11 Leadership Lessons From Terrible Managers

Eliza-May Austin
8 min readSep 10, 2021
11 Leadership Lessons From Terrible Managers

Lesson 1. Keep politics out of it.

It does not matter what, or who, your employees voted for in an election, what matters is their ability to do their job, and do it well.

During a stint at a large multinational company, a pub discussion with a manager (of a different team) really concerned me when it came to light various managers clubbed together to undermine a departmental leader for voting Brexit. Not cool.

How to avoid getting caught up in a world of politics:

Don’t bring it up in the first place. If someone else raises the conversation just avoid getting stuck in, regardless of how tempting it may be. Avoiding an argument isn’t you being submissive, but rather avoiding unnecessary tension. Politics can be both controversial and divisive, save it for discussions with your non-work colleagues. Furthermore, being in a position of authority can inadvertently create a perception that your views represent the company.

Lesson 2. Don’t send your employees on outbound work trips if it makes them physically vulnerable.

Once upon a time, I worked as an intern, on an intern’s wage, for a company that sent me halfway around the world, having told me they’d cover costs. When I arrived in the country, in the evening, knowing no one, I was told by the hotel that I’d need to pay a deposit of £3k for my room. I didn’t have £3k of disposable income, which left me in a very risky situation.

How should the manager have avoided the situation?

Some people won’t have the money to pay upfront costs to claim back later, so make sure large expenses are paid in advance by the business.

Lesson 3. A sense of humour matters.

Chances are that your role is important, maybe stressful, perhaps it’s even critical!

It’s paramount that teammates have the freedom to ‘banter’, being playful can instil a sense of camaraderie in an otherwise stiff or hostile work environment. Having a sense of humour keeps you awake on those slow night shifts, helps a group to bond and generally builds a stronger team.

Working in an IR team for a large organisation, on 12-hour shifts, was surprisingly more fun than it sounds. However, our manager at the time would jump in with “if you’re laughing you’re not working”, at the slightest giggle. It made that particular financial company incredibly dull, dry and tedious, and the shifts felt like they lasted 5 years!

How should the manager have avoided the situation?

By butting out, a happy team holds conversations and makes jokes. Maybe your team are dancing on the tables naked, doing roly-poly tequila shots (don’t try that at home) and laughing like a pack of hyenas, in which case — yeah you should do something about that.

Lesson 4. There is no such thing as a stupid question, stupid people don’t question things!

Have you ever researched and studied something for a while, only to be none the wiser, realise you’ve wasted hours getting nowhere, so pluck up the courage to ask the office ‘expert’ about it, only to have them turn around and say “google it”? Me too. This can be pretty damaging, especially when permitted by management.

There was one particular instance I remember, where a forensic analyst asked for help analysing a MacOS version of something; this person hadn’t analysed on a Mac before and wanted to run a few things past colleagues that had done. This went down very badly with the manager saying “… look, if you’re just not capable then that’s a problem (stares at the person for an eternity in the middle of a team meeting)”. Asking for help on a task is a sign someone wants to do a good job, or maybe shows a lack of confidence, but it shouldn’t ever be a reason to put your entire team culture in jeopardy, not to mention the services that go under-delivered because an employee is too scared to ask for help.

How can you create an open learning culture?

Make it common knowledge that you appreciate lifelong learners, whether it’s a supermarket shelf-stacker wanting to learn more about product placement optimisation, or a cyberdefence analyst with questions about offensive security, be sure to help your team help themselves and even if that involves a bit of time, do it. I always ask that someone at least try to learn something themselves, so as not to be too put upon, but sharing knowledge is powerful and individuals that proactively try to sabotage that should be called out by management, and absolutely should not engage in it themselves.

Lesson 5. Protect your team like a Momma bear!

Do you know what happens to weak managers?

They get walked all over.

Do you know what happens to the underlings of weak managers?

They get walked all over by proxy, taken advantage of, overloaded with work that doesn’t belong to them, blamed for mistakes that are not theirs and end up stressed, unhappy and looking for another job.

Ok, so this little story isn’t about a terrible manager, he really was a nice guy; in fact, he was so nice he rarely said “no”, to the great delight of other managers who wanted to offload work to his team. Managers like this are almost as painful to work for as tyrants.

How to push back when people take advantage of your team?

Stop being a people pleaser.

Say “No”, avoid saying “Sorry, no”, a simple no will do.

