How To Fire A Team Member (And Still Sleep At Night)

Firing someone 😬

It’s the ultimate dirty word in People Ops circles — especially now, when the job market sucks, layoffs are high and competition for new roles is frankly insane. For many of us, firing someone is often perceived as we’re doing something morally wrong or evil. 

But let’s take the emotion out of firing someone for a minute. Why is this such a huge issue for People Ops? 🤔

The reality is, terminating someone’s employment doesn’t happen in a vacuum. I’ll bet the employee was underperforming. Or perhaps a bad culture fit. Maybe they were impacting team morale. Or worse… all of the above. 

I think the biggest issue for People Ops teams is when the (inevitable) firing doesn’t happen fast enough. Waiting to cut someone loose if they aren’t a good fit (or frankly doing a sh*t job) can pull down the rest of your company — and your bottom line. 

In this guide, you’ll learn Toggl’s playbook for firing people the right way without trashing your reputation.

Why not firing employees is a mistake 

Retaining employees doesn’t just help teams do better work. On paper, it keeps hiring costs down, creates long-term team relationships, and keeps skilled employees in your company. 

In reality, keeping employees around doesn’t always work out like this. High employee retention is goal for People Ops departments, but it should never mean shying away from terminating contracts if a team member isn’t a good fit or is hurting company culture. 

I would go as far as saying the biggest issue People Ops departments make around terminations is they don’t make the call as fast as they should. 

This was (definitely) once the thinking for Toggl’s People Ops team. The company prided itself on employee tenure, where many team members had been with the business since it began. Mistakenly, I thought this was the best indicator of a healthy company culture and how good things were for employees. 

This was misguided. 

Our decision not to fire people ended up holding our company back. Like many companies, we avoided firing team members in the hope behavior or poor performance could be turned around. Instead, we focused on improving employee experience (something 47% of HR leaders also prioritize) and cultivating an environment where every employee would do their best work. 

We thought not sacking employees who underperformed or didn’t mesh with our culture would impact team morale. But not taking action actually ended up negatively impacting everyone’s workflow. 

Now for a controversial take that probably shouldn’t be controversial. 

Not all firings are equal, and parting ways in some situations can be the best thing you can do for your team and your company.

Let’s take a look at how we built a playbook at Toggl to handle underperforming or bad-fit employees and decide when it’s time to let them go 👇

Lessons on how we learned to fire people the right way

Lesson 1. Don’t jump to firing people — try to improve the situation first

Team members are just that, members of your team. Firing shouldn’t (and isn’t) the first step you take when someone isn’t performing or meshing well with the rest of the team. 

We came across this with a veteran developer lead we had at Toggl (let’s call him John). He wasn’t rude or dismissive, but his long tenure and deep knowledge made him less approachable over time. When team members asked for feedback or advice, it was usually correct but also delivered in a way that made the rest of the team feel inadequate 

Time and time again, conversations like this would land in my Slack inbox: 

Daria: I just found out the marketing team messed something up. Again. 

Me: Oh no, what happened this time? 

Daria: They didn’t come to ask for help. Instead, they went ahead and did things on their own. 

Me: That’s frustrating. We really need to encourage them to collaborate more, especially when they’re unsure about something.

Instead of reaching out to John for help, the marketing team didn’t want to deal with the toxic communication style and tackled the issue themselves. Over time, these mistakes became very expensive and started to hurt the business.

We tried giving John feedback multiple times to adjust his communication style using our Performance Improvement Plan (PIP). 

This tool, created for our management team, gives employees with recurring performance issues — anything from not delivering results to a certain value mismatch, communication issues, or poor behavior — a chance to fix them and get back to their day-to-day roles. 

Setting up a PIP to monitor an employee’s performance is a three-step process: 

💬 Step 1: Conversations. Before putting someone on a PIP, team leaders must have had several conversations (1:1s) about the performance issues, so it doesn’t come as a surprise being put on a plan

🤝 Step 2: Bring in People Ops. Next, the team leader brings in the Head of People (me!) to give me the heads up that an employee who is struggling and needs more than just regular support

🧑‍🤝‍🧑 Step 3: Assign a PIP buddy. Then, someone in People Ops reaches out to be the team member’s PIP Buddy. The PIP Buddy is the go-to person for doubts or questions while we try to get the employees’ performance back up. They also support management and the team member by ensuring the root cause of the issue(s) is looked at and action steps are understood and precise.

