I have walked into more than one team where the culture was the problem and nobody wanted to say it out loud. The bad habits were baked in, the loud ones were obvious, and the quiet structural ones were doing most of the damage. Both have to go, and you cannot fix either by firing your way out.
TL;DR: Resetting a bad culture is slow, uncomfortable work. The temptation is to replace people right away. The smarter move is to change the systems that created the behavior first, then figure out who can actually operate in the new environment. Culture change takes 12 to 18 months, not a quarter.
What bad culture actually looks like up close
People throw the word toxic around like it means any team that is hard to lead. It does not. High stress and a broken culture are two different animals, and confusing them is how new leaders make their first mistake.
High stress looks like long hours, tight deadlines, and people who are tired but still talking to each other. A broken culture looks like silence in meetings and side conversations in the parking lot. It looks like decisions getting reversed three times because nobody trusts the first call. It looks like the same two people getting blamed for everything while the actual sources of dysfunction sit untouched.
When I started at MetalMaster-RoofMaster, I spent the first two weeks doing almost nothing but listening. Not asking leading questions. Not pitching my plan. Just listening. You learn more about a culture in the first thirty days than you will in the next six months, and most leaders waste that window trying to look decisive.
Here’s what you’re looking for. Where does information get stuck. Who gets talked about when they’re not in the room. What problems keep coming back. Which meetings exist only to protect somebody from accountability. Those four questions will tell you more than any climate survey.
Change the systems before you change the people
Most new leaders walk in and start swinging. They fire the loudest problem in the first 60 days, bring in a couple of their own people, and call it a reset. Six months later the same patterns are back, just wearing different faces.
That happens because behavior comes from the systems around it. If your compensation plan rewards hoarding leads, people hoard leads. A meeting structure that punishes whoever raises a problem first teaches people to stop raising problems. A promotion path that runs through one favored manager teaches everyone to perform for that one person. That is a design problem, and design problems have design fixes.
Before I evaluate a single person, I audit the systems. How are bonuses calculated and who decides. What is the cadence of one-on-ones and are they actually happening. Who can approve what without going up the chain. What gets measured and what gets ignored. How does feedback travel up, down, and sideways. If the answers point to the same bad incentives, you have your starting point.
Then you change the system in public. Announce it, explain why, and tie it to a specific outcome you want to see. People do not trust quiet changes. They trust changes they can point at and say, that one is real.
How to shift norms without losing the people you need
Every broken team has people who are quietly miserable and waiting for someone to give them permission to operate differently. They are your first allies. You don’t have to convert them. You have to find them.
I look for the person who keeps raising the same uncomfortable point in meetings and getting shut down. The over-delivering manager with no political cover is another. So is the new hire who hasn’t yet learned to play the bad game. Those three show up on almost every team I’ve inherited, and they tell you where the healthy version of the culture wants to grow.
Once you find them, give them air. Back them publicly the first time they raise a hard truth. Reverse a bad decision they flagged. Promote one of them inside the first six months if the work supports it. Other people are watching, and they are calibrating what the new rules actually are based on what you reward, not what you say.
The flip side matters just as much. The people who built their power inside the old culture will test you. Not always loudly. Sometimes it is a missed deadline that used to be acceptable. Sometimes it is a sideways comment about the new direction in a group setting. You have to respond every single time, in proportion, in private when possible, in public when the behavior was public. If you let the first three tests slide, you have told the whole team the new rules are negotiable.
When to coach and when to part ways
I get this question more than any other from new leaders. When do you give someone a chance to change, and when do you accept that the fit is wrong.
My honest answer is that most people deserve a real shot in the new environment, but the shot has to be real. That means clear, written expectations about what changes. A defined window, usually 90 to 120 days. Specific behaviors, not vague vibes. Regular check-ins where you are honest about what you are seeing. And a decision at the end that you actually act on.
The people who change are usually the ones who were unhappy in the old system and did not know there was another option. The people who do not change are usually the ones who built their identity around being the kind of person who survived that old system. Identity is harder to move than skill.
You’ll know the difference within 60 days. Watch whether they bring you problems early instead of hiding them, whether they own a mistake without redirecting blame, and whether they operate differently when you’re not in the room. If two of those three aren’t happening, the next 60 days aren’t going to fix it.
When you do part ways, do it cleanly and respectfully. Severance, a real reference if you can offer one, and a private conversation. How you exit people is part of the culture you are building. The rest of the team is paying attention.
The 12 to 18 month timeline nobody wants to hear
Culture change takes a year and a half of consistent, repeated, often boring decisions that point the same direction. If you’re looking for a faster timeline, you’re looking for theater, not change.
The first 90 days are listening, auditing, and changing the most damaging systems. The next 90 days are testing the new rules and seeing who is operating inside them. Months 6 through 12 are when the personnel decisions start landing and the new normal becomes visible from the outside. Months 12 through 18 are when the culture starts holding itself up without you having to be the enforcer.
The biggest failure mode in year one is impatience. You will get pressure from your boss, your board, or your own ego to declare victory at month four. Do not. The work you are doing in months six through nine is invisible from the outside, and it is the most important work of the whole reset. If you rush it, you end up with a thin layer of new behavior over the old structure, and the old structure wins every time.
The practical takeaway
If you just inherited a team and you suspect the culture is the real problem, here is the order of operations.
- Spend the first 30 days listening more than talking. Map where information gets stuck, who gets blamed in absence, and which meetings exist to protect someone.
- Audit the systems before you audit the people. Compensation, promotion, meeting cadence, feedback flow, decision rights. Fix the worst incentive first and announce the change in public.
- Find your three allies. The truth-teller, the over-delivering manager, the new hire who has not learned the bad game yet. Back them visibly and early.
- Respond to every test of the new rules. Small consequences applied consistently teach the team faster than one big firing ever will.
- Give every person a real 90 to 120 day window in the new environment with written expectations. Decide based on whether they bring problems early, own mistakes, and operate the same way when you’re not watching.
- Plan for 12 to 18 months. Resist the pressure to declare victory at month four. The invisible work in months six through nine is where the reset actually lands.
None of this is glamorous. No speech fixes it, and no off-site resets a year of bad habits in a weekend. What works is the quiet, daily work of changing what gets rewarded and what gets tolerated, and the patience to let the team prove who they are inside the new rules.
If you’re sitting on a culture problem you haven’t figured out how to solve, I’ve probably lived some version of it. Get in touch.
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.
Common questions
What are the signs a team culture is actually toxic vs just high-stress?
High stress looks like long hours and tight deadlines with people who are tired but still talking to each other. Toxic looks like silence in meetings, side conversations in the parking lot, decisions reversed multiple times because nobody trusts the first call, and the same two people getting blamed while the real sources of dysfunction sit untouched.
How do you change team norms without alienating the people you need to keep?
Find your three allies first: the truth-teller who keeps getting shut down, the manager over-delivering without political cover, and the new hire who has not learned the bad game yet. Back them visibly and early. The people you want to keep are usually quietly miserable and waiting for permission to operate differently.
When should you replace team members vs work to change their behavior?
Give every person a real 90 to 120 day window in the new environment with written expectations. Watch for three things: do they bring problems early, do they own mistakes without redirecting blame, and do they operate the same way when you are not in the room. If two of those three are missing at 60 days, the next 60 will not fix it.
How long does a genuine culture reset take?
Twelve to eighteen months. The first 90 days are listening and fixing the worst systems. Months three to six are testing the new rules. Months six to twelve are when personnel decisions land. Months twelve to eighteen are when the culture reinforces itself without you having to be the enforcer.