Like a Boss

Actually, nobody likes a boss. So why are there so many of them?

We’re mid conversation -- door open, obviously informal -- when a staff member appears at the doorway. My colleague gives me a knowing look as he turns his attention to the visitor.

“How can I help you?”

“Um, my daughter’s school just called. She’s sick -- I’ve gotta go pick her up.”

“There’s no one else you can call to pick her up instead?”

I watch in horror.

“I, uh --” (the visitor, stuttering)

“Look, go if you must, but make sure you have someone cover for you. And don’t be late with that project we talked about.”

The visitor leaves, shell-shocked. My colleague turns to me, his expression somewhere between pride and the solemnity of having done one’s sworn duty.

“You’ve gotta be careful with these people. This week it’s a sick kid, next week their dog died. Give ‘em an inch...”


After the better part of two decades in the working world, I feel qualified to ask: why are there so. damn. many. abysmal ‘leaders’ out there? And by that I mean *people in leadership positions, which turns out to have nothing to do with actually being capable of leadership.

The above scenario is a true and specific story, but I’ve witnessed the same sort of thing a thousand times: in colleagues, in people I’ve reported to, in stories from others who’ve dealt with the same, and so on. It’s all anecdotal evidence, but I have enough of it -- you probably do too -- to suggest that the bad-boss problem is rampant, to the point of being possibly systemic.

That word -- ‘boss’. Let’s use it. It’s a good one to distinguish between an actual leader and the mess I observed that day with my colleague. So many bad choices in, what, 20 seconds?

  • Zero apparent concern for the staff member

  • Zero apparent concern for the child

  • Automatic, reflexive mistrust

  • Immediate emphasis on what was important to him

  • Presumption that the staff member would neglect their duties

...and probably a bunch of others, if I wanted to work myself deeper into frustration by thinking more about it. Every time I see or hear about a situation like this, wherein the boss figure is a wrecking ball of blatant self-concern, I have some version of the same bewildered thought: WTF, it’s not that fucking hard.

And it’s really not. Sure, the art of leadership is grounds for infinite study, nuance, elegance and so on -- there’s a lot (of really cool stuff) to explore there. But the ‘boss’ type doesn’t need to worry about all that yet. First they just have to get over one simple hurdle:

A leader serves their people. A boss expects to be served by them.

Now, I’ll grant that making this leap is slightly easier said than done -- but only slightly. I think a lot of bosses get caught up in the pressures of being accountable to whoever / whatever is above them: their own bosses, the company as a whole, etc. When the going gets tough, they retreat into their egotistical fears, amplifying and cascading -- rather than absorbing -- the pressure as it rolls downhill, needing to secure their own air mask before helping with anyone else’s. But still, there are lots of ways to navigate those pressures without treating people as servants. And guess what? These characters would have a much better time if they could figure this out.

Anyway -- details aside -- if as a leader you have the basic mindset of being there to help your people, rather than the opposite, you’re already doing better than a large proportion (the majority?) of people in leadership positions. And if you genuinely care, rather than having to make a conscious effort of it, you’re in rarer company still.

Back to my earlier question: how the hell can this be? I mean…I imagine most of us have been subjected to a bad boss at one time or another, and I can’t imagine many of us have enjoyed the routine degradation that comes with it. So why is this experience so pervasive in working life? Shouldn’t the bad, self-serving bosses have been rooted out by now?

Here’s my theory: many workplaces are political, and political cultures systematically select for the self-serving type.

Let’s unpack that.

First, what’s a political culture? It’s one in which people are primarily motivated by their individual interests as opposed to shared goals. It arises, best I can tell, out of a thorny challenge: at a certain size/scale of a company*, it becomes tough to measure or even gauge a particular individual’s contributions to overall outcomes. So the job of deciding who’s doing a good job gets left to human judgement -- farmed out to a set of managers throughout the company, each responsible for assessing performance (often subjectively) in their respective area. 

(*I’ll use the word ‘company’ here, but the idea applies equally to any organization with a collective mandate.)

In that moment of tasking a specific person with identifying talent or a job well done, getting ahead in the world becomes -- in a strict sense -- about impressing that person, rather than about contributing to the company’s mission. They’re meant to be the same thing, but they’re not. Now, in addition to being competent in your job, there’s such a skill as managing others’ perceptions of you. Someone who’s good at that and does justokay work is not uncommonly rewarded more highly than the person whose work is way better but who isn’t particularly skilled in the art of looking good.

For example, ever meet the ‘firefighter’ type? The person who runs around pointing out emergencies and making as big a show as possible of being in the middle of reacting to them? It’s very likely that the fire preventer -- who stops problems from occurring in the first place -- is much more valuable to the team, but because their contributions are by nature less visible, this person may go underappreciated relative to their dramatic counterpart.

Anyway, all of this is to say -- political cultures are common and super hard (if possible at all) to avoid. And in political cultures, advancing in your career has at least a little and possibly a lot to do with impressing those above you. 

Those who are motivated to play the political game are naturally better at it. Those who aren’t either grow disinterested and disengaged, or get frustrated and opt out entirely. The politically motivated crowd are happy to brownnose their way up the ladder. Meanwhile, the act of voicing a dissenting opinion now has to come with a calculation of the political cost of doing so. You get the point: repeat this cycle a few times and you get an environment where it’s not leadership talent that gets you ahead, it’s the will to outlast others in the political ringer, which in turn favours those who are persistently self-interested. 

Voila -- the origin story of The Boss, who has now earned his moment in the sun and will take advantage of the opportunity to be served by the next generation of subordinates, just as he made sure to serve those before him.

This is all a touch cynical of course, but I come by this view of the underlying cause and effect sincerely. I think the problem is systemic, owing to the effects of a political culture, which is itself owed to a root problem of organizational behaviour.

Final note: to be a great leader is to have the will and skill to navigate corporate politics, and the strength of character to not buy into them. This is a rare breed indeed, who uses their political savvy as a means to a collectivist end: that is, to acquire power and influence for the purpose of better serving those around them.

Of course, anyone who operates this way will never lack for opportunity, gratification, status or whatever else our inner ego monsters are after -- so it’s not like there’s any real sacrifice involved in being genuinely about your people. It’s a shame more bosses don’t recognize this.