Lessons Learned from Bad Bosses: Transforming Negative Experiences into Leadership Success

I’ve had a colourful career in Finance to say the least with many highs and lows and can say at this stage my only regret is not having experienced serving under non-Finance leaders sooner. Not because I think they are better, but it’s a different perspective and emphasis.

Looking now as an IT professional I am currently working for someone who I would say is the best boss I’ve ever had and am now engaging more frequently with very senior Global Finance leadership for another organisation and seeing very admirable characteristics, traits and behaviours which I find an interesting contrast.

Also, I’m learning a huge amount of new skills and developing new perspective shifts which has given my career a second lease of life that I am extremely grateful for.

However, having given half my career to Finance as a qualified accountant and I still like to practice financial modelling and reading corporate financial statements plus still having the foot in finance as I work on solution delivery for Finance teams.

I consider myself fortunate having both business and digital skills. However, pure Finance is no longer a development priority as I now devote most of my development time to change management, coding, process engineering, systems, data architecture and leadership which is my current area of business need.

So reflecting back on my career to date here are some of the personal lessons I’ve received working for bad bosses as a guide on “how not to do leadership”.

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A manager who competes instead of collaborates with you

The first and worst boss I ever had was an expert, but a rude, unhappy person with a grudge. The red flag was that the manager had been off with long-term health concerns due to getting into HR related issues with my predecessor and I had to be interviewed by his manager (the CFO) and HR.

As a newly qualified accountant in his early-twenties I tried my best to work with my manager explaining that I was trying my best to understand the new systems and new industry. I had moved industries from manufacturing building materials to pharma so there were nuances.

However, in all fairness I switched jobs for the pay increase which my previous company weren’t willing to step up and offer (until I tendered my resignation) – the job was doing pretty much what I’d done previously, but with different systems and processes with the difference being medical regulation e.g. FDA compliance. Within a couple of months I was bored!

This boredom led to complacency which when the manager eventually returned from long-term sick leave he got straight to work questioning everything I had done. He made it a habit of publicly pointing out my errors and dropping remarks like ‘I don’t see it in you’ to the point that I had completely lost my confidence.

Eventually I was second-guessing everything I knew with the only thing I thought keeping me from dismissal were my strong Excel skills. During this period I was demoted and had my salary reduced 30% and put on a PIP for 6 months where I would either be sacked or have my original salary reinstated (HR’s Performance Improvement Plan) where I had to document everything all my task performance.

I managed to work my way out of that, but when I had the meeting with my manager he advised me that he thought I would be sacked and therefore hadn’t budgeted for my salary reinstatement so I wouldn’t receive my original salary.

At that point I decided enough was enough so I started looking for work as I had zero trust in my manager. The week after that I had another job and I left as soon as I could (taking unpaid holiday to eliminate the notice period as far as possible).

After telling this he had to go red faced to his boss to explain the news, I don’t think it reflected well for him. I found out the following month through a former colleague that my replacement had been dismissed within the first week for sending 250 emails to her boyfriend.

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A manager who makes snap decisions on pure emotion

This character was the craziest boss I ever had, he was the Finance Director of a growing company, technically the strongest Accountant and Finance professional I have ever worked for with a great sense of humour.

However, he also had the strangest personality of someone I have ever worked closely with, including a reduced sense of personal boundaries.

To say his behaviours would never fit into a corporate environment would be an understatement – he would frequently be getting myself and the rest of the Finance team to work all the hours to try to get books closed and move projects forward whilst also saying things that were racist, sexist, misogynistic and other forms of inappropriate banter.

On my first day there he thought it was funny to demonstrate the spyware he was using to monitor the other employees as they were working whilst we were offsite and then take control of the computer to create a new email on their desktop and start writing a ‘love letter’ to himself. Needless to say it created a massive scream from the office worker (a lady in Accounts Payable) who subsequently left the company a few weeks later.

I wasn’t so fortunate in the sense that I stayed there for three and a half years during which time my work-life balance disappeared as we were getting more and more work to manage with various competitor acquisitions that needed to be integrated into the business with as little customer attrition and as many synergies (staff reductions and supplier rationalisations), as possible.

It was a badge of honour how long and hard we could work to meet increasingly more difficult targets and before I knew it I’d become a workaholic. All throughout this Finance Director would openly boast how he had the highest performing (and cheapest) team in the group.