We designed the PIP to have three possible scenarios once it’s done: 

Unfortunately, the PIP we put John on led us to scenario #3. While his expertise was invaluable, it ended up being a concrete barrier that blocked collaboration. The cost of keeping him was too high, and we made the tough decision to part ways with him. While John’s history with us was important, it couldn’t outweigh the need for a supportive and collaborative work environment.

Lesson 2. Listen to your team when there are warning signs

Hiring for culture fit is always a difficult task, especially when it happens remotely. 

We’re not alone in this struggle. 15% of HR leaders struggle to integrate remote workers into remote company culture, and 32% of new hires will leave in their first three months if they don’t vibe culturally with their new team. 

Getting culture fit right is (arguably) more important than any skillset a new hire will bring to a position. And although it’s something we focus on a lot, we still don’t get it right 100% of the time. 

This was true for one developer our Engineering team hired a couple of years ago, Mark. While his technical expertise was unparalleled, and during the hiring process, he was just what we were looking for, we knew soon after onboarding there was a problem. 

While Mark found bugs the team hadn’t noticed and pointed out inefficiencies confidently, he was also quick to point fingers at others in the Engineering team. His Slack messages were laced with a negative, condescending tone, and he would question the competence of fellow employees. 

It’s the kind of behavior that Amy Gallo from Harvard Business Review describes as a risk to psychological safety. She says it’s important for a team to think it’s OK to take risks, express ideas, speak up with questions, and admit mistakes without fear of negative consequences. 

Unfortunately, Mark’s behavior was having a negative impact on our Engineering team’s psychological safety. It flew up enough warning signs to initiate Toggl’s Red Flag Process, which team leaders use to gauge conflicts:

The last bullet point — the impact on our culture — meant we had to act quickly. 

The culture we had worked so hard to build — one of collaboration and healthy debate —was being bulldozed by one person’s need to be right at any cost. Every day, my inbox and Slack DMs were filled with complaints from team members who felt frustrated, demoralized, and angry. 

Before Mark even completed his onboarding, we knew we had made a bad hire and made the difficult decision to part ways with him. 

It taught us a valuable lesson. No matter how technically brilliant someone is, if they’re not a good fit for the culture, the cost of keeping them is too high. It’s better to cut your losses early, recognize when something isn’t working, and move on. 

The biggest lesson of all? Listen 👏to 👏 your 👏 team 👏. 

Lesson 3. Create a “termination” checklist to help leaders navigate the most difficult decision

In business, firing is usually looked at as a dirty word. As if you’re doing something morally wrong or evil. 

The decision to terminate an employee must be grounded in understanding. This involves getting everyone on the same page and agrees the call to take this step is what’s best for the team and overall — what’s best for the business. 

Just like any other decision managers make, terminations should have a concrete process to follow. At Toggl, we created a termination checklist (which you are free to steal) to help team leads navigate through the process: 

🤝 Step 1: Coordinate with People Ops and get legal advice. The team lead’s first port of call is to loop in People Ops and highlight the performance issues with the team member they want to terminate. They must show they have followed company policy and attempted to address the issues through the PIP/Red Flag process before jumping the gun. Once we give the green light to proceed with the termination, we loop in our legal team to avoid any fallout in case of disagreeable terminations.

📅 Step 2: Schedule the termination meeting. Team leads must book a face-to-face meeting over video with the team member to break the news. These calls mustn’t be made right before, during, or right after the team member’s vacation or leave period. Be empathetic and make it fair. 

📞 Step 3: Prepare for the call. Focus on facts, not emotions, during the termination process. If a team lead is struggling with this, People Ops helps them prepare for the call and can even join in to help them deliver the news.

🗣️ Step 4: Inform the rest of your team ASAP. Terminations are made between People Ops and team leads, so the rest of the department won’t know what’s going on. It’s important for team members to be told as soon as the call is made and given room to ask any questions about what happened.

