Have you ever had a conversation you have been putting off for weeks? You know what you want to say and who needs to hear it. But whenever the right moment comes, something always gets in the way.
The real issue is never the timing. We usually delay difficult conversations at work because we are trying to protect something we haven’t identified yet.
Usually, we’re trying to protect the relationship. Sometimes it’s the team’s mood, our reputation as the easygoing person, or someone else’s pride. No matter what it is, we don’t notice the cost of waiting. By the time we finally talk, it’s no longer about the original issue. It’s about everything that has built up since then.
I see this happen a lot. A leader tells me about someone on their team whose work is slipping. We talk for half an hour about what is going on, what they want to say, and what they are worried about saying. By the end, they have practiced what they could say the next day. But when we meet again a couple of weeks later, the conversation still has not happened, and the leader cannot really say why.
It’s because we tell ourselves we’re being considerate by waiting. But waiting and avoiding look the same from the outside, and the person on the other side feels it. They know something’s off. They just can’t name it. So they start making up their own story, and it’s almost always darker than the one we were going to tell them.
Difficult conversations at work get heavier the longer you carry them
Marshall Rosenberg, the psychologist who created Nonviolent Communication, once wrote:
“What others do may be the stimulus of our feelings, but not the cause.”
I read that line years ago, and it changed how I think. It also planted the seed of what I now call Subtle Shifts, and made me realize that our reactions are not caused by others. They are caused by the sense we make of another person’s actions.
But I also believe the opposite is true for the person waiting for a conversation we haven’t started. Our silence triggers their thoughts. They fill in the gaps, and the longer we wait, the more complicated their story becomes. This is the cycle where most difficult work conversations get stuck.
Have you ever sat down to address one specific thing and ended up dealing with six weeks of unspoken assumptions? This happens all of the time. When we fail to promptly address conflict by having a difficult conversation, the other person fills the silence with their own story, and now you’re not unwinding one conversation; you’re unwinding all of it.
So here is the subtle shift
Stop waiting until you’re ready to have the perfect conversation. Begin with the imperfect version now.
That might sound small, and it is. The change isn’t in your words, but in lowering the bar for what counts as starting the conversation. It could be a short text message naming the topic, a meeting invite that hints at what’s coming, or just asking someone for five minutes. Any of these can break the silence, and once you do, the conversation will take its own shape.
Try this sometime this week. Choose something you’ve wanted to say and say it out loud, even if it’s not perfect. Say what you need to say and then let the other person process it. Most of the time, they will resist what you initially tell them, only to appreciate the candor later.
Difficult conversations at work get easier the moment we stop waiting for the perfect version. And once you take that bold step, please reply to this email to tell me how it went. I’m always thrilled to hear about the subtle shifts you are making.
