Difficult conversations: should you have them via email?

Written by Investors In People

Difficult conversations: should you have them via email?

The clue’s in the title, right? A conversation can only take place face-to-face.

That’s what I always thought. But when I consistently had poor face-to-face conversations with one person, I wondered if there was a better way – email.

And it worked for me, kind of. It certainly helped.

Let’s find out how and why.

Shouldn’t all tough conversations be face-to-face? Maybe not – I certainly found there were shades of grey.

I manage eight people and one relationship is by far the most challenging in terms of mutual trust, respect and communication.

Every time we have a tough conversation, we hit a brick wall. I get frustrated. She gets frustrated. We make no progress. We get stubborn. We both lose.

I always wondered whether having the tough conversations via email would take the sting out of the process, but I shied away because I thought I was being a coward.

And as a manager, the last thing I want to be is a coward. I pride myself on facing my problems head on.

But is this always a good strategy? It massaged my ego, that’s for sure. I was being brave and that’s what counted, despite the poor outcomes.

When I reflected, this didn’t seem very smart. Shouldn’t I prioritise the outcome over my ego?

So I took the plunge and had a tough conversation via email.

What happens during a difficult conversation via email? Here’s what happened to me before, during and after.

The catalyst was a really negative face-to-face conversation where I was essentially stonewalled. We both left the meeting in a bad mood.

My employee emailed me soon after and apologised for their behaviour and suggested we try again. At this point I suggested the email conversation.

She was open to it, but asked me to kick it off. So I emailed her my honest feedback around the points in question and I waited.

Because it was a long email, I didn’t put in next steps, because I wanted her to absorb the information rather than be concerned about replying quickly.

Unfortunately, she had a pretty negative reaction to the email and I found out several days later she hadn’t even finished it. Next time I would definitely put in expectations around replying, because emails can be ignored easily.

Eventually I nudged her and she sent a detailed reply. Normally she is not vocal in meetings so it was refreshing to actually know her opinions. I sent her a placeholder text telling her I needed to absorb the email and I would get back soon.

Which I did, and at this point I proposed a face-to-face conversation after she absorbed the content of my email. She seemed more engaged at this point. We had a follow-up conversation and I sent an agenda in advance of the points based on our email chain.

Although this meeting was by no means perfect, the fact that we’d ‘got out’ our thoughts in the email and had actually made progress meant that we had a more open, honest conversation and agreed some actions.

I think what the emails did was turn what was no progress into some progress and this allowed us to start from a positive place when we got face-to-face, rather than both feeling like we were staring into the abyss.

Difficult conversations via email: when should you use them? It comes down to if you’re using them for the right reasons.

I’m glad I started my difficult conversation via email. It helped overcome a blocker that I was just not shifting. But the whole process didn’t exclusively happen via email.

If I’d expected email to replace the whole process, I think it would have fizzled out and got nowhere. Email is an enabler, not a silver bullet.

It’s not a good idea to use email to have your difficult conversation if:

  • It’s your first attempt at a tough conversation with that person
  • You’re trying to avoid negative feelings around confrontation
  • You’re tired and don’t feel like doing it but have to get it done
  • You think it will replace the face-to-face element

It’s worth considering email to have your difficult conversation if:

  • Previous tough conversations with this person have ended badly
  • There’s a lot to say and absorb and reflect on
  • You appreciate that email is a catalyst for a better face-to-face meeting
  • There’s a strong personality clash that makes poor outcomes likely
  • You can’t get out of the starting gate and need something to kickstart progress

Difficult conversations: 3 tips to do them over email

1. Set rules and expectations

I wish I’d been clearer early on exactly what the use of email was trying to solve. I should have said it was a conversation starter.

Otherwise the process seemed a bit endless, like a tennis match. I think that’s why my employee took ages to respond.

Next time I would have set some expectations around timeframes on when each person should reply and how we’d move the conversation off email to a place of resolution.

I would also be clearer on tone and language: both sides should say, for example, “I feel that…” rather than “You always…”

Basically, all the guidance around being human in difficult conversations face-to-face applies to email as well.

2. Set the boundaries on topics

Without boundaries, the email could start about one thing and – three emails later – turn into something else.

Are you tackling a specific issue or getting everything that’s been festering out on the table? Be clear early on and make sure you reference it throughout the conversation.

Check yourself to make sure you haven’t accidentally gone down a tangent or used the safe environment of writing an email to raise something you shouldn’t.

It’s supposed to be a conversation via email, which means you should be primarily responding to the other person.

3. Follow up with a face-to-face meeting

Context gets lost in emails and you can’t use positive social cues, such as leaning in, to build trust.

It’s also easy to take offence from emails when none was intended. This may be doubly true when the email is about a tough topic.

If someone does get hurt in a face-to-face difficult conversation, it’s obvious and therefore easier to repair the damage.

But via email, it may not be so obvious, so it’s important to remember that having a follow-up face-to-face meeting also allows you ‘come together’ and strengthen your relationship.

Looking to have better face-to-face difficult conversations? Take a look at our five tips to help you take control of difficult conversations at work.

About Investors in People

Investors in People have been working with a huge range of big and small organisations from Public Sectors, SMEs, Charities, PLCs and anything in between for over 30 years. We have accredited more than 50,000 organisations and our  accreditation is recognised in 66 countries around the world, making it the global benchmark when it comes to people management. So we know we speak your language and can offer the specific kind of support and guidance your organisation needs.

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14th Nov 2023 | Old Billingsgate, London



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