The Questions Advantage:How Questions Expand Strategic Thinking (and Answers Shrink It)

Part One of a Three Part Series

TL;DR:

• Answers narrow strategy; questions expand it.

• Leaders signal safety and unlock thinking through curiosity.

• Teams do their best work when the leader's ego steps back and their questions step forward.

• The quality of strategy is correlated with the leader's level of curiosity.

Questions are the Answer:

I thought I was in a live-action theatrical production of 5 Dysfunctions of a Team. I even caught myself waiting for a camera crew to jump out from behind a false wall and yell "Cut!"

But it was real.

We had great technology, a high-powered leadership team, strong market position, and deep financial backing.

We also had a leader who opened every meeting with "declarations."

Unfortunately, Kathryn was not coming to save us.

The team underperformed. Factions emerged. There was no disagreement in the room, but plenty of dissent behind closed doors.

It didn't have to be that way.

A series of well-placed questions, instead of declarative statements, could have unified the team and focused its energy.

That experience cemented something I now believe deeply: questions have always been at the heart of effective leadership.

And that belief didn't start in the boardroom.

When I was younger, on long car trips with my Dad, we listened to Anthony Robbins tapes (yep, I am that old). Robbins said, "The quality of your life is determined by the quality of the questions you ask yourself each day."

Years later, selling pots and pans door to door, my mentor introduced me to Zig Ziglar, who famously said, "Questions are the answer." A zealot of don't tell — ask.

More recently, Marshall Goldsmith and Byron Katie, giants in the world of executive coaching, have attracted my attention. Their work is powered by short, incisive questions that cut straight to the truth.

Different fields. Different philosophies.

One common thread:

Great questions unlock great leadership.

Statements Close Conversations. Questions Open Them.

This is true in life, and it is exponentially true at the executive table when forming strategy. 

In every strategy session I run, I can predict the quality of thinking based on a single variable: the number of open-ended questions the leader asks.

When leaders lead with statements, the conversation contracts; when they lead with questions, the conversation expands.

Strategy is an exploration. It's the search for the best possible set of choices under uncertainty. Answers prematurely collapse that exploration. Questions widen it.

Teams mirror the leader's intellectual posture; curiosity begets curiosity.

The Moment Teams Stop Thinking

I've watched this pattern play out dozens of times; in fact, I have been that leader:

A leader opens a conversation with a strong statement.

• The room goes quiet.

• The risk-taking evaporates.

• People switch from thinking to complying.

• Strategic options shrink to the safest possible answers.

  
  

Leaders, as I did, leave the room patting ourselves on the back, thinking "I nailed that". But in reality, nothing kills a strategic conversation faster than a leader trying to prove they are right or the most intelligent person in the room.

Teams don't need leaders to be right. They need leaders to be curious.

Why Questions Work: Biology and Psychology

If you don't believe me, believe science. Questions don't just change conversations, they change brains.

Biologically, questions shift people out of threat mode.

Neuroscience shows that when a leader makes a strong statement, the listener's brain activates its defensive circuitry. The amygdala lights up, cognitive resources tighten, and the priority becomes safety, not insight.

A question does the opposite: it triggers exploratory neural networks, increases dopamine, and opens up the prefrontal cortex — the part of the brain responsible for problem-solving, creativity, and strategic thinking.

In simple terms:

Statements make people protect their position. Questions make people explore possibilities.

Psychologically, questions lower status risk.

Lencioni's model tells us that vulnerability-based trust is the foundation for productive conflict.

Edmondson's research shows that psychological safety allows people to dissent, test ideas, and speak up without fear.

Questions signal:

"Your voice is valued."

"Your thinking is welcome."

"It's safe to disagree."

That one signal often determines whether a room explores boldly or retreats into silence.

As Samantha Shikira Clarke, a giant in the psychological safety realm states, all humans seek to be safe, seen, soothed and secure in order to perform.

Put the biology and psychology together, and the conclusion is clear:

Questions deactivate ego threat and activate collective intelligence, the exact conditions required for meaningful strategy work.

Five Leadership Questions That Change the Room

So what are great strategic questions to lead with? Glad you asked.

Short, open-ended questions have a disproportionate impact because they avoid signalling your bias.

Use these:

• "What do you see that I don't?"

  • Redistributes hierarchical power

• "What's the real problem here?" 

  • Moves the team past symptoms

• "What must be true for this to be the winning move?" 

  • Forces a hypothesis, not opinion

• "If we could only make one bet, which one has the highest leverage?" 

  • Surfaces tradeoffs 

• "What would we do if we were starting this company today?" 

  • Exposes limiting beliefs

    
    

Strategy improves not because the team becomes smarter, but because the leader becomes quieter.

But beware, questions can be weaponized:

For example:

• "Don't you think the real issue is X?"

• "Shouldn't we be focusing on Y instead?"

• 
  

Thinly veiled statements masquerading as questions that lead the group to the leaders agenda.

Why Now? Because the Leadership Environment Has Never Been More Uncertain:

There is urgency. 

In 25 years, I have never seen a moment with this level of volatility: technology disruption, geopolitical tension, shifting trade patterns, rising capital costs, and an increasingly fragmented workforce.

The variables leaders must navigate have multiplied, and the half-life of a good decision has shrunk.

No single leader can see the whole picture anymore.

A Questions-First approach isn't a soft skill; it's a necessity.

You need more eyes, more insight, and more truth in the room than ever before.

Questioning as a Strategic Operating System

Importantly, curiosity is not a personality trait; it's a leadership discipline.

To make questioning a system rather than an afterthought, these strategies:

• The Two Question Rule: Ask two questions before offering one opinion.

• The Speak Last Rule: If you are the most senior person in the room, always offer your opinion last

  
  

When leaders consistently ask questions, teams think harder, learn faster, and solve problems sooner, accelerating execution.

Strategy becomes stronger because the team feels safe enough to contribute fully.

Leadership Takeaways

• Questions are a lever for influence — answers are a lever for control.

• Curiosity is the primary strategic skill for leaders, and it is underused.

• When leaders lead with questions, teams lead with thinking.

• Strategy improves when the leader's voice creates space rather than pressure.

  
  

➡️ Practical step: In your next meeting, hold off on giving your perspective until you've asked two questions. Start with: "What are the choices we haven't considered yet?" Watch how the energy and the quality of thinking shift.

Stay tuned for the following two issues of Leadership on the Edge, where we will explore:

Part 2: The Executive's Guide to Discovery: Questions That Strengthen Sales

Learn my secret to being named "The most effective sales executive."

Part 3: Coaching Through Questions: The Art of Developing Leaders

Learn how I used questions to build leadership capacity and future executives.