“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: dismissals lacked transparency and firings largely came as a surprise to departing individuals plus the wider team. This was just one instance in a pattern of employee dismissal 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. Letting go of someone remotely — disconnecting their profiles and revoking account access — can feel especially abrupt and cold. It’s the office equivalent of having someone pack up their things in a cardboard box and having security escort them out of the building.
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.
The lack of a transparent process 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. This article will cover:
- The systems we use to build transparency and accountability into our work so managers can spot performance issues early (yes, it is possible to know if someone is doing their job well without seeing them in the office)
- How we address performance issues with "radical candor" — combining honest and direct feedback with questions to open a dialog
- What our Performance Repair Process looks like including the possibility for temporary leaves of absence if the employee needs it
- How we've evolved our off-boarding to be as humane and transparent as possible, for the person being fired and for the larger team
- Why we stopped immediately cutting off access to our team communication tool, Twist, when we fire someone.
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 makes a hard situation as respectful, compassionate, and transparent as possible.
Catching performance problems early
On a remote team, performance problems can be 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 identify 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. fewer 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 situations where people stop delivering on their work and go radio silent. Yet, those times are far outweighed by team members who have been entrusted with responsibility and put in thousands of highly productive hours into the company each month.
Build clarity, transparency, and accountability with a centralized project management system
A culture of trust must also be tied to one of high expectations and strong accountability that allows 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 and it's still a work in progress. 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. These teams are so small that when someone drops the ball, it doesn’t go unnoticed.
Aside from the DO 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.
Use one-on-ones to get ahead of potential 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 preferred 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.
You've identified performance issues with a remote team member. Now what?
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 Kim Scott, the author of Radical Candor.
Build a culture of radical candor that flows in both directions
Inspired by her experience as a leader at Google and Apple, Scott coined the term "radical candor" to describe how bosses should think about and approach 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.
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 compassion and providing an opening for a two-way dialog. 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.
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:
...at 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 behaviors or performance problems, using radical candor to ensure all parties are aware of “the issue, the impact, and an alternative approach.”
Find the balance between providing the right feedback to emphasize the seriousness of a situation while not presenting it as an ultimatum. When feedback is shared as a "final warning" it applies immense pressure on the recipient. 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.
Here are the three steps to our formal Performance Repair Process:
- 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.
- 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.
- Consider a decision-making leave of absence: 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 on the team
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 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 made us reconsider that inflexibility.
Unfortunately, transitioning roles isn't 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 someone go as a last resort
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 a conversation where all parties feel heard and respected. Finally, announcing a termination to the wider team should be done as transparently as possible, without sharing any compromising or confidential information.
Ending a professional relationship should be a conversation where all parties feel heard and respected.
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 finishes off outstanding work and hands over any projects depends on what's sensible in the giving situation. This is agreed upon by both sides.
- Inform the person's team in 1:1 calls so the announcement doesn't come as a surprise.
- The company announces the termination internally while the person is still on Twist.
- Give the person the opportunity to write and share a farewell message to 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 humane and transparent.
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.
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.
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 as transparently as possible
I briefly touched on the backlash created when a layoff isn't backed with transparent reasoning. A termination can create a lot of uncertainy across the company, especially among newer employees. But handled with care and compassion, it can also be an opportunity to reinforce your company's values and ensure that anxiety and resentments don't fester.
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 the team a greater understanding of the situation 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.
Keeping the terminated person on your communication platform during the off-boarding process pushes you to think every step through carefully — your team will let you know if your communication isn't on par with your values.
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 — you'll quickly know if your communication isn't on par with your values.
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.
What’s Twist? Twist is an async messaging app for teams burned out by real-time chat, meetings, and email.
You don’t need to use Twist to get a ton of value out of this newsletter and community. But if the topics we talk about resonate with you, there’s a good chance the app will too. See what makes Twist different →
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