‘Best boss’ discussions are often total garbage

Best Boss

There are probably about 1.9 million articles on the Internet around how to be the best boss you can possibly be. This morning, when I couldn’t sleep for some reason prior to a brewery fun run, I found one on Fast Company: “The 10 Habits Of Well-Liked Bosses.” It makes some good points — we’ll get to them in a few moments — but I just kept thinking about how many articles exist that purport to make you the best boss possible.

In a way, any best boss convo is total bullshit. Let’s be clear about a couple of things (we’ll elaborate in a second):

So the sheer fact of the matter is, most bosses aren’t great. The best boss is pretty far off. And this too makes sense — management isn’t really intuitive, honestly. The targets you hit to become a manager aren’t really the targets you need to hit once you manage other human beings; it becomes way more about managing human energy and way less about managing tasks and deliverables. Most managers don’t understand that, and this is a core reason why best boss discussions are pretty far off.

Let’s dive deeper for a second.

Best boss discussions: Where do they fall apart?

Let’s go back to that Fast Company article I linked above. It’s about 10 habits of well-liked bosses, or people that are theoretically in this best boss category. Here are the 10:

  • Clear communicators
  • Trust employees
  • Consistent
  • Understand your work
  • Let you make mistakes
  • Self-aware
  • Manage up
  • Appreciate you as a person
  • Believe in your development
  • Have your back

I just ran my last manager down this list. She hit maybe 2/10. 20 percent, eh? Hardly a best boss — but within that company, she was loved and revered.

See, this is the thing. This is why most best boss discussions are total business journalism bullshit. You need to follow this bouncing ball:

  1. First off, there’s a difference between a ‘manager’ and a ‘leader.’ In all likelihood, your employment situation leads to a manager being your boss and a leader being your mentor. That’s how it works for most people — if you believe mentorship is still alive.
  2. Managers are often tasked with hitting targets: This is kind of where the idea of a best boss falls apart. Managers are people who are vetted by an organization with authority. Leaders are inherent managers, but standard managers got a promotion and became someone who has ‘direct reports.’ Now look, in reality middle management makes almost no sense anymore and needs to die. But until it actually does, most managers will be tasked with hitting targets. You report up to an exec, and the exec tells you “Hey Bob, this is a priority now. Go get it.” You work on that priority for a few days/weeks and then the same exec tells you “Hey Bob, forget that other thing. We’re chasing a new revenue play. Get your people on that.” This is how most jobs work. It’s total garbage and priorities are completely unclear, but it’s the best way we can think to manage a hierarchy and a set of tasks.
  3. Because of a managerial focus on tasks and deliverables, people slide to the background: This has been happening for years, and it’s part of the major problem with Human Resources these days.
  4. Because of this task focus, bosses can’t really be a ‘best boss:’ They construe their job as hitting targets for those above them, plain and simple. Those below are workers. They’re interchangeable. Ignore them for three weeks at a time? Sounds good, so long as my boss is happy!

This is why all these types of Fast Company articles about what makes a best boss are bullshit — there are great bosses in the world, but you can’t learn to be a best boss through some business journalism article. You need to understand how to remove yourself from pleasing your own boss (managing up) and seeing how the whole ecosystem of purpose, mission, culture, revenue, and profit fit together where you work.

Look at the bullets above — the list from Fast Company about what makes a great boss. “Clear communicators” is one of the main ones, right? We’d all love our direct boss to be a better communicator — “I can’t read your mind!” — but nary a soul manager-wise tends to care about communication, because the ROI can’t be tossed on a balance sheet and breathlessly debated in a 1:00pm stand-up. Another one is “trust employees” — that would make a best boss, baby! — but virtually no managers understand accountability and most operate according to some principle that “If an employee isn’t directly in front of me, they’re jerking around somewhere.” Another best boss characteristic is “Understands your work,” but research keeps proving that most people aren’t really sure what their direct reports even do.

I could go on and on.

The yin and yang of a manager is that they need to manage up — which heck, is on this bullet point list of best boss traits above — but they also need to manage down and explain to you what’s going on and what matters in the company right now (even if that changes every six days). Most managers I know, and I’ve worked with, only manage up — because getting closer to the power vortex means more perks and scratch for you, and that’s what most people are chasing, Daniel Pink keynote speeches be damned.


At one of my last gigs, my role was totally unclear. I had a boss who was accountable to a whole different set of priorities that didn’t involve me, and she could have given 0.22 shits about what I did. It was a great way to feel every day. I had a guy in a different city who was closer to my work, so sometimes I’d ask him if I could help out in some way. He regularly threw himself on The Temple of Busy and apparently once told a superior that it ‘annoyed’ him that I was asking for work that would help him out. This is a super common attitude in management: “I’m so slammed, I don’t actually have the time to talk to or acknowledge someone that might help me out with what I’m slammed with.”

That guy I was asking for work? That’s a standard middle manager right there. He was trying to manage himself up and get himself in a better position for perks, bonuses, trips, scratch, and more. That was the goal. Where in that equation is a better employee experience? (Jeopardy music.) The answer? Nowhere. And that’s why any ‘best boss’ discussion is bullshit. For someone to become a great boss, they need to care. They need to care specifically about: people, their lives, their workflow, their tasks, their intentions, their purpose, etc.

Most bosses care about themselves first and foremost — which makes sense, because Country Club Management is all the rage post-2008 crash and since your company has no real incentive to take care of you, someone needs to look out for No. 1.

You can’t be the best boss if you only care about yourself. It’s that simple.

Any other thoughts on this?

Ted Bauer


  1. Ted, you make an excellent point that “manager” and “leader” are two distinct roles. “Boss” is just a convenient label to name a position (i.e., supervisor), though Sydney Finkelstein has taken that discussion to a different level with this book, “Superbosses.” I would add “coach” as a third role that is distinct from “leader” and “manager.” The single “boss” can sometimes be good at two or more of those roles but not at the same time.

    • My other argument would be that for someone to become a ‘great boss’ or ‘best boss,’ the true No. 1 thing is caring … but most ‘bosses’ tend to care about (a) pleasing their own boss and (b) “revenue plays.” That won’t make you a best boss.

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