Stories about Software


Help, My Boss Sucks!

I might be accused of link bait for a title like this, but I actually get a decent amount of questions that, when you distill them down to their bare essence, amount to this title. The questions are often packaged in narrative (possibly rant) form and almost invariably summed up with an apology for all of the detail. Please don’t apologize for that level of detail. It’s not that I enjoy hearing about your miseries, but I think that there’s definitely a shared catharsis that occurs when recounting or listening to tales of corporate stupidity with a narrator that’s powerless to stop it.

My Expert Beginner series and eventual E-Book resonated with a lot of people largely, I think, because of this dynamic. The experience of dealing with an entrenched incompetent is so common in our industry that thousands and thousands of people read these posts and, thought, “hey, yeah, I had to deal with a guy just like that!” And I’m small potatoes — the DailyWTF is an entire, vibrant site with tens of thousands of subscribers and a number of authors and editors dedicated to this kind of thing. If you want to go even bigger, think of Dilbert and his pointy haired boss or the Peter Principle.

Assuming, however, that commiseration with others isn’t enough to bring the joy back into your life (or at least to remove the angst from it), the question then follows, “what should I do?” It’s at this point that one might expect to stumble across some kind of insipid faux-answer on LinkedIn or something. It’d probably go something like this:

Top Ten Tips to Tame a Terrible Tyrant

  1. Take up meditation or yoga and learn to take deep breaths when your stress level is getting high so that you can react calmly even in the face of irrational behavior.
  2. Ask yourself if you’re not part of the problem too and do some serious introspection.
  3. You don’t have to like someone to respect them.
  4. Talk to human resources and ask for discretion.
  5. Have a heart to heart and explain your concerns, being courteous but firm.
  6. Enlist the help of a mentor or respected person in the group to make things more livable.
  7. Empathize with their motivations and learn why they do what they do so that you can avoid their triggers.
  8. Heap praise on the boss when he or she avoids behaviors you don’t like in favor of ones that you do.
  9. Seek out a project that puts you on loan to another group or, perhaps, minimizes the direct interaction with your boss.
  10. If all else fails and you’re at wits’ end, perhaps, maybe, possibly, you might want to consider some kind of change in, you know, jobs — but do a ton of research before you do anything and make lots of idea webs and charts and make really, really sure that this is what you want to do because it’s a huge decision.

Honestly, go out and google something like, “what to do about a bad boss” and this is the sort of platitudinous, enumerated non-answer to which you’ll be treated.  It’s manicured, politically correct, carefully considered, diplomatic, and a load of crap.

Let’s get real.

What To Do When Your Boss Sucks

  1. Form an exit strategy.  That’s it.  There is no 2.


Wait, Wat?

Yes, you read that correctly.

I don’t advocate that you take up yoga or work it out on the heavy bag or recite “calm blue ocean” or empathize or anything else.  If you find yourself miserable at work day after day because of a boss with whom you are fundamentally incompatible or if you find yourself googling “what to do about a bad boss” or if you find yourself writing to someone like me to ask for advice on what to do about your bad boss, you’re in a fundamentally awful position that’s probably shaving hours and days off of your life.

Whatever appeasement strategy upon which you may choose to embark is only going to mitigate that — it won’t alter it.  You need to take control of your destiny and that requires an executable, measurable, and tangible plan of action.

I’m not advising you to rage quit or do anything rash — that’s an awful plan (or perhaps a non-plan).  What I’m suggesting that you do is start laying out a sequence of events that removes this person from your life.

There are a lot of ways that this could happen.

Obviously, you could quit and work elsewhere, but you could also plan to stick it out until the boss retires in 18 months.  Perhaps you start taking classes at night so that you can transfer into a different group or maybe you find some team-lead type that acts as a buffer between you and Mr Spacely.

It could be that you do something as unusual as becoming a huge advocate for your boss to upper management so that he’ll get that promotion that will take him to another division or, at least, away from dealing with you directly.  Maybe you initiate controlled explosions inside of your own ears so that you never have to hear his terrible voice again and he can’t deal with you unless he learns sign language.

Go make yourself a brainstorming list — no idea short of criminal malfeasance too farfetched — and capture every imaginable path to your emancipation.  Once you’ve got that list in hand, start narrowing it down and firming it up until you have several strategies that you can work simultaneously, all timeboxed and with contingency plans.

