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Awkward is the New Authentic

Most leadership advice says, “Stay in your lane.” That’s exactly why so many high performers never become real leaders. Not because they lack courage, but because they’ve been rewarded their entire career for staying focused, prepared, and “on point.”

Your lane is safe.

But progress happens when you step into the awkward. Read this article to explore why awkwardness may be the most reliable sign that you’re leading well, and how high performers can learn to lean into it, instead of avoiding it.

Staying in Your Lane Is Hurting Your Leadership

He asked the question. And immediately regretted it. Not because it was wrong, but because it made the whole room shift. Eyes darted. Someone coughed. The air changed. And in that pause, he realized: he’d just stepped into someone else’s thinking, uninvited, unpolished, and unsure.

But also…right where he needed to be.

When You Only Stay in Your Lane, You Miss the Work That Matters

We often think leadership happens in our strengths. In the moments when we’re composed, prepared, and confident. But real leadership happens in the stretch. It happens when we step awkwardly into someone else’s mental space. Not to fix their thinking, but to move it forward. To meet people where they are, and then help them get where they haven’t gotten yet on their own.

High performers are conditioned to avoid these moments. We’re taught to lead from what we know, not curiosity. To deliver answers, not dwell in unknowns. But that mindset can limit your influence to the space you already understand.

Real influence lives where other people are thinking. And the truth is, it’s awkward. It means asking questions that might disrupt the room. Risking being misunderstood, so that the real issues can finally surface.

Because the goal isn’t to look smart. The goal is to help the thinking get better.

When you’re willing to step into how they see the problem, everything starts to move. You stop trying to be impressive and start helping them think more clearly. Instead of giving answers, you uncover what they already know and what they haven’t considered yet. That’s where influence begins. And that’s how teams unlock their best thinking and move forward together.

Awkward at a Glance

“This isn’t even my conversation…” ran over and over through his head.

Matt was shifting in his seat. He was hesitating, trying to figure out whether to say something or wait it out. The meeting was running long, and the marketing team was deep in the weeds about messaging strategy. Not his department. Not his decision.

But the real issue was bigger than marketing. It was about how his team was interpreting the company’s direction. He felt it, but didn’t know what to do with it. So he leaned forward.

“I might be out of my depth here,” he said, glancing around the room. “But I think we might be missing something important… Can I ask a clarifying question?”

The room went quiet. Not the polite kind of quiet, but the kind that lingers when something real is being said. Matt wasn’t trying to take over or prove something. He was doing what great leaders do: stepping into the gray space of someone else’s world to get more understanding.  Hoping the bigger picture would start to come into view.

And in that little moment, awkward as it was, his question changed the direction of the conversation entirely. People started thinking out loud.

Awkwardness Is a Signal, Not a Symptom

You don’t need to be polished. Your team needs you to be present, not just focused on what you’re saying but tuned into how they are thinking. Awkward moments can feel uncomfortable, like something to avoid, but they often signal that it is time to lean in. That is where fresh ideas appear, trust grows, and breakthroughs happen. Avoiding it might make you feel safe, but it keeps your team stuck.

I’ve learned this slowly over my career. The moments that mattered most were the ones where I didn’t protect myself. I chose to step into someone else’s thinking, even when it was messy, outside my lane, or full of unknowns. Instead of trying to look confident, I leaned in and said, “I don’t have all the answers – can we think this through together?” That honesty opened the door, and they walked through it.

This is how leaders stretch, not by doing more, but by thinking with others. By noticing where someone feels stuck and helping them think through what’s next. It’s not about fixing. It’s about opening up space for new thinking.

So the next time you feel awkward, don’t pull back. Step in. Here’s the framework:

  • Sense: Notice the moment someone seems stuck or the conversation stalls. Trust your instinct that it’s time to step in.
  • Test: Start with a gentle question, like “Can I ask something to clarify?” or “Help me understand your perspective.”
  • Engage: Listen without judgment, asking follow-ups like “What’s making this tough for you?” to deepen the dialogue.
  • Progress: Suggest a small next step, like “Could we try this approach?” to move the conversation forward together.

Example: Matt used STEP when he sensed the marketing team’s disconnect, tested with a question, engaged their ideas, and proposed a new direction.

Try It: Whose thinking are you avoiding right now? Awkwardness might be your clearest indicator that it’s the right place to create something new. Step into it this week, and see what changes.

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