How to Approach Difficult Conversations in the Workplace

October 20, 2023

Difficult conversations are unfortunately always a part of our lives. This includes in the workplace. I'm sure we’ve all had our fair share of uneasy or awkward discussions and have figured out how to deal with them the best way we know.

Generally, you are left to your own devices on how to handle these uncomfortable situations. But in the workplace, when a certain level of professionalism and ethics needs to be met, it makes it slightly more difficult to navigate. So how do we approach these situations?

I’ve dealt with this quite a few times at work. The first thing I take into consideration is the person’s emotions and knowing that they are going to be running high. And it's almost impossible to have a difficult conversation with someone if they are defensive or not in a clear headspace.

I've learned that what made the biggest difference is to make sure the person feels heard, cared for, and validated. Make sure you hear their side of the story. If this doesn’t happen these conversations will become more difficult and the problems themselves will become more pressing.

So, to approach the situation, it’s helpful to ask a general question before like “how are you doing?” or “how’s life been?” just to start the flow of conversation and bring people's guards down. Then, when you bring up the issue at hand, address it very clearly but make sure to see what’s happening from their point of view as well. Bring up your side and what you've seen so they understand where you’re coming from. Follow up asking how you can help the situation.

There is much more going on in people's lives than you think. Many small issues can be fixed just by having a conversation and giving an employee a little extra help or making them feel understood.

The last thing that will completely change the game is to take account of anything that you know you should’ve done in the situation or could do better. This builds trust, opens communication, and makes things much easier moving forward.