One trick I learned to fire your staff without getting sued, tears and shouting

One trick I learned to fire your staff without getting sued, tears and shouting

Hi Alex, Thanks for sharing this and was an amazing read. This hits right at point where I was struggling a lot. Cheers, Ajeet G.

I’ve hired a lot of people. A lot. I’m talking hundreds. With that volume of people, there is going to be voluntary churn. There is also going to be… involuntary churn. That means firing people.

I’ve been sued for wrongful dismissal. I’ve been in more than one termination and had people either freak out and shout, or at the other end of the spectrum, start crying.

None of this is fun. Maybe you can relate?

But do you know what? I was fundamentally firing people wrong.

But how I was firing people in meetings was not wrong. I was respectful, I let people talk, I was prepared and I did meets when no one was about so it wouldn’t be awkward. So what was I doing wrong?

I did one thing different and changed the lawsuits, shouting and crying to “Alex, thanks for giving me a shot.”

I’m going to explain this one key learning to you.

Crazy land

We were in super-aggressive hire mode. I was flying around launching new cities and attracting salespeople by hook or crook. I needed people to hit targets and I had the budget. But I needed the right people, performers.

When I started, I didn’t think. As my saying went, ‘don’t think, just do!’ I just hired people that performed in interviews. Then did proper onboarding one on one. I would pair them with another sales person to share learnings.

FYI, I learned it was more efficient to do hire in groups, with a min of two, as they always had the same questions and some were more forward at asking questions. Also frees up way more time personally and you can compare each’s performance against one another which is a more informative sample. This is a great learning if you are more normal, meaning can only hire a few people! Don’t hire one person, hire two.

I did a lot right to get salespeopleĀ prepped and ready to start selling. But I didn’t set them up for failure. And not how you think.

Things get dark

I hate firing people.

Don’t tell anyone, but, I used to cry sometimes in the toilet when I was sure no one was listening, just before I had to do the dirty deed.

I’d pulled people from a steady job into my world and now I was canning them. Now, I’m not even talking after 3 months. I’m talking 4 weeks. In fact, my performance test shortened to 2 weeks… 2 weeks!

No shit. I would literally fire people after two weeks, and sometimes a week. They had a week to close a deal and two weeks to close 5 deals in a week. I figured out that people either performed or not. Time didn’t have a high r2 to performance. That’s brutal I know.

Do you think people were happy?


I got sued once (The guy was desperate). People cried. People shouted.

I felt like shit.

The change

I had an epiphany.

It wasn’t just that I was firing people (Which is clearly not sunshine and rainbows) that was the issue. I realised that I hadn’t properly set expectations for success and failure clearly.

  • I hadn’t set out clearly agreed goals
  • They weren’t purely about performance (and not soft things)
  • They weren’t personal, so they could save face
  • I didn’t have clear timelines to deliver

In short, for performance orientated people that make money by selling stuff, I wasn’t quantitative and definite.

Before hiring people, I said something like this:

Look, I’ve been doing this a while. It’s not for everyone. You may be a high performer for other products, but here, sales people either are great or they fail. It’s nothing to do with you as a person. It just works or it doesn’t. For you to hit your OTE (on target earnings) you want to be a performer. Why do you want to be here if you aren’t making a lot of cash? And yeah, our folk are making out like bandits! We’ve figured out that people either do great or not at all. So here is the deal. You have one week to get a deal. In your second week you need to do 5 deals. If you don’t, then it’s not going to work. Your min goal is 5 deals a week on a rolling-basis anyway. Is that clear?

That’s not exactly what I said. I made that up, but it’s probably what I said, lol ;).

But do you know what? I never once had someone not take the offer. And let’s be real, no salesperson thinks they won’t make the cut.

What happened after

OK, so salespeople don’t make the cut! Yes, I had to fire people a lot. But, it was better.

I remember the first time I implemented this. It was a chap in Melbourne, I’m clearly not going to name. I’m going to be honest. The prep spiel above was spontaneous, I just said it as I was tired of hiring, training, firing and feeling crap. It just turned out to work.

