EXTRACT | Great leaders aren’t defined by the answers they give – but by the questions they dare to ask

What’s the difference between Donald Trump and a leader? Leaders listen. Then they think. They process. And they act based on a thoughtful assessment of all the available information – not just what flatters them or fits their agenda.

Mike Stopforth has created a smart, practical, and deceptively simple resource for business leaders who want to think better, lead better, and ask better questions. 52 Big Questions for Business Leaders isn’t prescriptive. It doesn’t pretend to have all the answers. What it offers instead is something far more valuable: the right prompts to help you shape your own.

Some questions will land more powerfully than others. That’s to be expected. We’re all at different points in our leadership journeys – some navigating growth, others facing reinvention, and many managing the everyday friction of people, process and change.

In over two decades of studying founders and companies they build, I’ve learned this: the most effective leaders are those who are uncomfortable with certainty. They do not default to quick fixes. They sit in the discomfort of complex problems long enough to ask questions that matter most. Because often, the quality of your question determines the quality of your decision.

— Bruce Whitfield

52 Big Questions for Business Leaders isn’t just a collection of prompts and provocations – it’s a guide to sharper, more intentional thinking. Whether you’re leading a start-up or a global enterprise, the questions in these pages will help you pause, reflect, and lead with clarity.

Drawing on decades of leadership experience, Mike Stopforth infuses wisdom, wit, and practical insight into the art of inquiry – because crafting big, beautiful questions is a skill worth mastering. This isn’t a book to read once and shelve; it’s a tool to return to whenever you need fresh perspective, focus, or inspiration.

In the end, great leaders aren’t defined by the answers they give – but by the questions they dare to ask.

EXTRACT

The Art and Science of Crafting Big Questions

“Hi. How are you?” We ask questions every day, often just in passing. We are asked and usually answer them without expending a single cognitive calorie. There are questions, and then there are questions. You’ll know when you’re asked a great question because it’ll stop you in your tracks.

The world is full of lazy, vague, and uninspired questions that fill space but don’t move us forward. Seeking out, crafting and sharing truly great questions is a blend of art and science.

What Makes a Great Question Great?

A beautifully crafted question will be precise enough to focus your thinking, yet open enough to spark possibility. It will challenge your biases, invite curiosity, and demand deeper thought.

Lukewarm questions draw out the things you already know. Great questions reveal what you didn’t know you knew (or what you didn’t know you didn’t know). That’s where growth happens.

Consider the disruptive possibility of a straightforward business question:

What is the problem I solve for my customers?

And its provocative follow-up question: What’s the most interesting or creative way to solve that problem?

Airbnb’s origin story is a powerful case study in asking great questions. The traditional, established, highly competitive hotel industry Airbnb famously disrupted was focused on metrics like property ownership, occupancy rates, and seasonal pricing – all important but internally facing. This is not an uncommon trait of saturated industries where, as marketing guru and author Seth Godin puts it, everyone is in a “race to the bottom”. What the hotel industry failed to ask was:

What problem are we really solving for travellers, and is there a more creative way to solve it?

Airbnb’s founders, imbued with the luxury of objectivity and a complete lack of legacy thinking to overcome, answered precisely that. What’s the job of a hotel? A hotel is there to provide me with a safe, clean, convenient and affordable place to sleep when I’m not at home. What’s the most interesting way to solve that? Well, now there’s a big question.

Airbnb’s leadership team also realised that the problem wasn’t just accommodation but affordable, flexible, local, and human connection. Hotels offered standard rooms and predictable services (again, a by-product of trying to win the race to the bottom) but little in the way of personality or authenticity. The founders questioned assumptions: Do we need to own property to provide hospitality? Can we leverage what already exists? Is there inventory out there that nobody is monetising?

Consider another historical pivot off the back of one beautifully crafted and articulated question:

What happens if we go to the moon not because it is easy but because it is hard?

In 1961, President John F. Kennedy stood before the U.S. Congress and posed one of the most audacious challenges of the 20th century: “What could we achieve if we committed to landing a man on the moon and returning him safely to Earth within the decade?” It wasn’t just a policy goal – it was a question designed to inspire a country to dream bigger, think differently, and unite in purpose.

JFK’s big question wasn’t about technology or politics. It was about possibility and ambition. In the shadow of the Cold War, this brilliant challenge reframed America’s self-perception – not as a nation reacting to threats but as a bold innovator leading humanity’s next giant leap. It takes a pretty remarkable question to coalesce hundreds of millions of people.

What made JFK’s question brilliant was its inherent tension: the goal was wildly ambitious, incredibly difficult, and laced with uncertainty. Yet, it was precisely that audacity that captured imaginations. Scientists, engineers, politicians, and ordinary citizens rallied around the idea and transformed what seemed impossible into reality eight years later.

The DNA of a Great Question

Want to start asking better questions? These are the building blocks of a truly great question: Building Block 1: A big question challenges assumptions.

Bad questions accept the status quo and often pass judgement:

Why is the economy in a slump?

Why are people so hard to motivate?

A big, beautiful question will interrogate the status quo and your assumptions with it:

What would we do differently if we started over?

What beliefs do we hold that could be wrong?

What problem are we solving that might not exist?

Building Block 2: A big question opens new possibilities.

Good questions don’t (just) critique; they create space for new ideas and lateral thinking:

What if growth wasn’t our primary measure of success?

What would we do if resources weren’t a constraint?

Asking big questions allows us to creatively connect the dots in ways we might have thought impossible.

Building Block 3: A big question is simple but not easy.

Impactful questions are short and sharp but require deep thinking:

What business are we really in?

Building Block 4: A big question is a catalyst for action and change.

Carefully considered and constructed questions force you into new solutions: What would it take to become the most customer obsessed company on Earth?

Why do we do things this way, and how would somebody really good at this do it?

How to Craft Big Questions

Luckily, the 52 big questions in these pages aren’t the only great questions you can ask of yourself and your teams. This book is just the tip of the iceberg. Maybe the best thing about big questions is that you can create your own! Doing so and forcing yourself to articulate your problem or challenge in fresh language is often valuable in its own right.

Step 1: Start with a clear challenge

Write down the real issue you’re trying to solve. Don’t overcomplicate it. The clearer the challenge, the sharper the question.

Step 2: Make it open-ended

Instead of asking: Is this strategy working? Ask: What tells us this strategy is or isn’t working?

If you can answer a question with a simple yes or no, it’s not a great question. Well, not a great strategic question. There is, without a doubt, a place for questions with yes or no answers, but not in the realm of self-discovery and planning in the face of uncertainty.

Step 3: Add some tension

Questions become powerful when they force trade-offs:

What would we do if we had to double our impact with half the budget?

Step 4: Make it personal

Instead of asking: What’s our vision?

Ask: What vision would make you proud to share with your kids?

Step 5: Consider time horizons

What will this look like in five years? In 50 years?

If future generations judged us on this decision, would we be proud?

For more on the art of great questioning, add these to your reading list:

• A More Beautiful Question by Warren Berger
• The Book of Beautiful Questions by Warren Berger
• The Coaching Habit by Michael Bungay Stanier
• The Art of the Question by Marilee C. Goldberg

52 Big Questions for Business Leaders is published by Tracey McDonald Publishers. Recommended retail price: R270. Available online and in all good book stores. Extract provided by Janine Daniels (J Doubled Publicity).