A grounded guide to employee termination — and how clarity and compassion can make even the hardest decisions feel aligned.
Letting someone go never feels good.
Even when you know it’s the right call — your chest tightens, your mind second-guesses, and part of you wonders if you’ve failed.
I’ve been there more times than I’d like to admit.
And for a long time, I made it harder than it needed to be.
I’d delay the decision.
Convince myself things might change.
Hang on because I liked the person.
But here’s what I’ve learned (the hard way):
When you keep the wrong person in the wrong seat, everyone loses.
You lose time, clarity, and confidence.
They lose the chance to thrive somewhere they truly fit.
In this episode…
I shared what happened when I finally got this right — literally minutes after letting someone go.
How I prepared for the conversation.
Why it felt calm, not chaotic.
And what shifted in me as a leader.
Because when you hire slow and fire fast — with honesty and heart — it’s not about being ruthless.
It’s about being real.
If you’ve ever dreaded that conversation or dragged your feet on a decision you already knew was right…
This episode will help you see it differently.
🎧 Listen to the full episode — and find peace in doing what’s right, not just what’s comfortable.
KEY TAKEAWAYS: Lessons for Confident Employee Termination
- Don´t Be Afraid to Let People Go Quickly: Use each new employee´s probation period properly. Review performance objectively and, even if you like them personally, don’t hang on to anyone who isn’t the right fit. Delaying tough decisions makes things harder for everyone.
- Prepare Well and Be Upfront: Think through what you’re going to say. Be honest, clear, and kind when sharing the news, and explain why they do not meet your business's needs. This helps everyone know where they stand and shows respect for the person, while enabling you to keep your business moving forward.
- Right Person, Right Role: Strong skills and a good attitude matter, but so does matching expertise to job requirements. Hire for the role you need filled now, don´t compromise and inadvertently hire someone with potential who needs lots of training up.
- Learn From the Experience: Every time you have to let someone go, whether that is at the end of their probationary period or later, pause and review why things did not work out. Use what you learn to change how you hire and run things in the future.
BEST MOMENTS: Honest Reflections During Employee Termination
00:01 – 💬 “ Letting people go or sacking people is pretty rubbish. As a business owner, it can make you feel terrible inside. It does for me anyway.”
02:24 – 💬 “I´ve learned that hanging on to people just because you like them isn't a good recipe for running a business, and what happens is it eventually just starts eroding away at you as a leader.”
10:11 – 💬 “ Do it quickly, do it fairly, do it concisely, don't drag it out, or just hang on for a few weeks hoping for the best.”
TIMESTAMPED OVERVIEW
00:00 Managing the emotional aspect of letting someone go
03:33 Preparing, being clear and showing respect
06:11 Explaining your decision
09:08 Recruiting in a way that minimises the need to sack people
Episode Transcript
Please note: This transcript was generated using automated transcription tools and may contain typographical errors or inaccurately captured words or phrases.
Dr Steve Day: Letting people go or sacking people is pretty rubbish as a business owner. It can make you feel terrible inside. It does for me anyway, and today I want to talk about actually the latest time fact to let somebody go. The reasons behind that decision and, how actually, I feel pretty good about it, even after the fact of literally, it was just two minutes ago that I did it.
I thought I\'d record this episode while it\'s on my mind, I\'m in the moment. So I can share what I\'m feeling right now, how this has changed dramatically from previous times that I\'ve had to let people go. And what I feel going forward, this has taught me about hiring and firing.
Okay, so today I had to make the decision to let somebody go.
Now, I\'ve done this at, I think, the right time. That is literally at the end of their short probationary period at the beginning of their employment. Doing this with confidence. Going into this decision, thinking I\'d been very clear on why I hired this person and what the requirements were for this role. And then comparing those very strictly against this, the person\'s skills and their abilities.
And what they\'ve managed to achieve in their probationary period. I did it with that objective mindset, that objective framing. And that allowed me to detach from the fact that I really liked working with this person. That I enjoyed their energy, I enjoyed their enthusiasm. That I actually really got on with them, and it was just such an easy person to work with.
And in those cases in the past, sometimes I\'ve let that sort of cloud my judgment about whether I should keep somebody on because you know, it\'s nice not to have to sack with somebody is. Especially when you\'re hiring people from places like the Philippines, where often you know them getting a job is a huge, huge difference to their whole family\'s lifestyle.
So taking that away is the opposite, that it can actually really be negative on their lifestyle. And so it\'s always that tough decision. But over the years, I\'ve learned that hanging on to people just because you like them isn\'t a good recipe for running a business. And what happens is it eventually just starts eroding away at you.
