When to Break Up with a Friend or Employee

If you’re trying to decide whether to fire someone or cut them out of your life, you’ve already waited too long

My executive assistant, Holly, came running into my office and blurted, “Sanjay, there’s a crazy woman in the lobby, screaming she’s going to sue us!”

Moments later Holly and I were in the lobby and approaching a woman yelling at the receptionist, demanding to be let in to the building. I interrupted, asking the woman, “What’s going on? How can I help?”

She responded, “Who the fuck are you?” and before I could answer, shrieked, “My husband is having an affair with some whore in your company and I’m going to sue you!”

I was then told through a cascade of swearing and tears that our head of IT, her husband, had been having an affair with another employee at the office, and we had facilitated the affair by providing a venue for them to meet and ‘carry on’, making us liable for some unspecified legal damages.

We eventually tracked down the wayward husband and sent him and his wife home, but here’s the thing. That IT manager had been a thorn in our sides for months. He was unreliable and a negative influence, but I had resisted firing him because his skill set was important.

Worse, when I did fire him in the aftermath of his wife’s revelation, an anonymous hacker took down our company’s servers and threatened to destroy all our customer files. Yep, solid character that guy. Fortunately a call from the RCMP Cybercrimes unit settled that problem quickly because we guessed it was him.

We’ve all been there. Resisted firing that troublesome employee too long. Gone weeks or years not having the courage to end a romance or a friendship or a marriage.

Humans used to exist in societies where the most important survival trait was being able to get along with others and to have the protection of the tribe. That isn’t true any more, but because of our evolutionary history, it still feels like a dagger to the heart when deciding to end a relationship, and it hurts even if you’re the one holding the dagger.

There’s a maxim in psychology that if you’ve having trouble deciding whether to break a relationship, then because of your emotional investment, you’re already way past the line when an objective person would’ve decided to part ways.

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Humans wait for certainty, or for a push. Learn to be more rational. — by author

I’ve hired and fired hundreds of people in my career. I have never regretted a single one of those firings, other than for having waited too long.

What you have to understand is that even the very best interviewers are wrong 50% of the time. The only time you have all the knowledge you need is once you’ve already been in the relationship for a while. When you hire, you’re right 50% of the time, but when you fire, you’re right 100% of the time.

Focus on making the right decision once a person shows you who they really are.

Second chances don’t work, although there is one exception. Not even the best relationship is perfect all of the time, but in good relationships, people surprise and please you more often than they disappoint you.

If an employee or a romantic partner or a friend has in the past been stellar, than sometimes a conversation or a warning can result in improvement. Sometimes people are fundamentally good, but get distracted or otherwise stumble.

In my 20s as an engineer I was considered a star. But when a new manager came in, I was ignored, and I started to come in to the office later and later every day. After two weeks, as I wandered in at 1pm to start my day, this new manager came to stand by my desk, pointedly looked at his watch, and started yelling at me in front of twenty of my colleagues.

For about 10 minutes I got a non-stop litany of how great everyone had said I was and how badly I had disappointed him. I was shaken, but in the end was left with one major thought, ‘holy shit, he’s actually been paying attention to me this whole time?’

I came in the next day at 7am and returned to being a star employee, earning raves from this same manager a few month later on my annual review. I had been a star. I could be a star again.

But for a new employee or a new friend? When they show their flaws, trust that this is really them. As with online dating, where you should assume that whatever pictures they’re sharing are the absolute best pictures they have, when you’re first getting to know someone, they’re on their absolute best behaviour. Stumbles at this stage should be taken as massive warning signs.

The marketing associate who proudly claimed she didn’t drink or do drugs, but when I caught her smoking up she said cannabis didn’t count because it’s a plant. The accounting graduate who was pretty, but couldn’t do simple math. The field service rep who put an ‘!’ at end of every! single! sentence! when he was emailing customers. I waited too long to fire each of them.

How you do anything is how you do everything. People of quality show it in their most mundane actions. They show up. They do what they say they’re going to do. They don’t make excuses.

Firing low quality people or friends is you allowing them to learn from their own mistakes. It’s you doing them a favour by letting them work for and be friends with people who’ll appreciate them for who they actually are, not who they’d like to be, or worse, who they’d like you to think they are.

You? Your expectations are higher.

My best hires and my best friends have been with me for 20, 30, 40 years. For those I’ve cut ties with over the years, it was them, not me. Which is not what I told them at the time of course.

Conventional wisdom is that you hire slowly and fire quickly. I would amend that to say you should both hire and fire quickly. Spending a ton of time on due diligence is going to increase your chances of success very slightly. You’re better off getting better at firing. Work on your dagger grip.

At my companies we’ve always had a three month probationary period, and when I was actively managing the process, our probation fail rate was 50%, far higher than the 10–20% fail rate of most companies. Not because we didn’t screen well, but because after three months we asked a critical question — ‘how would we feel if a competitor were to hire this person?’

If the answer was anything less than ‘terrified’, the person would not pass probation. Most of the executive team I put in place at Audiobooks.com has been there for nearly 20 years. Much of that success is due to the leadership of Ian Small, who took over as CEO after I sold the company, but boy, we fired a lot of people along the way.

When you have that termination conversation, you will always hear “Give me another chance, I’ll improve!”

Do they ever improve? No. They never do. They might plod along, barely avoiding getting sacked, but they’ll never be a star. And that’s what your job is as a hiring manager. Finding stars. Every butt in a chair is taking up space that could be filled by a star. Your job is to find stars, not to put butts in chairs.

Steve Jobs famously said “A’s hire A’s. B’s hire C’s.” and he worked tirelessly to avoid letting any B’s into his company. You can’t be successful at this all the time, but when someone reveals themselves to be a B or a C, take action, fast.

You may wonder, ‘but what will people think?’, worrying that people will question your judgement or your loyalty or your compassion if you fire a bad employee. Trust me, everyone knows they’re a bad employee.

With your social circle, there’s no need to tell a friend that they’re fired, just stop returning their calls or making plans or inviting them to parties. No need to be dramatic about it. The desire for constant drama is one of the hallmarks of bad friends and bad relationships.

People who suck have bad reputations. You will always look good breaking up with them. At least a dozen times, I’ve had a fired employee tell me, “If you fire me, everyone else will quit!” It never happens. Everyone else is happy they’re gone.

I’ve been told by friends after two bad relationships that they’d known all along the person was wrong for me but they were afraid to say anything. I get it, don’t interfere in other peoples’ relationships, it will only backfire on you (it will). The point is that when you finally do make the decision, you’ll be applauded, not criticized.

You’re judged by the company you keep. You may think you’re being compassionate, or inclusionary, by keeping people of questionable motives, wisdom, or humour around you, but trust me, people of quality are judging you and spending less time with you as a result. Your best employees are thinking of leaving because you have low standards.

Mark Manson says, “Nobody ever left a good marriage.” And nobody ever left a relationship that was working for them. Stop worrying about whether you’re making the right decision.

Be a manager of quality people. Be a person with quality friends. Have that difficult conversation now.

You’ve already waited too long.