Learn from your bad bosses
Then leave them, of course
Thanks for reading Oscillations - a newsletter where I look for lessons in growth from all aspects of work & life, making them applicable to all areas of work & life. Why’s it called ‘oscillations’? I explain it here.
By my count, I’ve reported to close to 30 bosses, managers or supervisors since I took my first cash job aged 15, cleaning fish boxes and shelling prawns in a deli in Dublin. I’ve watched countless other bosses – to whom I didn’t report directly – do their thing, from varying distances. Each led in their own particular way. Each affected their teams based on how they led.
Some were inspirational, visionary, thoughtful; others were aloof, arrogant or downright deranged - at least some of the time. Of course, you strive to emulate the former; you track their careers and, in some cases, hope to work with them again. But what about the latter group? Why don’t we talk about them and what we learned while hitched to their chafing yoke?
WE DON’T TALK ABOUT BAD BOSSES - WHY?
Even from the worst experiences, there is always something useful to take away as you move on through your career. If you keep an open mind and review your experiences of bad leadership roundly, if you cultivate self-awareness, if you care about self-improvement, you should emerge a better leader for having spent time in those situations. But oddly, bad leadership rarely gets talked about as something useful or educational. Scan LinkedIn for posts on bad bosses and you’ll find a litany of ‘Here are the traits’ posts, talking about how harmful bad leadership is, how to spot it, what to do when you encounter it, how to tell if you are the bad boss. None of them tell you to pause, breathe it in, seek to understand what’s behind bad leadership and deeply observe it before you pull the ripcord and move on.
Why do we not talk about bad bosses? A host of reasons, including the ones that caused this post to sit in drafts for several years. It’s impolitic to publicly describe our nasty workplace situations other than in whispered chats, DMs or anonymous Glassdoor posts, lest people attribute what you’re describing to an individual, or themselves. We fear retribution, which is totally natural, especially as you strive to ascend in your career.
A boss who feels slighted by a description they feel applies to them may act vindictively, overtly or covertly. Also, we expose ourselves to criticism from those who may not see us in the same light as we see ourselves. Life is subjective. If we say ‘I learned from that and bettered my self and/or my own management style’, there’s every chance someone feels that in fact, we are not quite so evolved as we would like to think, or that the incident in question was actually our fault. If you read this and have worked with me, and you think - ‘Hey, you’re guilty of that too, Markham’ - I’d love to hear from you about when and why. I’m always on a mission to do better.
It’s risky, in short, but by holding back from discussing bad leadership, the lessons bad bosses teach us are suppressed, which is a loss. The greatest way to help others succeed is to guide them past known pitfalls, to help them avoid the mistakes you’ve made and the setbacks you’ve encountered. So we need to find a way to lay out the learnings without pointing the finger too directly.
So, in no particular order, here’s some of what I’ve learned from bad bosses or moments of bad leadership experienced during my two-and-a-half decades in the workplace. To those who would play the ‘I definitely know that person’ game - I wish you luck. Almost every scenario here is an amalgam, not a singular experience. There is commonality in leadership failure, unfortunately. It recurs, you get better at spotting and mitigating it once you’ve seen a trait or trend for the first time. If you think it’s about you, it’s most likely not, but every point made in this is something we can all work on in ourselves. So, you’re welcome.
Here’s to the bad bosses, and to the good bosses who occasionally did bad things. Here’s to the lessons they inadvertently taught us and the betterment they brought about. Thank you, one and all.
WHAT I LEARNED FROM BAD LEADERSHIP
✍️ Bosses who spoke in riddles and never put clear details or expectations down in an email taught me how emphasizing and committing to clarity of communications demonstrates that you value accountability, which puts teams at ease and makes people more inclined to work with you. Defining up front, to yourself and your team, how you plan to communicate is critical. I like to set expectations and the rules of engagement early when I land somewhere new. Letting your team know how to communicate with you effectively – through which channels they can expect slow responses, which channels to hit if they need quick decision-making versus a considered response – takes stress out of those interactions and bakes accountability and transparency into every interaction. Also be clear on times of day when you do or do not expect responses, and how you’ll signal exceptions to that rule should they occur. (Schedule send is such a great tool). Lots of people now create ‘personal manuals’ to this effect, and on balance, that’s probably a good thing.
🤞 Bosses who constantly promised things they couldn’t deliver taught me to always be clear about what you definitely can deliver on and what you maybe cannot, on what you can share with the team and what you cannot. That clarity is fundamental to building long-term trust with your team. If you raise an expectation and then fail to deliver on it, you’re essentially taking something away from the recipient that they have mentally built into their future. It feels like a betrayal, particularly if that expectation is related to anything financial. Be careful not to do that.
