Diary of a Leader: How Relatable Leadership Builds Real Trust

Lindsay Sheldrake
Jun 2
4 min read

Updated: Jun 3

Welcome to "Diary of a Leader" - Real Stories, Leadership Lessons, and Personal Growth

Lindsay Sheldrake - How Relatable Leadership Builds Real Trust — Diary of a Leader: How Relatable Leadership Builds Real Trust

Ah, leadership. It’s messy, rewarding, and full of lessons you can only learn by doing.

Welcome to Diary of a Leader—a behind-the-scenes look at what it really takes to lead high-performing teams and deliver results in project-based businesses.

Whether you’re scaling operations or managing creative chaos, this space is for leaders who want to grow with clarity, confidence, and impact.

If you lead a design firm, creative studio, or project-driven team, you’ve probably felt it—that internal pressure to be the one who has it all together. To be positive. To be prepared. To be polished. All the time.

As a Fractional COO and project leadership partner, I see it all the time: leaders trying to stay strong for their teams while navigating their own uncertainty.

At first, it feels like leadership. And in many ways, it is.

But when this becomes the pattern, it can prevent the very trust and connection we want to build.

That’s the tension—between leading from strength and leading from shared experience.

Let’s unpack how that showed up for me, and what it taught me about being a relatable leader.

Why We Think Leaders Have to Be Flawless

Most of us step into leadership believing we need to have all the answers. That we have to model confidence, optimism, and unwavering direction. And yes, there is power in presence.

But when presence turns into performance, something critical gets lost: connection.

As Brené Brown writes in The Gifts of Imperfection, it’s not our masks that build relationships. It’s our humanity.

Trying to lead flawlessly doesn’t inspire trust. It creates distance. Because no one relates to perfect. But everyone relates to struggle.

Adversity as a Bridge, Not a Barrier

We often talk about experience like it’s a resume. But the most impactful experience? Adversity.

When you’ve walked through something hard—and come out wiser—you gain more than resilience. You gain perspective.

That perspective is what makes you relatable. It allows you to say, "I know what you're going through," not as a tactic, but from truth. And when that truth is shared with humility, it creates a bridge.

A Conversation That Changed Everything

A few years ago, I had a team member who didn’t get a promotion she was hoping for. She had the skills. The drive. The leadership potential. But the role went to someone with more seniority.

She was gutted. And honestly? She struggled to accept it.

Not long after, she announced she was pregnant and would be heading out on maternity leave in six months. Before she left, we had a real conversation—not about performance or handoffs, but about life.

We talked about ambition. About identity. About what it means to pause one part of your life to make room for another.

As a mother myself, I knew exactly how she felt. And I told her: "If there’s anything good to come from this, maybe it’s the clarity this time will give you. About what matters most."

I shared moments I had missed with my own family in pursuit of career momentum. Not as a caution, but as context. And I encouraged her to fully unplug, to give herself that space.

A year later, she called me. She was ready to come back. Ironically, the role she originally wanted had just opened up. And do you know what she said?

"The reason I called you—the reason I even want to come back—is because of that conversation."

That’s the power of relatable leadership.

What Makes Relatable Leadership Work

It’s not just about being vulnerable.

It’s about being grounded in your values, confident in your imperfections, and generous with your wisdom.

Relatability isn’t something you manufacture. It comes from showing up. From failing, learning, and sharing.

From letting others see not just what you do well, but what you’ve walked through to get there.

How to Lead with Relatability (Without Losing Authority)

Show up, don’t show off. You don’t need to perform strength. Just be present.
Share your why. People don’t need your whole story—just enough to understand your empathy.
Use your story to empower others. Keep the focus on their growth, not your spotlight.
Practice humble transparency. Admit when you’re learning too. Invite others into the process.
Encourage dialogue. Being relatable doesn’t mean fixing everything. It means being a safe space.

The Leadership Lesson

People don’t follow perfect leaders. They follow real ones.

Because trust doesn’t come from always being right. It comes from being honest.

It comes from sharing what you’ve learned through adversity.

And it grows when your values show up in how you lead—not just in what you say, but in the space you create for others to be human, too.

Wrapping Up (Because Time is Precious)

Relatable leadership isn’t soft. It’s strategic.

It builds trust. Strengthens culture. And creates the kind of connections that keep great people coming back.

Wisdom is forged in crisis. And when you share that wisdom with courage and humility, you don’t just lead more authentically—you lead more effectively.