Leadership & Team Building

Building High-Performing Teams

What I learned about hiring, accountability, culture, and trust while growing companies from five employees to 180.

Why I talk about teams

I have built teams from scratch three times. At Penebaker Enterprises, I started with a truck, a phone, and a willingness to work harder than anyone else. We grew that commercial roofing company from $1.5 million in revenue to $15 million with 50 employees. At Roofed Right America, I helped scale operations to $35 million with 180 employees across multiple markets. Now at Great Day Improvements, I manage four markets spanning Chicago, Madison, Milwaukee, and Minneapolis.

Each of those experiences taught me something different about what makes teams work. The first company taught me that hiring the wrong person is more expensive than having no one at all. The second taught me that systems matter more than talent once you get past 50 people. The third is teaching me that inheriting a team requires a completely different leadership playbook than building one from day one.

This page is a summary of what I have learned. Not theory. Not frameworks borrowed from books I read on a plane. These are lessons that came from making mistakes, fixing them, and sometimes making them again before the lesson stuck.

Hiring for character over credentials

The best hire I ever made was a guy who had never worked in construction. He had been a restaurant manager for eight years. What he knew how to do was show up on time, manage chaos, and treat people with respect under pressure. I could teach him roofing. I could not teach him those things.

The worst hire I ever made had 20 years of industry experience and came with glowing references. He also had a habit of cutting corners when nobody was watching and blaming his crew when jobs went sideways. It took me six months to undo the damage he did to team trust in three.

After enough of those experiences, I built a hiring filter that prioritizes three things: integrity, work ethic, and coachability. Skills can be developed. Character is mostly set by the time someone walks into your office for an interview. I look for people who take ownership of their failures during the interview, not just their wins. Anyone can talk about what they built. I want to hear about what went wrong and what they did about it.

In construction, this matters more than most industries. You are putting people on rooftops, managing six-figure projects, and trusting crew leaders to represent your company when you are not on the job site. A resume does not tell you whether someone will do the right thing when it costs them something. The interview, the reference calls, the way they treat your receptionist when they walk in, that tells you.

Setting clear expectations from day one

Most team dysfunction I have seen comes from the same root cause: unclear expectations. People are not lazy or incompetent. They are confused about what success looks like. They think they are doing a good job because nobody told them otherwise, and then they get blindsided during a review or, worse, when they get let go.

At Penebaker Enterprises, I made this mistake early. I assumed my crew leads understood what “quality work” meant because they had been in the trade for years. They did not. Quality meant different things to each of them. One guy thought it meant no leaks. Another thought it meant clean lines on the flashing. A third thought it meant getting done on time regardless of how the finished product looked.

Once I started defining expectations in specific, measurable terms, things changed fast. Every new hire got a written document on day one that spelled out exactly what we expected. Not vague statements about “exceeding customer expectations.” Concrete things. Response time to customer calls. Photo documentation requirements. Cleanup standards before leaving a job site. When you make expectations specific, accountability becomes a conversation about facts, not opinions.

The same principle applies at the leadership level. When I took over at Great Day Improvements, one of the first things I did was sit down with each team member individually and ask: what do you think your job is? The answers were all over the place. People in the same role described completely different priorities. That gap between what leaders think the team understands and what the team actually understands is where performance problems live.

Accountability without fear

There is a version of accountability that works and a version that destroys teams. The version that destroys teams is the one where people get called out publicly, where mistakes are treated as character flaws, and where the loudest voice in the room sets the standard for how problems get addressed.

The version that works is quieter. It is consistent. It starts with the leader holding themselves accountable first. When I make a mistake at Great Day Improvements, I name it in front of the team. Not in a performative way. In a factual way. Here is what happened, here is what I should have done differently, here is what I am doing to fix it. That sets the tone. When the leader is transparent about their own errors, it gives everyone else permission to be honest about theirs.

At Roofed Right America, we built an accountability system that tracked key metrics weekly. Revenue per sales rep, close rates, installation quality scores, customer satisfaction. The numbers were visible to everyone. Not to shame low performers, but to create clarity about where things stood. When everyone can see the data, the conversation shifts from “I feel like things are going okay” to “here are the numbers, and here is what we need to do about them.”

The hardest part of accountability is consistency. You cannot hold someone accountable for missing a deadline this week if you let it slide last week. You cannot enforce quality standards on one crew and look the other way with another because their lead is a friend. The moment accountability becomes selective, the entire system breaks down. People stop trusting the process, and they start managing around the leader instead of with them.

What changes when you scale past 50 people

There is a breaking point somewhere between 30 and 50 employees where everything you used to do stops working. The personal relationships that held the team together when you were small cannot scale. You cannot have a one-on-one relationship with every person when you have 80 people. You need systems.

At Penebaker Enterprises, I could walk a job site and know every person by name, know their family situation, know who was having a tough week. At 50 people, that was still possible if I worked at it. At Roofed Right America with 180 employees, it was not. I had to trust my managers to carry the culture. That meant hiring managers who understood that their job was not just to hit numbers but to build people.

The scaling process also exposed every weakness in our processes. Things that worked fine at 20 people, like informal communication and handshake agreements with subcontractors, created chaos at 100. We had to formalize everything. Project management systems, documented procedures, standardized training. The entrepreneurs who resist that formalization are usually the ones whose companies stop growing at a certain point or, worse, grow and then collapse because the infrastructure cannot support the volume.

