Lessons From Turning Around Broken Teams

I have walked into broken teams three times in my career. The first time, at Penebaker Enterprises, I broke the team myself through poor hiring decisions and then had to fix it. The second time, at Roofed Right America, I inherited a division that was underperforming because the previous leader had checked out months before leaving. The third time, at Great Day Improvements, I took over a region with documented quality problems, falsified records, and a team that had been through enough leadership changes to be skeptical of the next one.

Each turnaround was different in the details but similar in the fundamentals. Broken teams share the same symptoms regardless of industry. Low trust. Unclear expectations. Inconsistent accountability. People protecting themselves rather than collaborating. The fix is not a single dramatic action. It is a methodical process of rebuilding the foundation that should have been there all along.

The first 90 days: assessment over action

TL;DR

I have walked into broken teams three times in my career. The first time, at Penebaker Enterprises, I broke the team myself through poor hiring decisions and then had to fix it.

The biggest mistake leaders make in a turnaround is moving too fast. They walk in on day one with a plan they developed from the outside and start implementing changes before they understand the actual situation. That almost always backfires. The team feels like the new leader does not respect what they have been through. The changes address symptoms instead of root causes. And the leader burns credibility on initiatives that do not work because they were based on incomplete information.

At Great Day Improvements, I spent the first 30 days doing more listening than talking. I met with every team member individually. Not to evaluate them. To understand their perspective. What was working. What was not. What they thought the real problems were. The answers were not always what I expected. Some issues the team identified were obvious from the outside. Others were invisible until someone on the inside explained the history.

During those conversations, I also learned who on the team was trustworthy, who was part of the problem, and who was somewhere in between. That assessment informed every decision I made over the next six months. Not every person on a broken team needs to go. Most of them are good people in a bad system. The leader’s job is to separate the system problems from the people problems and address each one appropriately.

When I took over the Upper Midwest region at Great Day Improvements, my first instinct was to start fixing things immediately. The previous leadership had left quality problems and staff turnover that needed urgent attention. Instead of rushing to fill positions and launch training programs, I spent the first three weeks sitting in on appointments, reviewing job files, and talking to every employee individually. What I discovered changed my entire approach. The quality issues were not a training problem. They were a supervision problem. The sales issues were not a motivation problem. They were a lead management problem. If I had acted on my initial assumptions, I would have invested in the wrong solutions.

Establishing the new standard

After the assessment phase, the next step is establishing what “good” looks like going forward. Not as a vague aspiration. As a concrete set of expectations that everyone can understand and measure themselves against. At Penebaker Enterprises, that meant written quality standards for every type of installation. At Roofed Right America, it meant documented sales processes and customer communication protocols. At Great Day Improvements, it meant reestablishing accurate record-keeping as non-negotiable.

The point is to communicate the new standard clearly and then enforce it consistently from day one. Not with threats. With calm, persistent follow-through. “This is what we do now. I will support you in meeting this standard. I will also hold you to it.” The team needs to see that the new leader means what they say. That takes weeks of consistent behavior, not a single announcement.

I also learned to pick my battles carefully during this phase. You cannot fix everything at once. Trying to overhaul every process simultaneously overwhelms the team and creates resistance. I identify the two or three changes that will have the biggest impact on performance and team morale, focus there first, and let the smaller issues wait until the bigger ones are resolved.

This is where most turnarounds fail. Leaders announce new standards in a meeting, send a follow-up email, and assume the work is done. Standards are not established through communication. They are established through enforcement. The first time someone violates the new standard and nothing happens, you have told the entire team that the old rules still apply. At every company I have led through a turnaround, the first enforcement moment was the one that mattered most. Not because it was punitive, but because it proved the words were real.

The people decisions

Every turnaround involves people decisions. Some are straightforward. The person who falsified records needs to go. The person who was actively undermining the previous leader needs to go. Those decisions are not pleasant, but they are clear.

The harder decisions are the people in the middle. The solid performer who has developed bad habits because the previous leader allowed them. The experienced team member who is resistant to change but has institutional knowledge you need. The person who is trying hard but may not have the skill set for the role as it needs to exist going forward.

My approach is to give everyone a fair chance under the new standard. Clear expectations, adequate training, reasonable time to adjust. Then evaluate based on results and effort. The people who embrace the new direction, even imperfectly, get my full support. The people who actively resist, after being given the tools and time to adapt, need to move on. That is not cruelty. It is clarity. And the rest of the team is watching how you handle both groups.

I have made every version of the wrong people decision. Keeping someone too long because I liked them personally. Promoting someone too fast because I needed the role filled. Hiring based on resume instead of character. Every one of those mistakes cost me more than the hard decision would have. At Penebaker Enterprises, I kept a project manager for eight months past the point where I knew it was not working. By the time I made the change, three of his crews had developed habits I spent the next year trying to break. The ripple effect of a delayed people decision goes further than you expect.

At Roofed Right America, I kept 80 percent of the team through the turnaround. The 20 percent who left were a mix of people who self-selected out when the standards changed and people I had to let go because they could not or would not meet the new bar. The 80 percent who stayed became the core of a team that went on to outperform every metric from the previous regime.

Building momentum

The early wins in a turnaround matter more than the big ones that come later. When a team has been demoralized, they need evidence that things are actually changing. Not promises. Evidence. Small, visible improvements that prove the new approach is working. A customer complaint that gets resolved faster than it would have before. A quality score that ticks up for the first time in months. A team meeting where people actually engage instead of sitting in silence.

I make those wins visible. Not in a self-congratulatory way. In a way that gives credit to the team. “The Milwaukee team’s customer satisfaction scores improved 12 points this month. Here is specifically what they did.” When people see that their effort is producing results and that the leader notices, discretionary effort comes back. That is the tipping point in every turnaround, the moment where the team stops going through the motions and starts actually caring again.

One of the most effective momentum builders I have found is the visible scoreboard. Not a complicated dashboard with twenty metrics, but a simple tracking board that shows the three things you are trying to improve. At Great Day Improvements, I put close rates, customer satisfaction scores, and installation quality ratings on a whiteboard in each branch. Updated weekly. When the numbers move in the right direction, the scoreboard does the talking. When they move the wrong direction, it starts the conversation naturally without anyone feeling singled out.

The long game

A turnaround is not a sprint. It is a sustained commitment that takes six to twelve months before the changes are fully embedded. The biggest risk is declaring victory too early. I have seen leaders relax their attention after three months of improvement, and within two months the old behaviors start creeping back. The new culture has not had enough time to become self-sustaining.

At Great Day Improvements, I am still in the middle of this process. The early indicators are encouraging. Quality scores are improving. The team is more engaged. Communication is more open. But I know from experience that the real test comes at month eight, month ten, month twelve, when the initial energy of the turnaround fades and the daily grind of maintaining high standards takes over. That is where discipline matters more than inspiration.

The teams that successfully turn around share one characteristic: a leader who is willing to do the uncomfortable work for as long as it takes. Not the flashy, motivational version of leadership. The quiet, consistent, showing-up-every-day version. The version that has the hard conversation on a Tuesday afternoon and then does it again on Wednesday when the next issue surfaces. That is not glamorous. But it is what works.

The truth about turnarounds that nobody wants to hear is that they take longer than you think and look different than you planned. I have never completed a team turnaround in less than twelve months. The first quarter is assessment. The second quarter is setting standards and making people decisions. The third quarter is where you start seeing results. The fourth quarter is when the team starts to believe the change is permanent. Rushing any of those phases means doing the turnaround twice.

Khary Penebaker

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.

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Last updated: March 9, 2026

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