questions lies not in the questions themselves, but in the motives behind them.” What emerges from Lalley’s reflections is a leadership philosophy centered on intentional curiosity—one that replaces the illusion of knowing with the discipline of discovery.

His insights offer a roadmap for leaders seeking to unlock genuine learning, collaboration, and innovation within their organizations.

From Technical Expertise to Empathic Inquiry

Lalley traces the origins of his transformation to a pivotal experience at Stanford University’s d.school, where he encountered the principles of design thinking. “Up to that point in my career,” he recalled, “I based everything I created on two things: what the business wanted—money, market share—and what was technically feasible.” He was a product manager and user-experience designer focused on specifications and execution.

But after attending a session at the d.school he encountered a different approach: solving problems by applying empathy and iteration.

It was there that Lalley heard the story of Doug Dietz, a GE designer who reimagined the MRI experience for children. Instead of sedating 80 percent of young patients, Dietz and his team engaged with the children and their families to redesign the environment as an adventure—a “pirate ship MRI.” The result? The sedation rate dropped to nearly zero. Lalley described his reaction as “a pivotal moment where I changed my relationship with questions.” The story taught him that genuine inquiry starts with curiosity about people, not processes or profits.

“I realized I had never really asked or looked at the experience of people,” he admitted. “I came back from that program pretty changed.”

The Motives Behind the Question

Central to Lalley’s thesis is his observation that “the questions we ask aren’t always what they seem.” In workplaces, curiosity can easily be replaced by pretense—questions asked to assert power, confirm biases, or perform intelligence rather than to learn. Lalley described this as “the slow degradation of pure motives behind questions.” He catalogued several types of these impure inquiries that plague teams and stifle innovation: the Power Move Question, the Hero Question, the Selfie Question, and what he calls the Time Machine Question.

The Time Machine Question—“How will this scale?”—illustrates how misplaced motives derail learning. As Lalley explained, “It can bring the entire team to a grinding halt because the problem hasn’t even been figured out yet.” When a leader jumps ahead to implementation before understanding, they shift the team’s focus from defining the problem to defending assumptions. The Power Move Question is even more corrosive: a leader firing rapid questions in public to demonstrate authority rather than curiosity. “The motive behind that really isn’t curiosity,” Lalley observed. “It’s to show the group what a visionary thinker I am.” The consequences are predictable: “People detach, defer, and hold back their own ideas.”

Lalley’s insight here is as much psychological as managerial: motives matter.

A question’s form may appear benign, but its intent can shape culture. “You need quantity first so that you can eventually get to quality,” he said. Genuine dialogue thrives when questions invite exploration, not evaluation.

Escaping the “Curiosity Theater”

In what he calls “one of my favorite and most cringe-worthy chapters,” Lalley introduces the concept of Curiosity Theater—the illusion of inquiry without the substance of discovery.

Drawing from his years on conference panels, he described how moderators and panelists often script both questions and answers in advance: “Each panelist would share three or four questions they wanted the moderator to ask them—they knew the answers. It was theater.” The result, he noted, was a missed opportunity for authentic learning. “You’ve got this group of people with really interesting experience and backgrounds,” he lamented, “and there really wasn’t an opportunity for us to interact with each other.”

The antidote to Curiosity Theater is what Lalley calls the workshop mindset—spaces where hierarchy gives way to honesty and leaders ask questions they genuinely don’t know the answers to.

“If you can break down the corporate speak and the adherence to hierarchy,” he explained, “people can have real dialogue and ask questions that they don’t know the answers to—which is very unlike the panel experience.” The principle is simple but profound: ask questions you don’t know the answer to, but want the answer to.

Signals of a Culture That Has Stopped Learning

Lalley’s emphasis on questions as cultural indicators offers one of the book’s most practical leadership lessons.

“If you really want to know a company’s culture,” he advised, “attend some meetings.”

He described a familiar scenario: a leader opens by declaring that “all ideas are welcome,” but then adds, “by the end of this, I want you to get to X.” That single statement, Lalley said, “blocks new thinking” because it sets predetermined outcomes. Another red flag is the leader who leaves the meeting early—signaling that the topic isn’t a priority. Even small habits like consistently arriving late to meetings, he noted, erode a culture of respect and curiosity: “That becomes kind of the culture, where it’s OK not to really respect other people’s time.”

These seemingly minor behaviors accumulate to create what Lalley calls “tell-tale signs that a team has drifted away from asking questions to learn.” Leadership, in his view, is as much about modeling curiosity as commanding direction.

From Brainstorming to Question Storming

Among Lalley’s most actionable contributions is a method he calls Question Storming—a deliberate inversion of the classic brainstorming session. “Brainstorming sessions feel great during the actual meeting,” he said, “but they often fade out right after.” The reason: most ideas are “solutions in search of problems.”

Question Storming flips this pattern by focusing exclusively on questions.

“You may pose a problem to a group,” Lalley explained, “but instead of thinking about solutions, you can only think of questions. When did this start? What do we know about it? What have we heard from customers?”

The process begins with five minutes of silent, individual writing. “It only works if you start silent,” Lalley emphasized. “If you start with discussion, somebody will dominate.” The silence ensures inclusivity and diversity of thought: “Everyone has to participate, and probably everyone has different perspectives.” This practice, he added, “democratizes meetings and stops the derailing by the expert or the talker.”

The Power of Subtraction

In another of his inventive techniques, Lalley advocates for subtraction workshops—sessions designed not to add more initiatives but to intentionally stop doing certain things. “Most workshops result in something new,” he observed. “The word ‘priority’ has stretched into a plural.” Lalley and his team experimented with reversing this dynamic: “We said, let’s explore what we can just stop doing.” The effect was liberating. “We cleared space for the things that are really important and let go of things that weren’t effective.”

