The Questions That Keep Leaders We Admire Up at Night

Leadership isn’t about having all the answers. In my 30 years of working with executives and organizations, I’ve found that true transformation rarely starts with a perfect solution. It begins with a powerful question(s). These aren’t the easy, surface-level inquiries asked in meetings just to check a box. They are the questions that follow you back to the office and to home, the ones that echo after the workday ends.

These are called HAMS questions. They’re the kind that make you tilt your Head, have an "Ah-ha" moment, and Make you Stop what you’re doing to reflect. These are the questions that distinguish good leaders from great ones. They don’t just challenge a strategy; they challenge a perspective. They push you to look beyond the immediate and to consider the deeper currents shaping your leadership and organization.

If you’re a leader who wants to build a thriving, resilient organization, you understand that these HAMS questions are essential for value creation. The questions might be uncomfortable because they reveal the gap between your current state and your goals. However, as I learned from Dick Beckhard and other NTLers many years ago, embracing that dissatisfaction is a first step toward meaningful change.

Here are seven of the questions that I’ve seen keep exemplary leaders up at night. I invite you to sit with them, reflect on them, and see what they unlock for you and your team.

1. What's the Real Cost of Untapped Potential in Your Team?

We all have talented people on our teams. But are we truly unlocking their full potential, or are we just scratching the surface? This question forces you to look beyond headcount and job descriptions to see the latent energy within your organization. Untapped potential isn’t just a line item you can find on a balance sheet, but its costs are very real. You can read more about this in my recent book, The People Dividend: Leadership Strategies for Unlocking Employee Potential.

It shows up as disengagement, where team members do just enough to get by but have stopped bringing their best ideas to the table. It manifests as quiet attrition, where your most promising people leave not for a bigger paycheck, but for an opportunity to feel challenged and valued. It’s the innovation that never happens because people are afraid to fail or don’t feel psychologically safe enough to speak up.

Think about your last team meeting. Did you hear from the same three people (I did), or did you create space for every voice to be heard? When was the last time a team member surprised you with a new skill or a passion you didn’t know they had? The cost of untapped potential is the future your organization could have had. What are you willing to do to claim it?

2. Are You Leading, or Just Managing Chaos?

Many leaders spend their days in a reactive whirlwind. They are masters of crisis management, juggling competing priorities and putting out one fire after another. They are busy, effective, and often exhausted. But is that leadership? Or is it just managing chaos?

Leading is a proactive state. It’s about stepping back from the daily whirlwind to set a clear, compelling direction. It's about communicating that vision so effectively that your team can make decisions without you. It’s about building systems and structures that reduce chaos, rather than just getting better at navigating it.

When you are truly leading, your team feels a sense of purpose and stability, even when the market is turbulent. They understand the "why" behind their work, not just the "what." This question asks you to assess how you spend your time honestly. Are you an indispensable problem-solver, or are you building an organization that can thrive without your constant intervention? One creates dependency; the other creates empowerment.

3. What’s the ROI of Trust in Your Organization?

We often consider trust a "soft skill," a desirable cultural trait. When leading executive development programs at Marriott, I was lucky to work closely with Steve Covey, who taught so much about trust. When trust is strong, the speed of execution significantly increases. Teams work more openly, innovate more confidently, and solve problems more effectively. The need for bureaucratic oversight and constant check-ins decreases, allowing people to focus on their best work.

Conversely, a low-trust environment is incredibly expensive. It creates a "trust tax" on every single interaction. Projects move more slowly because every decision requires multiple layers of approval. Politics and self-preservation replace open dialogue. People withhold information, hide mistakes, and spend more energy managing perceptions than driving results.

So, what is the ROI of trust in your organization? Look at your employee turnover rates, your engagement scores, and the speed of your project cycles. Notice how readily people share difficult news or admit mistakes. Trust isn’t just a feeling; it’s a performance multiplier. Investing in it is one of the most strategic decisions a leader can make. When you can’t trust, you need to work on purpose, mission, and vision.

4. Are Your People Aligned with a Purpose or Just a Paycheck?

A paycheck gets people to show up. A purpose gets them to commit. In a competitive market, you can always be outbid on salary. But it’s much harder for a competitor to replicate a deeply embedded sense of purpose that connects your team to something bigger than themselves.

This question isn't just about having a mission statement on your website. It's about whether that mission is alive in the daily experiences of your people. Do they understand how their specific role contributes to the organization's larger goals? Do they see leadership making decisions that are consistent with your stated values?

When people are connected to a purpose, their work becomes more than a job. It becomes a source of meaning. They are more resilient in the face of setbacks, more willing to go the extra mile, and more likely to act as ambassadors for your brand. If your people left tomorrow, would they miss the work and the mission, or just the money? The answer to that question reveals the true strength of your culture. Work on values.

5. What Is the One Thing You Are Avoiding That’s Holding You Back?

Every leader, and every organization, has an elephant in the room. It’s that difficult conversation you’ve been putting off, the underperforming team member you haven't addressed, or the structural problem everyone complains about but no one wants to tackle. We avoid these things because they are complex, messy, and emotionally charged.

But avoidance has a powerful and corrosive effect. The issue you’re ignoring doesn’t go away; it festers. It drains energy, erodes credibility, and creates a bottleneck that holds everyone else back. Your team sees you avoiding it, which signals that specific problems are undiscussable. This silence can be more damaging than the problem itself.

Facing these issues requires courage. It requires a willingness to be uncomfortable and vulnerable. But confronting the thing you’re avoiding is often the key that unlocks the next level of growth for you and your organization. What conversation have you been rehearsing in your head but never had? That’s your starting point. I typically find that what I avoid takes less energy to perform than my anxiety costs.

6. Are You Building a Culture of Resilience or a Culture of Burnout?

It’s easy to celebrate "the grind" and mistake constant activity for progress. We push our teams to do more with less, to be always on, and to hit ambitious targets. But there is a fine line between a high-performing culture and a culture of burnout.

A resilient culture is not one where people never feel stress. It’s one where they have the resources, support, and autonomy to navigate stress effectively. It’s a culture that prioritizes well-being, encourages people to disconnect, and models sustainable work habits from the top down. It’s a culture where people feel safe enough to say, "I need help." We might further describe this as psychological safety.

Burnout, on the other hand, is the slow erosion of passion, energy, and effectiveness. It leads to cynicism, higher rates of illness, and increased turnover. Resilient organizations can weather any storm. Burned-out organizations crumble at the first sign of pressure. Which one are you building?

7. What Legacy Are You Creating as a Leader?

This is the biggest question of all. When your time in this role is done, what will you leave behind?

Your legacy isn't something that gets decided at the end of your career. It's being built every day, in every decision you make, every person you mentor, and every interaction you have. It’s the sum total of your impact on the people and the organization you lead. It’s a fair and accurate summary.

Thinking about your legacy, despite the challenges of time and tempo, compels you to lead with a sense of purpose that goes beyond short-term wins. It motivates you to invest in people, act with integrity (for more ideas, see my book Integrity by Design: Working and Living Authentically), and create something that will endure long after you're gone. Great leaders don't just build successful companies; they develop better leaders. They leave behind a stronger, more capable, and more humane organization than the one they inherited.

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The HAMS don't have easy answers, and that’s the point. They are meant to be a starting point for reflection, conversation, and intentional action.

Which of these questions resonates most with you right now? I would love to hear your thoughts in the comments.

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