The Cost of Avoiding Hard Conversations
Some people are naturally gifted at having hard conversations; by nature, I am not one of them. And it’s not because I don’t care—on the contrary, it’s usually because I do care, deeply. And having a hard conversation means that someone’s feelings will end up being hurt.
But lately I’ve thought a lot about the cost of not having the hard conversation, whether it be personally or professionally.
Difficult conversations rarely become easier with time. Problems don’t typically fix themselves. Instead, problems become patterns that are hard to break. And in the workplace, these patterns of avoidance often create resentment and frustration among other team members.
Because kindness without clarity is not actually kindness.
In my last newsletter, I wrote about the truth often living in the middle, and about the importance of holding both sides accountable with empathy. But accountability requires something many of us would rather avoid: a dreaded hard conversation. This is Management 101 — we know this, and yet we avoid it. Why?
The easy answer is that there is a temporary reward that comes from avoiding the conversation—the avoidance of conflict and disruption. There is also a fear that the person you address the conflict with could leave the organization or create further disruption in the workplace.
But I also think it’s more nuanced than that. I think for many people it stems from a genuine care and concern for the other person. And often, we don’t know how to have the hard conversation in a way that is proactive, clear, and still respectful.
Here is the challenge: the hard conversation needs to happen before the cost of avoiding it becomes greater than the discomfort of addressing it.
When hard conversations are avoided, the issue does not disappear. It is quietly transferred—to coworkers, clients, culture, productivity, or you, the leader carrying the frustration. What I have seen in myself is this: when I avoid the hard conversation that actually needs to happen, I focus on the minutiae that aren’t actually the root of the problem. Or, other team members can end up taking the slack.
Sometimes it may feel easier to live with your head in the sand (I can empathize). But eventually, the issue finds its way to the surface. By that point, the conversation is usually more emotional, the frustration has had time to build, and the person receiving the feedback may reasonably wonder why no one told them sooner.
Of equal importance is that clarity does not require cruelty.
Feedback can and should be clear, timely, and direct, while still being kind. This is actually, in my opinion, one of the most important reasons to “keep a short account” and not enter the conversation from a place of frustration.
It can sound as simple as:
“Here is what I am seeing.”
“Here is the impact it is having.”
“Here is what I need to be different moving forward.”
“And I would like to understand what you are experiencing as well.” In fact, “help me understand” is one of my favorite conversation tools.
Because the goal is not to win the conversation. The goal is to create clarity . . . this distinction matters.
When leaders enter difficult conversations determined to prove a point, people become defensive. When leaders enter them willing to be honest, curious, and direct, the conversation has a much better chance of producing growth.
And sometimes, even when the conversation is handled well, the outcome will still be uncomfortable. Someone may be disappointed. They may disagree. They may even choose to leave (which may be a good or a bad thing!).
Here is the bigger point: Clarity does not guarantee the outcome we want. It simply allows everyone involved to make decisions based on what is true.
I am still learning this. My natural instinct will probably always be to preserve harmony for as long as possible. But I am beginning to understand that real harmony is not created by avoiding what is difficult. It is created by addressing problems early enough that trust, accountability, and respect still have room to grow.
The hard conversation may feel unkind in the moment.
But done thoughtfully, clearly, and with genuine care, it may be one of the kindest things a leader can offer.