I started at Great Day Improvements on December 1, 2025. Within my first week, I discovered that the region I was inheriting had falsified sales records, lost half its staff to resignations, and had quality complaints stacking up across four markets.
The leadership books don’t cover that chapter.
TL;DR: The first 90 days in a new leadership role are about listening, not fixing. I inherited a region with falsified records and staff turnover. Here’s what I actually did in those first three months versus what the playbooks say to do.
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 falsified records were the loudest issue, but they weren’t the root cause. The root cause was a culture where people felt pressured to hit numbers at any cost. When the pressure got high enough, some people faked results instead of asking for help.
That’s a leadership failure, not an employee failure. The system created the behavior. If I just fired the people and kept the system, the same thing would happen again with different names.
So I changed the system. New reporting requirements. Weekly check-ins that 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. When someone told me the CRM was broken and nobody had fixed it for six months, I had it fixed in 48 hours. Not because it was the most important thing on my list, but because it showed my team that when I said I’d look into something, I actually did.
I picked five small, visible problems and solved them fast. Office supplies that had been backordered for months. A scheduling conflict that nobody had escalated. A training gap that was causing quality issues on installs.
None of these were strategic priorities. All of them showed the team that this new boss followed through.
Month 3: Start building forward
By month three, I had enough context to start making real changes. Hired two new design consultants. Restructured the weekly meeting cadence. Started a SWOT analysis practice with corporate that gave us 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, my region isn’t fixed. But it’s moving in the right direction, and the people doing the work believe it’s possible. That’s what the first 90 days are actually for.
About Khary Penebaker
Khary Penebaker is a Regional General Manager at Great Day Improvements, overseeing operations across Chicago, Madison, Milwaukee, and Minneapolis. He previously built Roofed Right America from startup to $35M+ in revenue with 180 employees 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 experience in construction, operations, and civic engagement.
Frequently Asked Questions
What should a new leader do in the first week?
Listen. Meet every person on your team one on one. Ask what is working and what is not. Do not change anything yet. You need to understand the real situation before you act.
How do you earn trust as a new boss?
Follow through on small things first. If you say you will look into something, report back within 24 hours. Trust is built in the follow up, not the first meeting.
What mistakes do new leaders make in their first 90 days?
The biggest one is moving too fast on changes before understanding why things are the way they are. The second is trying to be liked instead of being clear.
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Last updated: March 25, 2026