PDF Summary:The Curious Leader, by Jon Bassford

In today’s rapidly changing environment, traditional leadership skills like decision-making and goal-setting are no longer enough to keep organizations in the game. In The Curious Leader, Jon Bassford contends that curiosity—an active drive to probe deeper, ask harder questions, and seek out what others overlook—is the quality that separates leaders who innovate and grow from those who stagnate. To lead with curiosity, Bassford says leaders must transform in three key areas: They must adopt a growth-oriented mindset, build a culture that rewards inquiry and exploration, and apply that same questioning spirit to their operational processes.

This guide explores what Bassford describes as the essential components of curiosity-driven leadership and the steps required to put them into practice. We’ll also include input from other sources on curiosity and leadership like Seek by Scott Shigeoka and Trust and Inspire by Stephen M.R. Covey.

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Third, Covey echoes Bassford’s clarification that servant leadership isn’t passive. He argues that leaders must set specific expectations and hold people accountable while granting enough autonomy that employees don’t feel micromanaged—a balance he calls “extending faith.”

Get Curious About Your People

Once you’ve adopted the servant leadership philosophy, the next step is to put it into practice by learning about each team member as an individual. Bassford argues that leaders who understand what each employee does well, what drives them, and where they want to grow are better positioned to assign work effectively, build stronger teams, and retain talent. People produce their best work when they’re engaged in tasks that match their interests and abilities—so making the effort to learn what drives each individual isn’t a soft exercise but a practical strategy for better performance and fewer mistakes.

(Shortform note: Gallup’s research confirms Bassford’s claim that strengths-based management is a practical strategy, not a soft one. Using survey data from 1,003 US workers, Gallup reported that engagement was far higher (61%) among employees who felt their supervisors emphasized what they did well than among those who felt completely overlooked (2%). This suggests that even imperfect efforts to learn what your people do well will dramatically outperform not trying at all.)

Gathering these insights requires deliberate effort; it won’t happen on its own. Bassford recommends several approaches for learning about your team, ranging from formal to informal. On the formal side, he suggests rethinking performance reviews as forward-looking conversations about goals and motivations rather than backward-looking assessments. The knowledge leaders gain should feed into personalized plans for growth that align each person’s growth with the organization’s needs.

(Shortform note: In Empowered, Marty Cagan and Chris Jones offer a concrete framework for the forward-looking reviews Bassford recommends: Perform a skills assessment for each team member and build a tailored development plan focused on no more than three growth areas at a time. This narrow focus prevents conversations about goals and motivations from becoming unfocused wish lists that never translate into real growth, and it gives both you and your employee a clear, manageable target to work toward together.)

On the informal side, Bassford favors lower-pressure methods, such as casual check-ins, firsthand observation of how people do their jobs, and everyday conversations that reveal interests or abilities formal meetings may miss. Cross-departmental collaboration—where employees work alongside people from different teams—can also reveal hidden strengths and create new connections across the organization.

(Shortform note: In You Win in the Locker Room First, Jon Gordon and Mike Smith add that during the informal interactions Bassford recommends, listening matters more than talking. Rather than just observing how people work, actively ask thoughtful questions and pay genuine attention to the answers. They also emphasize making yourself visible beyond formal settings—showing up in break rooms and hallways—so team members see you as approachable, which makes them more likely to share the interests and abilities that formal meetings often miss.)

Scale Your Curiosity

With the right philosophy and people-knowledge in place, leaders can begin shaping the organizational culture itself. Bassford defines culture as the habits, management practices, and norms that shape how people act every day—particularly the elements that directly drive performance and results.

Bassford asserts that culture must be shaped and driven through leadership. Left unmanaged, cultures form on their own—and the result is rarely what an organization needs. Leaders must be intentional about what behaviors they want to see, then actively reinforce those behaviors through how they run meetings, respond to ideas, handle mistakes, and allocate resources. Stating values on paper means nothing if leaders don’t actually use them to guide their decisions and behaviors.

