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Questions That Drive Change

Questions Part-3

By Rick Aman
on

Progress is not the same as transformation. Leaders must ask the questions that reimagine, not just improve.

In 1978, a United Airlines DC-8 circled Portland International Airport because a small warning light failed to illuminate. The pilots weren’t sure if the nose landing gear was properly extended and locked, so they stayed in a holding pattern, focused on troubleshooting. As they analyzed the reason for the lack of three gear down indications they missed a far more urgent issue, fuel. Despite subtle cues and lack of situational awareness, the aircraft ran out of fuel and crashed six miles from the airport, killing 10 people. The cause wasn’t mechanical; it was a failure to ask the right question at the right time. It’s not just about flying, it’s about leading. The same holds true in boardrooms and executive teams.

One of the most common traps in leadership is mistaking motion for progress. We reorganize departments, implement new software, add KPIs, and call it change. But activity isn’t the same as transformation. It’s possible to stay busy and still be stuck, especially when what’s really missing isn’t effort, but imagination. I’ve seen this firsthand in higher education. As a former community college president, I’ve helped guide institutions through budget crises, accreditation reviews, and strategic planning. I’ve led retreats and restructured teams. But I’ve also seen well-meaning leaders pour energy into surface-level improvements while the deeper issues remained untouched, not because they lacked dedication, but because they lacked the courage to ask different questions. And that failure often begins with the questions we never think to ask.

“The difficulty lies not so much in developing new ideas as in escaping from old ones.” — John Maynard Keynes

Improvement vs. Transformation

Here’s the distinction: Improvement asks, “How can we do what we’ve always done a little better?” Transformation asks, “What needs to change so we can do what we’ve never done before?” Improvement is essential, but it doesn’t always go far enough. Especially now. We’re living in a time of accelerated disruption. AI, demographic shifts, political volatility, and workforce realignment are reshaping the landscape faster than most strategic plans can keep up. In this environment, fine-tuning isn’t enough. We need leaders willing to reframe the challenge entirely. And that reframing starts with asking different questions.

How Boards Can Drive the Right Dialogue

Governing boards play a unique role here. Their distance from daily operations is a strength but only if they use that perspective to ask bold, unfiltered questions. I’ve worked with boards who fall into two camps:

One focuses on oversight. The other shapes vision. Strategic boards don’t just review reports, they ask questions that disrupt comfortable assumptions. They make it safe to revisit the core. And they challenge leadership to think not just about managing risk but embracing opportunity.

Four Questions That Signal It’s Time for Change

If you’re a CEO, board chair, or executive leader sensing that your organization is “busy but stuck,” here are five questions worth asking at your next meeting or retreat:

“What would we build if we started fresh today?” This question allows leaders to step outside the constraints of legacy systems and rethink their institution from a clean slate. It encourages bold visioning, innovation, and alignment with future needs rather than past assumptions.

“What are we doing out of habit rather than purpose?” It invites honest reflection on long-standing routines, traditions, or programs that may have outlived their usefulness. By challenging inertia, leaders can refocus energy on actions that serve the mission.

“What assumptions are we holding that may no longer be true?” This question surfaces outdated beliefs about students, learning preferences, or institutional roles. It helps leaders stay adaptive and grounded in current realities, not past paradigms.

“If our funding model changed tomorrow, what would survive?” It reveals which programs and practices are truly mission-critical and self-sustaining. At the same time, it highlights vulnerabilities that require rethinking, streamlining, or innovation.

These aren’t just philosophical. They’re deeply strategic. They help expose misalignment, surface hidden risks, and create urgency around what matters most.

A Real-World Example: The Transportation Question

One of my favorite cautionary stories comes from Arthur Levine’s The Great Upheaval, where he describes how the railroad industry failed to adapt to air travel in the 1920s. Rail executives stayed focused on improving trains and timetables. What they didn’t ask was the better question: “Are we in the railroad business, or the transportation business?” It wasn’t a failure of technology. It was a failure of inquiry. Many colleges and nonprofits face a similar crossroads today. We’re improving our schedules, marketing, and course delivery, but are we asking the right fundamental question about what our communities need now and next?

Culture Change Begins with Courageous Curiosity

Culture doesn’t change through slogans or strategy documents. It changes through repeated, courageous questions. I’ve watched organizations unlock new momentum not through major restructures, but through leadership teams that made questioning a discipline. One CEO I worked with opened most leadership meetings with the same question: “What’s one thing we’re doing that no longer fits our future?”

Over time, it changed how people thought. It created space for candor. It gave permission to challenge tradition. And it built a culture where transformation didn’t feel threatening, it felt necessary.

Boards, CEOs, and the Discipline of Disruption

If you’re in a leadership seat, whether as a trustee or executive, the best thing you can do right now might not be to act faster. It might be to pause and ask better questions.

Strategic disruption isn’t reckless. It’s responsible. Especially when it’s grounded in mission and guided by inquiry.

So, before launching a new initiative or approving a five-year plan, step back and ask:

You may find that the most powerful leadership move isn’t answering quickly, it’s asking slowly.

Summary: Questions That Move the Needle

The organizations that thrive in uncertainty will not be those that move the fastest. They’ll be the ones that pause long enough to ask, “What needs to change?” In a world reshaped by complexity, the leaders who drive transformation aren’t the ones who speak first. They’re the ones who listen well, question wisely, and create space for bold, honest dialogue. Because real change doesn’t start with answers. It starts with the courage to ask the right question.

“If I had an hour to solve a problem, I’d spend 55 minutes thinking about the problem and five minutes thinking about solutions.” — Albert Einstein

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Aman and Associates

If your board or leadership team is ready to move beyond incremental change and start reimagining what’s possible, I’d welcome the opportunity to help. At Aman and Associates, I facilitate customized retreats that guide organizations through strategic visioning, preferred future planning, and board development. Reach out to explore how we can shape the future—together.

Rick Aman, PhD

Aman and Associates

rick@rickaman.com / http://www.rickaman.com/articles