Leading with story

“You could have the best strategy in the world, but if people don’t understand it and don’t connect with it, it doesn’t matter how good the strategy is. To bring a strategy to life, you need lots of stories.” — Gabrielle Dolan

I can’t remember exactly when I first heard the statement: “If it’s too obvious, it can’t be trusted.”

This thought comes to mind when I am speaking with Gabrielle Dolan, a leader I have come to know over the past decade and feel so fortunate to have done so.

The fact that we immediately connected is no surprise. Her leadership builds on the power of story, its nuance, and relatability. Our capacity to draw on personal lessons and learnings to understand self and what’s important to us, whilst developing the confidence to draw on these insights and tell our story to build a deeper connection with others and a commitment to a shared purpose and plan.

I love storytelling, its memorability, and therefore its timelessness. The emotions it can evoke, the extremes, the best and worst of our human experiences, told as high-performance leadership coach Shane McCurry describes in Episode12 of ‘In the Arena’, in a ”healthy way”.

Mostly, however, a story’s capacity to express what truly matters, your values and principles, that once told holds you accountable, as your credibility will now be judged by your capacity to live them, especially when it gets hard, as it will.

I doubt, therefore, whether there is a more important skill for leaders than storytelling, including our capacity to tell our own.

I understand this statement would be very challenging, if not confronting, for many leaders.

Supporting and coaching leaders to find and express their story authentically is Gabrielle Dolan’s mastery, which we explore in this podcast.

For more than two decades, Gabrielle has worked with leaders across business, sport, and government, helping them move beyond jargon that can’t be trusted and into meaning that can.

Her work challenges a flawed leadership assumption that clarity comes from data. Instead, she reminds us that understanding, alignment and commitment are built through story.

All great strategy come from a compelling story

Strategy needs many stories. It cannot be carried by one story alone.

As Gabrielle describes, it becomes real only when people can see how it connects to their roles, decisions, and everyday work. This requires many stories, told over time and from different perspectives.

Leadership often falls into the trap of searching for the story, the single narrative meant to explain everything. But strategy doesn’t live in a paragraph, a slide deck, or a slogan. It is complex, layered, and constantly evolving.

When leaders try to compress strategy into a single explanation, it often collapses into jargon. When they allow multiple stories to emerge, strategy becomes something people can understand, buy into with energy, and bring others along with them, all of which is fundamental to the successful execution of strategy.

It is the power of the story that delivers on the promise of the strategy.

Data informs. Story connects.

People don’t engage with strategy because of a compelling spreadsheet. They engage when they understand why it matters and where they fit. Story bridges the gap between direction and belief. It moves leadership from instruction to meaning, and from compliance to commitment.

This is leadership as sense-making to create meaning-making, spaces where expertise and ideas can surface.

When people can link an organisation’s purpose to their own experience, something shifts. They don’t just understand the strategy, they start to own it.

As Gabrielle relates, story gives people language they can carry into conversations with others.

It allows strategy to travel beyond the room where it was first introduced because it carries emotional weight and human relevance.

The most powerful story is the one where you didn’t live the value

Gabrielle explains that the stories that shape culture are rarely heroic. More often, they are the uncomfortable moments, the moments where leaders fall short of the values they now speak about.

These stories take courage to tell, but they build trust in a way polished success stories never can. They turn values from words on a wall or a mousepad into standards and expectations that will always ask a lot of leaders.

They remind people that leadership isn’t about perfection; it’s about honesty, reflection and learning.

As Gabrielle reassures us, vulnerability isn’t oversharing. It’s sharing scars, not wounds. When leaders are willing to tell these stories, values stop being aspirational statements and start becoming lived behaviours.

Notebook ready…

Play on!