Horrible Bosses

Iain Smith
7 min readOct 1, 2020

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When it is my wife’s turn to choose a film for us to watch I have one specific rule. It can be any film she chooses, whatever she wants, any film at all . . . as long as it hasn’t got Jennifer Anniston in it.

It’s a time saving rule of thumb. You can assume that if JA is in a film it is a terrible film. Always fabulous in Friends, consistently substandard on the big screen.

Sure, my rule’s not 100% fool proof (Marley and Me, We’re The Millers) but it will keep you safe on the whole.

The last time I ignored the rule was to watch Horrible Bosses. That’s one hour and 38 minutes of my life that I’m never getting back.

So to glean some measure of value from that time I lost I’m using the film to segue seamlessly into four valuable lessons I learned from the most horrible boss I ever had.

Glory Days

About twenty years ago I worked as an events fundraiser in the charity sector. It was a brilliant time and a lot of fun but I realised quite quickly that it wasn’t the career for me. The year and a half I ran events taught me a heck of a lot.

One reason I learned a lot was because for the second half of the year 2000 I had the best boss I’ve ever had.

The best boss was amazing. I often share things she did like using her diary by stapling every single event, ticket and notice into it.

She never lost a single piece of paper or missed an appointment. Everything was in her diary and always at hand.

Then, from 2nd January to 11th November 2001, I had the world’s worst boss. Or at the very least the worst boss in the London Borough of Merton.

Rocky Ground

The world’s worst boss was even more amazing than the best boss. Amazingly awful that is.

To be fair I’m sure I wasn’t a world beating employee either but he was stunningly awful as the guy in charge.

He was awful to everyone but seemed to be even worse to me. Our small team of sparky twenty-somethings quickly cottoned on to this and shared glances when he would blank my outstretched hand or offer biscuits to everyone but me. Happened more than once!

Much of the low level stuff like that we found amusing but these next few examples of everyday behaviours might give you a fuller feeling for him.

  1. He would give short shrift to ideas that we, his fundraising team, would come up with in meetings, then pass them off as his own to the Managing Director, taking full credit for them.
  2. He would ignore my comments in meetings, then when someone else purposely said the exact same thing he would nod enthusiastically and declare it to be “A very good idea. Very good.
  3. He would micro-manage us over menial tasks, having the team work on unproductive and worthless jobs.
  4. Least enjoyable was when he would try to be matey with me, making laddish, lewd suggestions when the female staff members were away or just out of earshot.

Brilliant Disguise

The Office was released in July 2001 and one reason for its success was that everyone recognised elements of David Brent in their own boss.

Many people felt Ricky Gervais must have based his character on their boss.

I knew differently however, David Brent really was my boss, just not as charismatic or nuanced. Yeah, I know.

In terms of long time learning, I’ve decided that terrible bosses are often just as good as, if not better than, the best bosses. The worst bosses give you lessons that stay with you forever because they’re so awful.

That’s definitely my take on it. Although you need to make sure you learn five times as quickly as normal to ensure you don’t get stuck with them for too long.

They are really valuable if you are able to view the things they teach you in a useful light. Looking back you can assess:

  • what you could have done better in response
  • how you would act now
  • what you would do if you were in their role. Hint — it’s usually the exact opposite!

Born To Run

As a charity we used to pay thousands of pounds for a handful of places in the London Marathon.

I remember that we paid £3,250 up front for each ‘golden bond’ that would allow entry for the next five years.

We had bought five golden bonds and it was a lot of money to pay out in advance, in the hope that our runners would raise more in the following years.

Our runners would ‘buy’ a place from us on the understanding that they would commit to raising a substantial amount. We were paying out £650 for each runner we recruited before they even tied their laces.

When you factored in the cost of the debenture, running kit, advertising, admin etc I think we only started to make any money once the runner had raised over close to a thousand pounds.

And I knew from the previous income figures that not all of the runners brought in what they initially pledged.

I had an idea. In the previous year I had somehow dragged my sorry backside over the 13.1 miles of a half marathon called The Great North Run.

It was a fantastic event that stirred up a lot of passion and could only get bigger.

I’m On Fire

I suggested that we should buy five places for the Great North Run and trial it by asking runners to pledge £350. If it worked we could buy more the next year and review the numbers.

I felt it was a no brainer because:

  • In 2001 a place in The Great North Run cost the princely sum of £25.
  • Our charity already had all the systems in place to support our runners with kit and training materials etc.
  • We were a nationwide charity and had supporters all over the country.
  • Our runners could pledge a much smaller, achievable amount and yet generate much more money with very little chasing from us.

My boss turned my idea down. He knocked it back flat, commenting disparagingly about fat, sweaty northerners wobbling through desolate council estates in cheap sweatpants.

That’s what he said. Told you he was a great guy didn’t I?

I ran the Great North Run that year anyway. I bought my own place, ran for my employers and raised £350.

My time was slow but I was very quick to tell everyone how great the numbers were for such little investment from the charity. You do the math!

Lessons From The Boss

But what lessons did I learn from my Horrible Boss?

Lesson 1
Conviction of belief. If you know something is right or true or a good idea you should believe in yourself and your own knowledge.

If I’d had conviction in my belief I could have have pushed on the potential of this event to raise money for the charity. That was my role and here was an easy win.

I knew the event. I’d run the thing. I understood that The Great North Run was not some provincial jog in the park.

It was a huge international event with the potential to raise large amounts of money for very little outlay in terms of cash or effort.

Lesson: Believe in yourself and bet bigger.

Lesson 2
Strategy. I could have predicted that my boss would have turned me down. He was a London based cultural snob so it was naive of me to think he would have agreed to an idea of mine.

These days, given the same scenario I think I would have had an earlier casual chat with the MD and dropped the idea in to gain tacit approval.

Once that had been ensured then I’d have floated the idea in a meeting with the clear suggestion that our MD already thought it was a great idea.

Lesson: Strategise. Manipulate. Be a bit cute if need be.

Lesson 3
Recognise my boss was a Hippo. I’m not being rude (although I got pretty close at times!). HiPPO refers to the Highest Paid Person’s Opinion.

There’s a tendency for lower paid employees to defer to the opinion of higher paid people whenever a decision is being made. That’s exactly what I did. These days I’d get my hippo gun out.

Lesson: Listen to the idea not the person speaking.

Lesson 4
From any decision, good or bad, there is always a lesson to be had. Hey, that rhymes! It’s like a quote on an inspirational poster.

What I mean is that by dissecting that snub from 20 years ago we’ve got a handful of half decent takeaways. There’s always something to learn.

Lesson: Look out for the learning

You might have had a horrible boss at one point. You may have one right now or could in the future. How would it benefit you if you treated it as a learning opportunity?

If any of those lessons my old boss kindly gave to me are useful to you then he has done us all a favour! And so has Jennifer Anniston. Thanks Jen!

Iain helps busy people get more done, in less time and with less stress. He delivers inspiring training courses across the UK and internationally. You can contact him here.

He offers a three day training programme based on the MET Model. A day each of Mindset, Energy and Time. You can book three days in a row or spread the three days out over the year. Or simply pick and choose one or two days as stand alone trainings — Mindset, Energy or Time. To find out more contact Iain here.

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Iain Smith

Writing about Productivity, Communication and Wellbeing.