Ms ZiYou Bad Boss

What I learnt from my worst bosses

Over the years as a job hopper, I’ve worked for many people. A few were great bosses, most in the range good to mediocre and a few were really bad.

And you know what?  I actually learned more working for those bad bosses than I did working for the better ones. Albeit it took me a long time to realise this.  So here are a few tales.

ConsultantMs ZiYou Boss

This was at a top end consultancy, where everyone was expected to give 110% all of the time. And work very long hours. At this place, I worked for one of the directors, who would make a fabulous case study in management techniques. Let’s just say he truly believed clients came first, then him, then his family, his dog….. and staff were then way down his list.

Strategic Pressure

This dude’s modus operandi was pressure. And you know what – you can achieve more than you thought possible with pressure. He proved that you can always get more work out of people by applying strategic pressure.

Obviously, I did not pressure my team to the level he demanded all the time, but I did learn that when it is necessary and you carefully monitor people it can work well. If you need a one-off miracle, pressure is a useful tool in your arsenal.

Team Bonding

Another thing where this dude excelled was team cohesion. Despite the pressure cooker environment, he excelled at bonding the team. This was achieved through a solid team identity and creating a cohesive team. Given the high amount of pressure and workload, we all needed to work together and rely on each other.

Head of

Ms ZiYou BossThis boss had scaled the greasy pole to a Head of the department role. As well as being able to do every job in that department, this boss had also spent time in an audit type function. Unusually, this boss was female. So the head of knows everything, which should be good yes?

Sadly she was lacking on the people skills. On my second day, I attended a team meeting. Well, it was badged as a team meeting, but in fact, it was a rant session. She stood in front of the whole team and ranted for an hour. And the piece-de-resistance? She stated the whole team had let her down. I was singled out for not specifically having let her down yet, but she was sure I would.

State your assumptions

Weirdly, this boss was obsessed with finding mistakes in everything. She couldn’t review anything without finding fault in some way. Despite being very difficult to work with, this did encourage me to really think through every option and have an answer for them all. I did have to level up my output and think strategically about what I shared with her.


So yeah, working for a tough boss is hard – and this taught me a lot about grit and resilience. You have to work with your boss no matter what, so it’s time to learn coping mechanisms. And this is where the importance of work friends come in. Having people to have lunch with that see your boss in action can help you contextualise things, and have a bit of a rant yourself.

Expert System Navigator

Ms ZiYou Boss

Early in my career, I worked for this boss who had worked his way up and was very ambitious. And he knew how to play the system expertly. Some found him frustrating as he never read emails or answered the phone unless you ranked above him. Yet he sailed effortlessly and was respected by those around him. Even his team begrudgingly respected him, despite being a difficult boss to you know, get hold of.

Manage expectations

One of the skills I still appreciate today that I am glad I learned early was to manage expectations. This dude was epic at stakeholder management and making sure his team never overpromised. He regularly did that team lead task of adding contingency into project plans which I have since made sure I always do.

Let them shout

Ultimately it’s your boss and their bosses opinion that matters. This boss was epic at ignoring the noise – and rarely did anything unless people complained to his boss.

At one point he actually cleared everything off our work list and requested we down tools on those tasks to work on something new. The noise was incredible, but he stood firm throughout and not much of the noise got through his boss and back onto the work list.

A very good lesson was learned there – the noisy people tend to not have the most urgent or important work in the scheme of things.

That ‘perfect’ boss

Ms ZiYou BossI have once had a perfect boss. Like we were on the same page about everything. It made day to day a pleasure – work was easy and I know all my decisions would be backed up and not challenged.

Thinking back, working for this boss was easily the best working relationship I’ve had with a boss. We took very similar approaches to everything, such as expecting staff to work hard for 7 hours days, but not stay late. And expecting stakeholders to negotiate through any changes rather than us take the hit.

But was the boss really perfect? No. Was I pushed enough or made to develop?

Life was too easy

In reality, it was just all too easy working for someone like me. There were no awkward conversations – as we instinctively thought the same. I was never challenged to expand my thinking. Similarly, it was all very much focused on getting through the day to day and then getting out to enjoy our lives. There was no scope for development or alternative opportunities pushed my way.

My Perfect = Easy

So in summary, my perfect boss is someone who gives me an easy life. And as I’ve matured, I’ve come to realise an easy life is actually not that good for me personal development wise.

Hence nowadays I appreciate more the difficult bosses I’ve worked for, and what I have learned from them. As without the difficult bosses, I would not be where I am today.

Over to you

  • What are your thoughts?
  • Have you worked for nightmare bosses?
  • Do you believe there is such a thing as a perfect boss?

Thank you for reading – please leave a comment below and join in the conversation. You can also connect on Twitter or contact me privately.


12 comments on “What I learnt from my worst bosses

      1. I moved a lot within one company but didn’t learn as much as you it seems.
        One nice thing about my job now is that I get to see how other companies work and how people behave. It is an eye opener how even say the same company but a different floor or department is from I e another.

  1. I had a brilliant but self destructive boss who flew up the company ladder to the top job with me staying right next to him getting a promotion every time he did. He was basically unable to handle the execution of his genius plans but I excelled at it so he had to keep me as his right hand guy. Then when he had the top job he naturally got fired and as usual I got promoted into it. I think it is an even better plan than job hopping if you can hitch your wagon to an amazingly gifted but tragically flawed mover and shaker. Just follow them until they self destruct leaving a gaping hole you have been pre-groomed to fill. I guess that sounds self serving but in fact I did not realize things would turn out that way at the time. I just loved getting promotions and raises then one day I went off on vacation and when I got back my boss was history, and I was in charge of a very large company. I learned both good and bad lessons from that guy!

  2. I learned a lot from my first boss, who was female, who I liked and respected. Attention to detail, no cutting of corners, follow the processes but challenge the processes if they don’t work. Sadly, she had her favourites in the team and I wasn’t one of them and that nudged me to move internally in the company. I guess I should thank her for that!

    A couple of remote bosses later, then the boss who I worked for the longest who wasn’t perfect but who was pretty close. Like your ‘perfect boss’, working for him wasn’t a challenge, although I did learn how to compose calm emails in the face of a sh*tstorm! Still, I was the one who brought up uncomfortable conversations in our 1-1s but at least he listened and he had my back when it counted. I’m on my second boss already at my current place of work – the first one was remote, my current one I think could have turned into a great friend had she not become my boss! Despite her youth, I’ve already learned a lot from her and hope I can still develop as I enter the last years of my career.

    1. You’ve had some cool bosses there – so sad that your first boss had faves and I can’t imagine why on earth you would not be one of hers.

      Yeah, that’s cool but weird she could be a good friend if she wasn’t your boss.

  3. Oh, I missed one boss who said I was a ‘trouble-maker’ because I voiced an opinion about the amount of time smokers took away from their desks (he was a smoker).

  4. Ahh few things are worse than an awful boss but I feel you can learn so much from them, especially how to navigate difficult people. I’ve definitely mastered tuning them out when they go on their rampages 🙂 Nothing chases good employees away from their jobs than their bosses. Whats the quote? “Employees don’t leave companies they leave managers”

What do you think?