🤬 I have no idea what bosses who shout at and insult their reports hope to achieve. You’re not Gordon Ramsay, mate. In one incident, a boss berated & insulted me for 30 minutes down the phone because they found solutions I presented to fix some broken processes & technology personally challenging, let’s say. While I emerged from that exchange and its aftermath more resilient, I quit shortly after. I’ll never work with or for that personality type again. I’ll never replicate that behavior. Nobody should.
😐 I’ve seen entire hierarchies of leaders paralyzed by fear of how the quixotic Alpha-boss at the top ‘might’ react, and refuse to try something new or deviate from a dated but unchallenged directive that has become baked in to a collective psyche. It reminded me that if you want a team to innovate, you need to first hire people who will question everything, manage your structure for maximum efficiency, then give clear parameters and empower your team leads to act with autonomy, challenge directives no matter whence they emerge, and create an environment where there is room to try and fail, then try a different solution. Otherwise, your teams will repeat mistakes month after month, quarter after quarter, robbing you of potential.
🥳 I watched more than one boss who couldn’t maintain professional distance from their team. Not necessarily in a sleazy #metoo way (but yeah, I saw that too), just sometimes too familiar or pally to allow them maintain functional objectivity. Those experiences taught me the value of healthy personal relationships with your team, the importance of balancing bringing your authentic self to work with the need to keep a safe moat of mutual respect between colleagues, particularly as you ascend to leadership. I saw how managing that in a professional way allows you operate with greater executive function. Some distance is healthy. Knowing when to close out the after-work drinks tab and leave your team to enjoy themselves at the bar is healthy. In more hierarchical organizations, that safe/healthy distance often increases depending on ‘power distance’ and other contextual factors - and the distance can become too great. It’s often closer and muddier in smaller or flatter organizations. On the other hand, I’ve seen bosses who navigated the spectrum of workplace closeness with mastery. Displaying genuine humanity in the workplace is immensely powerful if you are attentive enough to get it right, but the more senior you are, the more it’s a tightrope to walk. You will never please everyone. Protect yourself.
😵💫 I’ve seen many bosses who are all vision but no focus. These ‘blurred visionaries’ taught me that as fun and fulfilling as blue-sky thinking might be, if you can’t link it to execution, it is as ephemeral as the clouds.
🤑 I saw bosses who prioritized their personal journey over team & company, either unaware or ambivalent to how visible it was to everyone. That underscored to me just how closely every action and omission is analyzed and interpreted the more senior you become. Everything you do is amplified. It’s critical to telegraph the values that you want to permeate through your teams, and the only real way to do so consistently is to live those values. You can’t ask people to do what’s right for the company if they see you doing what’s right for you, even if that’s at the expense of the company.
🔥 I’ve seen more than one boss come in and effect scorched-earth regime change all around us. Watching the spectrum of how they did that confirmed to me how sometimes, the working world is tough. At some point you’re going to have to make hard calls, and you’ll be unpopular with a lot of people because there is no way to restructure that makes everyone happy. But if you need to make changes, best to move decisively, communicate as clearly as circumstances allow what you want to achieve and how everyone can play a part in that. Only then you can muster the survivors to turn a ship around. Otherwise you risk screwing it all up, stripping out a culture, or continuing to sail your ship in the wrong direction while your remaining crew and/or money gradually go overboard.
👋 I’ve seen many colleagues move on, and left plenty of roles myself. I’ve seen bosses react to resignations with self-obsessed fury. That taught me that how you treat people who choose to leave your team is as important as how you treat them while you’re working side-by-side. They made me better at productive farewells (where possible - it isn’t always), helping people to be successful as they move on (I often recommend this book to people on their way to a new job) and building a good network of former colleagues. Word of mouth matters. Your relationship with a colleague doesn’t end when someone hands you a notice of resignation, it enters a new phase. Think of it as the coffee/dessert at the end of a long meal. If the meal was poor, great coffee and dessert can drastically alter someone’s perception of the experience as they prepare to tip and walk out the door. If the meal was great, terrible coffee leaves an awful taste in your mouth.
🤫 Similarly, don’t be the boss who takes a resignation serenely, only to persistently badmouth the departed soon after they leave. Many people spend time building a broad network of relationships of trust and friendship within their organization and beyond. Those networks only grow more interconnected over time and sour grapes will be seen for what they are.
🥱 At some point in your career, you will have at least one boss who baffles you with their total absence of work ethic, expertise or inability to connect with their team. Don’t forget them. Their behavior sets the low-water mark for you in terms of leadership and gives you something to refer back to any time you feel impostor syndrome creeping in. Don’t settle for being better than the worst boss you ever had, but do know that no matter how bad a day you feel you’re having - you’re most likely still outperforming that boss on their best day.