I hired him ‘on trial’ with a girl. It was also the first time I started training multiple people at once since I had only just got to the point where I had enough candidates (Managed to find the right head-hunters).

He was a decent chap, but nothing spectacular. He asked a lot of questions. I liked him. I went on sales calls with him (How else do you get respect from salespeople?). He leveraged his relationships to get meetings…

But, no deals. They just didn’t close.

His one-week milestone hit. I scheduled a meeting with him after work hours on a Monday.

After I had dried my eyes and didn’t look like a soppy little girl, I walked into the meeting room, a folder in hand (Termination letter).

Me: “How did you think the week went?”

Him: “I had a fun time, but it was harder than I thought”

Me: “Yeah. It really isn’t.”

Him: “Look, I know. I just want to say thanks for the support and for giving me a shot.”

That was sort of the end of it. We shook hands and did the BS small talk.

I felt good. Well, better.

Why was this different?

There was no need to explain. Anything.

It wasn’t personal. It wasn’t like Mary in HR doesn’t like you or some political BS.

We agreed on clear targets and why they needed to be hit.

He didn’t want to work for me if he wasn’t making money either.

There were no grand promises and prospects. Everything was clear cut.

But, what about for non-sales people?

Good point. For most jobs, it isn’t so clear, at all. I’ll tell you what I do.

I set out exactly what I want people to do for me on a small scale, despite the potential scope of their role. I make sure once they start I support them, but also that they immediately start delivering on their core job.

I hire people who can think for themselves, even with VAs (Virtual Assistants). To do that you have to make clear that failing is cool… so long as they ask for feedback proactively. Failing has to almost be encouraged. When they fail, you need to allocate time to teaching and with zero spite. When you do that people feel comfortable ‘having a go.’

I think a month is a fine test period for pretty much anyone. If they can’t execute on their core job for defined tasks, you are on to a loser, so take the advice and fire fast. If they execute immediately above expectations, give them more, and make the test period 3 months.

Set expectations with people as follows:

  • You have 1 month to demonstrate you can execute on your core capabilities and can add value to the team. We expect you to ship a quality SQL based dashboard as we need to get better at our reporting. If this isn’t done, we aren’t going to be a great fit as we need people to operate independently.
  • You then have 2 further months to demonstrate you can expand your role to the full expectations of your role in business intel and have the potential to grow and advance in our company. I need you to identify at least three optimisations and figure out how to increase our conversation rates on page by 3%. Is that clear?


By being really clear with staff on your expectations, you are not only doing yourself a favour, you are also ensuring the hire finds the right home themselves and doesn’t waste their time. They don’t really need to put their 1/2 month stint on their CV either, right…?

Think about setting clear goals when hiring people, so firing becomes a formality the hire knows is happening without a surprise.

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Comments 5

  1. I heard a quote once that has stuck with me due to its utter simplicity and profundity:

    “Fail early.”

    Unfortunately, I don’t know who originally said it (it wasn’t me).

    It definitely applies in many aspects of business.

    1. Post

      Hey Chris – There’s a lot of variations of that in startup land. ‘Fail fast’ is the most common one.
      I always actively find reasons why I’m going to fail as quick as possible instead of believing blindly that you can push through. You only make money if things work.

  2. I have always clearly defined expectations then reviewed weekly for new starters. The end result people who did not perform called the meeting most times to say thanks but not working. Where I am somewhat different is that during that trial periods and self/joint review, I often found they suited another role better or a role they had not tried but showed great aptitude in. Works well in multi discipline environments.

    1. Post

      Hey Gareth – That’s going to depend on your company. I picked this up when hiring sales folk- I just need them for deals. In the earlier phases of a normal startup and you hire ‘smart kids’ to do whatever, then your approach totally works. e.g. running ecommerce, they can get involved in customer care to supply chain management

  3. This quantifies what is otherwise a very murky world between startup bosses and their rapidly deployed staff. As a startup, you feel a bit undercooked to dictate terms anyway, and firing someone who is clearly under-performing is just excruciating.

    Setting even simple goals / KPIs up front and sticking to them, even in a grossly inhumane sort of way, at least lets that sendoff discussion be less debatable. Awesome Alex.

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