Navigating a Nightmare Boss: Are You Working for the Worst?

I won't sugarcoat it; writing this story felt intensely personal. Maybe it's because, like many people my age, I've ridden the tumultuous rollercoaster of having a bad boss.

Don't get me wrong - I've also had the privilege of working with incredible, inspiring leaders who have profoundly influenced my personal and professional growth. But, I know what it's like to be thrown into the chaos, self-doubt, and daily humiliation that comes with having a truly awful boss.

Working with a bad boss is kind of like having Gordon Ramsay as your mentor on MasterChef. He scrutinises every slice, measures every grain of salt, and incessantly delivers critiques and instructions. It leaves you confused, disoriented, and trapped in your own Hell's Kitchen. Except, in this case, the soundtrack is a never-ending loop of a Microsoft Teams ringtone, and there's no way out.

When sharing bad boss stories with others, it can feel more like swapping war stories, where each one seems more shocking than the last. These stories range from overstepping personal boundaries and discussing divorces and affairs, to relentless micromanagement, the insistence on proofreading all company emails, or even demeaning a team member by referring to them as an assistant. Some have even gone so far as to use your annual review as content for an op-ed on the problems with millennial workers for their LinkedIn profile (yes - seriously). It feels as though almost everyone has a traumatic experience to share.

I experienced my first bad boss at 22. Still very green and a little naive, I took a job at a not-for-profit, excited by the idea of making a difference. Interestingly, my boss was also new to the role, having transitioned from working on the Republican campaign of a previous US election. She was abrupt in a way that seemed to come naturally for most New Yorkers, but every day was a guessing game of deciphering her directions and mood. Then, one Tuesday, about 6 weeks in, sitting in our very public, open-plan office, she yelled to me:

In hindsight, I probably didn’t. If I could go back in time, I would tell that mortified 22 year-old with tears stinging her eyes that it's okay not to know and that without guidance, direction or constructive feedback, you’re never going to know.

It's been quite a few years since then, and I've learnt and experienced a lot. I have confidence in my training and enthusiasm, and I'm genuinely proud of what I've accomplished. Yet, every now and then, that voice still echoes in my head: "Do you even know what the fuck you're doing?"

The concept of what constitutes a bad boss, admittedly, is very subjective; however, the consequences can be observed clearly. The ‘Great Resignation’ was the buzzword across most Fin Review articles of 2021. A 2022 survey by McKinsey stated that uncaring and uninspiring leaders are a big part of why people leave their jobs.

As most of us have a boss, and some of us are becoming bosses, how do we deal with, and make sure we don’t become, a really horrible one?

That’s where Rebecca Veksler comes in. A natural-born leader, Rebecca started her first business, Sol Cups, in 2016. The company quickly became one of the top four reusable cup companies worldwide with operations across Australia, NZ, China, USA, Europe, and the UK - all achieved by the age of 21. She can make shit happen but has learnt that it can be done quicker with an incredible team around her.

Rebecca always had an underlying knowledge that she didn't have to be perfect. Her mission was to build a world around her where people could live and thrive. "I'm okay to put my hands up and say, 'I have no fucking idea what to do here' instead of pretending that I do," she says.

Rebecca stresses that a leader is bad due to two reasons: ego or fear. Often, bad leaders are made bad by their own issues, a lack of personal development, or unmanaged imposter syndrome. And, while it’s important to be compassionate about a boss' individual mental health challenges, it’s also important to protect yourself from the toll that it can take.

In January 2023, the Australian Mental Health Index (MHI) surveyed workers from across Australia to discover that managers have higher mental health scores (meaning: better mental health) than non-managers. This is not to mention the known mental health risks of a toxic work environment.

"If you have a terrible boss, it's really tough. Culture is so ingrained in an organisation, and it's rare that you walk into a team that's brand new so you really only have two options," Rebecca says. “If you do decide to leave and you're in the process of applying for something new, then ask about the company culture as your first question in the interview: does it align with your lifestyle, values, and beliefs?” If yes, go for it.

But what happens if this is your dream job or you're not in a financial position to leave? The Reserve Bank of Australia, with a characteristic finger on the pulse, suggests that job retention can prevent financial hardship. Big news, indeed.

If you’re not in a position to consider a career change, Rebecca suggests being an advocate for cultural change. “This is also relevant to your whole life. The absolute best thing that you can do is speak up. If that causes short-term isolation, that's okay, it's all part of the bigger picture.” She compares a working relationship to a marriage, encouraging a shift in mentality from opposing your boss to understanding what makes them tick. Similar to learning a love language.

For me, I decided to take the first option and find a company that was more aligned with my values, and that might have been the right decision for my future colleagues, too.

A study on models of abusive supervision in the workplace suggests that supervisors at lower levels, after experiencing abusive conduct from their higher-ups, might start using similar management methods, either intentionally or without being aware of it. This could lead them to become more controlling, overly critical, or mistreat their own team members.

If you are starting in a leadership position and want to be a good boss, Rebecca suggests doing deep personal development. “Tune in. Make sure your life is well looked after from a mental and spiritual health perspective.”

As a Managing Director, founder, mentor, and Learning Chair of the Entrepreneurs Organisation, Rebecca coaches and advises many leaders. One technique she recommends is called a “WIFLE (What I Feel Like Expressing) Session”. It's a weekly team meeting where she encourages open discussions about both personal and work-related matters. The entire team comes together to share their achievements, discuss challenges they're currently experiencing, and collaborate on finding solutions.

Rebecca says, “A good leader would be the first one to talk and set the example.”

This could start with the following prompts:

This is what I'm really proud of.

This is who I'm thankful for.

These are the problems I'm facing.

I'd love if anyone could help with.

The road to change isn’t easy if you have a truly shit boss. Whether you decide to seek a new opportunity and protect your peace or create a cultural change for the greater good, the road ahead is rocky and you need people to lean on for support to help you be the best version of yourself. 

A big thank you to Rebecca for sharing your incredible energy to ignite change with us and for inspiring the confidence that it’s ok to not know what the fuck we’re doing at times.

Also, thank you to those who have been wonderful bosses and colleagues who’ve built us up, not torn us down. Appreciate you.

Image credit: Hea Lin Kwon