Wendy Harris
There’s one sitting in most of our inboxes right now. Or hovering somewhere in the back of our minds between the school run and the weekly shop.
A conversation we know we need to have. One we’ve been quietly postponing.
Maybe it’s with a colleague whose behaviour has been affecting the team. A client relationship that’s drifted somewhere neither of you intended. A friend you haven’t been honest with, even though you probably should be. Or simply someone you’ve let too much time pass with, and now the longer you leave it, the harder it feels to begin.
September has a particular energy to it. Back to school, back to business, back to the things we put off over the summer. And yet the conversations we most need to have are often the last ones we schedule.
We tell ourselves we’re waiting for the right moment. But if we’re honest, we’re usually just hoping the situation will somehow resolve itself without us having to say anything at all.
It rarely does.
In my experience, the anticipation of a difficult conversation is almost always worse than the conversation itself. We build it up.
We rehearse worst-case responses in the shower. We draft and delete messages on our phone. All of that energy, spent on a version of events that usually never arrives.
Because here’s what tends to happen when you actually have the conversation: quite often, the other person is relieved too. They’d sensed something was off. They’d been waiting for someone to name it.
What makes a difficult conversation difficult isn’t usually the subject matter. It’s the fear that honesty will damage something. But the quiet damage that builds when we stay silent – the unspoken tension, the growing distance, the slow erosion of trust – costs far more in the end.
I’ve worked with people who’ve spent months managing around a problem conversation, adjusting everything else to avoid it, until eventually the relationship or situation they were trying to protect had already quietly fallen apart.
The commercial cost is real too. Deals stall because nobody names the real objection. Clients drift because nobody checks in when the relationship starts to feel different. Teams underperform because nobody says the thing everyone can already sense. None of that shows up as one dramatic moment. It shows up as slow erosion, and by the time it is visible, it is already expensive.
The conversations that feel hardest to start are often the ones doing the most harm by not happening.
There’s no perfect script for these moments. What helps is intent. Going in with genuine care for the other person. Not to win, not to vent, but to understand and be understood. That changes everything about how it lands.
Start simply. “There’s something I’ve been meaning to say, and I’d rather say it than leave it unsaid.” That single sentence does more work than most people expect. It signals honesty. It signals respect. And it opens a door that both people, more often than not, are quietly glad someone finally opened.
Autumn is a season of clearing. Leaves, clutter, the things we’ve been carrying since summer.
Perhaps this year, one of those things is a conversation that’s been waiting long enough.
Wendy Harris is the founder of Konpasu and a commercial conversation strategist. She believes businesses grow when conversations do. Find her at konpasu.co.uk
