What does a lollipop have to do with leadership?

How leadership in everyday moments shapes connection, trust, and impact

In a world where leadership is often equated with authority, strategy, and decision-making, The Power of a Lollipop: A Model for Inspiring Leadership invites us to consider something far more human—and far more powerful.

A lollipop.

Not as a gimmick. Not as a metaphor for quick wins. But as a moment of connection that reveals what leadership truly is.

This was the basis for an amazing discussion I was fortunate to have with Feena in a recent MRG webinar (you can watch the full recording of that here).

A moment that changed everything

Feena May opens her story not in a boardroom, but on a battlefield.

“Guns and uniforms had created tension, but guns, uniforms and lollipops had changed the moment… we were all human again.”

At just 24 years old, leading a convoy through conflict, she offered lollipops to frightened children—and then to armed soldiers on both sides. What followed was extraordinary: guns lowered, laughter emerged, and humanity resurfaced.

That moment didn’t come from authority. It came from a choice. A choice to lead.

Leadership is not a role—it’s a choice

One of the most powerful ideas from Feena’s work is deceptively simple:

“You get your managerial role because… somebody gives you the job… That makes you a manager. It’s a choice to step into the leadership space, to become a leader.”

This distinction matters. Management is assigned. But leadership is chosen.

And that choice is not reserved for those at the top. It exists in everyday moments—how we show up, how we respond, how we connect.

Leadership begins the moment we decide to take responsibility for making a positive difference.

The Lollipop Model: A practical path to inspiring leadership

Through years of field experience, global research, and two doctoral programs, Feena distilled leadership into five essential elements:

1. Presence: Leadership starts with showing up—fully, intentionally, and self-aware.

“If I don’t stand in the space, then nothing else can happen.”

2. Relating: Understanding people and context through deep listening and connection.

3. Sense-making: Turning vision into shared understanding—not just ideas in your head, but clarity across the group.

4. Action: Moving from insight to decision and forward motion.

5. Service: The real heart of leadership.

“What is it that’s driving me to be bothered to take an act of leadership?”

Service, as Feena defines it, is the intention to make a positive difference at all levels—for yourself, your team, and the broader system.

So what does it mean to fully choose to be a leader?

It’s more than stepping up when convenient. It’s a conscious, ongoing commitment.

To fully choose leadership means:

1. You take responsibility beyond your role. Not because you have to—but because you care enough to.

2. You act with intention, not just reaction. You ask: What difference am I here to make?

3. You invest in knowing yourself. Because without self-awareness, everything else rests on “wobbly bits.”

4. You create space—for yourself and others. In a fast-moving world, reflection becomes a leadership discipline, not a luxury.

5. You lead in small moments, not just big ones. The “lollipop moments”—those seemingly small acts of connection—are often where leadership lives and leadership habits are born.

What gets in the way of leadership?

Despite the simplicity of the model, leadership is not easy.

Feena points to a few consistent challenges:

• Lack of time for reflection
• Uncertainty and complexity
• Underdeveloped self-awareness
• Forgetting why we lead in the first place

“People who can answer… what is driving them… step into the role so much better.”

Without that clarity, leadership becomes mechanical. With it, leadership becomes meaningful.

Leadership, at its core, is human

Perhaps the most striking insight from Feena’s research is this:

Across hundreds of leadership stories from around the world, power never came up. What did?

“I had the space to learn and grow.”

Great leadership isn’t about control. It’s about creating environments where people can thrive. It’s not about being impressive. It’s about being present.

Leadership in everyday moments: A final reflection

Near the end of the conversation, Feena shares a simple but profound truth:

“You don’t have to like everyone… but if you don’t love them, you can’t offer the love up.”

Leadership, in this sense, is not abstract. It’s deeply personal.

It’s found in how we show up for others—even in difficult moments.
It’s expressed in small acts that restore connection.
It’s sustained by a commitment to service.

So… what does a lollipop have to do with leadership?

Everything… It reminds us that leadership isn’t about grand gestures or formal authority. It’s about choosing (again and again) to step in, connect, and make a difference. Sometimes, all it takes is a small act of humanity to change the moment.

And that’s where real leadership begins. Leadership in everyday moments is what ultimately defines a leader’s impact.