Sharing Difficult News with Remote Teams

18 minutes, 1 link


Updated March 23, 2023

You’re reading an excerpt of The Holloway Guide to Remote Work, a book by Katie Wilde, Juan Pablo Buriticá, and over 50 other contributors. It is the most comprehensive resource on building, managing, and adapting to working with distributed teams. Purchase the book to support the author and the ad-free Holloway reading experience. You get instant digital access, 800 links and references, a library of tools for remote-friendly work, commentary and future updates, and a high-quality PDF download.

When a group of people experience the same challenges in the same physical space, human connection can form naturally, without any further effort. This connection can make dealing with bad news a little easier—the small act of looking across the room to see someone else struggling can be enormously important as a group recovers or tries to solve a big problem. Remote teams don’t have the same social outlets, the cues of “we’re all in this together” that help individuals process difficult emotions like shock, grief, uncertainty, and fear. In remote teams, each person can experience their own individual bubble of painful emotions, without the communal processing of grief that allows one to feel less alone. Managers will want to take extra care and pay attention to many subtle details when communicating challenging information.

Voluntary Departures

Voluntary departures—when someone chooses to move on to a new job on a different team or at a new company—can be sad or disappointing, but also can be a chance for the team to express its community feeling. In a remote team, the departing person should receive the same, if not more, celebration and well-wishes than you’d give for the last day of a valued in-office co-worker. It’s easy for a remote team member to just disappear as if they were never there, and the temptation can be to let this happen. We strongly recommend that you not do this; it hurts morale by making people wonder what ‘really’ happened, and by creating the feeling that the company doesn’t care if remote team members leave.

To counteract this, it’s best to be intentional about how voluntary departures are handled. You can encourage the team member to share a company- or team-wide announcement themselves, communicating their decision to move on, and providing personal details so that co-workers can keep in touch. A message from the teammate themself helps dispel any rumor that they were dismissed.

On their last day, you may have their manager organize a goodbye video call, where everyone shares what they appreciated about that person and wishes them well. Having a “cheering you on” celebration by sharing GIFs and messages in the company chat room can also send people off on a positive note. Making sure departures are handled gracefully helps to nurture a culture that your company is both a good place to work, and also a good place to have worked: people go on to good things and aren’t resented, or gossiped about, for leaving. Counter-intuitively, this helps the remaining people feel that the job they’re currently at is a good one, rather than a toxic place where people gossip about those who move on.


In a distributed team, dismissing someone is a precision operation where rumors and panic are the default setting. You don’t have the ability to have a private, in-person meeting and escort the dismissed person out of the building, and then address your staff all together afterwards. As soon as you have a video call to dismiss someone, you will lose control of the narrative and rumors will spread. Your staff will have heard the dismissed person’s side of the story via instant message or online on social media as soon as the dismissal happens.

People rarely expect to be fired, even with serious feedback and performance improvement plans. In a remote setting, when you don’t visibly see your teammate dejected after a meeting with a manager, or appearing stressed or under-performing at work, people will often have no inkling at all that someone else’s job is at risk until they disappear from the company. Given this environment, it’s easy for people to believe that the dismissal was a complete surprise, and that if a surprise dismissal happened to someone else, then they might be abruptly fired, too. The worst case scenario here is rumors of layoffs framed as “firings” starting a panic. In this case, you run the risk of top performers (who will most easily find another job) preemptively quitting before they get “laid off.” This is an expensive mistake.

The best antidote is clear, consistent communication. Following a firing, it’s important that every single line manager tell the same essential story. Broad strokes of that story can be shared to the whole company. You, and all managers, will need to be kind, attentive, and available to your team. Should people across teams discuss the dismissal among themselves, they’ll all enter with the same set of facts, having observed the same calm, caring behavior in the manager who dismissed their peer. This goes a long way to prevent panic.

Chronological Communication Plan

A dismissal will involve planning and communicating carefully in the leadup, during, and after the actual firing:

Unlock expert knowledge.
Learn in depth. Get instant, lifetime access to the entire book. Plus online resources and future updates.
  • Several days before. Preparation.

    • Informing HR and your line manager (if appropriate).

    • Writing your script for the actual conversation, and rehearsing it several times.

    • Getting severance agreements ready. This includes agreeing on the severance pay amount and getting it approved. You will want to have this exact amount in writing for the teammate.

    • Informing any partners or close stakeholders whom you can trust to remain confidential.