Yet, as he noted, subtraction is psychologically harder than addition. “Clients would love the idea but often get nervous as the session approached.” To illustrate why, Lalley shared a personal story: running out of hangers and instinctively reaching for his phone to order more—before realizing he could instead remove unused clothes.

“I solved the problem through subtraction instead of addition,” he said. The metaphor extends seamlessly to leadership: growth often requires letting go.

Flipping the Script: Outroductions and the Five Hows

Lalley’s flair for reframing routine behaviors extends to meetings themselves. He proposes replacing introductions with outroductions. “What happens in most meetings,” he explained, “is that introductions take half the time and subtly reinforce hierarchy.” When someone begins with “I’m the vice president of X,” others naturally defer.

Lalley suggests flipping it: “Start the meeting and say, ‘We’ll leave introductions until the end.’”

By then, participants have context and urgency, making introductions concise and meaningful. "It makes people uncomfortable,” he admitted, “but it works.”

Similarly, Lalley’s “Five Hows” technique pushes teams beyond vague strategy to concrete action. After identifying a goal—say, creating a customer advisory board—he encourages teams to ask, How will we do that? and repeat the question five times, drilling down to specifics: “If those little things don’t happen, the big thing probably doesn’t happen.” The process enforces accountability and bridges the gap between aspiration and execution.

How Might We? Reframing for Possibility

Few phrases capture Lalley’s design thinking roots better than the simple but powerful How Might We…?question.

Each word, he explains, serves a purpose: How signals curiosity, Might allows for possibility, and We implies collaboration. “It involves everyone and sparks new thinking,” he said. By exploring opposites—How might we make people want the middle tier instead of the top?—leaders can reveal hidden insights and expand their creative range. “It probably opens up the possibility for different answers,” Lalley noted. In bureaucratic systems where assumptions calcify quickly, such reframing can be revolutionary.

Learning Through Discomfort

Curiosity, Lalley insists, is inseparable from discomfort. He recounts his experience performing stand-up comedy as an exercise in “getting comfortable with discomfort.” Standing before an audience, “you immediately know if your joke is funny—you see people’s reactions right away.” The experience mirrors leadership: feedback is often instant and unfiltered. “There are very few things where you deliver the product and immediately know how people react,” he observed. The key is embracing that vulnerability as data, not failure.

He also tells a humbling story about accidentally sending a “reply all” email to 50,000 customers. “The most common reply-all message was, ‘Can we all stop replying all?’” What he learned wasn’t about better processes but about mindset: “The instructions were really good. The process was fine. It wasn’t the tool—it was my mindset. I was in a rush.”

His conclusion carries a timeless management lesson: “People often jump to redefine the process when they should rethink their thinking.”

Avoiding False Compromise

In both personal and professional life, Lalley warns against what he calls “false compromise”—solutions that split the difference but satisfy no one. He illustrates this through two anecdotes: a workplace debate about hybrid work and a domestic dispute between his children over an orange. His initial instinct was to “cut it in half,” but later discovered that “one wanted to make juice and one wanted to bake.” By asking why each child wanted the orange, he found a true win-win. The same principle applied to hybrid work. “Instead of dividing the week between home and office,” he said, “we asked people about the kinds of tasks they did.” Some required collaboration, others concentration. “It’s not about the days of the week—it’s about the motives and the goals.”

In other words, leaders should resist defaulting to balance and aim for understanding.

Mindset Over Playbook

Perhaps the most profound takeaway from Question to Learnis Lalley’s rejection of rigid playbooks in favor of adaptable mindsets. “I talk a lot about mindset, skill set, and tool set,” he explained. “Without the mindset, the judgment isn’t there.” Playbooks—like standard operating procedures in government—offer structure but can become stale. “Many situations have their own unique challenges,” Lalley noted. “Almost every time, I would change something along the way.” Instead, he advocates for “smaller building blocks” and empowering teams with the judgment to know when to apply them.

The distinction is crucial: procedures provide consistency, but mindset provides agility.

The Art of Listening

The book’s dedication—to Lalley’s father, Frank—encapsulates its human heart. “He was one of the greatest listeners I’ve ever known,” Lalley wrote. “He was totally fine with silence and would wait patiently for the answer.” From his father, he learned that listening is not the pause between talking, but a form of attention. “He didn’t fill silence with anything,” Lalley recalled. “He just waited. He didn’t have a second question prepared. His second question was based on your answer.”

This, Lalley argues, is the essence of questioning to learn: to listen not for confirmation, but for revelation.

His favorite question embodies this spirit: How did you come to feel that way? It avoids accusation and invites empathy. “The ‘why’ question can feel like an interrogation,” he said. “‘How did you come to feel that way?’ opens dialogue. It helps you learn the steps that got someone there.” Whether applied to customers or colleagues, the question transforms interaction into understanding.

A Leadership Philosophy of Curiosity

Across every story and exercise, Lalley returns to a single conviction: leadership begins with curiosity.

When leaders replace performative certainty with genuine inquiry, they create conditions where innovation and trust can flourish. His message is particularly resonant for government executives, whose environments often prize procedure over exploration. As Lalley demonstrates, the skill of asking better questions is not ancillary to leadership—it is leadership. It fosters empathy with citizens, understanding across agencies, and learning within systems that too often reward answers over insight.

In a world awash in information, Question to Learn reminds us that wisdom starts with wonder. Lalley’s father modeled it through listening; Dietz embodied it through empathy; Lalley himself teaches it through practice. As he told me, “Ask questions you don’t know the answer to—but want the answer to.” In those moments, leaders do more than manage—they learn, and in learning, they lead.