Ways to Navigate Difficult Conversations (on both sides!)

Difficult conversations are called such for a reason – they are not fun to have. This might be anything from a “Hey, we need to let you go” to “That plan we had didn’t work” to “We need to talk” – and the anxiety and discomfort around them doesn’t always get easier the more you have them.

We’ve been hearing a lot of talk on mitigation over the past few months, and that’s the best strategy for difficult conversations…mitigation. You’re working to lessen the severity, seriousness or painfulness of the difficult conversation. Here are a few tips to make those conversations a bit easier – and much more effective – no matter which side you’re on.

Understand the situation

Have you heard of the metaphor of running away from something in the woods? In case you haven’t, think about something chasing you. You keep running and running and running, and you never once look back. That thing chasing you gets scarier and scarier in your mind because you don’t know what it is, so all of that anxiety around it increases.

The moment you turn around, and see what is chasing you, you start to think of plans to get away from that thing.

This happens when we shy away from situations – if we’re avoiding a difficult conversation, we keep building it up. When we finally decide to have it, we get to a place where we work to figure out how to handle it. Look at the conversation that you may or may not be avoiding – take a big step back and work to understand the situation as much as possible. Running from it makes it worse, so schedule time (officially or unofficially) to have the conversation.

Listen more than you talk

This is true in most situations: if you listen more than you talk, you’re probably going to be in better shape for all conversation. This is especially true in ones that are highly emotionally charged. Too often we react instead of responding to people and stimulus when we are feeling less than great. That often leads to projection: you’re placing your annoyance or hurt onto that other person.

Use active listening to guide your responses: work to summarize what the other person is saying to you to make sure that you understand their meaning. Listen for bits of information that you can use in your response or a clarifying question, and try to avoid the word BUT. BUT often pits two ideas against one another, and when there is an argument, the last thing you want to do is make it worse by using an inflammatory word like BUT.

If you’re on email, get in-person – phone, video or in real life

If the difficult conversation is happening over email, then move to phone, video or real life – as soon as possible. Text and words can be misunderstood – and all of that overthinking around meaning and what someone was “actually” saying – or not saying – can get muddy fast.

If you’re using email, use it to make an appointment to be face to face, as much as possible, and as soon as possible. Stewing on emotions and meaning isn’t good for anyone.

Think about the middle

In difficult conversations, especially arguments and disagreements, someone is almost always going to be disappointed. The best way around massive disappointment from either side of the conversation is to think about the middle – diagnose what you want out of the situation and what they want out of the situation. Then, figure out the middle. What is the outcome that is not perfect for any one person, but falls somewhere between the two?

Start small with these tips and while we can’t guarantee that difficult conversations suddenly become easy, you might find a bit more space to handle things in a way that is a little bit less stressful for all parties, on all sides.


Subscribe to Our Newsletter

Stay up to date with our events and get exclusive article content right to your inbox!

Latest Stories

Other Featured Articles


All Article in Current Issue

Subscribe to our Newsletter

Stay up to date with our events and get exclusive article content right to your inbox!