Identify Your Organization’s Current Culture

In Primal Leadership, Daniel Goleman, Richard Boyatzis, and Annie McKee support both Bassford’s definition of culture as the norms and habits that drive daily behavior. They also echo his warning that unmanaged cultures form on their own, and they offer a method for taking control of the process.

Their first step is to uncover the cultural reality of your organization by asking employees at all levels open-ended questions about what’s helping or hindering their success and what they care about. The shared language that emerges will reveal the true norms shaping daily behavior—which may differ significantly from whatever values leadership has posted on the wall. Only once you understand this gap between your stated and actual culture can you begin intentionally reinforcing the behaviors Bassford describes.

The Practices Behind Curious Cultures

Bassford recommends several practices to build a culture where curiosity flourishes. First, pose broad, exploratory questions that push people past habitual assumptions. You should also show real interest when others contribute, and build recurring forums where disagreement and suggestion-sharing are normal parts of work. Bassford is especially insistent on holding your opinion in reserve until everyone else has weighed in—when a leader shares their perspective first, it pulls the room toward agreement and away from independent thinking. By waiting, you create space for everyone to contribute honestly.

(Shortform note: Research on how employees share ideas and bring up questions suggests that the practices Bassford recommends are necessary but may not be sufficient on their own. Studies found that the strongest predictor of whether employees actually speak up isn’t the existence of forums or open-door policies—it’s whether employees perceive their manager as genuinely open to input. Even well-intentioned leaders can inadvertently suppress workers’ speech through subtle cues like responding dismissively or not fully listening. Bassford’s structures may only work if leaders consistently demonstrate through their responses that contributions are genuinely valued.)

Bassford also emphasizes the value of new employees as a source of fresh perspectives. People who are new to an organization see inefficiencies and assumptions that long-tenured employees have become blind to. Yet in most workplaces, new hires face the strongest pressure to conform and the most resistance when they speak up. A culture grounded in curiosity inverts this—treating new perspectives as assets and building structured opportunities for new hires to share what they observe (such as feedback sessions in the first few months).

(Shortform note: Research on organizational socialization confirms Bassford’s concern about new employees losing their fresh perspectives. Studies show that new hires choose whether to stay with their employer within a very short period, during which the primary pressure they face is to conform to existing norms. This means the window for capturing their outsider’s perspective is narrower than most organizations realize—making Bassford’s recommendation for structured feedback sessions in the first few months especially urgent.)

Beneath all these practices lies what Bassford considers the essential foundation: psychological safety, identified by psychologist Amy Edmondson as the shared belief that it’s safe to express ideas, admit mistakes, and take risks without fearing punishment or humiliation. Research shows that psychological safety is the single most important factor in team performance—more than individual talent or team structure. Without it, no culture-building practices can function, because people won’t participate honestly. Building psychological safety requires leaders to consistently demonstrate that questioning is welcomed, mistakes are treated as opportunities for growth, and vulnerability is met with support rather than judgment.

(Shortform note: While Bassford presents psychological safety as the essential foundation of team performance, Edmondson’s research reveals an important caveat: Psychological safety alone isn’t enough. It must be paired with high accountability to drive results. High safety with low accountability creates a pleasant but stagnant environment where deadlines slip and standards erode, while high accountability without safety creates fear that suppresses honest communication. Peak team performance occurs only when both are present — when people feel safe to speak up and are expected to deliver.)

Applying Curiosity to Operations

Bassford argues that curious leadership also means understanding the operational side of your organization—not just on the surface, but deeply enough to spot strengths, friction points, and opportunities to improve performance. Rather than accepting how things have always been done, leaders must continuously evaluate their systems and processes to ensure they’re delivering the outcomes the organization needs without wasting time, money, or effort. Without this ongoing scrutiny, inefficiencies pile up, outdated systems persist, and the organization gradually falls behind.

