Why Leaders Struggle to Tell the Right Stories

And what it’s costing them in trust, clarity, and connection

We’ve all heard that storytelling is a “powerful leadership tool.” But at our October #PeopleBeforeStrategy Roundtable, one thing became clear:

Most leaders don’t know when, where, or how to actually use story.

They overthink it.

They try to sound like someone else.

They avoid vulnerability because they fear it will weaken their authority.

And in doing so, they miss the opportunity to build trust, clarify the why, and create real connection.

Our guest expert, ghostwriter and developmental editor Emily Crookston, brought refreshing clarity to this messy, often misunderstood topic.

This recap captures three key takeaways from that conversation, insights that are especially relevant as we head into performance reviews, year-end wrap-ups, and strategic planning.

Reframing Storying Telling

Storytelling isn’t about long speeches or cinematic moments.

In leadership, story means:

• Anchoring your message in human emotion

• Clarifying why something matters

• Helping people connect with the bigger picture

Whether you’re sharing a metric, giving feedback, or aligning on goals, story gives your words meaning.

“It’s really hard to get a lesson across unless you start with a story. That’s what sticks in people’s minds. That’s what gets people interested in paying attention.” - Emily Crookston

Here are three things you can keep in mind:

1️⃣ Don’t Confuse Structure with Strength

Most leaders overthink storytelling. They try to sound “professional” or default to slides and jargon. But the most effective communication? It’s clear, conversational, and rooted in your real voice. Emily shared that even in book writing, leaders freeze up because they forget how to talk like themselves.

If you’re struggling to connect:

• Start with a story you’ve told in conversation

• Don’t over-edit yourself into a robot

• Focus on clarity, not polish

🟣 Action Step: Record your thoughts out loud before writing them down. Then transcribe and shape.

2️⃣ Storytelling Isn’t Separate from Data. It Guides It

Especially in technical teams, there’s a tendency to think data speaks for itself. But Emily reminded us: Story is the context. It gives your metrics meaning.

Ask yourself:

• “Why are we measuring this?”

• “What changed and why does it matter?”

• “How should this data shift how we work?”

Without a story, your team just sees numbers. With a story, they see direction.

🟣 Action Step: The next time you present a KPI, start by sharing why it matters to you and the business.

3️⃣ Vulnerability Is a Leadership Advantage

Many leaders fear that if they’re too real, they’ll lose authority. But what builds trust today isn't perfection. It’s grounded self-awareness. You don’t have to share your life story. But when you name a doubt, own a mistake, or reflect on a lesson? That’s when people lean in.

🟣 Action Step: Think of one leadership story you’ve avoided sharing. Could that story actually deepen the connection with your team?

Heading into performance review season and strategic planning, many leaders will focus on frameworks, numbers, and plans. But don’t forget the story.

Because story is how we:

• Build trust

• Inspire alignment

• Lead with clarity

And the good news? You don’t need a perfect story. You just need to remember the “why” and who it’s for.

Join the next free monthly Roundtable designed for leaders who understand that businesses are people. Each session is a live, facilitated space where decision-makers, team leads, and people professionals connect, learn, and grow together. Register here.

Originally posted 10/20/2025 on LinkedIn.