A client called. He’s forming a temporary partnership with another business. The two companies trust each other and have a long history.

The president of the other company likes to keep things feeling relational and move fast. To do so, he wants to make a gentlemen’s agreement and skip the hassle of drafting up formal documents. But my client has asked that they document their agreement.

This has earned him pushback. The president of the other company doesn’t see the point. Just shake hands and get to work.

This creates a problem for my client. Should he risk friction by insisting on a written agreement?

The problem with nice leaders

Most leaders want to be liked. And if they can’t get that, at least they want to avoid conflict. Makes sense. Who doesn’t want to be liked? What sicko really wants conflict and stress?

Here’s the problem. Nice leaders are prone to allow poor behaviors and practices. They rarely work to create the right ones.

Why? Because to do either requires challenging someone or the status quo. And that doesn’t feel good. That feels like conflict. And nice people don’t do conflict.

Nice leaders try to get through the moment as opposed to building a future. As an accidental result, nice leaders create problems and hurt people over time.

They don’t want to. But that’s what happens.

Eight ways nice leaders hurt people

As you’ll see, being nice is a slippery slope. Many of these behaviors are connected to each other. If you struggle with one, the chances are high that you struggle with at least one other as well.

1. They avoid tough conversations
   What it looks like: Letting poor performance or behavior slide, not giving candid feedback, avoiding hard truths.
   Cost: Declining performance, frustrated top performers, tolerance of toxicity, and cultural drift.

2. They keep poor performers too long
   What it looks like: They avoid confronting or firing toxic employees or chronic underperformers.
   Cost: Morale suffers, high performers leave, and productivity drops. The good employees are asked to carry others’ slack and tolerate poor behavior.

3. They don’t provide accountability
   What it looks like: They let people miss deadlines or violate expectations or standards without consequence.
   Cost: This creates a culture of low trust and low standards. It leads to general disrespect for the leader.

4. They fail to set or enforce boundaries
   What it looks like: They allow the biggest, loudest, or most urgent voices to dictate priorities or how others are treated.
   Cost: Resentment, burnout, inefficiency, turnover.

5. They pursue consensus at any cost
   What it looks like: Needing everyone’s agreement before making decisions, or watering down decisions to avoid conflict.
   Cost: Slow decisions, purposeless strategy, and missed opportunities.

6. They let charismatic or respected individuals off the hook
   What it looks like: Giving exceptions to founders, key execs, or well-liked individuals when they misbehave.
   Cost: Cultural hypocrisy, power imbalances, and long-term brand risk.

7. They tolerate misalignment or undermining
   What it looks like: Not confronting a leader or department head who is out of sync or working at cross-purposes.
   Cost: Organizational confusion, silos, and stalled execution.

8. They over-prioritize harmony in meetings
   What it looks like: Minimizing debate, not allowing ideas to be challenged, avoiding conflict.
   Cost: Groupthink, poor decisions, and unresolved issues.

Don’t be a jerk.

But people need leaders who do the right things and have the right conversations, even when they are uncomfortable. They won’t always feel good. But a good leader is courageous enough to do it anyway.

My client is 100% correct in his sense that he needs a written agreement with his partner. I know both companies. I know the partner company has had problems in the past over a ‘handshake’ deal gone bad. I’m surprised that they want to risk this again.

Here’s what I said to my client:
“You are going to feel uncomfortable either way. Better now, with a difficult conversation now than later, with broken trust and conflict.”

He’s a good leader and is able to be courageous. He’s respectful enough to enter into a tough conversation well. This simple, difficult conversation won’t hurt either of them – but could end up saving both of their bacon (and their relationships) down the road.

Nice leaders often default to avoiding tough decisions for the sake of comfort, but that comfort comes at a cost to team performance and culture.

In what contexts do you tend to default to being nice and avoid the tough work of leadership?

What is one area where you realize wanting to be liked is allowing problems to continue or be created?

Take good care,
Christian