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How to hold difficult conversations online

I was once told that what we want is on the other side of the difficult conversation we’re unwilling to have. 

That’s proved to be true a number of times in my life, personally and professionally. 

Leaders embrace difficult conversations to make necessary changes, build relationships and earn respect among colleagues. 

But how do you do that when you’re unable to meet in person? 

Knowing how to hold difficult conversations online is vital.

It requires great skill, preparation and a willingness to change your habits. 

Read on. 

1. Choose your time and medium carefully

retail, how to hold difficult conversations online, pink elephant

When I was 17, I was sacked from my part-time retail job. 

To be fair, I had it coming.

My skills clearly lay elsewhere.

What annoyed me was that it was done on the shop floor, in front of both staff and customers. 

If I’d have wanted to mount a counter-argument, or I’d got emotional, that would have reflected poorly on both of us.

And that’s down to the poor choice of medium. 

Pick the ideal time and medium to allow someone else to see your point of view.  

Avoid the 4.30pm Friday phone call just because it’s now over in time for the start of your weekend. 

You might just be ruining the start of someone else’s. 

Instead, set up a video call early morning or early afternoon. 

Turn your camera on so people can see the whites of your eyes.  

Make sure it’s a time when they’re likely to be able to take things in fully, reflect and ask questions. 

Your goal is to remove stress and facilitate a healthy discussion. 

2. Take your time 

take your time, how to hold difficult conversations online, bill mcfarlan

We speed through difficult conversations for the same reason we speed through presentations. 

We feel vulnerable and threatened by the uncertainty ahead, so we skip through it quickly, hoping for a swift resolution and acceptance. 

That rarely happens when we rush. 

So instead, prepare carefully.  

Set aside enough time to show the importance of the issue. 

Put 45 minutes into the Zoom call rather than 15.

That allows for questions and a healthy discussion. 

Slow down and breathe. 

You’re giving yourself a better chance of getting your points across clearly, and you’re demonstrating to the other person that you’re comfortable asserting yourself. 

3. Get to the point  

how to hold difficult conversations online, pink elephant, get to the point

For three decades, we’ve helped organisations communicate difficult decisions through the media. 

Interestingly, most first drafts of press releases fail to mention the job losses in the opening paragraphs.

That’s because they’re written by those unaffected. 

When that makes it through into the public domain unchecked, it appears unsympathetic and cold. 

Far better to get straight to the point. 

By all means, make sure the other person can hear you properly at the start of the call but avoid getting into chit-chat.  

Address the issue quickly and practise your opening line to make sure it comes out correctly. 

Let your audience know at the first opportunity what’s been decided.

Or, if you’ve yet to decide, let them know what the conversation will be about. 

The context, the background and the next steps can wait.

4. Identify common ground  

how to hold difficult conversations online, pink elephant, identify common ground

Your audience needs to know that you’re on their side if you’re going to build trust. 

So focus on “us”, “we” and “our”.

Attach those to the common goals you’re both aiming for.  

That helps to put the point above into context and helps you both establish the next steps. 

5. Be specific  

how to hold difficult conversations online, pink elephant, be specific

Be direct and stick to the facts, however uncomfortable, so the other party knows exactly what’s expected.  

If someone has been late for a call three times during the week, say that. 

If they’ve let you down in an important meeting by being unprepared, tell them. 

Now make it very clear what’s expected of them, so they know where they’ve fallen short and how to avoid it in the future. 

11 years ago in my first professional role, I did something that fell below the standards expected of me. 

I was talked to extremely directly, stating the facts and making it very clear where I’d fallen short. 

My attitude changed, my productivity rose and I vowed to raise my professional standards way higher than before. 

And through it all, I felt I’d been treated fairly. 

6. Demonstrate empathy  

how to hold difficult conversations online, pink elephant, empathy

One of our clients told us that she’d seen someone yawn in the front row of a talk she was giving. 

Frustrated, she asked: 

“Are you tired?” 

Then came the response:

“Yes, I am.

“I’ve been up all night caring for my mother.” 

It’s impossible to recover the moral high ground from there. 

That’s one of the reasons it’s so important to stick to the facts and ask questions about the person’s behaviour. 

And when you find out that something negative has influenced the behaviour, show empathy. 

“I’m so sorry to hear that” is a natural reaction socially. 

But we can be reluctant to use it professionally. 

So be direct, show empathy when it’s needed and now you can both move on to discuss a solution. 

Especially during a pandemic. 

7. Accept responsibility  

how to hold difficult conversations online, pink elephant, accept responsibility

Difficult conversations, in my experience, are rarely one-way. 

However negative the behaviour, I always find there’s something I can do to make the other person’s life easier. 

So accept responsibility if a task has been unclear and discuss what you can both do to find the solution. 

Work hard to understand and clarify objections, before committing to make changes. 

If you are announcing a job loss, for example, accept that it’s a decision that was within your control. 

It’s often easier to say “the global situation means it’s out of my hands”. 

It’s more honest to say “I’m sorry to say we’ve decided to make your position redundant”. 

And it’ll strengthen your grasp of how to hold difficult conversations online.

8. Make the next steps crystal clear  

how to hold difficult conversations online, pink elephant, make the next steps clear

If you think back to the most difficult news you’ve received, it’s likely to be a blur. 

Your head is simply unable to process bad news in a logical way.  

It’s common for doctors delivering bad news to ask the question: 

“Do you understand what I’m telling you?” 

Appreciate that your audience can experience shock too with the onset of news about their job changing, or disappearing. 

And eventually, when the shock wears off, they’ll start thinking about what to do next. 

So the burden’s on you to offer that certainty by making the next steps crystal clear.

And to make sure that it’s been received and understood. 

9. Show the change  

how to break bad news, colin stone, pink elephant communications

If you’ve asked someone to change their behaviour, highlight the positive change when you see it.  

Catch people doing things right, and praise them publicly for it.  

Similarly, if you’ve been asked to change, demonstrate it through positive action. 

Make it clear that you’ve embraced the feedback and adapted. 

In an ever-changing world, it’s those who adapt most quickly who’ll benefit.  

So what’s hiding behind your difficult conversation? 

Follow these steps on how to hold difficult conversations online.

Put pen to paper, decide your action and set up the meeting. 

You have everything you need to get to the other side safely and respectfully. 


Andrew McFarlan is Managing Director of Pink Elephant Communications in Glasgow.

You can read his full profile here.


Photos in How to hold difficult conversations online blog by Pink Elephant and Pexels.
How to hold difficult conversations online blog edited by Colin Stone.

How to hold difficult conversations online

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