The final piece of our process is to draft a termination announcement to be shared in the main Slack channel. There are a few areas to cover here:

• Tone and wording. Avoid using harsh formal words like “voluntary/involuntary,” “fire,” or “terminate,” and use “leave” or “part ways” instead. Remember, the rest of the team won’t know about the decision until it’s posted in the Slack channel, so it needs to be gentle. 
• Provide context. Without sharing personal details that might put the leaving employee in an awkward position, instead explain the reasons related to their job role about why the company is parting ways with them. Add in any important details like the team member’s last day and any other relevant information.
• Highlight the positives. Sometimes, the team members we part ways with have been with Toggl for years. Employees have genuine bonds with them, so we always take a moment to appreciate the good things the team member brought to the company. A big thank you for their time and efforts will encourage the rest of the team to share happy stories about working with them. 
• Be respectful. Finally, stay on the high road. Keep everything in the announcement professional and avoid negative comments.

If you decide to steal our process above, make sure there aren’t any lingering questions from team members. As long as everyone is aligned and happy to move forward, reach out to the Talent Acquisition team to get the vacancy filled as soon as possible.

Lesson 4. Offboard a terminated employee respectfully (and quickly)

After the dust has settled from the termination, agree with the team member on when their last working day will be and start the offboarding process. 

The main aim of aligning on this ASAP is to avoid legal issues. It’s standard for the employee to stay on for a couple of days to do a handover to the rest of the team. Other times, it’s not that simple. If the person is toxic to the team or might harm the company due to access to certain tools, the termination requires a stricter approach — like immediate termination or mutual agreement on a date that doesn’t breach their contract. 

Along with agreeing on a last working day, try to schedule an exit interview. After all, the team member is on their way out, so they’ll be more comfortable spilling the tea about what they didn’t like about working with you. 

Not every company takes advantage of exit interviews — a Harvard Business Review study found 75% of companies conduct them — but they are one of the most honest ways to find flaws in your company. Ask questions like: 

• How did you perceive the communication leading to your termination? And what could we have done better? 
• Did you feel treated with respect throughout the whole process? 
• How can we improve our training and development?
• Do you have enough opportunities for promotions and to grow professionally? 
• Are our values well-implemented in our daily work? If not, how could we improve?
• What could be done to make this company a better place to work?
• Were you happy with your benefits, perks, and other incentives? 
• Do you think our company offers competitive compensation for your position? 
• Do you believe your work was adequately recognized and appreciated?

Any answers you get after the person has been let go won’t always be what you want to hear. But these hard truths can help you make positive changes internally. 

For example, a lot of the folks leaving Toggl in the past was down to the lack of career development options available. It stung, but this feedback helped us carve out our Career Development Framework to give our team more options to grow with us.

Lesson 5. Look after team members after you part ways

A huge part of firing people the right way comes down to treating people with respect, offering support, and setting them up for the next chapter. 

We offer a generous severance package to every team member we part ways with based on their tenure, reasons for termination, the person’s role, and the impact they made at the company. On top of that, we write references for employees if they ask and direct them to our Career Transition Resource Hub.

It’s full of information about navigating new job searches, negotiating salary packages, and coping with career transitions. We even offer terminated employees the option to book a one-on-one consultation with a member of our Talent team to discuss career aspirations, review their resume, or help them prepare for an interview.

We’re not saying all of this to give ourselves an ego boost. At the end of the day, firing people is hard. 

But there’s a better way to do it than just cutting the employee loose. If you can navigate the process with dignity and respect, it will reflect well on your company’s reputation — and give the terminated team member a head start at finding their next position. 

Firing people isn’t easy — but it’s our job

Firing is still a dirty word for many People Ops departments. For us at Toggl, firing people just wasn’t in our DNA. We really struggled with making those tough calls until the issues became impossible to ignore. 

The reality is firing people isn’t easy. But it’s often the best thing you can do for the team, for the company, and even for the person involved. 

Make the process easier by having processes in place. Attempt to resolve issues and get the employee to step up before you move on to talking about termination. And if it comes to that, work through a checklist to keep your emotions out of it while still treating the team member with dignity and respect. 

Not only will it make the whole ordeal less stressful, but it’ll also leave your company’s reputation intact. 

📚Dajana’s handpicked People Ops reads 

• “First, Break All the Rules” by Marcus Buckingham and Curt Coffman: This book discusses how great managers make tough decisions, including firing underperforming employees, to build strong teams.
• “Crucial Conversations” by Patterson, Grenny, McMillan, & Switzler: This book provides insights into how difficult conversations, including those that lead to termination, can be handled in a way that is both respectful and effective.