He would always create a work emergency and have me and the rest of the finance team working late evenings (with takeaways so I gained even more weight). Over time this became the norm and therefore unquestioned. I later found out that he was having personal issues which, happily, he managed to resolve a couple of years after I’d left.

Meanwhile at that time my personal life was in tatters – I had no social life outside of work and I kept blowing off a girl I was trying to date at the time (there was always a work emergency so I’d end up finishing between 10pm and midnight) until she got so fed up she found someone else.

This lack of a personal life caused both the Finance Director and the Managing Director to openly question my sexuality -- they reassured me it would be okay if I was gay. I thanked them and informed them I wasn’t.

How did I eventually leave this employment situation I would liken to Stockholm syndrome? Well he basically dismissed me.

The Managing Director had decided that he was getting too ‘cocky’ and took an opportunity to blame a minor mishap on me. Because this, as the FD was always prone to emotional outbursts, he stormed to my desk area and told me that I needed to find another job.

I was absolutely shocked so I went out to call my dad who told me immediately “Congratulations!! You always complain about working there – why are you upset?”. You know what? He was totally right. Having been told this on Monday, I updated my CV and started applying for jobs and got another job Friday the same week. I then handed in my notice which I think shocked the FD (it certainly shocked the MD when the FD told him).

He then admitted perhaps he might have been a little ‘hasty’ (one of his favourite expressions was ‘I’m always right except when I’m wrong, but then we don’t talk about that!’). I was able to talk him out of that, that it was completely the right decision and he should find someone better, so we wouldn’t have the awkwardness of my departure and relationships remained civil.

In a nutshell my replacement didn’t last long. Initially my boss had to get his hands dirty again with the close and the management reporting, but I was informed again by a colleague a year later that it took him 3 months to start saying ‘I wish Dante was here’ and he’d been saying it ever since.

He actually called me late one evening – I suspected he’d been on another late working session and had consumed lots of alcohol with a late meal. With the call I sensed he thought it was a probably a good idea to see if I was open to returning.

I’d been sent to work in Moscow at the time and I told him that I was having an amazing time working for my new company. He said he was so happy for me, thankfully that ended the idea before it ever got off the ground.  

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A leader who overpromises, underdelivers and talks way too much

This lesson is about expectation management and then avoiding over disclosure in an effort to try to absolve yourself from any blame. The manager in question was a bold and brash corporate alpha-individual with a ‘big mouth’.

I served under this CFO during an overseas secondment and he didn’t need to do this, but went out of his way to make a big promise as an incentive for me to take the assignment and work for him “If you deliver 95% by fulfilling your remit I’ll deliver the 5% and ensure you get on an accelerated career path”.

Long story short, as this Finance Leader wasn’t that interesting as a character (except he loved to go into battle against his operational peers which I found most times highly amusing) I over-delivered on meeting my 95% by exceeding my objectives and even running an additional department during my assignment, but he couldn’t deliver the 5%.

It turned out that he’d been building up my expectations that the right next role was an early stage approval in PD Finance that would help accelerate my career by giving me the right exposure (getting that all-important ‘Facetime’) in order to ensure that I got promoted to the next level.

It is essentially the only career game in town for the UK with declines in Accounting (outsourced to India), Sales and Marketing Finance (outsourced to Hungary) and Manufacturing Finance (making cars anywhere else).

However, in fairness to him, he had very little political influence being an American in the European Finance Personnel Committee.

He had a great way of not mincing his words, but on this occasion he tried to twist it that it was my own fault somehow that my traits and skills weren’t sufficient to convince the committee that I was worthy of a PD role. He made a point of saying that they were looking for people who were proven as ‘analytical’ and that I wasn’t considered strong enough to be deserving.

There were no other overseas Finance assignments available. So I ended up back in Accounting when I returned to the UK. My mentor advised me that it was to provide me a soft landing and allow me to settle back in my home country (very nice, but after what my former boss said I knew it was an attempt to butter me up).

I’d already had my perspective stretched from working overseas plus being on the coal face I could see the implications of what happens when PD Finance screw up (hint: expertly cover their a**es). So I felt like I had a lot to offer, but the decisions were already made with no account of my input and the organisation was happy to allow me to stagnate as my career growth wasn’t their priority.

I did have one amazing advocate who did make an effort and eventually found me a great development role.

