Leadership Begins With One Difficult Question

There’s one question I ask almost every senior leader I coach.

Not in the first session. That comes later, once we’ve built enough trust for the conversation to move beyond performance reviews, organisational change and career ambitions. It’s the point where people stop giving the answers they think they ought to give and start giving the honest ones.

The question itself is deceptively simple.

Is the ladder you’ve spent your career climbing actually leaning against the right wall?

It’s a question that almost always catches people off guard. There might be a nervous smile, a thoughtful pause or a moment of silence before they answer. More often than not, the response is something along the lines of, “I’ve never really stopped to think about it.”

I find that fascinating because these are experienced, accomplished leaders. They’ve worked hard, earned promotions and built careers that many people would admire. Yet somewhere along the journey they’ve become so focused on reaching the next rung that they’ve rarely paused to ask themselves why they’re climbing in the first place.

I don’t think that’s unusual. In fact, I think it’s one of the biggest challenges facing leadership today.

Purpose Isn’t Something You Put on a Wall

Over the years we’ve managed to turn purpose into a corporate exercise. It becomes another workshop, another values statement or another beautifully designed poster hanging in reception. Organisations spend weeks crafting the perfect wording, only for it to disappear into the background while everyone gets on with the real work.

The truth is, purpose isn’t found in mission statements. It’s found in decisions.

It reveals itself when the pressure is on, when priorities compete, when budgets are tight and when there’s no obvious right answer. It’s easy to talk about values when everything is going well. The real test comes when living those values costs you something. That’s when you discover whether purpose is something you genuinely believe or simply something you’ve written down.

People Believe What They See

One of the greatest misconceptions in leadership is that people judge us by what we say. They don’t. They judge us by what we consistently do.

Teams are remarkably perceptive. They notice who gets recognised and who gets overlooked. They notice whether poor behaviour is challenged or quietly ignored because the individual delivers results. They notice whether wellbeing is genuinely important or simply appears in a presentation once a year.

I’ve seen organisations proudly declare that “people are our greatest asset” before making decisions that tell employees precisely the opposite. Every time that happens, another little piece of trust disappears. Eventually people stop listening to what their leaders say because experience has taught them that actions tell a very different story.

Leadership credibility isn’t lost in one dramatic moment. It’s usually lost in the small gap between our words and our behaviour.

Five Questions Worth Asking Yourself

In The Purpose-Led Leadership Playbook, I encourage leaders to spend some time reflecting before rushing into another framework or development plan. The questions themselves aren’t complicated, but answering them honestly often is.

Ask yourself:

·      What experiences have shaped the leader I’ve become?

·      What do I believe, fundamentally, about how people should be treated at work?

·      When have I been at my very best as a leader, and what was present in those moments?

·      At the end of my career, what do I hope people will remember about the way I led?

·      Complete this sentence: My leadership exists to…

It’s the final question that usually proves the most difficult. Not because leaders don’t care, but because very few have ever taken the time to define their purpose in a single sentence. We spend years learning how to lead without ever asking ourselves why we want to lead at all.

A Simple Filter for Difficult Decisions

Leadership rarely becomes difficult because we don’t know what needs to be done. More often, it’s because every option comes with consequences.

When I’m supporting leaders through difficult decisions, I encourage them to slow down and ask themselves three simple questions.

Does this decision align with what I say I believe?

Could I explain this decision openly to every member of my team and feel comfortable doing so?

Five years from now, will I still believe this was the right decision?

They’re straightforward questions, but they’re surprisingly demanding. They force us to move beyond short-term convenience and consider the kind of leader we’re becoming every time we make a difficult choice.

Culture Is Built One Decision at a Time

People often ask me how to build a purpose-led culture. They’re usually hoping I’ll recommend a framework or a programme that can be rolled out across the organisation.

The answer is both simpler and much harder than that.

Culture isn’t built during an away day or through a new set of corporate values. It’s built every day through hundreds of seemingly ordinary moments. It’s built when you challenge behaviour that doesn’t reflect your values, even when it’s uncomfortable. It’s built when you take the time to explain why someone’s work matters. It’s built when your decisions consistently reflect the standards you expect from everyone else.

People don’t remember the presentation you gave about values.

They remember whether you lived them.

One Question to Take Away

If there’s one thing I’d encourage you to do after reading this article, it’s this.

Think about a recent decision, a conversation you avoided or a moment where your actions didn’t quite reflect the leader you aspire to be. Not because you’re a bad leader—far from it—but because every leader has moments where intention and behaviour drift apart.

Don’t ignore it. Learn from it.

Purpose isn’t found in a strategy document or a vision statement. It’s found in the choices we make every day, particularly the ones nobody notices.

Perhaps that’s the real measure of leadership. It isn’t how high we’ve climbed, how impressive our job title sounds or how many people report to us.

It’s whether we were climbing the right wall in the first place.

About this article

This article is inspired by The Purpose-Led Leadership Playbook, Book Five in my Trusted Leadership Series—a collection of practical, evidence-based leadership books written for leaders who want to build trust, lead with purpose and create workplaces where people genuinely thrive.

If this article resonated with you, I’d love to hear your thoughts. And if it reminded you of someone else, please share it with them. Sometimes the most valuable thing we can do for another leader is ask them one difficult question.