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Not long ago, a young entrepreneur asked for my advice on how to fire a remote employee.

They’d never parted ways with a team member before, remote or otherwise, and they were nervous about it — I didn’t blame them. I remember being terrified when I had to let someone go for the first time, especially since an in-person conversation wasn’t an option. Sadly, I’ve made my fair share of hiring mistakes, but the silver lining is that I’ve learned a lot about how to make the best of a tough situation.

I shared the following advice with the entrepreneur, and I heard back later that the conversation went better than they originally feared. So even though firing is a difficult subject, I’m sharing the advice here in case it can help anyone who needs to let go of a remote team member.

7 steps for parting ways with compassion

I don’t want to suggest that firing someone is anywhere near as unpleasant an experience as being fired. For the person being let go, it’s a scary, life-altering moment — which is why you want to remove all the pain and uncertainty you can from the process. Put yourself on the other side of the table, and make it about them. The decision has been made; now it’s your job to deliver the news with sensitivity and compassion.

1. Use video

When you can’t be across the table from the team member you’re letting go, video is the next best option. The person needs to see your face, read your body language, and understand that you care deeply for them and are sincere in helping them move on in a positive way.

I’ve fired someone over the phone once, and I will never do it again. It was awful — I felt like a total jerk. The person started crying, and I wasn’t prepared for what a cold experience it was for them. It’s been several years and I still feel terrible about it.

2. Don’t wait

The conventional wisdom is to wait until Friday to fire someone, but I couldn’t disagree more. It’s pointless and cruel to hang on to a team member after you’ve already decided to part ways.

It should happen the morning after you decide. Imagine what a crummy feeling it is to know you just worked an entire day for the company that fired you.

Don’t let anyone work a full day before you let them go.

When you hold the conversation first thing in the morning, it gives the person the whole day to let it sink in, take a walk, whatever they need to do. It also gives them time to consider how they will share the news with people close to them.

And don’t schedule anything in advance — ask the person to chat right away so they don’t see a meeting with you on their calendar and fret all night about what that might mean.

3. Have someone else in the room

This conversation could be difficult for a number of reasons, both for the manager or the person getting fired — so it’s useful to have an advocate from People Ops/HR there who can buffer any difficult conversations, explain benefits, and keep the conversation focused on next steps.

In most cases it’s not necessary, but occasionally what’s said during this type of meeting can become the subject of a lawsuit. For this reason, it’s also a best practice to have a witness present to observe what happens and hear what gets said.

4. Get to the point

Don’t beat around the bush or try to make small talk at the outset. It should be clear what’s happening after the very first sentence.

The separation details (e.g., today is your last day, here’s what the severance package looks like, we’ll do everything we can to support you in the transition, etc.) should only take a minute to explain — try to cover everything before giving them a chance to speak.

Go over next steps and walk them through what happens next. Outline what’s required before you can pay any severance. This varies based on the situation, but usually it includes returning (or purchasing) company property and signing a termination agreement. It’s also a good idea to give a confidentiality reminder.

Make it clear you’ve been thoughtful about setting them up to land on their feet. Ask if they have any questions when you are finished explaining your part, and then …

5. Stick around to answer questions

At this point, the person might have questions about why this is happening. Only get into the reasons if they ask. If you do it right, they’ll know the decision has been made and there’s no going back, so it’s pointless to discuss the why — it’s best to talk about logistics and what’s next.

This time is for them, so make it clear you’ll hang around to answer any of their questions and make sure the details are clear. Give yourself a few hours before you have another commitment.

Stay as long as they want, and let them end the conversation.

Try to end on next steps, so they know you’re motivated to help them find a good fit elsewhere and be their advocate. Remember, it’s all about them.

The conversation will likely be a blur to them — survival instincts kick in and make it hard to remember how any of it happened — so it’s critical for all the logistics to be written on paper as well. Make sure you or your People Ops person is available to communicate after the fact.

Finally, we always attempt to schedule an exit interview at a separate date and time. It’s an opportunity for the person to speak with someone from People Ops, provide feedback, and maybe even vent a bit. We get value out of the conversation, but again, it’s also about making sure they walk away with closure.

6. Coordinate login removals

Make someone else on the team responsible for removing the person’s logins and company access during your meeting. By the time the call is over, access is shut off. Have the person’s email forwarded to you or someone else on the team for a while so nothing slips through the cracks.

In some cases, we leave Slack access on for a short time so the person can say goodbye to teammates.

7. Have a plan for informing the team

In most cases, it’s a good idea to inform the person’s immediate team members before the termination meeting, so they’re not surprised.

When it’s called for, we pull the person’s larger team together in a Google Hangout so everyone knows right away.

We also share an announcement in Slack with the whole company to provide context, thank the person for their contributions, let team members know how to get in touch with them should they wish to reach out, and talk about next steps.

All of that is drafted before the fact, and it’s published as soon as the conversation is over.

It’s no fun to be good at firing

It’s sad that firing people is a skill I’ve acquired. Four out of five times I’ve had to fire someone, it was due to a bad hire — and that’s on me. It’s my fault for making the wrong decision, failing to set the person up for success, or failing to set clear expectations.

At the very least, as I’ve learned more about how to hire the right folks, I’ve made fewer and fewer mistakes. I’m proud of the wonderful team we’re building at Help Scout, and I’m thankful that this isn’t a skill I need to use much anymore.

If you’re in the unfortunate position of needing to fire a team member, remember that this is a day the person on the other side of the table (or computer screen) will likely never forget. It’s critically important that, when they look back and reflect on the experience, they find that you conducted yourself with compassion, empathy, and an authentic desire to see them succeed elsewhere.

How to Handle Termination Meetings

How to Handle Termination Meetings

Download this checklist to ensure you handle termination meetings on the up-and-up.

Nick Francis

About the author: Nick Francis is CEO of Help Scout.