The most expensive problems my clients face aren’t complex or sophisticated contract disputes. They’re conversations that never happened. The partner who should have been confronted about their underperformance three years ago. The vendor relationship that just limped along, burning money, because nobody wanted the discomfort of renegotiating the contract terms. The employee whose problematic behavior metastasized into a toxic workplace because management kept hoping it would resolve itself. These situations started small and could have been manageable, and fixable with a single uncomfortable conversation.
Conflict avoidance in professional settings doesn’t keep the peace. It creates a slowly spreading rot that corrupts every adjacent relationship and decision. Think about what happens when a business owner dodges that conversation with a business partner about their spouse meddling in company decisions or a problematic employee. That avoidance tacitly creates a culture where discomfort is more dangerous than dysfunction, and that lesson gets reinforced every single day no one speaks up. Meanwhile, the actual problem grows over time and becomes much more difficult to resolve.
The brutal irony is that people massively overestimate how bad these conversations will be. In my experience, about seventy percent of the “difficult” conversations my clients finally force themselves to have are better and easier than expected. We build these interactions up in our minds anticipating how horrible they will be only to discover that most reasonable people on the other side of the table are just waiting for someone to be direct with them. And even when the conversation goes poorly, even when it ends a relationship or leads to a departure, you almost always look back and wish you’d done it sooner.
I challenge you to write down any professional relationships or situations that drain your energy when you think about them. The partnerships that feel off, the arrangements that don’t work, the boundaries that keep getting violated, the expectations that need resetting. Most people can identify between five and ten issues where they’re actively choosing silence over resolution. Now imagine that you handled all those this month with basic directness and professionalism. It will benefit your business, your stress level, and allow you to reclaim mental real estate.
My bet is you are about eight awkward conversations away from the professional life you actually want. The question isn’t whether you can afford to have those conversations. It’s whether you can afford to keep avoiding them.
As always, this post and others can be found on my blog, Business Law Guy.