How to Be a Horrible Boss

I’ve been working in the tech sector for over two decades now. That means I’ve had more bosses than I can remember. The ones who left an indelible impression in my brain were in the extremes: either great or horrible. There are many books written about how to be a great boss, for example Managing Humans. Today I’m going to take the contrarian position, and tell you how to be horrible at it.


Why is this useful? I don’t know, perhaps you were such a great programmer that you were promoted. You reluctantly accepted your role as a manager, you hate it, and you want out. Of course you could figure it out with your superiors, but let’s assume you’re an introverted nerd with zero social skills 🙂 Seriously, here is a list of things that would make you a horrible boss. Do not try these at work!


Talk a lot, do not listen much. This trait would make you an annoying person in real life. You know the guy or gal who cannot stop talking about his/her own world: “enough about me, now let’s hear what you think about me.” As a manager, this is a cardinal sin. Why? Because unlike your friends, your direct reports won’t usually call you on it. You will have a self-reinforced view of what’s happening to them, and they will grow alienated from you. “The boss is out of touch.”


Be patronizing. Tell people how to do their jobs, and explain the obvious many times. If you were promoted to manage an awesome team, there surely will be stars who know more about their jobs than you do. The tech industry is not an assembly line with lots of turnover. For example, you may be managing a senior software architect with ten years of experience. If you ramble about how it’s important to “remember to design for scalability” or to “always consider security,” it will reflect poorly on your ability to trust him. My father-in-law was a successful manager for a pharmaceutical company for most of his career. He puts it this way: people become what you expect of them. If you treat your direct reports like children, that’s how they will act.  On the other hand, if you place lots of trust in them from day one, they will be compelled to prove that they deserve the trust.


Be as cryptic as possible, never direct. Another cardinal sin for a manager is to not tell people what she expects from her reports. Expecting people to read your mind or learn things by osmosis is a terrible idea; to make things even worse, criticize people for not doing what you knew you wanted but never expressed. If you want to take it up a notch, go behind people’s backs and talk smack about them to your peers or superiors. At that point your reports will have no recourse, because you are their proxy to the upper strata of the organization.


Encourage bureaucracy, and demand visibility into everythingIf you’re a horrible boss you probably don’t find too many people worthy of your trust. Never fear! The solution couldn’t be easier or more time-consuming: ask them to document every little thing they do. If they ask why, the answer is “because I need to know.” What if a senior executive asks you about the current status of the Lisp rewrite of FizzBuzz, and you don’t know it was delayed because there’s a temporary shortage of odd numbers for testing? Obviously you’d look like a clown if you said: “I don’t know, but I’ll ask my team and get back to you in a few minutes.


Show them who’s boss. If there is one thing that’s proven to demoralize a team, it’s a boss who constantly reminds them he’s in charge. There are limitless ways to do this, for example:


  • Tell people to do things without explaining the rationale for them.
  • Have weekly status meetings even if there is nothing new to say, or if it can be said over email. In Peopleware,  Tom DeMarco says this about weekly status meetings: “though its goal may seem to be status reporting, its real intent is status confirming. And it’s not the status of the work, but the status of the boss.”
  • Punish people with menial tasks (“hey senior engineer, go make copies of these handouts because my time is too valuable”). Bonus points if you do this in front of others.


Don’t learn about management. After all, you already went to school for programming or whatever it is you do. It is obvious that your experience doing X qualifies you to manage people doing X. Why waste time taking classes or reading books?


At this point many of you may be thinking “hey, you’re describing my boss to a tee!” in which case you should be updating your resume and your LinkedIn profile.


I’m lucky to work in Silicon Valley, where these types are relatively rare. There are not very many Bill Lumberghs or Michael Scotts around here these days. In other industries, they are probably still the norm. However, there was this one time of rapid growth in the late 90s when the rising tide would lift all types of idiots into management. I’m not going to talk about these characters and how they destroyed companies, morales, and souls. Instead, I’ll re-read this post. Then I’ll go back to think about how many of the above sins I have committed in my career, and keep this post as a checklist. If you report to me and you see me doing any of these things, please call me on it. If you let me get away with it then I will end up like Bill Lumbergh, and my life will suck as much as yours:



21 Replies to “How to Be a Horrible Boss”

  1. . I started a website which collects stories of horrible bosses and we’re taking names. So other people know about such horrible bosses. I find it extremely unfair that these guys can background check you before hiring you, This is the reverse, Check if someone has been reported on my site. The full site will be live soon

  2. Really nice article !I do not have much experience yet but I can already say that I experienced most of those situations. At the end I think that I can “forgive” all of those as long as the manager in question is ready to take responsibility when things go down…Which seems to be never the case with horrible bosses lol

  3. There’s a subtle conflict between “Be patronizing” and “Be cryptic.” It’s good to be direct and explicit, but it’s also good not to waste others’ time by stating the obvious. Getting that balance right is a real skill.

  4. @sowbug: Agreed! What I try to do is explain the high-level objective as clearly as possible, along with the reasons for it. Then I trust my team to figure out the details. They have never let me down. In particular, there was a time during the fundraising phase of IndexTank in which I was spending most of my time driving around the Bay Area as a single founder. The team knew what to do most of the time, and when they didn’t they asked me.

  5. Great post. You can write an entire book on this topic as well as its corollary that I’ve always used with clients “Most companies get the unions they deserve”. You’ll find a lot of these bosses working there, which is not a coincidence!

  6. Gripe about your bosses to your reports.It kills morale and makes us think that there is no real system or reason to what we are being told.

  7. Hi There. I actually wrote the book on horrible bossing, ‘How to Be a Horrible Boss in 23 Easy Lessons.’

  8. Love the article. And what’s funny is, I posted a near identical article yesterday – I call it “Failing up – how to fail your way to the top”. Check it out – Michael Baer

  9. “I’m not sure why but this weblog is loading incredibly slow for me. Is anyone else having this problem or is it a issue on my end? I’ll check back later and see if the problem still exists.”

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