Difficult conversations at work: should you have them via email?

The short answer to this question is – no, you shouldn’t.

The long answer is nuanced.

It’s based on my personal experience  – and boy did I learn a lot.

So let’s find out why, when and how you should use email in your quest for difficult conversations that actually make a difference.

difficult conversations over email

Tough conversations at work: why I resorted to using email

Basically, the face-to-face approach was not working.

For the fifth or sixth time, with the same individual.

We would butt heads and reach a stalemate or, when I thought my message had been delivered, her behaviour post-conversation suggested otherwise.

Why was it so difficult? There was a personality clash: we spoke very different languages and at times it felt like we were having different conversations.

In our ‘final’ face-to-face conversation – after about an hour of chatting – we hadn’t made much progress. We left it there and agreed to pick it up another day. 

Then she emailed me as a follow-up to our conversation. When I responded, I summarised the issues I had gone over and why they were problematic, while responding to the comments in her previous email.

It was positioned as a way for us to reach a shared understanding. Since we couldn’t agree on the issues and reach a shared understanding face-to-face, could we do it via email?

I wasn’t tackling every stage of the tough conversation, just the first stage – trying to reach the point where we could ‘agree to agree.’

What happened after I sent the first ‘tough conversation’ email?

She took a long time to come back to me – but eventually did. Then I sat on my response for a couple of days before I emailed back.

Then I never got a response, so I prompted her.

But she was just going on a week long trip and said she wasn’t ready to respond, so we postponed any further discussion until then.

The emails, by the way, tended to take a similar format: we would respond to the other person’s comments and then add our thoughts above.

Mostly it was going over the same issues, but adding colour each time.

In the heat of the moment in a conversation it’s hard to remember everything you want to say. But over the course of a few emails, it comes back to you.

In this way, email allows you to build a more well-rounded, 3D picture of the issue.

Tough chats via email: what were the outcomes?

When she came back from holiday, we had a private conversation and quickly admitted we should have ‘gone into a room sooner.’

But I’m not sure either of us were in the right place emotion-wise to do this prior to our email exchange.

We needed a break, which her holiday provided. 

We also needed perspective, which the emails provided: we were able to reflect on each other’s points and the whole, well-rounded, 3D image they created.

This helped us see the other person’s point-of-view – much easier when it’s all articulately written down available for you to refer back to.

Off the back of our shared understanding, we made a plan based on admission of shortcomings on both sides and with a renewed interest in making our relationship work.

Hard conversations: what did I learn from this experience?

It’s impossible to hold a conversation via email

Email increases understanding – it allows you to organise thoughts and send them to someone else. Email is a useful way of explaining something that is much harder to explain in person.

Email isn’t ‘instant,’ which is both good and bad

The nature of email means people take longer to respond as they ‘craft’ a response. In the void of silence, bad feelings can fester. On the flipside, the built-in delay to email conversations means your words can be chosen more carefully.

Email is permanent: does this discourage the ‘human’ connection?

When you send an email, it lasts forever. It’s harder to be human via email knowing that, if things turn sour, there’s an entire message chain that could be made public.

You’re much more likely to be ultra-professional and stilted: this is fine, as long as you see email solely as a means to build up a shared understanding. If you’re looking for compromise and reconciliation or agreement, don’t look to email. 

Sometimes something has ‘to give’ – but email is not the solution 

A change – like my direct report’s holiday – can help break the deadlock when a tough conversation just isn’t going anywhere. It resets emotion. Holidays, social events, positive news – they all can have the same effect. But email is not one of these things.

In fact, email raises the tension because it’s a really non-human way of communicating. It only worked in my case because it was combined with a genuine ‘change’ – the holiday – which provided a chance for her to decompress and for me to reflect.

Do not use email to delay a conversation while emotions simmer down.

Tough conversations via email: what’s the conclusion then?

Basically, if you see email as something that…

  • …should not be used as a delaying tactic
  • …won’t provide the ‘solution’ a tough conversation needs to provide
  • …may be useful when used sparingly to develop shared understanding

..then you should consider using it where appropriate. That’s the conclusion.

Which sounds a bit like a politician’s answer to me.

But it’s honestly the truth.

Need to have that hard talk with someone? Go deeper into the topic by reading our five tips on how to take control of difficult conversations.