The first 90 days in a new leadership role: what actually matters

I started a new leadership role in December 2025. Within my first week, I discovered the region I was inheriting had serious performance problems: staff departures, quality complaints across multiple markets, and trust issues that had been building for months.

The leadership books don’t cover that chapter.

Week 1: Shut up and listen

I met every person on my team one on one in the first five days. Not group meetings. Not team lunches. One on one, closed door, 30 minutes each. I asked three questions: What’s working? What’s not working? What would you change if you could?

The answers were consistent. People felt unsupported. Communication was one-directional. Promises had been made and broken so many times that nobody believed new ones.

I didn’t fix anything that week. I wrote everything down.

Weeks 2-4: Find the real problems

The loudest issues weren’t always the root cause. Underneath most performance problems I’ve seen is a culture where people felt pressured to hit numbers at any cost. When the pressure got high enough, some people cut corners instead of asking for help.

That’s a leadership failure, not an employee failure. The system created the behavior. If you just change the people and keep the system, the same thing happens again with different names.

So I changed the system. New reporting requirements. Weekly check-ins focused on pipeline, not just closed deals. Clear expectations with actual support behind them.

Month 2: Small wins, visible follow-through

Trust is built in the follow-up. I picked small, visible problems and solved them fast. A tool that had been broken for months. A scheduling conflict that nobody had escalated. A training gap causing quality issues in the field.

None of these were strategic priorities. All of them showed the team that when I said I’d look into something, I actually did.

Month 3: Start building forward

By month three, I had enough context to start making real changes. New hires on the team. A restructured meeting cadence. A framework for talking about problems without it feeling like blame.

The biggest shift wasn’t structural though. It was cultural. My team started bringing problems to me instead of hiding them. That only happens when people believe you’ll help solve the problem instead of punishing them for having one.

What the books get wrong

Most “first 90 days” advice assumes you’re walking into a functional organization. That’s not always the case. Sometimes you inherit a mess, and the mess is the job.

The books say to establish your vision early. I say listen first. Your vision doesn’t matter if nobody trusts you enough to follow it.

The books say to make quick wins. I agree, but with a caveat: pick wins that matter to your team, not wins that make you look good to your boss. Your team is watching which direction you’re facing.

Three months in, a region isn’t fixed by a new leader. But it can be moving in the right direction, and the people doing the work can believe it’s possible. That’s what the first 90 days are actually for.

About Khary Penebaker

Khary Penebaker is Division President at MetalMaster-RoofMaster, the Upper Midwest division of Wolkow Braker Roofing Corp. He previously built Roofed Right America from startup to $35M+ in revenue with 180 employees (2014-2025) and founded Penebaker Enterprises, growing it from $1.5M to $15M. A gun violence prevention advocate and former Everytown for Gun Safety Fellow, Khary brings two decades of leadership in commercial roofing, architectural sheet metal, and civic engagement.

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Last updated: June 28, 2026