(Shortform note: The urgency behind Bassford’s argument becomes clearer when you consider what operational inefficiency costs you. According to IDC research, inefficient operations can drain roughly one-fifth to nearly one-third of a company’s annual revenue. This figure shows that continuous scrutiny of your systems isn’t optional—left unchecked, operational blind spots don’t just slow you down; they quietly erode a significant portion of the value your organization creates.)

Probing Beneath The Surface

The foundation of operational improvement is learning to probe more effectively. Bassford emphasizes the importance of asking diagnostic questions over fault-finding when exploring operational issues. Questions aimed at assigning responsibility tend to shut learning down, while questions that uncover contributing factors make real analysis possible. Leaders who probe beneath the obvious—following up on initial answers, challenging comfortable assumptions, and looking at problems from angles others haven’t considered—uncover insights that lead to genuine improvement.

A practical point Bassford emphasizes is that the quality of an answer depends on the precision of the question. Vague or tangential questions produce incomplete information. Leaders get better results when they identify exactly what they need to know and frame their inquiry around that core concern, using open-ended questions rather than narrow ones.

Asking the Right Questions The Right Way

In Humble Inquiry, MIT organizational psychologist Edgar Schein provides an intellectual framework that deepens both of Bassford's points about effective operational questioning.

On the distinction between diagnostic and fault-finding questions, Schein argues that most leaders operate in a “tell” culture—asking questions that already have an implied answer, which functions as a subtle form of blame assignment and shuts down honest communication. Genuine inquiry, by contrast, requires asking questions to which you truly don’t know the answer, approaching problems with curiosity rather than from a position of authority.

When it comes to precision, Schein identifies three types of diagnostic questions worth distinguishing: those that help make sense of a situation, those that surface emotional reactions, and those that clarify what actions have been or need to be taken. Knowing which type you need before you ask dramatically sharpens both the question and the information it returns.

Bassford recommends several established tools to structure this inquiry: repeatedly asking “why” five times to move past surface explanations to root causes (the 5 Whys technique); framing questions that are specific, measurable, and tied to clear timelines; performing an organizational SWOT analysis (strengths, weaknesses, opportunities, and threats), though he warns this must go deeper than surface-level discussion; and comparing processes against industry benchmarks to identify gaps. He also advocates bringing in external consultants when internal biases and blind spots prevent objective evaluation—an outside perspective can ask the uncomfortable questions that insiders avoid.

When to Use Each Inquiry Tool

While Bassford presents the 5 Whys, SWOT, benchmarking, and external consultants as a general toolkit, each tool is best suited to a specific type of problem. Root-cause tools like the 5 Whys work best when the causes of a problem are unclear—they help uncover the root cause of recurring operational failures where the surface symptom is obvious but the underlying driver isn’t. SWOT, by contrast, is often a great starting point because it surfaces the most critical problems—meaning it’s better used for broad strategic stocktaking than for drilling into a specific issue.

A practical sequence is to use SWOT first to identify which problems deserve attention, then apply the 5 Whys to investigate the root causes of those specific problems. Benchmarking, meanwhile, is especially useful when you need external proof that a performance gap exists—industry data showing where your organization falls behind competitors provides a concrete basis for strategic decisions that internal observations alone may not.

Improving Processes

Beyond questioning, leaders must systematically evaluate and refine how things get done. Bassford outlines a four-part approach: First, pinpoint areas where processes may be underperforming; second, gather input from the people who interact with those processes daily (particularly frontline employees who encounter friction points firsthand); third, critically assess the data to identify overlaps, bottlenecks, and steps that don’t add value; and fourth, implement changes and monitor the results on an ongoing basis.

