Storytelling for Tech Leaders
If your message keeps getting ignored, this might be why. Your next presentation needs more human stories.
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You finish walking through the roadmap.
It’s clear, logical, and right on time. You included timelines, resources, dependencies, risks, and even some mockups.
A few heads nod. Someone says, “Makes sense.”
But as the meeting ends, you can tell something didn’t quite land.
No one’s pushing back. But no one’s moved either.
This happens more often than we think. Especially in tech.
People understand your point, but they don’t remember it.
They hear you, but they don’t feel connected to what you just shared.
And here’s the thing. It’s not because you missed a slide. Or needed more data.
It’s because you didn’t tell a story.
Not a long speech. Not a fake anecdote. Just a real, human story that explains what the work means.
I’ve seen this happen so many times…
Product managers who can talk about features but struggle to explain why they matter.
Engineering leads who give updates like status reports, instead of narratives.
Senior leaders who want teams to care, but forget that people don’t connect to slides. They connect to people.
Storytelling sounds like something only marketers or keynote speakers use. But in real digital leadership work, it’s a quiet superpower. Not to sell. But to create clarity, movement, and shared meaning.
So let’s walk through this together. I’ll show you why storytelling is not just helpful — it’s essential for leading in complex, fast-moving environments.
Then we’ll break down a simple way to start using it in your role, even if you’ve never thought of yourself as a “storyteller.”
But before we build anything, let’s first look at why storytelling matters more than ever in digital work.
Why storytelling matters more than ever in tech
Let me explain something that’s easy to miss when you’ve been in digital work for a while.
The more complex your work becomes, the more people around you will stop understanding what you actually do.
They’ll nod when you speak, ask for a timeline, approve a budget, but still walk away unclear about what’s really at stake.
That gap is normal. You might be managing platforms, integrating data pipelines, launching experiments, and working with dependencies across four teams.
And yet, you're still expected to make people care. You’re still expected to bring others on board, keep them aligned, and move forward together.
This is where storytelling helps. Not because it simplifies your work, but because it gives it a shape people can follow.
It turns abstract ideas into something that feels real.
In real life, it looks like this:
A roadmap becomes more powerful when you anchor it in a customer's successful story.
A technical decision makes more sense when you talk about what went wrong in the past.
A team retrospective becomes more valuable when someone says, “Remember when we almost missed the release but stayed up late together to fix it?”
Those stories are not nonsense. They are memory hooks.
They give meaning to the work. They show the human side behind the effort.
And you know what? That human part is what builds trust.
People follow stories more than instructions.
They remember how something made them feel before they remember what was said.
So the question is not, “Should I use storytelling?”
It’s, “What stories am I already living that I can share more clearly?”
Next, let’s talk about a common excuse that blocks many leaders from ever starting.
The myth: “I’m not a storyteller”
This is probably the biggest excuse I hear when I bring up storytelling in leadership.
“I’m not that kind of person.”
“I don’t know how to tell stories.”
“I’m more of a facts and logic person.”
And I get it…
When we hear the word “storytelling,” we picture someone on a stage, talking with perfect timing, dramatic pauses, maybe even using their hands like a TED speaker.
But that’s not the kind of storytelling I’m talking about.
You don’t even need to be charismatic. You don’t need to have a dramatic story. And you definitely don’t need to perform.
Because you are already telling stories every day.
When you explain how a problem happened.
When you walk someone through how a decision was made.
When you talk about a tough moment and what you learned from it.
Those are stories.
They are not polished. They are not exaggerated. But they connect people. Because they are real.
The myth is that you need to sound impressive. But the opposite is true. The more honest and grounded your story is, the more people will listen.
Think about it like this: a story is just something that made you think, or made you feel, or taught you something, and that you can now pass on to someone else.
And once you stop trying to sound like a storyteller and just speak like a person, the whole thing becomes easier.
In the next part, I’ll show you a simple way to structure a leadership story.
Nothing fancy... Just a pattern you can follow when you want to bring people closer to the work.
A simple structure for telling better leadership stories
You don’t need a storytelling course or a writing degree to do this well.
You just need a clear shape for your story.
Something your mind can follow and reuse in different moments, like in a team update, a stakeholder conversation, or even when mentoring someone.
So let’s keep it simple. Think of your story like this:
Start with a moment
Show the tension
Name the shift
Tie it back to now
Let’s walk through each of those, slowly.
1. Start with a moment
Skip the abstract setup. Don’t start with “we were trying to be more efficient.” That’s too vague. Instead, bring people into a real moment. A meeting, a decision, a stuck problem.
You might say, “It was 4:30 on a Thursday, and we were staring at the whiteboard trying to figure out why the last release caused so many bugs.”
This doesn’t need to be dramatic. It just needs to be real.
A moment is what makes people listen.
We remember moments more than we remember summaries.
2. Show the tension
Now talk about what made that moment hard, or uncertain, or frustrating.
What was at stake? What was confusing? What made people disagree?
Maybe it was time pressure. Or a conflict between speed and quality. Or someone feeling unheard.
This is where people start to see themselves in your story.
Tension is what creates interest.
It’s what makes someone lean in and think, “Yeah, I’ve felt that too.”
3. Name the shift
Every useful story has a shift. Something that changed.
It can be a small insight, a new approach, or just a decision that moved things forward.