Well, this is my experience that it erodes away at me as a leader, and I know the decision I\'ve made was not the one with the business\'s best interest at heart. And if I\'d only made that decision earlier, then I wouldn\'t be so emotionally involved in the whole process. And then it becomes more of a moral issue, whereas it should have just been a business decision.
So the take-home from this for me is about, I mean, the old adage is, hire slow, fire fast. And that\'s exactly what I think is the lesson for me in this case. It\'s, yeah, I did in this case, hire pretty slow. We\'ve been looking for someone for this role for a while. I thought I\'d find somebody really good.
I did have my doubts because of their level of experience in this particular type of role. This is a quite a technical systems, oriented role. Talking about automation, AI, doing prompt engineering, combining those three things together into building AI agents. It\'s quite a technical role. But this person was so enthusiastic about systems, about technology, about automation, about apps in general.
I thought they would just jump on it and grab it and, you know, they did to some extent, but not to the level that I needed this moment. Because I need someone who I can throw stuff at, they get on with it, build it, and then give me back. That\'s what I need for this particular role. Had I been in the position or what were I in the position to have an apprentice for this role that I was going to train up and bring up to speed?
She would\'ve been a great candidate. But actually that\'s not what I hired her for. Right now we have a need for someone to literally replace me in the business, not be trained by me. Because it sort of defeats the object if I\'m the one, then training them. Because the whole idea is want to move some of these high value or very technical tasks off my shoulders and onto somebody else.
And that is the role specifically that I\'m hiring for in this case. So, let me just break down if it would be useful, of how I approach this. And so the first thing I did was actually prepare for this meeting. And it may sound an obvious thing to do. But in some cases I haven\'t.
I\'ve been sort of so emotionally worried about the whole thing. I\'ve sort of just gone along and just, you know, it\'s sort of come out halfway through a conversational sentence. Or, you know, in the middle of a meeting for example, it\'s like, oh, I\'ve got something I\'ve got to say. You know, halfway through doing a normal one-to-one and then sort of throw in this bombshell. And it sort of just completely just messes up the whole feeling or the whole experience, I think, for both parties.
Whereas in this case, I prepared. And I literally turned on my camera, we\'re a remote-only business. So everything is done on Zoom. I turned on my camera and I started obviously just saying hello, you know, just niceties in the very beginning. And then I said, quite simply, today\'s the end of your official probationary period.
And I regret to say that I\'ve decided not to renew your contract, and that\'s how I opened it. So there was no smoke and mirrors. There was no beating around the bush. There was no big apology, there was nothing. It was just stating the fact really nicely, politely, but factually, the end of your probation period is today.
That\'s the reason we\'re having this conversation. So I\'ll frame why this is happening today. It\'s not because of anything she\'s done or not done like dramatically. And then state very clearly what the decision is. And then, just threw in there because I thought it would be ni nice in cases in the back of her mind so she can stop worrying about it.
I said, you\'ll be paid for any work you\'ve done to date, so just submit your time sheet as usual, and you\'ll be paid or your invoice as usual, and you\'ll be paid. And then I went straight into the decisions, which were very objective. Exactly what I described before. I said for this role, I need someone who is of a certain level of expertise. Who doesn\'t require handholding and isn\'t in that mode of sort of training up of how to do this stuff.
I need somebody who comes with that knowledge and experience so I can just delegate to. So exactly what I just said before. I literally just said that to her using those, pretty much those words. Obviously trying to do it in a nice tone and friendly and keep smiling so it\'s not like a, you know, a traumatic experience for anything. I\'m being just human about it basically.
And then I simply opened the floor to questions and said, you know. Oh, I actually also mentioned, you know, that I genuinely enjoyed working with her. And I also said, actually that, which I felt was a really good thing to say, if it\'s appropriate, obviously. But in this case, it was not a people issue, it was a position issue.
If you ever read Traction by Gino Wickman, he talks about position, sorry, people in positions, or people in roles, I think it is, people in seats, maybe. The wrong, the right person, the wrong seat. That\'s how he describes it. And in this case, it was the right person. Great values, great energy, great enthusiasm, you know, honest, dependable, got work done.
All those things were tick, tick, yes, yes, yes, yes, yes. But it was the wrong seat for her. Had I, or if I had a different position for it, opening the company that I needed somebody else to come in, I would\'ve moved her into a different role. Because I believe she was a, she is a brilliant employee for somebody. Somebody who either she leans into the skill she\'s already got or that she is in a training position to skill up.