(Shortform note: Bassford’s four-step approach aligns with W. Edwards Deming’s continuous improvement framework—the Plan-Do-Check-Act (PDCA) cycle—with a few minor differences. Deming’s “plan” step is the same as Bassford’s first step, but on top of figuring out what needs to change, he says you should plan how to make the change. The “do” stage requires some experimentation beyond simply gathering input—he says to do a trial run to see how planned changes actually pan out (for example, how they really affect frontline workers). The “check” stage is the same as Bassford’s third step, but you should also assess the result of your trial run from the previous stage. Finally, the “act” stage is virtually the same as Bassford’s fourth step.)

Technology is an important part of this evaluation—from project management and payroll software to communication and data analytics tools. Instead of layering on separate apps that teams must constantly patch together, Bassford says leaders should choose tools that fit into a coherent system and make coordination easier rather than harder. Too many unintegrated platforms create information silos and process breakdowns, so leaders should prioritize solutions that connect with existing systems and support the overall workflow, ensuring technology serves the organization rather than complicating it.

(Shortform note: Research confirms the operational risk Bassford describes. According to MuleSoft’s annual Connectivity Benchmark Report, organizations use an average of more than 1,000 different applications, of which 70% aren’t properly integrated with other systems. Eighty percent of organizations report that integration challenges are slowing progress, and building custom workarounds to patch fragmented systems together costs millions of dollars annually. This suggests that the problem of leaders layering on separate tools that teams must constantly patch together isn’t an edge case but the norm for most organizations, making the approach Bassford recommends an active corrective rather than simply good practice.)

Bassford also identifies four interconnected operational areas that leaders should regularly question and evaluate: 1) whether decisions align with organizational values and authority is properly delegated, 2) whether people at every level are ready and able to embrace change, 3) whether internal processes are strong and resilient enough to support the organization’s goals, and 4) whether resources like time, money, and talent are being used effectively.

These operational areas depend on each other—an organization that runs lean but resists change becomes brittle, and well-built processes mean little if leadership isn’t making coherent decisions. The curious leader’s job is to keep examining all four, since neglecting any one of them undermines the others.

(Shortform note: The elements Bassford discusses are important for more than just operational efficiency—they’re also crucial for organizational health (OH) and are part of the McKinsey Institute’s nine interconnected dimensions of OH. Bassford’s first area aligns with McKinsey’s dimensions of direction and coordination and control. His second area aligns with McKinsey’s dimension of innovation and learning. His third area also aligns with McKinsey’s dimension of coordination and control. Finally, his fourth area aligns with McKinsey’s dimension of capability.)

Putting Curiosity Into Practice

Even leaders who understand the value of curiosity will encounter forces that work against it. Bassford identifies three common barriers and offers practical guidance for moving past them and embedding curiosity into daily work.

Roadblocks to Curiosity

According to Bassford, the most pervasive barrier when practicing curiosity is fear. People hesitate to ask questions, propose ideas, or try new approaches because they’re afraid of failing, being judged, wasting limited resources, or speaking up in an environment where trust is low. These fears all connect back to the same root: Without psychological safety (the kind we discussed in the section on culture) people will default to caution over curiosity. Leaders address this not through one-time declarations but through consistent behavior that demonstrates that curiosity is safe and valued.

The second barrier is ego—specifically, the leader’s ego. When leaders are too attached to their own ideas, too quick to dismiss input, or too focused on maintaining control, they shut down the very curiosity they claim to want. Bassford argues that leaders should ask whether their own habits are suppressing inquiry—for instance, whether they become protective of their views, take up too much conversational space, or respond to mistakes by searching for fault instead of solutions. Recognizing these patterns isn’t a sign of weakness, it’s the starting point for creating real change.

The Connection Between Fear, Ego, and Leadership

While Bassford frames fear and ego as barriers specifically to curiosity, Brené Brown argues they’re barriers to courageous leadership more broadly. In Dare to Lead, Brown finds that fear itself isn’t actually the biggest obstacle—it’s the armor leaders put on in response to fear. This armor takes the form of self-protective behaviors: needing to be right, dismissing vulnerability, perfectionism, and false certainty—behaviors that closely mirror the ego barriers Bassford describes.