However, if the work is meant to be completed by your team, make sure people dishing out the work come to you first, you should establish yourself as an authority and you are the person who knows the strengths and weaknesses of your team members and delegation should come from the manager, aka, you.

Lesson 6. EVERYTHING is your fault :(

When something you are responsible for goes wrong, it is your fault, not the person who clicked the button, or the person who sent the email, not the tool that broke or report that did not get done, it’s your fault, plain and simple.

Why?

Because you’re the manager, you should have managed it.

Okay, I realise that is a little abrupt: allow me to explain.

Maybe it really isn’t your fault, maybe you showed Bob how to run that report 15x and he still messed it up, but the worst thing you can do is throw him to the wolves. Taking it on the chin helps you generate respect from the team under you and leaders above you.

How to get in the “it’s not them it’s me” mindset.

When the big bad wolf comes knocking, don’t be a little pig, be the farmer (my pigs, my problem).

Lesson 7. If you are a sexist or other “*ist”, keep it at home

We each have a right to our own internal private thoughts, which is how it should be and no one wants to take that away, but please leave these thoughts in your head.

A few years ago, I had a terrible experience with a manager who treated me so differently (in an incredibly negative way) that even my team and a team in another country knew about it. It became such a daily issue that I just had to report it to HR.

The response? “ <insert name> has never worked with a woman before, we are arranging anti-discrimination training”.

How should the manager have avoided the situation?

Leave it at home, quietly hate whichever demographic you want from the comfort of your own home.

Lesson 8. Don’t be jealous!

We’ve all seen those managers who appear to despise the most talented person in the team: it’s really not a good look.

If you are half-decent as a manager, you’ll be hiring people who are better than you, more talented and far more equipped for the job you hired them for. This is a positive thing, don’t let jealousy get in the way, they should be better than you, it’s a good reflection on you.

How should I avoid the situation?

The better your team performs, the better you look as a manager, it really is that simple. Surround yourself with top people.

9. Strictly Confidential

Treat your conversations with employees as strictly private, unless someone else is required to be a part of the conversation, for professional purposes.

Some years ago, a young man in the same office, disclosed to our manager that he’d been having an affair, was leaving his wife and needed a week off to move his belongings. Upon his return to the office, he was met with a rather frosty reception. I get it, none of us wants to be married to him but the manager really should have kept his mouth shut.

How should the manager have avoided the situation?

Avoid asking overly personal questions, but if someone divulges sensitive personal information to you, quietly treat the information as you’d like it treated if the roles were reversed.

10. Just because it’s not inappropriate to you, does not mean it’s not inappropriate.

‘What a minefield, I know’. A compliment, a hug, a dirty joke, or a 1am WhatsApp with heart emoji’s may seem like harmless fun to you, but not everyone feels the same. Cover your own back by avoiding any of that with anyone who works under you. Initiating a sexual relationship with an employee is heavily frowned upon, especially when you are in a position of power: save yourself the hassle and just don’t go there. There are plenty of attractive people out there who don’t depend on you for a living.

In a previous role, a rather eccentric C-level exec thought texting me cryptographic challenges at 1am was a fun, bonding experience, it wasn’t sexual and it wasn’t offensive, but it was a stupid move when I’d just finished a 12-hour shift.

How to avoid coming across as inappropriate?

Leave people alone out of their working hours, unless “ignore this till Monday…” is stipulated at the start of an email. Use legitimate company comms systems to speak with employees. If you should be calling or messaging via Slack, Teams or Google, do so, and avoid texting on non-company systems. Your team needs to know they have a clear separation from you, if they find you in a text, a voicemail, whatsapp and sliding into their instagram DMs, they can feel like they are being stalked by a velociraptor not a boss!

11. Don’t be too shy to say “Bye”

Not getting rid of lazy people, or repeatedly poor performers, is a slap in the face to the employees that consistently perform well.

We’ve all seen managers so concerned with being liked that they cannot bring themselves to fire a downright terrible employee. When everyone sees an issue and a manager doesn’t act, it’s an apple that rapidly starts to rot the whole barrel.

How should the manager avoid the situation?

Firing someone should always be a last resort, but it is always an option and not one you should be afraid to take, when necessary. Get familiar with your company’s policy surrounding dismissals, but remember, your team should be diverse in its opinions, skills and personalities: not liking someone is not a good enough reason to fire someone.

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Eliza-May Austin

CEO & Co-Founder at th4ts3cur1ty.company & PocketSIEM. Founder and Director of Ladies Hacking Society | Purple teaming enthusiast @Eliza_MayAustin