The Blog

difficult conversations at work, pink elephant team round the table

Difficult conversations at work: Three tips ahead of your next chat

Many of us actively avoid difficult conversations at work.

We’ve either been on the receiving end of one.

Or we’ve been the person bringing up the issue with our colleague.

I’ve done both.

And either seat can be deeply uncomfortable.

Confidence for a chat like that comes from proper preparation.

So what does that look like?

Preparing for your difficult conversation

difficult conversations at work, streisand effect, pink elephant communications, colin stone

I remember sitting in a small meeting room in 2014 when my line manager entered with a single A4 sheet.

As he sat down, I asked:

“What’s that?”

Slamming it on the table, he responded:

“A blank sheet of paper. A clean slate, if you will.”

I imagine my eye-roll reaction got us off to a bad start.

There are three simple steps to consider before you have a difficult conversation.

(Using clichéd figure-of-speech props is absent from that list.)

It’s important you give thought to these before you sit down.

Rather than attempt to recall them in the heat of the moment.

1. Be specific

difficult conversations at work, being late, be specific

For argument’s sake, let’s say this issue is about a colleague being consistently late.

Here’s how that behaviour is sometimes addressed in a sit-down conversation:

“You’ve been a bit late for work for quite a while now.

“I think it would be great if you could manage to get here just a little earlier.”

We often use vague language to avoid upset, or to tip-toe around a sensitive topic.

The problem is that you both leave unsatisfied with the outcome of your chat.

For difficult conversations to be effective, your language must be specific.

“For the last three weeks, you’ve arrived at work after you’re due to start.

“This has been anything from five minutes late to almost half an hour.

“You need to start arriving at work on time, as this is what’s expected of all our employees.”

It’s crystal clear, and it’s factual.

2. Get to the point

difficult conversations at work, being late, get to the point

We can go round the houses in difficult conversations at work.

We start with the background, the context, the timeline of why we’re sat there.

We’re keen to introduce this challenging topic gently.

But after a few minutes, you’ve been taken off-piste.

You’re now discussing a whole range of other issues.

And you fail to get to the main reason why you’re having this chat in the first place.

It’s why we must get to the point in the opening seconds.

We can add context and other information afterwards if necessary.

At least if you’re interrupted, you’ve already said the reason why you’re there.

3. Find common ground

rules of communication skills, pink elephant comms, bill mcfarlan, difficult conversations at work

Difficult conversations at work can spiral into an adversarial battle.

That’s how it was with my 2014 line manager.

You versus me.

Or the company pitted against the employee.

But pitching conversations this way only ends badly.

It puts up more barriers.

Instead, you must find mutual areas you both agree on.

“We all want the business to keep growing as it has in the last 12 months.

“We can only do this if every employee is held to the same standard.

“That means we all have to be at work on time.”

This is why preparation ahead of the conversation is so important.

It’s highly unlikely that this common ground will come to you when tension starts to rise.

Difficult conversations at work

difficult conversations at work, colin stone talks to camera

Difficult conversations at work can be among the most challenging you’ll ever have.

For many of us, colleagues and employees are also our friends.

And the threat of a bad conversation spoiling that relationship puts us off from holding it.

Inadvertently making the issue into something larger the longer we ignore it.

The resolution we want is on the other side of the difficult conversation we’re unwilling to have.

So do the preparation.

Be specific, get to the point, and find the common ground with the other person.

And build a stronger, more effective relationship in the process.


Colin Stone is Communications Lead at Pink Elephant.

You can read more about him here.


Photos in Difficult Conversations at Work blog by Pink Elephant.
Difficult Conversations at Work blog edited by Andrew McFarlan.

view all posts

Build Your Confidence

Some media trainers knock you down…and leave you down. Our media coaches show you how to deal with each knock…and still win through. So you have the presentation skills to perform – with confidence.

request a quote