It could sound like this: “That’s when we realized the way we were estimating work was hiding too much complexity. So we started asking different questions in planning.”
This is the part where you show what was learned. What moved. Even a small shift matters.
Because leadership is full of small shifts that lead to real change.
4. Tie it back to now
This is where you close the loop. Connect your story to the moment you are in now.
Why are you telling it?
What should we take from it?
You might say: “I bring that up because we’re facing something similar now. And I want us to pause and make sure we’re not rushing the same way.”
Or, “This reminds me of that time. And it helped me realize we might be thinking too narrowly again.”
That’s it. That’s your structure. Moment, tension, shift, connection.
You don’t need slides. You don’t need notes.
You just need to slow down and remember what you’ve already lived and what it taught you.
Where storytelling shows up in tech leadership
You don’t need a stage to tell stories.
You need moments.
If you’re working with cross-functional teams, managing people, or presenting to senior stakeholders, you already have the space for stories.
You just need to spot them.
Let me walk you through some common ones.
Vision and strategy conversations
This is where stories do a lot of heavy lifting. If you're trying to explain a long-term goal, a change in direction, or why something matters, stories help people connect with the why, not just the what.
Instead of saying, “We need to rework our infrastructure,” you can say, “Remember that outage in February? The team worked all weekend. That moment showed us what we’re risking if we don’t fix this now.”
Now it’s not about technical details. It’s about people. And urgency. And meaning.
Retrospectives and postmortems
It’s easy to turn retros into a list of bullet points: what worked, what didn’t.
But real learning comes when someone says, “You know what? That week when we shipped too fast and had to fix everything later, that stuck with me.”
Stories help us process failure without blame.
They help teams see patterns.
And they make the lessons easier to remember when pressure comes again.
One-on-ones and coaching
If you lead people, you’re probably guiding them through uncertainty.
They feel stuck. Or unsure. Or frustrated.
Telling a short, honest story from your own path builds trust fast.
You don’t need to sound wise. Just real.
You can say, “When I started leading, I also hesitated to speak in meetings. It took me months to feel comfortable saying I disagreed. What helped me was…”
That kind of moment stays with someone. It shows them they’re not alone. And it opens the door to real support.
Team updates and all-hands
When you give updates, it’s easy to list the progress: five tickets closed, feature deployed, roadmap adjusted. That matters.
But what makes people care is the story behind it.
What was hard?
What did we figure out together?
What are we proud of?
Who made a difference?
Stories bring meaning to the work.
And meaning is what keeps people going when things get hard.
Stakeholder communication
Sometimes you need to influence someone who doesn’t live in your world.
They don’t know the systems, or the code, or the product logic. They just want to know why it matters.
Instead of explaining everything, tell a story about a customer.
Or a bug that costs real time.
Or a moment where the team made a tough call and avoided something worse.
The point is not to impress. It’s to make things land.
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Common storytelling mistakes (and how to avoid them)
The truth is, most people who struggle with storytelling aren’t bad at it. They’re just trying too hard to sound like someone else.
So let’s name the usual traps, and walk through what to do instead.
1. Trying to make it perfect
You start thinking your story needs a beginning, middle, end, punchline, and maybe some emotional twist.
So you over-edit.
Or worse, you stay quiet.
What to do instead: Let it be messy. Focus on the point. If it’s something you've lived and learned from, people will feel that. Don’t polish the feeling out of it.
2. Making yourself the hero
It’s tempting, right?
You want to show what you did right.
But if your story is all about how smart or strong or right you were, people feel distanced.
They won’t relate. And they won’t trust you as much.
What to do instead: Be the guide, not the hero. Show what you noticed. Talk about what the team did. Share what challenged you, not just what worked.
3. Talking only about the outcome
A lot of updates sound like, “We solved the problem.”
That’s fine, but the story lives in how it was solved. What was at stake? What changed? What almost went wrong?
What to do instead: Tell the middle. The messy part. The thing that made it feel risky or human. That’s where the story is.
4. Forgetting the point
Sometimes a story is interesting, but people finish hearing it and think, “So what?”
That usually happens when you forget to connect it back to the present.
What to do instead: End your story by tying it back to the moment. Why are you sharing it today? What does it help us see or do differently?
5. Thinking you don’t have good stories
A lot of leaders skip storytelling because they think their work isn’t dramatic enough.
No big crashes. No turning points. Just everyday progress.
But honestly? The best stories are usually small.
They are about how we made a hard choice. How we recovered from a mistake. How we supported each other in a quiet way.
Those are the stories people remember.
Because they’re real.
One last thing to try this week
So maybe this all feels new.
Maybe it still sounds like something other leaders do.
Or something for a presentation later.
But you can start this week. You don’t need to wait for a big moment.
Try this: In your next team meeting, instead of just saying what happened, tell a short story from the week. A real moment. Something someone did. What changed. Why it mattered.
It can be one minute long. It just has to be honest.
And if you’re not sure which story to tell, ask yourself this:
What’s one moment this week that made me feel something?
Start there. That’s usually the story that sticks.
And if you try it, let me know how it goes.
I’d love to hear your story.
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✅ Reflective questions (Quiet Leadership style)
✅ Feedback prompts (Radical Candor made practical)
✅ A simple step-by-step conversation roadmap