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Best Practices for Letting Go of a Remote Team Member

Key Takeaways

  • Build a system of openness and accountability on a remote team to detect performance problems before they escalate. 
  • Create a culture of radical candor and honest feedback so team members know where they stand.
  • Implement a performance repair process to course-correct performance problems when they arise. 
  • How to let go of someone on your team as a last-resort, being communicative and compassionate throughout the process. 
  • Communicate the departure of a remote team member to the wider company balancing transparency with privacy. 


“Am I the only one feeling a bit déjà vu about this?”

We had recently made the hard decision to part ways with a Doist team member and announced the choice to the wider company. The backlash was instant. Among the criticisms: dismissals lacked transparency, firings largely came as a surprise to departing individuals plus the wider team, and this was just one instance in a pattern of employee discharges that generated widespread anxiety about our ambiguous termination process. 

The team was right. 

Over the last ten years at Doist, we’ve parted ways with approximately 25 team members. On a distributed team like ours, this can present unique challenges –– letting go of someone remotely, disconnecting their profiles and revoking account access, can feel especially abrupt and cold. It’s the in-office equivalent of having someone pack up their things in a cardboard box and getting them escorted out of the building with security in tow. While we thought we were handling these situations with respect and dignity, over time it became apparent that we’d failed in more ways than one. As a company that prides ourselves on communication and transparency, we weren’t living up to either value.

Previously, parting ways was often the result of an extended period of performance issues and a final incident we deemed the last straw. There was no well-documented process with feedback preceding the decision and no recommended remedy to solve the problem. Instead, our decisions largely evolved from a “gut feeling.” This was a mistake that left terminated team members feeling unfairly treated and allowed uncertainty to ripple through the entire organization. 

Through (unfortunate) trial and error, we’ve learned and changed the way we handle remote terminations over the years. At Doist, letting go of a team member is a last resort that we don’t take lightly. We make every effort before the question of termination is raised, including implementing our Performance Repair Process. But as remote work becomes mainstream, letting go of remote employees will become an unfortunate but necessary reality. 

This article will discuss how we’ve revised our own termination approach and discuss key three areas:

  • Navigating the challenges of remote work performance
  • Addressing performance issues head-on when they arise
  • Letting go of team members remotely as a last resort

Our hope is that sharing the lessons we’ve learned can help other companies avoid the same missteps we’ve made and approach remote termination in a way that’s both communicative and compassionate.  

Navigating the Challenge of Remote Performance 

On a remote team, performance problems are harder to detect. It’s more difficult to discern if someone is experiencing personal or professional issues through the screen, and your colleagues may be facing challenges you’re not aware of. These hidden challenges can manifest in visible work issues. 

But termination should come as a last resort. 

Remote companies can take steps to set their team members up for success, create a culture of accountability, and detect performance problems before they spiral out of control.

Default to trust

Trust is everything on a remote team. This means eschewing micromanagement, saying “no” to invasive time or screen tracking tools, and maintaining confidence that your colleagues will do what they say until shown otherwise. It's impossible to build a strong and long-lasting remote-first company unless you, default to trust:

Building a company culture that assumes your team can’t be trusted is like playing basketball with one hand tied behind your back: you might be able to do it, but you’re never going to reach your full potential. The companies that empower their workers are going to win over companies who monitor them. The future of work is trust, not tracking.

On a remote team, it’s important to acknowledge that a lack of visibility doesn't equate to a lack of hard work. In many instances, less visibility in a remote environment (e.g. less messages and meetings) is a sign that the person is doing focused deep work. 

However, this won’t always be the case, and “people issues” can fly under the radar for a longer time virtually than in a shared office. We’ve had people go radio silent or not deliver on their work. Yet, this has been outweighed by team members who have been entrusted with responsibility and put in thousands of highly productive hours into the company each month. 

Have a centralized project management system

A culture of trust must also be tied to one of high expectations and strong accountability, which allow problems to surface in a remote environment more quickly. This is where a project management system is crucial. 

It has taken us years to tailor our project management system to how we work. These iterations have led to our DO System: a cross-functional method that includes monthly cycles where we explore, plan, and execute on both company initiatives and product projects for Todoist and Twist. A “DO” can include a squad of anywhere from 1-5 people, creating transparency around the responsibilities of each squad member and accountability across the board. When someone drops the ball, it doesn’t go unnoticed. 

