I strive to avoid making others uncomfortable or wrong. Truly, I do. Yet I fail more often than I would like.

I suspect it is because I sometimes make one too many leaps in logic which effectively is inconsiderate. I have not fully partnered in the conversation.

It happened again the other day.

A client was musing aloud about letting go of a key employee. He doubted this person could help take the company to the next level.

Philosophically I disagreed. Full transparency, I have spent years helping ordinary employees become extraordinary. I tried, gently, to share my experience.

Wrong move.

I then bobbed and weaved, trying to sound less like a well-meaning busybody, but the damage was done. At that point it was clear: either he was right, or I was. There was no middle ground, no third option, no Switzerland.

In the end, I conceded: he knows his business better than I ever will. Regardless of my intention, expertise, or how carefully I couched my words, I had inadvertently set the stage.

Later, of course (because wisdom loves to arrive fashionably late) I realised my mistake. My words were neat and tidy, but they weren’t what I truly meant. What I really wanted to ask was whether he had thought through the consequences two or three steps ahead. What would the devoted clients say? His over-stretched team? How long would it take to replace someone with rare technical skills in a market tighter than a jar lid put on by an over-zealous relative?

In hindsight, I could have been more useful had I helped him prepare for the future. 

Even if dismissal was the right choice, and stakeholders still disliked it, it would sit better with everyone if they saw he had considered what mattered most to them.

So, here’s the lesson, neatly packaged for me: in difficult conversations, it’s rarely about displaying what I know. It’s about helping others see further, think wider, and make choices they can live with.

As my Uncle Ray is wont to say: “Hindsight is a perfect science”.