However, I’d resolved myself never to work in PD Finance even if it was the only Finance career game in the UK and if they didn’t want me I certainly didn’t want to be in their team (my own silent “F*** You!”).

So I stayed in Accounting longer than anticipated because I needed to bide my time until a suitable development role arose in Finance that was non-PD related – it was really satisfying each time I got to turn down a role in that team (got the opportunity a couple of times over the remainder of my time with this company).

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A manager who allows toxicity to flow down the team

Initially it was a struggle working on a Finance transformation programme classed incorrectly as a project. For starters I wasn’t formally trained (we didn’t do credentialled training once you got your Accountancy qualification).

So it was a tough slog hacking out results and trawling through complex processes to achieve what, at the early stages, seemed like limited returns. I almost gave up, but I found support from mentors and friends within the company plus an amazing transformation mentor outside the company (shout out to the amazing Gordon Tredgold).

Every two weeks I would be in Governance meetings and I was at the mercy of my manager’s moods (it was also dependent on how his manager treated him to be fair). I would allow my team the opportunity to present their updates and support if there were any tricky questions.

My manager was the sponsor for the project and had the right to challenge some aspects of the performance, but most times it felt more like an inquisition.

The questions swayed between fairly challenging the approach taken to complete tasks to outright questioning our (mostly my) competence and it was at those moments an emotional challenge to remain professional.

At the time I had a lot of withheld anger toward this boss, but time heals and I can now look back on this with relative indifference.

A couple of things happened that changed my perspective, first he had a personal crisis which made me sympathise with his situation and the second was I got to understand what his boss (the CFO) was doing.

Through my network I was informed that he had been sent on random tasks that were ‘worthless’ purely to fob him off and he was also being given a rough ride which he probably took out on his own team members, having less patience with what he saw as ‘incorrect’. I observed this when he was hiding in an office – the CFO needing him for something asked me where he was and I said I didn’t know would relay the message when I saw him.

My own personal experience of the CFO? I expect that he had his own challenges from his seniors. He was always supportive of me directly although I’m not sure he liked my personality. He could be a bit of an a**e in a few of our interactions, but generally I think it was more he had such high standards and rightly so.

At the end of the programme, because all of the transformation efforts were winding down and our team had achieved all the objectives I was now in a position of relative strength and comfort in the sense that I was leaving the company and the leadership team had congratulated and even thanked me for my contribution.

The relationship improved toward the end, but I think there was too much water under the bridge for me. I made a point to be very careful to never let negative emotion get out of control or take my own personal disappointment out on my own people.

Over a year after I left that position a member of my team told me they could sense my emotions (my anger toward my manager) when he got too aggressive in our status meetings. It apparently leaked out during those governance meetings and other interactions and they also noticed that my manager could sense when he had gone too far with me as he would back down afterwards.

I didn’t realise those emotions were on the surface as I thought I’d kept them hidden (at least verbally), but I won’t be learning to play poker anytime soon.  

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The well-used phrase is that people don’t leave bad companies, they leave bad bosses and that’s because it’s so true because you spend too much of your life on your career to be miserable.

However, looking back I can say that whilst they weren’t pleasant years they were ‘formative’ and in this regard invaluable because no matter how pressured I feel I am hyper vigilant not to let these attitudes and behaviours sink into my psyche and that has made me a stronger manager and leader.

I hope I didn’t demonise these characters too much because this is one-side of the story and whilst I emphasised their weaknesses to enhance my points I do acknowledge that they all had their own unique and relative strengths which mostly outweighed their quirks and admittedly we all have quirks.

In some cases I wonder if I could have done more to improve the relationships and in taking some moral high ground at the time, but acknowledge that these experiences have hopefully helped to strengthen my maturity. In my more spiritual moments I wonder if Karma has a role to play in where I am now which is still not where I’d like to be.

However, don’t expect anyone else to own your career but you despite whatever anyone might promise. It’s going to be hard to find people you work with who will care about your development as much as yourself so take charge. Create your vision, find mentors who will help guide you.

Be very grateful if it does happen that a manager will champion your development, but don’t expect that from your boss. At best hope they don’t pro-actively stand in your way.

At the time seeing the teams struggle after I’d left was super satisfying, but I made a point not to burn my bridges in front of everyone. All of those relationships were ones I didn’t want to maintain.

However, they have left strong impressions on my psyche which have, in turn, helped to frame how I build my own relationships with the people I manage.