How to Have a Difficult Conversation

Everyone in the world’s been in a conversation that’s turned awkward. For me, just witnessing one will increase my desire for a hole in the ground to swallow everything in sight.

Come to think of it, maybe politicians’ total awkwardness explains fracking?

Unfortunately, for most of us, the magic hole never appears. So you stand and watch, as the conversational titanic takes down everyone in the room.

If you’re the captain of this conversation, and you know the iceberg’s coming, it gives you time to prepare. There are plenty of times you’ll be the purveyor of difficult chat in recruitment.

But it’s probably one of those things you’re never truly comfortable with.

Still, there’s no reason to go down with the ship.

Here’s how to reach the shores of safety, when you have a difficult conversation at work.

1 Plan it

Most conversations in your job are planned. Even the most surprising of chats with the gaffer in the boardroom you probably know are coming. And whilst the term ‘planning prevents piss poor performance’ is a cliche, it’s definitely true in this case.

For all the bad news and negativity mongering you may have ahead of you, planning’s a real possibility.

Let’s say you’ve got to let a candidate down. The first thing you should deliver is the ‘No’ itself. The candidate will know why you’re calling. Therefore by discussing this first, you can work out other options and the call won’t end on a negative.

But more than this, having other options up your sleeve after the initial rejection will mean you’re always in control.

No one likes being turned down. But not knowing is far worse.


2 Manage emotions

Emotions will fly in difficult conversations. Especially when you’re talking face to face. But once again, planning the interaction will help you.

Not interrupting the other person will make a huge difference. Because even if you start on good terms, interrupting them will turn it sour quickly.

Maintaining an even eye level height is another solid tip.

If you’re standing up, and your counterpart’s sat down, they’ll feel affronted and lower down the chain. Which may get their back up. Something you’ll be keen to avoid at all costs.

Know going in, if this conversation is really tough, there might be tears. So researching and spending a little time understanding how to deal with them, will mean you’re helping both them and yourself. Watch this video to start yourself off.

3 Stay on topic

This chat isn’t one you want to veer off topic. Keep it relevant and methodical in how you approach the content. Yes it’s nice to natter every now and then. But delivering bad news or difficult opinions should be constructive.

Like all the times you see Graeme Souness whinge about Paul Pogba in relation to something totally unrelated, those who feel afflicted will want to bring it up. Often for no rhyme or reason.

Your job is to stay on track.

“Yes, I know Paul annoys you Graeme, but we’re talking about recruitment pal.”

Two people at Baker Street

4 Silence is good

You’ll know this little trick from your negotiation training. Hopefully.

Silence is a powerful thing.

And being comfortable with awkward silences will mean you don’t fill the void with spontaneous, unhelpful chatter.

Silence is also calming in delicate situations.

Whether the person you speak to is introvert or extrovert, silence helps frame a conversation and wrangles back awkwardness so you’re able to take control.

5 Enquire without opening fire

If you’re trying to understand an issue you need to understand the situation fully possibly from two sides. This means asking a lot of questions and not reacting immediately.

If you only interrupt to acknowledge their stance, your conversation partner will feel as though you’re on the same team. And then you can address the issue together.

Whether that’s a rejection from a client. The ‘letting go’ of said conversation partner. Or something even trickier.

6 Acknowledge and manage emotion

Emotions are going to be flaring in difficult conversations, so you need to manage them. Otherwise, you’ll find yourself knee deep in a conflict.

And this should be a resolution. Not a revolution.

To do this, you need to be aware of thwarting ploys and combative action. If for example, your counterpart starts using sarcasm, the best action is to address the sarcasm and understand why it’s being used.

“Is it fair to interpret your sarcasm as you understand the issue?” will address the problem, and ask for further clarity, whilst moving the conversation on.

You should also pay close attention to the location of the chat. A quiet room will allow privacy and make each participant feel safer.

After that, consistency is key. Stick to topic and guide the conversation clearly.


7 Finish well

When you started the conversation, you’ll have framed it by saying “I’d like to talk to you about …”

You’ve stuck to task. Managed the emotions. Kept quiet at the right times. Ask open questions. Been a sympathetic ear. Now, you need to close.

And you can do that in the same way as the beginning. State what you’d like to happen after the chat. Ask whether they have any questions about the topic, and crucially, be willing for a further conversation should they need it.

Have a phrase or go-to ending in mind, should you need it.

“OK, well I think we both know where we’re at. Let’s leave it there and I’m here if you need to clarify anything.”

You can even work out a follow up, with actions on both sides, if appropriate.

And then, instead of two people storming out a room, mentally throttling the other, you’ll have a calmer, more rational end to proceedings.

And if you’re really good, your partner will feel good about the chat.