Aside from our project management system, there are other mechanisms we have in place to create a culture of accountability –– including our weekly snippets. To keep everyone in the loop about ongoing work, each person in the company posts weekly snippets every Monday that summarize work conducted the previous week, plans for the week ahead, and any “blockers” that could prevent us from doing our best work. 

Having systems in place, where expectations are obvious and responsibilities are clear, is an important part of detecting when things go awry. This can present itself in a myriad of ways in team members:

  • They miss weekly or mid-project milestones
  • They block other team members from moving forward 
  • They do not respond within 24 hours to messages and mentions
  • They fail to provide weekly progress reports on their work
  • They continuously push the same work from one week to the next

A strong project management system shouldn’t only push work forward and drive projects to completion, it should create transparency around the projects-in-progress and generate a sense of accountability regarding who is responsible for what. In the absence of a rigorous project management system, it can be easy for people to fly under the radar and for performance problems to go undetected.


Tool Tip: At Doist, we use Todoist as our project management tool and Twist as our team communication app. Todoist allows us to plan projects from start to finish while assigning DRDs (Directly Responsible Doisters) and dates to each project task or milestone. Twist brings conversation into the open –– our channels and threads are public by default, allowing everyone at the company to see what’s happening on one project or another. 

Use one-on-ones to uncover performance problems

At Doist, Heads have mandatory monthly one-on-ones with their direct reports each month. Besides discussing work, these meetings also serve to check-in on a person's well-being, professional struggles, or anything else that might be preventing them from thriving at Doist. 

It’s important to use this time efficiently to dig into what’s working for your teammate and what’s not. Often, reports won’t volunteer the problems they’re facing –– especially in the case of personal issues affecting their professional performance. As a team leader, it’s your job to get at the heart of these issues by asking the right questions. 

Know Your Team has an excellent guide on one-on-one meetings for managers that’s worth reading. They dissuade managers from using one-one-one meetings as purely status updates, and provide guidance on the best questions to ask beyond “how’s it going?” to get “honest insights”: 

  • “When have you been frustrated in the past year? What can I do to help make things less frustrating for you, or get out of your way?”
  • “When have you felt dejected or demoralized this past year? What can I do to better support you, and make sure that’s not the case going forward?”
  • “When have you been disappointed with a decision or the direction that the company has gone in the past year? Was there an opportunity you think we squandered? Something you think we mishandled? How would have you pre- ferred we proceeded?”
  • “When have you felt bored in the past year? How can I create situations going forward so you don’t feel that way?”
  • “When have you felt stressed or overworked in the past year? What can I do to create a better work environment going forward so you don’t feel that way?”

The entire guide is chock-full of wisdom on how to have meaningful one-on-ones –– it’s been shared internally at Doist and much of its advice has been put to use by our Heads. By having more insightful one-on-ones, you can better detect performance problems as they arise and create a strategy to course-correct so termination can be avoided altogether. 

Addressing performance issues head-on

While we all experience highs and lows that can impact work, if someone is experiencing an extended dip in performance, it's a manager's job to address it head-on.  Performance problems shouldn’t be left to fester. We’ve had to learn this over time and our evolution has been partially inspired by two women who’ve set out to revolutionize the workplace –– Kim Scott, the Author of Radical Candor, and Patty McCord, the author of Powerful

Their approach to work and feedback has changed the way we work and nudged us towards addressing poor performance head-on and finding solutions more quickly. That includes creating our own internal Performance Repair Process

Embrace radical candor

Inspired by her experience as a leader at Google and Apple, Scott penned Radical Candor and coined the term to describe how bosses should approach leadership, especially in the face of difficult conversations:

Radical Candor’ is what happens when you put ‘Care Personally’ and ‘Challenge Directly’ together. Radical Candor builds trust and opens the door for the kind of communication that helps you achieve the results you're aiming for.

At Doist, we often use radical candor as an ice-breaker for sharing feedback. Providing radical candor isn't about nitpicking or being a jerk. It's about giving honest feedback to nudge the other person in the right direction. 

Here’s what convoluted, vague, and unclear feedback sounds like…

  • Is this your best effort?
  • I think you could have done a better job. 
  • Could you try to have this completed earlier next time?

Here’s what radically candid feedback sounds like…

  • Your contributions on x were some of your best work! I didn’t see that same level of quality on your latest project. In what ways was this project more challenging?
  • It’s clear to me that you take pride in your work, that’s been evident across projects x, y, and z. This work feels rushed and is not consistent with what I’ve come to expect from you. What happened?
  • I know you care about your teammates. But when you consistently submit your work late, it holds up the entire team. How can I support you in sticking to deadlines for the future? 

