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Having tough conversations remotely

How to share bad news remotely (and mainly how to anticipate these situations)

Daniel Jarjoura

Earlier this week, someone I know had to inform a person in her team that they were being let go. The decision had been made before the coronavirus crisis and, since everyone is in lockdown, she had to deliver the bad news remotely.

While there is never a good time to have a tough conversation with someone in your team, there is a good probability that you’re going to have several of these conversations in the coming days. And you’re going to have to have them remotely.

Delivering big/bad news

In the movie Up in the air, George Clooney plays a corporate downsizing expert flown around the United States to have difficult discussions with employees, instead of their managers. In the real world, it’s your job as a manager (and your duty towards people in your team) to have these discussions.

There are several cases that qualify as big/bad news. It can be telling someone that the project they were working on for some time (and were very passionate about) has been canceled. Or that they’re dramatically behind what anyone thought in terms of productivity. Or it can be that they’re being let go or have their contracts terminated (for contractors). But, whatever the news, chances are you’ve been doing the conversation in your head for some time now and waiting for the right moment to have “the talk”. Don’t.

Here is a framework I’ve used over the years to deliver bad news:

  1. Start early: whether you’re letting someone go (the last resort), giving feedback about bad performance/behaviour or announcing the end of a project, you’ve had the signs for some time. Don’t wait for your team member to be right over the cliff before giving them feedback. Start communicating one-on-one as soon as you realise something is wrong. The more you wait, the worst it will be for the other person (and the less you will be inclined to have a conversation)
  2. Announce bad news like a surgeon: a clean, straight cut, and then manage the blood. When you started the conversation (and probably since you sent the meeting invite), your team member already knew something was off. Instead of doing some small talk or beat around the bush, start the meeting with the bad news and stop talking. Let the other person digest the news before you start rationalising the decision
  3. Start a Performance Improvement Plan (PIP): if the conversation is about performance, put together (in coordination with HR) a reasonable and fair PIP. In my former life, as an employee, I was offered a PIP which was so unreasonable that the only conclusion was my dismissal. There’s usually two reasons for bad performance: lack of skills or lack of motivation. Both can be improved with there’s a willingness to progress on the other part. That’s what PIPs should be about: measurable actions and results over a fair period of time
  4. Be authentic, empathic, and as honest and transparent as possible: don’t forget that we are all human beings. It’s OK to feel bad about bad news and shouldn’t start acting like a robot to protect yourself. On the other hand, don’t be overzealous when showing empathy. The last thing your team member wants is to feel that you pity them

The remote factor

At some point in the Up in the air movie, George Clooney’s new colleague (played by Anna Kendrick) has a brilliant idea to cut costs for their company: let people go over video conference. The problem is that she does everything wrong: she’s cold, unempathetic and doesn’t take into account that the other person might want some time to digest the news and express emotions without a camera zooming on their face.

If you have to deliver bad news over video conference in the coming weeks, here is how I would prefer to do it:

  • Include a Zoom in the meeting invite
  • Dial-in to start the zoom (without launching the app so you don’t see your team member’s face)
  • If applicable, ask the HR person to also only call into the meeting
  • Deliver the decision
  • Explain clearly that you didn’t want to put the person on the spot with video from the start of the conversation, but if they’re OK with it, you’d like to jump into the Zoom app so that you can turn on the video

If in doubt, rely on your relationship with the person to make the right decision. Remember, every bad news had roots that go back days or weeks before. Don’t have huge tough conversations when it’s too late. Have a lot of small tough conversations as soon as you see the signs.

Additional resources

If you’re interested to dig deeper into this topic, I recommend the following resources:

📖 Radical Candor: Be a Kick-Ass Boss Without Losing Your Humanity - a must-read to handle tough conversations, but also prevent them

📄 Delivering Big/Bad News - a very concise guide by Michael Lopp (aka Rands), Engineering Leader at Apple and the author of Managing Humans

💻 5 Must Haves in Performance Improvement Plans

Project Management