Offboarding with Heart - Making the Last Chapter Counts

Letting people go used to be one of the hardest parts of my job (and sometimes it still is). I would lose sleep over it, overthink conversations, and feel an overwhelming sense of guilt. In the beginning every offboarding used to feel personal, and I struggled to separate my emotions from the process. But over time I realised that offboarding is not just about endings, it is about transitions, and it is about turning goodbyes into growth. It is a human experience that requires empathy, honest conversations, and a commitment to ensuring respect for everyone involved.

It is also good to understand that there comes a point when holding onto a professional relationship does more harm than good, both for the individual and the company. Whether it is a mismatch in expectations, a shift in business needs, or simply a role that no longer fits, saying goodbye sometimes is crucial. While done right offboarding is not just about closing a chapter, it is about helping a company or someone who works there turn the page to the next opportunity.

personal struggles

In the beginning of my HR journey offboarding felt like that one part of the job that I wasn’t sure how to navigate. The awkwardness, the uncertainty, and the whole “I don’t want to say it, but I need to say it” moment. I have never seen offboarding as just another task to check off in a list. For me it has always been much more than that.

When I hire someone, I do deeply believe in them. I see potential, I imagine how they will grow within the team, and I invest in their success. So, when the moment comes to let someone go, it probably always may feel a bit personal. It is not that I don’t understand the reasoning behind the decision. It is that delivering this type of news has always been one of the hardest things I might have to learn. It made me feel like I had failed them - failed the employee, the team, and the organisation. As if I had created a problem rather than solved one, and that I had wasted both the candidate’s time and the company’s.

And honestly? It is also because I genuinely like the people that come. They are my team. I have never believed in bad intentions - only in circumstances, mismatches, or situations that didn’t unfold as we hoped.

making a transition

Over time I have come to see offboarding differently. It is not just about ending a chapter. It is about setting the stage for the next one. Sometimes, letting someone go is not about rejection, it is about redirection. Keeping them in a role that is not the right fit doesn’t do them any favors. It just keeps them from opportunities that could be much better for them.

I know this might sound like sugarcoating. But it is not. I genuinely cheer for every person I have to say goodbye to. I know that for them this moment is often one of the toughest in their career. That is why I approach it with empathy, honesty, and as much support as I can offer. It is still sometimes difficult for me, but I have also learned that no matter how much I want something to work out, sometimes it just won’t - and that is okay.

It’s the same when someone leaves the company I work for. I always feel a bit sentimental. I cheer them on and fully understand they have their own reasons for the decision, but a part of me still feels sad that it didn’t work out. At the same time, I really admire their courage to make a change.

leaving a positive legacy

I have always believed that the true measure of collaboration is not about how we start working together - it is about how we part ways. There was a reason we begin this journey together. It could not have been all wrong. No one forced us into it. Along the way, there were wins, lessons learned, and moments worth remembering even if in the end things do not turn out as planned.

Offboarding is not just a formal goodbye, it is a reflection of your company’s culture and how you treat people - even when they are leaving. A poorly handled offboarding process can leave a sour taste, not just for the person leaving but for your remaining team, too. If your company prides itself on being a great place to work, then the way you handle departures should reflect that. A well-executed offboarding process shows you care even when things are not going according to the plan. It is about making sure people leave on good terms.

Not everyone is suited to lead an offboarding process. Too often, I hear about managers handling it mechanically, like choosing what to eat for breakfast. I get it - stress plays a big role in these situations. But if you can’t approach offboarding with empathy and respect for the person affected, it is better to step aside and let someone who can.

When I go through an offboarding process, I see a person - a human being - not a job title. So, if this chapter is coming to a close, the least I can do is make sure it ends with dignity, respect, and a genuine appreciation for the time we shared. Because at the end of the day, offboarding is not just about paperwork.

consequences of holding on too long

l admit there were times when I held on to a person or situation a bit too long. I have tried to convince myself that somehow, magically or with huge effort of both sides, everything would work out. Maybe after the next sprint, or maybe after the next release, things would click. Any honestly sometimes they did, but usually they didn’t.

If someone is not the right fit for the job, sticking with them for too long just causes friction both for them, the team, and the client. It is like trying to force a square peg into a round hole, no matter how much you try, it is just going to get worse. But it works both ways. If you start feeling that the company or the role isn’t right for you, the result is often the same - frustration, burnout, or simply a sense of not belonging. Letting go, even if difficult, can be the healthiest choice for everyone involved.

It is even harder when accoriding to you everything is going well, but sometimes it is the best choice for both sides. For the individual, it opens up the opportunity to take a role that actually fits and lets them thrive. And for the company, it frees up resources to bring in someone who will add more value. In the very long run it is a win-win.

how to end collaboration with empathy

All managers and leaders have awkward moments where the “exit interview” feels more like a bad breakup than a professional conversation. But the secret tool is empathy. There are a few tips to make the process smoother and a little less cringe:

• Be honest, but kind. You do not need to sugarcoat things, but at the same time, do not turn the conversation into a list of all the things the person did good or wrong. Be transparent about why the decision was made, but also acknowledge the contributions. Every team member, no matter how long they were with you, brought something valuable. Recognize it. 
• Offer support. Offboarding does not mean cutting ties completely. Depending on the situation, offering career advice, sharing job opportunities, or simply connecting them with your network can make all the difference. Don’t be afraid to help someone get to the next step, even if it is not within your company.
• Keep the door open. Don’t make the departure feel like the end of the world. Who knows, maybe you will cross paths again down the line or they might come back to your team as a boomerang employee. In the tech world you never know when a past employee could be your next colleague. Keep the relationship cordial and professional.
• Respect the decision. When an employee decides to leave, it is important to handle the transition with gratitude. Their decision may come from a desire for growth, a career shift, or personal reasons. Regardless of why they are moving on, showing kindness in their departure leaves the door open for future connections and reinforces a positive workplace culture.

growth through change

Looking back I have come to understand that offboarding is not a failure, it might be a part of the journey. It might be about growth not only for the person leaving, but for the team and the organization, too.

At the same time I believe some offboardings can be avoided. Clearer expectations, better onboarding, regular feedback, and honest conversations, especially early on, can help spot misalignments before they become too big to fix. When we invest in mutual understanding and ongoing support, we give people (and ourselves) a real chance to grow in the right place.

Adam Grant once said that You don't have to have it all figured out to move forward. You just have to be honest about where you are at. This quote captures something essential about healthy team dynamics as the key to progress is not perfection it is honesty. In the workplace we often avoid tough conversations because we feel we need to have all the answers before we speak up. But when we are honest early about mismatched expectations, unclear roles, or personal challenges, we can adjust, support each other, and prevent situations from escalating into disconnection or offboarding.

Regular feedback loops, check-ins, and psychological safety allow everyone to be transparent about what is working and what is not. That’s how teams evolve together. We do not do it by pretending things are fine, but by having the courage to say that we need help moving forward.