Radically candid feedback addresses the problem head-on, while also infusing that feedback with care and compassion. By providing feedback and asking questions,, you may uncover answers you didn’t expect –– like poor team dynamics, personal problems creating distractions, or unclear expectations that can be solved. 

Build a culture of feedback

Patty McCord, Netflix's former Chief Talent Officer, played a central role in building Netflix's culture and wrote the book Powerful about her experience there. Taken by the advice in her book, in 2019 we invited her to our team retreat in Açores, Portugal. 

One of the things we took with us from that encounter was using one-on-ones for providing two-way feedback, rather than feedback that flows in one-direction. For a period, every one-on-one contained a feedback session where both a report and their manager both would provide mutual feedback in the format “start doing, stop doing, and do more of.” It was a great exercise to say complicated stuff constructively. 

While this practice has waned (it becomes difficult to spot and find new things each month),  we've since built career paths with functional mastery and leadership tracks focused on professional growth. With the new system, feedback has become less forced. Now everyone has concrete development goals with regular check-ups on progression. It means feedback flows more naturally and challenges surface before they become actual problems. The need for feedback continues to be omnipresent. Currently, it happens primarily on a team level. Our goal is to get it out of the silo and spread across functions. Our future plans include further focus on feedback by rolling out 360-reviews to everyone in 2021.

While a culture of feedback is something we continuously strive for, it’s important to acknowledge the impact of critical feedback –– even when it’s provided with compassion. Find the balance between providing the right feedback to emphasize the seriousness of a situation while not presenting it as an ultimatum. It applies immense pressure on a person if feedback is shared as a “final warning.” It's hard to work and recover from feedback when there’s an expiration date attached. Instead be clear and firm, but leave out the feeling of finality. 

Implement a Performance Repair Process

At Doist, rather than standard “disciplinary conversations,” “corrective actions,” or “performance improvement plans,” we’ve developed something we feel is more conducive to truly addressing performance problems: a Performance Repair Process. This process is included in our employee handbook, accessible to all Doisters, and is described as follows: Doist, we genuinely want to see everyone thrive and grow. In alignment with this, we see these conversations as an opportunity to repair performance, not punish poor performance or force anyone out the door. At the heart of these conversations are clear expectations and communications between you and your leader. We want to make sure every Doister is clear on how they are performing, especially if something isn't working.

While these conversations aren’t always easy, it’s the responsibility of our team Heads to engage early when they observe poor behaviours or performance problems, using radical candor to ensure all parties are aware of “the issue, the impact, and an alternative approach.” 

Here are the three steps to our formal Performance Repair Process: 

  1. Identify The Issue and Talk About It: Heads are charged with identifying the issue, discussing expectations, and discussing concrete steps to address the issue. This is also an opportunity for a report to ask questions, seek understanding, and commit to specific actions moving forward. 
  2. Formally Document The Issue and Solution: In the case that a performance problem persists, performance issues and the agreed-upon solutions, as well as a clear timeline, are documented to ensure there is a “clear plan for what needs to change and by when.” This process is meant to be collaborative, including the Head, their report, and potentially, assistance from our People Ops team. While performance is being repaired, regular check-ins to discuss progress should be scheduled. At the end of the agreed-to-timeline, there should be a formal 1:1 meeting to discuss progress. If performance is repaired, the process can come to a close and People Ops will ask a Head for a note indicating performance has been improved. If performance problems persist, a Head can choose to extend the timeline or move to the next step of the process. 
  3. Decision-Making Leave: In the case where performance issues can’t be resolved, a Head may choose to work with People Ops to coordinate a decision-making leave. This temporary leave of absence provides a team member time to decide whether or not they’re willing to fully commit to meeting the performance expectations and standards of the job, or voluntarily resign their position. The length and status of the decision-making leave is determined by People Ops in conjunction with a Head. 

This process is meant to truly address performance issues head-on and align expectations for a role moving forward through honest conversations about the future. 

Consider a new place for them

It’s important to acknowledge that your organization changes with time, and so do people. It's not unusual that a person's passion and enthusiasm shift over time. Be open-minded towards changes and consider new areas of responsibility to assign, or a role transition, to facilitate continuous growth for individuals. If someone isn't firing on all cylinders and you’ve worked with the person over an extended period to improve the situation, start thinking beyond the current role for unexploited options to resurrect the person's tenure and career. 

