Storytelling for Leaders with Robert Kennedy III [Episode 402]

There’s a pattern I’ve seen over and over again when it comes to how leaders communicate…

They tend to share too much information and end up communicating too little.

More information typically leads to less communication.

And one skill to work on is to say less, but if you need to communicate something important, you can share more through the power of story.

Stories can build trust.

Stories can change behavior.

Stories get remembered.

Our brains are wired to hold information in the form of stories.

I recently had a conversation about the power of stories with leadership communication expert Robert Kennedy III, and it pushed me to think more deeply about how we, as nonprofit leaders, can use storytelling every single day to make our work easier and our results better.

Robert said something that stuck with me:

“Storytelling is important because it humanizes us. It humanizes every organization.”

That word—humanizes—is everything.

When you humanize, you build trust.

Data matters too, but data should be part of the story, not in place of the story.

But our brains aren’t wired for spreadsheets. They’re wired for narrative.

When you share a story with context, characters, conflict, and conclusion, something powerful happens. The listener’s brain begins filling in gaps. It creates images. It searches memory. It feels something.

And once someone feels something, trust becomes possible.

Trust is the real currency of communication and leadership.

Robert breaks strong stories into four elements:

• Context

• Characters

• Conflict

• Conclusion

When we lead with conclusions—“Here’s the program,” “Here’s the new process,” “Here’s the solution”—we skip the human entry point.

And that’s why people disengage.

Instead, strong leaders often start with the conflict.

• What problem are we facing?

• Why does it matter?

• Who is affected?

When people recognize themselves in the story, they lean in.

In my experience starting with the conflict makes introducing the context and characters easy.

The next thing to share is the process that was used to get to the conclusion. And once that is done, the conclusion is the last thing to share, and takes up the least amount of time.

So next time you need to communication a conclusion (a.k.a. A decision you have made) try this formulat:

Step 1: Share the conflict, context, and characters

Step 2: Share the process you used to figure out the conclusion. Include some wrong turns if you took them. For example: “we tried this and it didn’t work so we pivoted” or “we considered x,y, and z, but decided they weren’t the right approach for us”.

Step 3: Share the conclusion 

Robert outlined three core types of leadership stories, and I believe every nonprofit should intentionally develop all three.

1. The Personal Story

This is the story of you.

A moment of failure.

A turning point.

A hard-earned lesson.

When leaders share appropriate vulnerability, they normalize growth. They remind staff that mastery takes time. They lower the emotional temperature of failure.

Your team doesn’t need a superhero.

They need a human.

2. The Origin Story

This is the “why.”

Why did this organization start?

What problem existed?

What injustice needed solving?

Even if your organization is 100 years old, your origin story still matters.

And here’s the important nuance: origin stories aren’t frozen in time.

Current-day testimonials are simply modern expressions of the original why.

When you show that your founding purpose is still alive in today’s work, you build continuity and credibility.

You signal: We haven’t drifted.

3. The Strategic Story

This is where leadership gets interesting.

Strategic stories explain:

• How we solve problems (process stories)

• Why our solution works (product stories)

• How collaboration amplifies impact (partnership stories)

This is especially important during change.

When introducing a new process, you can’t just announce it. You have to tell the story of why the change is necessary, what challenge emerged, and how this solution evolved.

Otherwise, people experience change as disruption instead of progress.

There’s research showing that information embedded in story form is significantly more memorable than random facts.

We’ve all experienced this.

You can’t remember a list of 20 unrelated words.

But if those same words are embedded in a narrative—suddenly, you can recall them.

Story creates structure.
Structure creates memory.
Memory creates influence.

And influence is leadership.

One of the most practical tools Robert shared was simple:

At the end of each day, write down five things that happened.
Then, beside each one, write the lesson or meaning.

That’s it.

It sounds small.

But here’s what it does:

• It trains you to notice.

• It turns mundane moments into meaning.

• It builds a personal “story vault.”

Most leaders think they don’t have stories.

They do.

They just haven’t trained themselves to capture them.

And when you practice assigning meaning to everyday events, two things happen:

• Life feels more intentional.

• You become far more interesting.

And yes—being interesting matters.

Nonprofit leaders don’t need to be entertainers.

But they do need to avoid being forgettable.

Here’s the final insight I want to leave you with:

Your stories are organizational assets.

Just like:

• Your brand

• Your programs

• Your donor relationships

• Your systems

They require development.

They require refinement.

They require practice.

The leaders who seem “naturally good” at storytelling have almost always worked at it. They’ve tested versions. Edited language. Rehearsed delivery. Noticed what lands.

Storytelling is not magic.

It’s muscle.

And like any muscle, it strengthens with repetition.