Brown frames these as a single underlying dynamic: When leaders can’t tolerate vulnerability, they default to self-protection, which shuts down the honest exchange that both curiosity and courageous leadership require. Seen through this lens, Bassford’s two barriers aren’t separate problems but two expressions of the same defense mechanism—fear causes us to act with our ego as a defensive shield—and addressing one means addressing both.

The third barrier is organizational inertia—the human tendency to stick with what’s familiar. Bassford explains that inertia is best addressed gradually rather than through an immediate organization-wide overhaul. Bassford recommends starting small—testing new ways of working in limited, manageable trials so people can see practical benefits before broader change is attempted. When people see that a new question or approach leads to a concrete improvement, momentum builds. Leaders can reinforce the new norm by openly acknowledging useful inquiry, praising inventive responses to problems, and treating experimentation as a normal part of how the organization works.

(Shortform note: Bassford’s recommendation to address organizational inertia gradually reflects a principle at the core of John P. Kotter’s change management framework in Leading Change. Kotter found that generating short-term wins is a distinct and critical step in succeeding in any change effort—not a byproduct but a deliberate strategy. Visible early successes serve as proof points that make continued change feel safe and credible, creating the “time and space” for broader transformation to take root. This suggests Bassford’s gradual approach isn’t just practical advice but a response to a well-documented psychological reality: People need to see change working before they’re willing to commit to it.)

Get Started Now

Bassford closes with practical steps leaders can take immediately. He first urges leaders to make routine scrutiny part of their work, drawing from Toyota’s kaizen method: Revisit accepted beliefs, inspect workflows closely, and assume even familiar systems can be improved. Effective organizations spread responsibility for improvement among all employees despite seniority, so people across the company can raise concerns quickly and help fix problems before minor friction grows into larger operational failures.

(Shortform note: Bassford grounds this recommendation in Toyota’s kaizen philosophy, and research confirms that the approach has proven effective beyond manufacturing. Studies on its application in health care, for example, found that when responsibility for improvement was distributed across all staff levels, organizations identified and resolved problems significantly faster, and employees reported greater ownership over their work. This suggests the principle Bassford describes isn’t industry-specific: Any organization that spreads scrutiny and improvement responsibility across its people, rather than concentrating it at the top, gains both a faster feedback loop and a more engaged workforce.)

The second step is to develop fluency with data. Collecting information isn’t enough—leaders must understand what their data means, what it implies for the future, and where the gaps are. The difference between a leader who glances at a report and one who digs into the numbers can be the difference between catching a serious problem early and discovering it too late.

(Shortform note: Bassford’s point that leaders must understand what their data means—not just collect it—reflects a challenge that extends beyond leadership. A 2024 report found that only 36% of employees feel confident working with data, and organizations with strong data literacy programs show 35% higher productivity than those without. This suggests the gap Bassford describes isn’t just a matter of individual diligence at the top—it’s a systemic capability that organizations need to build at every level. A leader who has developed data fluency but hasn’t cultivated it in their team still faces the same blind spots, just one level down.)

Third, reframe how you see mistakes—both your team’s and your own. Bassford observes that our expectations often shape what stands out to us: If a leader watches for errors, they’ll see errors everywhere; if they watch for potential, they’ll find that instead. This isn’t a call to ignore problems, but a reminder that the lens through which a leader views their team shapes what that team is willing to try.

(Shortform note: Bassford’s observation that leaders find what they’re looking for stems from what psychologists call the Pygmalion effect. In the original study, teachers who were told certain students were likely to excel saw those students improve significantly—even though the students were randomly selected. The only difference was in the teacher’s expectation. A later study replicated these results across workplace settings, finding the same dynamic between managers and employees: When leaders hold high expectations, performance improves; when they hold low ones, it declines. This suggests that the lens through which a leader views their team can shape what their team achieves.)