And so this was the debate with me when I was actually thinking about this is do I train her up or not? And I was like, no, I\'ve gotta go back to basics. Why did I hire this person? Why was it, why do I need this role right now? And so therefore, the objective, Steve came back in and the decision was made.
So I made it very clear. Yeah, state the reasons why. State the, for me that actually this isn\'t a people issue. And I even said that actually if she skills herself up and she wants to apply again to work with me and the position\'s open, she would be welcome with open arms. And that is genuine. So I said it.
I wouldn\'t say it if it wasn\'t genuine, but in this case it was. And then I just opened the floor to questions and I said, you know, do you have any questions at all? And the first thing she said was, thank you for telling me so clearly, and I can\'t exact words she used actually. But thank you for telling me so clearly and explaining it in the way you have.
And she just thanked me for the opportunity and the training she\'s had so far, and she said, I\'ve got no other questions at all. And then I just basically finished by recapping any admin that needs to be done. So I said, please do submit your invoice. I\'ll ask you to provide evidence that you\'ve deleted or handed over access to a couple of accounts. And that will be it. Then we\'ll release your final pay. And that\'s it. And I said, I wish you all the best.
So that was my experience of letting somebody go, but leaving that meeting actually feeling quite positive. I\'ve freed up some time now again, because I was actually spending time training her and, actually supporting her in this role. So I\'ve now got time back, which is a positive. Yup, I\'ve not filled that position yet, so I\'ve gotta go back into the whole recruitment thing again. But luckily that\'s something that I\'m relatively, familiar with and they\'re actually just built an entire automated, AI driven recruitment system.
So it shouldn\'t be a big deal to actually, get somebody else. Some more candidates into actually try and fill this role with someone who is at the right level of expertise. And now I\'ve got those lessons that I\'ve learned or taking somebody in. I realize actually, I need that level of expertise. Whereas before, I wasn\'t a hundred percent sure.
I thought maybe she would just pick it up enough as we go along. And I realized actually what I\'m asking people to do is pretty damn technical. This is stuff that I spent years getting to be an expert at. And so expecting somebody to pick it up in a matter of weeks is actually not really practical. I need somebody who knows what they\'re doing.
And so, I\'ve learned a lot from this experience. I learned a lot from this experience of actually the way I approached this whole dismissal process. So do it quick, do it fairly, do it concisely. Don\'t drag it out and you know, just hang on for a few weeks hoping for the best. It\'s like, make the decision. That\'s what probation period should be for.
I haven\'t always, honoured that in the past and it\'s come back to bite me emotionally. And then ending up being much more of an issue when you do let somebody go. Because you know if someone\'s worked with you for six months or 12 months. And you\'ve always known in the back of your mind, they\'re not the right person. It\'s far, far harder to let them go.
Whereas if it\'s the first two, four, whatever weeks, or the probationary period, it\'s much more transactional. And therefore, the emotion doesn\'t need to be in it. And it\'s not such a big hit for that person. Because they\'re not totally like, they\'ve not been reliant on your income for months and months and months and suddenly you\'re taking away. It\'s, you know, a new opportunity for them. And then hopefully they can go and take that energy and, look for another job.
So that\'s it. Hope you found that helpful, insightful. If you have, I\'d love to hear your comments on how you approach this. If you do things differently or if you\'ve got any tips for me to make my life better in the future, then I\'m happy to take them.
But if you found useful, equally, I\'d love to hear. So please do comment on whatever medium you are listening to this on right now. If it\'s on a podcast, you could leave us a review and just mention this particular podcast, so we can pick them up that way. If not, reach out to me at, come to our website systemsandoutsourcing.com and on there you can click a button to book a call with me and chat about your business and how we can help.
Or just ping me an email, steve@systemsandoutsourcing.com, and I\'ll be happy to have a chat and just explore this further with you. So thank you very much. If you find this useful, it\'s a good chance other people you know will as well. So please do share this widely with anyone you know who you think might benefit from hearing this about how I approach the dismissal process in my business.
Thanks so much. Your time is super valuable and I really appreciate you chose to spend it with me today. Take care.
LINKS TO CONNECT WITH THE HOST
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ABOUT THE HOST
Steve moved to Sweden in 2015 and transformed how he ran his businesses—switching to a fully remote model. A former NHS doctor, with a background in computing and property investing, he now helps overwhelmed business owners systemise and outsource effectively. Through his courses and coaching, Steve teaches how to automate operations and work with affordable virtual assistants, freeing up time and increasing profits. He runs his UK-based businesses remotely with support from a team of UK and Filipino VAs, and is passionate about helping others build scalable, stress-free companies using smart systems and virtual support.
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