The Reason You Hate Difficult Conversations (and 4 tips to help)

Leaning into difficult conversations is a sign of strong leadership, yet we all struggle with it.

What is it that makes these conversations so uncomfortable, that many of us prefer to avoid them altogether? ... even though we know it's going to cost us in time and effort if we don't deal with it head-on.

Why do we prefer to put up with something rather than dealing with it?

Why don't we want to talk straight with the person involved, and clear the air (even when it bothers us so much that we invest time and effort in complaining about it to the people around us).  Often its clear we want a resolution, yet we don’t take the direct route to resolving it.

Well, we have been looking into this for you.

And the answer is pretty straight-forward…Difficult conversations are uncomfortable. They are uncomfortable because they are dealing with personal topics such as someone’s behaviour, an embarrassing situation, or the future of a relationship (such as their ongoing employment). 

Communicating successfully in uncomfortable situations is difficult because its unpredictable, we don’t have a lot of practice with it and it usually provokes emotional responses in others, that we don’t feel equipped to deal with.

So, we feel a sense of threat in our brains, whenever a situation arises that calls for a difficult conversation. This threat is driven by fear.

This fear tends to be focused on the feeling that the conversation will not go well and you will feel uncomfortable during it. You may worry that you will say or do the wrong thing that makes things worse, and then you will feel bad afterwards (guilt, sadness, frustration, worry), and it may lead to unproductive behaviours from the other person that could result in the need for further difficult conversations.

It feels big and exhausting, and it seems easier to avoid it, than to deal with it.

What’s interesting though, is that this sense of threat is often unnecessary.

In school we learn about the Normal Distribution Curve. Its also called the "bell curve" because its shaped like a bell.  Its important because if we apply it to the conversations we have on a daily basis, it means that around 80% will fall within the middle "average" or "okay" space. Only 10% will fall in the "went awesome" space and only 10% will fall at the lower end, in the "was terrible" space.  This means that if we step-up and have difficult conversations 8 out of 10 are going to be okay. 1 in 10 are going to go great - just like we hope. And 1 in 10 will be terrible. Those odds aren't too bad, right.

So how do I know if the conversation is going great?

When the difficult conversation goes well, your message is met with positive emotions (the other party may express a sense of relief - they were thinking the same thing or had felt like they should bring it up in conversation with you, they may express gratitude for your help and support, or a sense of hopefulness that they can improve and deliver whats needed). When the conversation goes well, you not only feel good about the conversation afterwards, your relationship is stronger, based on mutual respect and you can both deliver what needs to be done. You progress forward, together.

How can we try to influence the probability that your conversation will fall in the top 10% and go really well?

There's a few things you can do to influence the outcome...

The following 4 tips are ways you can try to  Control the Controllables - to try to prepare and plan to help set the conversation on the right path (towards the top 10%).  And try to let go of the uncontrollables (things like, the way the other person will respond).

TIP 1 - plan the right TIME

Finding the right time is essential.

Make it in the morning. Don’t leave it to the afternoon when your brain is tired.

How do you do this:

TIP 2 - plan THE SPACE

Public places are not the right space for a difficult conversation. No one wants to feel vulnerable when their friends and colleagues are around.  Organise for a private space where the two of you can have an open and honest conversation. There are times where you may need to have a HR representative present, or a support person for the other party. Make sure the room is big enough (but not too big).

TIP 3 - plan YOUR INTENTION

As human beings, we often jump head-first into conversations without taking the time to think through what it is we really want to get out of it. Why are you having this conversation? Why are you investing your time in this? Is it even worth it, or should you let it go?

If it helps guide you, in our consulting practice, we share our feedback with the following intention - to engage the other person in a process, where we share data with them, for them to use. We have no judgment about how they will use the data. No emotion. No bad feelings. Its just data.

How do you do this:

TIP 4 – PLAN YOUR MESSAGE

Start with a polite greeting = Hi. Thanks for meeting with me.

Explain the situation – don’t keep people in suspense by dragging it out. 

There’s been a change of plans....

We need to talk about X situation...

I've been struggling with...

Think about:

1. Whats really bothering you. Be specific. Don’t generalise (always, never). Don’t label their behaviour (selfish, inconsiderate) personal attacks. Whats the specific behaviour and the specific instance that it occurred. Whats the impact (its distracting, it sets a poor example in front of the workforce). Avoid You statements (it comes across as an attack). Avoid harsh objectives (selfish, annoying). Avoid exaggerating and overgeneralising (always, never).   You could mention what you assume is their intention “I’m sure you meant no harm, when…” “you may not even realise this, when…”
2. Whats your ask – what are the specific behaviours you want them to do instead.
3. Finish up with a check-in = can you do that? Okay? Do you have any questions?

For more on this topic: check out the Pragmatic Thinking book we list in our Resources