Some workplaces have a "nice" problem. Everyone’s polite and pleasant, and yet people are too "nice" to give one another meaningful feedback.
You’ve probably been in one of these conversations. Maybe the same issue kept showing up even though everyone supposedly talked about it. Or there was a palpable "vibe," but the words being spoken didn't quite match, creating that pat-your-head, rub-your-belly feeling where what you’re hearing and what you’re sensing are pulling in opposite directions. Or maybe someone left a conversation thinking it went really well, only to hear through the grapevine that things had been left unsaid – or at least, unsaid to them.
It's reasonable to look at these situations and assume someone’s holding back because they're trying to be nice. But there’s something else beneath the surface.
When people skirt around issues, avoid difficult conversations, bite their tongues, or give a watered-down version of what they really mean, it's often less about being "nice" and more about self-preservation.
Kindness can absolutely be part of it. Most people don't want to hurt others or make them uncomfortable. But there's usually another calculation happening too: What could this cost me?
Our brains are really good at noticing potential risk and finding reasons NOT to stick our necks out. That’s by design! Historically, if you held back when you could have moved forward, you usually lived to try again. But if you made yourself too vulnerable, missed a real threat, or took the wrong risk...well, the stakes could be considerably higher.
Turns out, survival is a pretty great motivator – at least in the short-term.
Thankfully, most of us aren’t outrunning real danger during a Tuesday afternoon team meeting. But that basic wiring didn’t disappear when we started working in offices, hopping on Zoom calls, and scheduling performance reviews.
Say someone has information they genuinely believe could help a colleague. They've noticed something about that person's work, behavior, or how they're showing up, and it seems useful for them to know.
There are choices: they could say something, keep it to themselves, or wait until the "right" decision becomes obvious. And before they even realize it, the calculations start.
What if I speak up and they don't take it well...
What if they misunderstand me...
What if I say the wrong thing...
What if I speak up and sound like an incompetent bumbledoof...
Some of that calculation is genuinely about the other person. How might they react? Do they usually take feedback well? Do they even want to hear another perspective? Could this hurt them? Will they understand the intent is good?
But a bigger part of the calculation is usually about the person speaking. What could this cost me? Could it damage the relationship? Will they see me differently? Am I creating more work for myself? What if I end up in a conversation I don't know how to manage? Could this come back to bite me later?
And so easily, sometimes before there's been a conscious thought about it, waiting or watering down the conversation starts to feel like the best option.
Instead of talking themselves into sharing a perspective, people talk themselves out of it. And because intentions are generally good, they can even convince themselves they're doing the other person a favor.
People become REALLY good at calculating the potential cost to themselves of speaking up, while seriously underestimating the cost of their silence to the other person.
Because there's a cost on that side too.
The other person doesn't get information that could help them improve, and may have no idea where they really stand. Then the same issue happens again, frustration builds, assumptions get made, and maybe people start talking about the problem with everyone except the person who could actually do something about it. And eventually, someone is sitting in a performance conversation hearing feedback they could have used months ago.
This pattern shows up a lot with leaders, because their cost calculation can get even more complicated. Leaders often feel responsible for the weight of the entire conversation. They want to share their perspective well, manage the employee's emotions, make sure nothing gets misunderstood, influence what happens next, protect the relationship, and somehow navigate all of it toward a positive outcome. On top of that, how well they handle difficult conversations may affect how their performance is perceived.
Here's the truth of the situation: words can be chosen thoughtfully, emotions regulated, curiosity maintained, and the conversation approached with care, but no one can control how another person interprets what's said, what they bring into the conversation, or how they respond. The more good communication is defined as producing the "right" outcome, the more intimidating honest communication becomes.
The good news is that no one goes into a conversation responsible for delivering indisputable facts. It's possible to share an experience, what's being observed, or how something is landing, and then ask the other person how they see it. One thing is certain: the person sharing doesn’t have the whole picture, and they don’t need to. The goal is to bring what you know into the conversation and stay open to what you don’t.
That takes some of the pressure off, because good communication isn't about getting every conversation perfectly right. That's impossible. When perfection becomes the focus, it's easy to become so afraid of getting a conversation wrong that the real conversation never happens at all. People become "nice," avoidant, or even invisible, and none of those work well in the long run.
If you want to get better at real conversations, start here:
You don’t have to prove your perspective. You’re allowed to perceive and experience something differently from someone else with no additional evidence to back it up. Share what you’re seeing, then stay open to learning what you don’t see.
Before deciding you’re protecting someone else, ask yourself what you might be protecting yourself from. Discomfort? Conflict? Being disliked? Looking foolish? Getting it wrong? There’s nothing shameful about any of those things. Knowing what’s driving your choices gives you a better chance of making the decision you actually want to make.
“I’m noticing...” or “Here’s how this is landing for me...” leaves room for another person’s experience. “Here’s what happened” tends to shut down the room and only leaves space for people to agree with you or argue with you, not much in between. When you share your perspective and listen for others’, everyone learns and grows.
We’re really good at practicing difficult conversations in our heads. Unfortunately, the other person rarely follows the script we wrote for them. 😅 Share your perspective, ask questions, and listen. Let yourself be surprised! If you already know exactly how the conversation will go, you’re probably not leaving enough space for the person sitting across from you.
They don’t exist. There will always be a reason to wait until you’ve thought it through a little more, found better words, caught the person in the right mood, or reached a moment when the conversation somehow feels easier. Even if you found the EXACT right words and delivered them at the perfect time, you still couldn’t control how another person hears them, what they bring into the conversation, or how they respond. And the longer we wait for the risk to disappear, the easier it is for a small, manageable conversation to become a much bigger one.
Performance evaluations, I see you. 👀 Honest conversations are usually much easier when they happen close to the thing you’re actually talking about. If you’ve been thinking about something for six months and the other person is hearing it for the first time, you’re entering that conversation with inherent inequity. Talk sooner – it usually makes the conversation kinder for everyone.
Some conversations are going to go sideways. You will misspeak, someone will misunderstand you, feelings will get hurt, you will walk away from some future conversation thinking, Welllll...that could have gone better. That’s okay. Go back and say, “I don’t think I handled that well,” “That didn’t come out the way I meant it,” or “Can we try again?” Good communicators aren’t people who never get it wrong; they’re the people who know how to come back when they do.
Whether you’re talking with a leader, co-worker, friend, or partner – the goal isn’t to get every issue resolved in one sitting. It’s to stay connected enough that you can keep talking honestly and openly. If things start going sideways, notice it. Pause. Get curious about what just happened. Take a break if you need one. When the relationship is strong, one difficult conversation doesn’t have to carry so much weight. You have room to clarify, repair, reconsider, and come back again (and again), if needed.
People don’t become good communicators by eliminating risk. They get better by accepting that honest conversations carry risk, and by realizing there's usually more space, grace, and time to work through disagreement, misunderstanding, and mistakes than the nervous system would suggest.
So the next time something is being held back because it feels safer, the question worth asking is: What's being calculated here?
What could it cost to say something?
And what could it cost the other person if it goes unsaid?
Sometimes that second question changes the math.