    • Putting all the documented feedback into a folder online (such as Dropbox, Google Drive, your intranet) so that the company has a record of pre-termination feedback.

    • Writing up a company- or team-wide announcement. You’ll want to be kind, respectful of the person, and appreciative of their contributions. This includes being as specific with the reasons for letting them go as you can respectfully be.

    • Asking someone to read this over for you. This announcement will determine whether staff feel at ease with the company decision, or wary.

    • Writing a support plan for the affected team, detailing how tasks will be handled, who will fill the role, and what the plan is to hire again.

    • Writing talking points for managers of other teams, to answer questions about the dismissal.

    • Scheduling a meeting with the person who will be dismissed.

    • Scheduling a meeting for the person’s immediate team, without them.

    • Ensuring your people operations or IT person is ready to deprovision accounts.

  • The day of. Following your plan.

    • Giving your line manager a heads-up an hour before the dismissal meeting.

    • Having the meeting to dismiss the teammate (with your script) . At this point, rumors will spread, and the teammate may share angry sentiments. You will want to remove company communication access as soon as you can.

    • Deprovisioning accounts.

    • Having the meeting with their immediate team to share the news and answer questions.

    • Talking to anyone else who’s a close peer, or who will be directly affected.

    • Posting the company or team-wide announcement on the same day. The dismissed teammate will probably be talking to your team on social media, and is likely to feel shocked and surprised by the news, which will destabilize your staff.

    • Sending talking points to all people managers. Explain why it matters that all managers tell the same story (to avoid rumors and talk of layoffs).

  • The next day. Following up.

    • In the case of a higher-profile dismissal (a manager or leader), you will need to speak to senior individual contributors or veterans to ask them explicitly to help you stabilize their team. You can also ask for a pulse on how the news is being taken.

    • It’s important to ensure you hold office hours, should anyone want to speak with you directly. A calendar booking system can make this easier.

Reorganizations or Layoffs


With a difficult reorganization or when faced with layoffs of people on remote teams, several key risks need to be managed:

  • Preventing post-layoff quitting.

  • Trauma and low morale post-layoff.

  • Minimizing disengagement.

  • Rolling layoffs or repeated reorgs.

Your distributed team is going to have a harder time processing and recovering from this kind of news than a co-located team will, because shared venting and healing is harder when you can’t go for a meal or a drink together. People will feel isolated alone at home behind a computer, and this isolation poses a bigger threat to a remote team’s engagement after layoffs.

A bad outcome in this situation is post-layoff quitting: the remote environment can be just too sad and lonely, and confidence and morale so low, that key team members leave for a fresh start.

cautionThe worst outcome that the company leadership can cause is rolling layoffs: realizing after one wave of layoffs that you need to lay off a second, or even third group, in order to remain in business. Don’t do this. It’s best to cut deep, but cut once. Rolling layoffs are a disaster in any team, as everyone who can get another job will leave—they perceive clearly that their days at this company are numbered and the axe could fall at any time.

You’ll want to decide how you’ll lay people off. A principle of “first in, first out,” where the most recently hired people are laid off, can be less emotionally taxing to the team, as they’re not losing team members they’ve worked with for a long time. In these cases, layoffs can also be approached as a case of excessive or over-hiring, rather than direct existential business threat. In a remote team, keeping the remaining team members engaged is more difficult, so optimizing for the less emotionally draining layoff structure is even more beneficial.

An exception is when laying off a large percentage of staff. In this case, keeping only the top performing employees, and appealing to a sense of elitism, of being “chosen to save the business,” might be enough to galvanize the remaining team into action. “Us against the world” can be a powerfully motivating narrative.

You can adapt a lot of the same communication plan for dismissing one person for larger layoffs. Essentially, your goal will be to minimize rumors and panics and avoid post-layoff quitting and disengagement. Transparency and communicating genuine remorse for the pain of both those laid off and those who’ve said goodbye to colleagues, go a long way.


story “When Buffer did layoffs, we published a blog post from the CEO about what had gone wrong, how we’d reached that point, and what our plan was to recover. Our CEO met with each teammate individually (feasible at that current team size) to assure them and answer questions. In this case, the reliance was on good will: that the company can turn around, that the leadership did everything possible to prevent a layoff, that the layoffs were done as fairly as possible. While our employee NPS dipped 10 points, it remained highly favorable, and we didn’t have a single post-layoff resignation in the following year.” —Katie Wilde, VP of Engineering, Buffer

Holding a Town Hall (Public Q&A)

Directly after layoffs have been delivered, a company all-hands meeting with a live Q&A can help to create stabilization by:

  • Allowing questions to be submitted anonymously ahead of time

  • Sharing the anonymous questions before the all-hands meeting and allowing up-voting

  • Addressing the most voted-for questions live in the Q&A

  • Allowing time for live questions and follow-ons to be asked

  • Following up by answering every question in writing for the record and so that nothing is missed.

contributeWe’re looking for more examples or stories from remote companies that have gone through significant reorgs or layoffs. If you have any to contribute, please let us know!

