The Leader’s Lens: Why the Best Executives Ask Better Questions

Modern leaders don’t win by having the answers — they win by asking better questions.

For much of my career, leadership meant having answers. Early on, that made sense. In the 1980s, when I managed a supermarket, success came from knowing every job, giving clear direction, and making sure things got done the right way. Leadership was top-down, command-and-control — and in that world, it worked.

But that world is gone.

Today’s leaders operate in a vastly different environment — one defined by globalization, rapid technological change, and knowledge workers who often know far more about their roles than their managers do. This reality requires a complete rethinking of leadership.

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Seeing Through the Right Lens

There’s a well-known story from the space race: the U.S. spent millions developing a pen that could write in zero gravity. The Soviets used a pencil. Five cents. Same problem, different lens.

Leadership works the same way. The issue isn’t intelligence; it’s perspective. Leaders who rely on a single lens — usually their own — miss simpler, more effective solutions hiding in plain sight.

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Why the Old Model Breaks Down

Modern organizations depend on specialists: engineers, technologists, marketers, operators, and frontline experts. If a CEO knows more about marketing than the CMO, or more about finance than the CFO, that’s not strong leadership — it’s a selection problem.

Peter Drucker saw this coming decades ago: “The leader of the past knew how to tell. The leader of the future knows how to ask.” Leaders who cling to being the smartest person in the room slow decision-making, suppress innovation, and disengage talent.

Gallup’s data confirms the cost. Only 31% of employees are engaged today, while 17% are actively disengaged. Command-and-control leadership doesn’t just underperform — it drives people away.

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The Shift to a New Lens

Today, the most effective leaders aren’t searching for the right answer. They’re building the discipline to ask better questions, explore multiple scenarios, and challenge assumptions before acting.

At a beverage distribution company where I once worked, one of the owners described himself — after leadership training and coaching — as a “controlling and wimpy manager.” As he shifted toward humility, curiosity, and inclusion, everything changed: stronger cross-functional trust, better communication, and a more energized culture.

The impact extended beyond work and into his family life.

Change the leader, and the system changes.

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Practical Application: Three Shifts Leaders Can Make Today

1. Flip the meeting script

   Ask 3–5 open-ended questions before offering your opinion.

   
   

2. Check assumptions

   What “truths” are you carrying forward from a world that no longer exists?

   
   

3. Hold back once

   Withhold your answer on one decision this week until you’ve heard from at least three stakeholders closest to the work.

   
   

Small shifts like these can create ripple effects that transform how teams see their leaders and how organizations achieve results.

Conclusion

The leader’s lens shapes everything an organization sees — and misses.

In today’s world, the most effective leaders aren’t defined by certainty, but by curiosity. They don’t outthink their teams; they make their teams smarter.

This article is part of a collaboration between Dan Sitner (Clear Purpose Coaching) and Bill Sommers (Learning Omnivores) exploring how leadership must evolve for today’s world.