Every workplace has one.
The person everyone warns the new employee about.
- “Oh… just wait until you meet Sarah.”
- “Good luck working with Mike.”
- “Yeah… he’s just difficult.”
We slap labels on people pretty quickly at work.
Difficult. Negative. High maintenance. Drama.
But every time I hear someone described that way, I find myself wondering… Compared to what?
I’ve watched someone be labeled “difficult” in one organization and absolutely thrive in another. Same person. Different environment.
So before we decide someone is the problem, maybe it’s worth asking a different question. What is it about this environment that’s bringing out this version of them?
Sometimes the culture creates the behavior.
Think about a workplace where no one feels heard. People repeat themselves over and over because they don’t believe anyone is listening. Eventually they get louder. Then they’re called “aggressive.”
Or maybe expectations change every week. Someone keeps asking clarifying questions because they’re genuinely trying to keep up. They’re labeled “high maintenance.”
Or feedback only happens when something goes wrong. Now people become defensive the minute someone starts a conversation. They’re “hard to work with.”
Was that always their personality? Or are they responding to the environment they’ve been given?
That doesn’t mean difficult people don’t exist. Let’s be honest.
Sometimes people are disrespectful. Sometimes they’re unwilling to collaborate. Sometimes they’re simply not a good fit for the team.
This isn’t about excusing poor behavior. It’s about resisting the urge to assume the person is the only problem.
Because if every few months there’s a new “difficult employee”... there’s a chance the pattern deserves more attention than the person.
Culture isn’t what’s written on the wall. It’s what people learn.
- Whether speaking up is safe.
- Whether mistakes are held against them.
- Whether leaders actually listen.
- Whether conflict gets addressed or avoided.
- Whether asking for help is seen as weakness.
- Whether they can disagree without becoming “the difficult one.”
That’s culture. Not the mission statement. Not the values hanging in the lobby. The everyday experience of working there.
I’ve seen this happen in workshops. Someone who barely says a word suddenly opens up. Someone everyone thought was negative starts contributing incredible ideas. Someone who’s been labeled difficult becomes one of the most thoughtful people in the room.
What changed? Usually not the person. The environment.
For a few hours, they felt like they could show up without being judged. It’s amazing what people will share when they don’t feel like they have to protect themselves.
Here’s a question I’d encourage every leader to ask. When someone on your team feels “difficult,” ask yourself: What might they be responding to?
Not because the answer will always be culture. But because it’s worth being curious before being certain.
- Maybe they’re frustrated.
- Maybe they’re burned out.
- Maybe they don’t feel heard.
- Maybe they need clearer expectations.
- Maybe they’re carrying something outside of work that no one knows about.
Or maybe... they really are just difficult. That happens too.
But curiosity is a much better place to start than a label.
The best leaders I’ve worked with do one thing differently.
They don’t ask, “How do I deal with difficult people?” They ask, “What is this behavior trying to tell me?”
Sometimes the answer is about one employee. Sometimes it’s about the entire team. Either way, it’s usually the beginning of a much more honest conversation. And in my experience, those conversations are where better teams are built.
