If It Feels Comfortable, It Probably Isn’t Leadership

You don’t need another keynote telling you to “step outside your comfort zone.” You don’t need this blog post to tell you that, either. You already know growth isn’t easy.

But what you may not realize is where you’re still clinging to comfort and how it’s holding you and your team back from the results you’re capable of achieving.

In a recent episode of the Unconventional Leadership Podcast, Mike Sipple Jr. shared a powerful reminder:

“Maybe the thing you're avoiding is actually what you need to be doing.”

It’s an operational gut-check, not just a mindset shift. At every level of leadership - from first-time manager to C-suite executive - there are decisions, conversations and dynamics we know we should tackle, but don’t.

Why? Because they’re uncomfortable, and because we’ve convinced ourselves that “not now” is a valid strategy. Meanwhile, your team notices what you’re not addressing, and performance suffers in the gaps.

Let’s get specific.

5 Signs You’re Leading from a Comfort Zone (and What to Do Instead)

1. You haven’t had a truly uncomfortable one-on-one in months.
   You’re giving safe, surface-level feedback. You’re not confronting the passive-aggressive behavior, the low-level burnout, or the high performer who’s quietly checked out.
   
   Do this: Have the conversation, and give the hard feedback. Ask real questions: “What’s not working for you here?” “What am I not seeing?” “What are you holding back from saying?”
   
   
2. Your team has outgrown the org chart, but you haven’t touched it.
   You know the roles aren’t aligned. You know someone is quietly doing two jobs while another is underutilized. Restructuring feels political, risky or disruptive.
   
   Do this: Map the structure you would design from scratch, then compare it to what exists. Start making moves. One conversation, one reallocation, one updated title at a time.
   
   
3. You’re managing tasks instead of developing people.
   You’re tracking metrics and celebrating delivery, but you’re not stretching or coaching your team. Instead of building future leaders, you’re using them.
   
   Do this: Choose one person on your team and ask, “What’s the next level of impact you want to have here?” Then give them a project that scares them a little and support them through it.
   
   
4. You’re protecting legacy systems no one actually believes in.
   It’s the CRM that doesn’t fit your workflow. The hiring rubric that no longer reflects your values. The performance review process that’s become a box-checking ritual.
   
   Do this: Ask your team: “What’s one process we do that doesn’t help you do your job better?” Listen for what’s not working, and commit to dropping the dead weight.
   
   
5. You keep waiting for clarity before making a bold move.
   You want to be sure. You want buy-in. You want data. But as Mike said in the episode:

“We don’t lead with a flashlight. We lead with a candle. You only get to see a few steps ahead—and that has to be enough.”

Do this: Name the move you’d make if you were 90% confident. Then ask yourself what it would take to move from 70% to 80%. That’s your work this week.

The Cost of Staying Comfortable

This is the real work: the messy, sometimes frustrating and high-stakes stuff no title ever prepares you for. It’s also the difference between managers who maintain and leaders who move. When you avoid the uncomfortable conversations and decisions, your team feels it. Performance plateaus. Good people get frustrated. And the gap between where you are and where you could be keeps growing.

Check out the full conversation with Mike Sipple, Jr. and special guest Jordan Huizenga. 

At Talent Magnet Institute, we coach leaders through the pivots, the stretch seasons, the cultural rebuilds and the make-or-break conversations. Whether you're stepping into new authority or shaking off stagnation, we help you align, lead, and grow.

Ready to get uncomfortable for the right reasons? Let's start the conversation!