June 20

When is it time to fire an employee?


Please note that details have been changed (such as from ‘he’ to ‘she’ to protect the identity of the person spoken about.

It’s never nice to know that you might need to sack someone.

But you’re the manager. And you need to make real decisions about when someone is not performing.

You might be thinking of sacking the worst member of your team. But hold on.
You might be thinking of sacking the worst member of your team. But hold on.

You’re struggling. You wonder if what the person might be a little more time. Or if you should be more patient with him. Or if your standards are too high.

And here’s the truth.

You will never know if you made the right decision.

But if you’re thinking about whether it’s the time to ask someone to leave, it might just be the time for him to leave.

Here’s why.

Who am I to say this?

But you may look at my baby face on this page, and wonder who I am, really, to say this.

After all, it looks like I’m young enough to not only be your kid, but to be your baby.

Who am I to advise you?

If you’re here looking for the advice of gurus, I don’t have it. What I do have is the experience of asking 3 of our previous associates to leave, and then another 1 who decided to leave me voluntarily.

Ask them to leave, when their working style does not align with yours

Key differences You might prefer Your staff might prefer
Speed Work to be handed before time is up Work to be handed in on the dot
Communication Over-communication, where anyone you work with keeps you updated at most points Under-communication, where the staff only talks to you when stuff hits the fan
Commitment One task at a time
One major responsibility at one time
Many different tasks at one time
Many different gigs going on at a single time

I looked at my phone, and wondered if I should send off the angry message to my partner.

I had been waiting for him to pass me the work for the last 2 weeks, and nothing had happened. I had begged. Told him how urgent it was.

But I was hearing crickets.

Deep within, there was a sense of helplessness. I was trying to make this work out. But his refusal to even reply was making it hard for me to answer to my client, and even figure out a solution.

And finally, on the bus journey home, I had enough. I asked him to leave.

Perhaps the key question that changed my perspective was this,

Would you put up with this for the next 5 years?

Often we are willing to put up with short term pain, in hope of longer-term gain.

And you might be willing to give the younger colleague working with you the benefit of doubt, thinking that he would grow up.


But when we stop extending lifelines in hope that they will change in future, and simply accept them as they are, right now, you might realise less of the desire to help them grow.

Working styles are a key determinant of whether your working partnership will bear fruit.

If you can’t tolerate your staff’s working style, don’t try to change it.

If you can’t accept it, you’re better off sacking him. As I’ve worked with more teams around the world, I realise there are particular styles of working that I simply cannot tolerate.

Sometimes just choosing to have faith may be the worst thing you choose to do.
Sometimes just choosing to have faith may be the worst thing you choose to do.

Values do not align

One of the biggest alignments you need to have is the cultural values of the team you’re in charge of.

Values may sound fluffy and the stuff of dreams, especially in a place where you’re in the trenches, everyday.

But make no mistake.

It’s the thing that will bind you together.

For example, in my team, one of the unshakeable values was reliability. We needed teammates to:

say what you do,

do what you say.

An early associate was constantly talking, but not delivering on the work promised.

For months, I tried to change him. I tried to tell him what was okay, and what was not. But little changed.

Reliability simply wasn’t one of his core values. And trying to change that value in him, was like trying to force milk down his throat.

He just wouldn’t take it.

You might be in a place where you think that you can change someone over time, and help them to ‘become better’.

But if months have gone by, and little has changed…

Set a time limit for yourself and your staff

Learning to say goodbye to the working relationship may not be easy, but it may be necessary.
Learning to say goodbye to the working relationship may not be easy, but it may be necessary.

You’re right. You have performance targets to hit. And managing someone who’s just not meeting them, at the expense of the wider company, can simply be too much.

Over time, I’ve found that telling someone clearly what’s not working, and laying out for them what the stakes are (a possible sacking, reduction in pay, etc.), can help.

It would be unfair to expect them to know what’s happening, if you don’t tell them.

It’s your responsibility, rather than expecting them to guess what you’re thinking.

Try to place them on an Employee Assistance Programme (EAP)

Some of the more ‘woke’ employers today are realising the importance of providing counseling and mental health support for their Gen Y and Z employees.

It’s true. The younger employees may not necessarily be ‘softies’, but they might just need a little more support. They grew up in a different environment, and coming to work might be the biggest step up they may have to take.

Having them seek confidential counseling might just be the best way to help them share and address their  problems in an anonymous way, and hopefully bounce back stronger.

In Singapore, there are different EAP providers, which are either run by private, commercial entities, or charities. 

An EAP run by a charity, which I might recommend are Care Corner’s Employee Assistance Programmes.

They provide:

  1. Confidential counseling
  2. Peer support training for colleagues who are interested in being ‘mental health first-aid buddies’ for others in their company
  3. Mental health talks

Asking them to leave, may be the best thing you do for them

Sometimes the retrenchment letter may be the best thing you do for your staff
Sometimes the retrenchment letter may be the best thing you do for your staff

I once had a 20 year old Gen Z intern. For 6 months, she was helping me with our internal social media posts.

But she was constantly late with the submissions, and she was also asking for pay-raises every 3 months.

I kept telling myself that she was learning.

But it came to a point where I gave her a real client to work with.

And she was late with that too.

It became too much.

You may be there too. Wondering if you should give another chance to the person you’re working with.

But asking her to leave became the best thing I did for us, and for her.

I think it taught her to reflect on her poor performance, however painful the sacking was for her.

Not all sackings are bad. Sometimes things don’t work.

And as the manager, or the boss, just accepting that things aren’t working and not trying to force it through, may just be the best thing you do for both.



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