Darryl Stewart
By Darryl Stewart

How and when to start a hard conversation

Many other leaders ask me for advice when they are dealing with difficult situations. Often, the difficult situations involve an employee underperforming or causing disruption on a team. We discuss the situation and I inevitably ask: “Have you talked clearly and directly with this person about the problem?” Way too often the answer is no. 

The same thing used to happen in my own head all the time. I knew there was an issue with someone, and I would grind my mental gears for days trying to figure out why it was happening and what I should do about it. 

Whether I push a colleague to finally have the conversation or I push myself to get out of my head and get face-to-face with the person, almost always the result is: “Why didn’t I do this sooner?” Once the issue is out in the open, things get easier. It is the fear of starting the conversation that often holds us back. What do I say? When do I do it? 

Here is my brilliant way to start a hard conversation. I simply say: “We need to have a hard conversation.” 

Now that you know how to start, the only question is when. How about today? 

People typically wait too long to have these conversations. You are not alone in this. How often in life do we over-complicate things? We invent work to do and create distractions to avoid the things that we know really need doing. This is one of those things. I am learning to save myself all the time and energy spent avoiding the hard conversation and instead, just get it over with. Life is too short.

Looking for ways to have that difficult conversation? Check out a previous I wrote: The right way to deal with your problem employee


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