The Boss I never wanted to be

An image of thick ropes laying on the ground next to each other - Photo Credit: Matteo Pescarin

I started writing this article with a bitter sentiment. I thought lashing out words of disapproval and philosophising on life choices would have brought closure. After about a thousand words, I got nothing back and wasn’t even driving a point about it. I decided instead to make this a self-reflection post, where I can look back and see how I gained better tools to move forward over the different situations I got myself into.

When I first moved to the UK in 2009, I stepped down from many of the ambitions I had built up while I was in Italy working as a freelancer and embarked on the individual contributor’s path.
The ten years that followed were the most formative and meaningful I ever had, but that didn’t come without a series of problems that made me who I am.

Over the years, even up until now, I mainly had subscribed to the quote that recites:

“People leave their job not because of it, but because of their boss”.

But this is effectively a single person’s view. While at the time, I have left some positions because I was feeling unheard and left aside, or unable to achieve more than I could do, or tasked to do things that didn’t make any sense, right now, empathy seems to be prevailing and be about understanding who I was confronting and re-evaluating the context I was into.

While a better understanding of myself has been beneficial, it doesn’t take away that some of the “bosses” I had were misplaced and lacked the tools and support I was complaining about. I look back at myself and ask: “Who’s the fool now?”.

Core values

After a very demeaning and toxic experience in a small London company that I chose mainly for the vicinity to where I was living back then, I was left with a feeling of having been duped, tricked into joining a company that revealed itself for being completely different from what was shown to me in the first place. While they had reasons for changing their objectives and targets without having a proper and honest conversation with me, they decided to go a long way behind my back and trick my direct reports into saying things out of context that could be used against me.

I left that company, relieved of not having to play those games anymore, and started considering the need to stay true to my values and find ways to assess this before joining a company.
For me honesty and transparency have been the two values that I wish I had spent time inquiring about: for instance, by making sure there’s a decent flow of feedback, that the input received is evaluated and acted upon, that domain experts are brought into the picture without making assumptions on delivery dates or similar. Unfortunately, this is not easy to assess, but asking for my values to be reciprocated has become non-negotiable.

In my daily life, applying transparency in what I’m doing and expecting the same from the people I work with is an incredible instrument to understand where silos might be forming, reduce waste in processes, and optimise for efficiency.

Houston, we have a problem.

I cannot recount the number of times I sat down in one-on-one meetings detailing problems to my managers only to get blank stares or a calm “yes, sure”, with a long silence following it.

While working for a large retailer, during one of our one-on-ones, my manager candidly admitted to forgetting their hearing aid during an important meeting. I appreciated the trust, but this also left me wondering if this had happened before with me or any of my colleagues in a tentative to explain the nods and lack of actions on their behalf.

To another manager I had in the same company, I highlighted the toxicity problems I found in one of the employees in the team I just started managing. While expecting support to be able to remove this person as soon as possible, nothing came out of it, leaving me to deal with them for almost six months until this person decided to part ways, leaving a trail of destruction behind them.

More recently, I looked upon one of my managers to provide the proper support to handle uncertainty, at least with some suggestions and maybe cooperation for many problems, from messy architecture organisation, lack of clear boundaries between teams, unclear processes, and organically grown uncoordinated activities that spanned across the whole company. After months of mounting evidence, an increasingly chaotic situation around me, and a missing dialogue with my manager, my frustration took the best out of me, burning me out. The only feedback I had back then was to be more positive.

As a new joiner to companies that are in that hyper-growth phase (gosh, and my thoughts immediately go to Brook’s Law!) or that are just gone through a massive internal org reshuffling, I found myself having to firefight, clearing out problems in a systematic way by reducing useless complex processes and mapping complexity as a way to understand how to tackle it.

In these situations, I’ve witnessed many people on the leadership ladder dragged into countless meetings without time to sit down and strategise the workload. These busy schedules can lead to messy or missing communication from leadership, which I take as an indicator of a lack of clarity on what’s going on or what’s going to happen next. There’s nothing more stressful than that, and it has the potential of turning into burnout, as I experienced myself.

When thinking of these situations, I have to constantly remind myself that managing is always two ways: up and down. And both are equally important.
Shielding my reports from the above mess is good as long as there is an understanding that something is happening and going somewhere. My manager shouldn’t need to know the nitty-gritty details of my actions but know that something is happening. He can support me in the right direction based on their or the company’s expectations is equally important.

In these two scenarios, trust is foundational. And, as Frances Frei said, so is authenticity, logic and empathy.

Once there is a good level of trust in place, managing expectations and prioritising are the following two areas I would focus on.

Prioritising usually leads me to four primary responses:

  1. Tackle
  2. Postpone
  3. Delegate
  4. Ignore

Understanding which one to apply is also a matter of understanding the complexity of the problem, where frameworks like the Cynefin Framework have proven to be massively helpful to me.
In turn, understanding where the company, the group, and the team from a technical and product perspective are going allows me to handle problems and set priorities autonomously without having to be handheld all the time.

While on paper it looks simple, it’s sometimes a lot to digest and map out. Without the proper support from my peers or manager, the feeling of being lost can overcome any rational thought and undermine my own self. Sometimes I need to step out momentarily, look at the sky and breathe.

Competence and Bias

After all these twenty-plus years of working in the IT sector, a few things have emerged to be regularly misunderstood, downplayed, or neglected: competence, bias and, sadly, burnout.

Confidence is one thing that is usually mistaken for competence. It has regularly been a problem to assess, especially when interviewing people. While not always true, this is even more relevant when interviewing male candidates. It comes into various forms, like an over-abundance of words to describe something simple or expected (classic case of “writing documentation” as part of the skills in a CV) or glossing over important details, like missing information on who led a project and omitting to report on any substantial data that supports any claim.

Confidence is also neighbouring to bias, which works against inclusion and diversity. It wasn’t until after I was left inexperienced to set up the whole hiring process in one of the small companies I worked for that I realised I got some people who were not fit for the role after all. This initial situation was followed by a tedious process of trial and error, on top of reading numerous articles on the matter, to understand that the little white boys’ club I was sitting in was impeding me from seeing any further than my nose. Even so, after so many years, I keep seeing people in much more senior positions falling into the same trap and not understanding what is happening. Understanding, unfortunately, comes from a different place, and telling someone what’s wrong does not remedy much.


The last thought of this article is about burnout. I won’t talk about it more than what you can read around on the web or listen to during seminars. I will instead focus on two aspects alone.

The first is how inexperienced people in leadership positions can (likely, unconsciously) use bias and confidence to trigger a negative response in their peers, causing burnout. Gaslighting is the best way to describe this, but it might also appear under different shades. Micromanagement is a much broader known generic term that can trigger it.

Very early on in my career, in my mid-twenties, I took on freelancing because I was overly annoyed by the lack of knowledge some people I ended up working with had. I was cocky and presumptuous, thinking I knew more than anyone in the field I was working in. I’m glad I was not managing anybody back then, but this attitude took some time to undo. Many years later, I rejected competition and preferred cooperation as a value to stand on when working with individuals within teams.

While spotting burnout in other people is essential, especially when managing them, spotting it in myself and knowing when to stop is equally important. Especially after discovering how taxing it is for the mind and the body and how challenging and lengthy the recovery is. While finding yourself having negative thoughts, being depressed, or being unable to sleep is a well-known sign of possible burnout, with age, I also understood this might be way too late into the process. To me, discontinuing the work on myself, like stopping doing any courses, drawing, or being unable to leave work at work, has been the way to spot a potentially dangerous situation.

If there’s anything you want me to get into more details, or talk about more, let me know. I’d be happy to expand on any topics about management.