At Doist, we’ve seen people fade a bit in their position, only to relocate within the organization and blossom. We used to have a more hidebound view on role transitioning, but the success stories we’ve seen have changed this. Unfortunately, this is not always feasible. Sometimes the cost of training is too high compared to hiring an expert, and other times, someone’s personal interests don't match a company’s needs. However, it’s an option worth exploring for individuals in your organization who continue to show promise. 

Letting go of someone

Occasionally, all options have been exhausted and attempts at remedying the situation doesn’t turn things around. In these cases, if handled correctly, terminations will still be unfortunate, but shouldn't come as a surprise. Instead, ending a professional relationship should be more collaborative. Finally, announcing a termination to the wider team should be done as transparently as possible, without sharing any compromising or confidential information. 

A compassionate approach to firing 

As I mentioned at the outset of this essay, we’ve made some firing mistakes in the past. Here’s what it looked like before when we let someone go:  

  • We informed them on a call that their contract had been terminated, effective immediately.
  • They were instantly released from all duties. 
  • A severance of the current month plus an additional two months was provided. 
  • They received a couple of hours to clear anything personal from their work email, Google Drive, Dropbox, etc.
  • They were immediately removed from Twist with no chance to say goodbye to their colleagues.
  • The notice about their departure would be written and shared with the rest of the company. Their personal email would be included in the message, so anyone who wanted to could send a private goodbye message. 

Over time, we’ve refined this termination process to be more compassionate and in line with our core values. 

  • If possible, the person must be informed face-to-face in a video call, but otherwise, over a phone call.
  • The period in which the person finished off outstanding work and handover of any projects depends on what's sensible in the giving situation. This is agreed upon by both. 
  • Inform the person's team. 
  • The company announces the termination internally while the person is still on Twist. 
  • Encourage the person to write and share a farewell message to the Doisters before leaving. Either as a follow-up to the termination announcement or as a separate thread.
  • Explore the company's network and yours for alternative positions elsewhere to help the person move on. If appropriate, provide a reference and refer them to roles they may be better suited for. 
  • Agree on an end-date.
  • Having an exit interview where they can share feedback.
  • Discuss severance and any next steps.

Unfortunately, not all terminations can be amicable, so the nature of someone’s last few days should be addressed on an individual basis. But on a remote team, where terminations can feel particularly cold, these changes have provided a buffer and make leaving the company feel much more gentle. 

Provide a severance package  

Once the decision is final and the message is delivered, the focus should shift to helping the person to move on. . A severance package policy can help. Terminating someone can result in immense pressure for that person –– you don't want to add insult to injury by cutting their financial lifeline too.

Our severance package pays out departing team members the rest of their current month’s salary, and 2-4 additional months depending on a person's tenure. We operate with a three-month trial period for newcomers, but for severance, anyone is qualified for the running month plus two from the moment they join. 

A severance package is acknowledgement of the challenging situation you put a person in when they’re terminated and no longer earning an income. The intent is to give them some runway as they seek out new employment opportunities. Looking for a new role can be a full-time job in itself –– temporarily relieving someone’s financial burdens can help.

Offering a severance package also acknowledges that someone took a bet on you, even if it didn’t work out. It sends a signal that you take your share of responsibility for a failed working relationship.

Communicate the termination to the team 

I briefly touched on the backlash created when a lay-off isn't backed with transparent reasoning. Communicating clearly about terminations can be a hard balance to strike and, unfortunately, one we’ve struggled over the years to find.

The more context you can provide, the better. It gives a greater understanding and allows others to challenge the decision or the reasoning. At the same time, it’s crucial not to expose intimate details about the departing person or share sensitive information. 

Tip-toe between respecting your departing colleague and providing sufficient information for everyone to understand the fundamentals of the decision. Keeping the terminated person on your communication platform during the off-boarding process pushes you to think every step through carefully, and you'll instantly know if your communication isn't on par with the standard. 

Letting go of someone is always hard, but tough situations can be improved with intention.  Our current approach, iterated over years, is better aligned with our values and makes room for better communication and a dose of compassion.

As a company scales, team members are forced to adapt and adjust to a changing environment. Unfortunately, not everyone can grow with a company –– new demands emerge and a certain level of evolution is required. While challenging, letting someone go in the long-run can create room for opportunity –– for both parties. 


About the Author

Allan Christensen is the COO at Doist, the remote-first company behind award-winning productivity platforms Todoist and Twist, which collectively supports 25 million people globally. Doist has been in business for more than 14 years, employing 100 people in 35+ different countries, with a 90+% employee retention rate.

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