Revoking Access

Operationally, it’s more complicated to remove access from a set of remote tools than to remove a building fob or pass. To make sure you’re able to remove access to tools and virtual workspaces when someone leaves, it’s best to keep up-to-date records of who has what level of access to which tools. In many startups in particular, new tools are adopted and old ones dropped every month, so this needs to be regularly maintained.

Wherever possible, you can benefit from using single sign-on methods, such as Okta or Auth0. This allows you to remove access to most tools at once. To prevent some difficulty in the event of a dismissal or departure, you may wish to consider early on whether or not a team member needs access to the tool. It’s always good practice to grant the lowest necessary level of access. For example, one would not give out “administrator” access when a lower level of access will do. It’s much easier to grant or change access when it becomes needed, than to reverse the damage done by a disgruntled ex-employee who has administrator access to the key tool. These best practices are even more important in a distributed team, where you need to be able to quickly lock down access to a tangled web of online tools and portals, and this is hard to do in a hurry if you’re disorganized or under-prepared.

Other Difficult News

For communicating other difficult news (such as deaths, illnesses, leaves of absence, or upsetting public news) to a distributed team, you can use the following guidelines as a start:

  • It’s imperative to talk to anyone directly affected privately first (co-workers close to the affected colleague, team members on the same team, managers or direct reports of the person affected, or people directly affected by political news or traumatic events).

  • Next, share a public announcement of the news with the company. If it’s relevant, this would include details of how to support the person or family, such as meal trains or memorial service details.

  • If you’re supporting a colleague, you can create an optional way for co-workers to share support or grief, like a collection of quotes and messages from fellow employees that can be sent in a card, care package, or as part of condolences to the family.

  • It’s healthy to talk openly about grief, shock or challenges with affected teammates, and as a group. Experts recommend not simply “moving on” to business—it’s best to hold space for emotions. You may need to encourage people to take time away if they need to process difficult news.

  • Grief can take time to manifest. It’s a good idea to proactively check in with people 1–2 months down the road.

important This advice also applies to external or public events that may impact some or all of your team in potentially unexpected ways. Mass shootings, acts of violence against specific communities, natural disasters, and many other public events can leave people on your team processing grief or even potentially dealing with forms of post-traumatic stress disorder (PTSD). They’ll need similar support from you and the team.

story “When something happens in the world or your community that is scary or traumatic, you can’t all gather around someone’s computer watching the news roll in, so you wonder, ‘Do other people know about this? Are they taking a break? Looks like people are still working, but I don’t feel like I can. Should I pretend I didn’t see the news? Should I interrupt and ask if they did?’” —Rachel Jepsen, Senior Editor, Holloway


As managers, one of our responsibilities is to provide the safest workplace we can to those around us. How do we support our reports in this rapidly changing political environment?Lara Hogan, management coach; co-founder, Wherewithall*

Is Remote Work Right for You?5 links

You need to know what triggers your productivity, what distracts you, and what makes you feel anxious or focused. It’s also important to maintain social interactions, so warn your friends that they may receive some additional attention or that sometimes you will need their attention. Remote work is not only a job you do for your company, but also a job for your own personal growth.Vytis Marčiulionis, Email Deliverability Manager, Emarsys*

Remote work has many benefits for self-motivated, disciplined employees, and it’s a popular choice: 98% of respondents to the 2020 Buffer remote work survey said they want to work outside an office at some point in their career. For many of us, remote working is both a logical and a fulfilling choice—greater flexibility, more control over where and when to work, and closeness to family are powerful incentives.

At the same time, it’s important to understand what you’re taking on. There are unique demands that come with working outside a traditional office environment, and being prepared for those challenges will allow you to develop the right skills and approach to find success as a remote worker.

You’re reading a preview of an online book. Buy it now for lifetime access to expert knowledge, including future updates.
If you found this post worthwhile, please share!