I have seen both outcomes. Penebaker Enterprises grew steadily because we built systems as we grew. Roofed Right America grew faster, but some of the systems did not keep up. When I left, some of the problems that eventually surfaced were traceable back to processes that should have been tightened two years earlier. That is the lesson: build the infrastructure before you think you need it, because by the time you realize you need it, you are already behind.

Culture is what happens when the leader leaves the room

This is the test that separates real culture from aspirational slogans. If your team behaves differently when you are in the room versus when you are not, you do not have a culture. You have compliance.

Every leader says culture matters. Most of them do not actually know what their culture is. They know what they want it to be. They know what the poster in the break room says. But the real culture is the behavior that happens when nobody is watching. It is how your team talks about customers when the customer is not on the phone. It is what your crew does when they find a problem that the homeowner will never see.

At Great Day Improvements, I inherited a culture that had some real problems. Falsified records. Staff resignations. Quality issues that had been ignored or papered over. Fixing those problems was not just about changing processes. It was about changing what people believed was acceptable. That takes time. You cannot change culture by sending an email or hosting a team lunch. You change it by making decisions that are consistent with the culture you want, even when those decisions are uncomfortable.

The first time you address a behavior that used to be tolerated, the entire team is watching. They are not just watching what you do. They are watching whether you follow through next time. And the time after that. Culture change is not a single act. It is a pattern of acts that, over time, redefine what normal looks like.

I tell leaders this: if you want to know your real culture, do not ask your direct reports. Ask the newest person on the team what they noticed in their first two weeks. That person has not been acclimated yet. They can still see the things that everyone else has stopped noticing. Their observations will tell you more about your culture than any engagement survey.

Rebuilding trust after things go wrong

Trust is the most important thing on a team and the hardest to rebuild once it breaks. I have been through it multiple times. After a bad quarter where the numbers were ugly. After a leadership change that left people uncertain about their futures. After discovering that a team member had been falsifying reports for months.

The instinct when trust breaks is to over-communicate. Town halls. All-hands meetings. Reassuring emails. That helps, but it is not enough. Trust is rebuilt through small, consistent actions, not grand gestures. Showing up when you said you would. Following through on the commitments you made last week. Giving people information they were not expecting you to share. Those micro-moments are where trust gets rebuilt, one interaction at a time.

The other thing I have learned about trust: it is asymmetric. It takes months to build and minutes to destroy. A single act of dishonesty from a leader can undo a year of good work. That means you have to be relentlessly honest, even when honesty is uncomfortable. If the numbers are bad, say so. If a decision was wrong, own it. If you do not have answers yet, say that instead of making something up. People can handle bad news. What they cannot handle is finding out their leader was not straight with them.

Leading across multiple markets

Managing four markets simultaneously is a different challenge than running a single location. You cannot be everywhere. You have to trust your people, and you have to build systems that surface problems before they become crises. The lag time between something going wrong in a remote market and you finding out about it is where companies lose money and customers.

What I have found works is a combination of consistent metrics, regular presence, and empowered local leaders. The metrics tell me what is happening. The regular presence, being in each market often enough that the team knows I am paying attention, tells me what the metrics miss. And empowered local leaders, people who have the authority and judgment to make decisions without calling me first, keep things moving when I am in a different city.

The biggest mistake multi-market leaders make is treating every location the same way. Chicago is not Madison. The market dynamics, the customer base, the competitive environment, the labor pool, all different. What works in one market may not transfer directly to another. You need a framework that is consistent in its principles but flexible in its application. Accountability, quality standards, and customer experience expectations stay the same everywhere. How you achieve them might look different in each market.

Writing on building high-performing teams

These articles explore specific aspects of team building in more depth.

How to Rebuild Team Trust After a Bad Quarter

What I did when the numbers were bad, the team was shaken, and trust was on the line.

What Scaling to 180 Employees Taught Me About Accountability

The systems and hard lessons from growing a company past the point where personal relationships can hold everything together.

Why Culture Fails When Leaders Avoid Hard Conversations

The conversations most leaders avoid and why avoiding them costs more than having them.

Lessons From Turning Around Broken Teams

What it actually takes to rebuild a team that has lost its way, from someone who has done it more than once.

How I Build High-Performing Teams Across 4 Markets

Managing teams in Chicago, Madison, Milwaukee, and Minneapolis, and what multi-market leadership requires.

Frequently asked questions

What is the most common mistake leaders make when building teams?

Hiring for skills instead of character. You can train almost any technical skill. You cannot train integrity, work ethic, or the ability to take ownership of mistakes. The second most common mistake is assuming everyone understands what is expected of them without explicitly defining it.

How do you handle underperformers without damaging team morale?

Address it directly and privately. Never publicly embarrass someone. Have a specific conversation about what needs to change, by when, and what support you will provide. If the person cannot or will not meet the standard after a fair chance, moving them out actually improves morale. Most teams know who the underperformers are, and they resent it when leadership does nothing about it.

Does Khary Penebaker speak about team building at corporate events?

Yes. Building high-performing teams is one of my core speaking topics. I draw on real experience scaling companies and managing multi-market operations, not abstract theory. My talks cover hiring, accountability, culture, and the leadership behaviors that make or break team performance. Learn more about booking Khary for your event.

How long does it take to turn around a broken team?

Expect six to twelve months before you see consistent improvement. The first 90 days are about assessment and setting new expectations. The next 90 are about enforcement and building new habits. After that, the culture starts to shift on its own as the team internalizes the new standards. But it requires sustained effort the entire time. Most turnarounds fail because the leader loses patience or gets distracted before the change takes root.

Speaking Topic