You need to have measurable goals against which you can measure progress and you need to understand when to pivot.  A good plan would be something like:

“I’m going to get that certification that will make me a bit more cross functional and then I’ll start volunteering for work over in Bill’s group in my spare time.  Within 3 months of that, I’ll casually broach the subject of spending some time in that group and within 4 months, I’ll make it official.  While that’s going on, I’ll talk to HR within the next month about the idea of a potential transfer.  If after 4 months, none of that is going well, I’ll start interviewing for other positions.”

Now when you’re looking at your life, you’re not seeing an unending string of misery to be mitigated only with non-actionable platitudes like, “be more understanding” and “ask yourself if you aren’t partially responsible.”  Instead, you have a plan of action that you believe, if followed, will lead you to being happier.  Because here’s the thing — if you’re fundamentally incompatible with a boss then “who is responsible” is a non-starter and being more understanding isn’t really going to help.

There’s a Protestant Work Ethic, “Pain is Gain” underpinning to all of this that’s really not appropriate.  Is it an inappropriate sense of entitlement that must drive you to say, “I shouldn’t have to work somewhere that my boss makes me miserable?”  Many would argue yes, but I’m not one of them, and I think that’s silly.

If you’re overly picky or sensitive, you’ll wind up job hopping, getting stuck somewhere or, perhaps, have trouble finding work.  That’s how you pay the piper for being too picky or sensitive and, if those things start happening, maybe you should embark on a course of introspection.

But if you’re miserable under a boss, that’s real and there’s no way it’s entirely your fault.  It’s not your sole responsibility to figure out a way to prevent someone from making you miserable and you ought to view this as a no-fault problem to set about solving.  That’s where the plan comes in.

A boss is someone who should be removing impediments from your path to allow you to be as productive and awesome as possible.

That’s not feel-good BS — it’s the way to get the most value and productivity out of knowledge workers.  No boss that truly embraces this mandate should be making your life miserable, even if you are an over-sensitive, uber-picky prima donna.

If the boss is making you miserable on a daily basis then he’s an impediment and not an impediment remover.  Since you’re then responsible for removing your own impediments, there’s only one thing to be done with this boss: remove him from your life.

That’s All Well and Good…

I realize that this all probably sounds rash and maybe you think, “easy for you to say,” but it didn’t just happen to become easy for me to say.  I planned for it.

I’ve spent a lifetime optimizing for my own happiness and satisfaction with what I do and, when that temporarily wanes, due to a boss or anything else, I form a plan, follow it, and fix the problem.  And I do this by thinking in terms of diversification and dependency.

If you take a job at Acme Inc, settle in for a 10+ year stay, and let your resume gather dust, then you’re largely dependent on Acme Inc for your well being via income — you’re putting all of your eggs in that basket.  If Acme then burps out a bad manager and puts him above you in the org chart, you find yourself in the same position as a cable company customer: “yeah, we’re awful, but good luck doing anything else.”

If it seems daunting or hard to plan at this point, it’s because you’re pretty coupled to Acme.  You still can and should make a plan, by all means, but that’s why my advice might seem cavalier.

I have contingency plans all the time, and they range from W2 opportunities to 1099/B2B work to royalty streams to oddball, go-for-broke schemes like moving to the country to be a hermit and try my hand at writing novels.

Some of them are clearly more realistic or feasible than others, but they all exist and I’m in a constant state of assessing my happiness and weighing my options.

Don’t confuse this with fickleness or disloyalty in me and I’m not advocating those things in you.  If I could find something that made me consistently happy, work-wise, for the next 2 decades, I’d happily take the consistency and stability, and I cheerfully advise you to do the same.

But when life or companies throw crap situations at you don’t hesitate to start executing contingency plans to bring your happiness level back to where you want it.  Your happiness is something that you can’t count on anyone but you to monitor and it’s not just important to your quality of life — it’s important to your quality of output as a knowledge worker.  You and your reputation can’t afford for you not to be happy.

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Matt Keen
Matt Keen
9 years ago

Great post. I spent the first 6 months of this year desperately unhappy at work under terrible management. We had gone from start up a few years ago, and had expanded to the point where we hired a “VP of engineering”. Needless to say it was a terrible hire. People who had been at the company since the beginning, who had invested many weekends, were starting to leave because of it. Everyone else was going to numerous interviews. Myself and a few other developers talked to upper management multiple times about how unhappy we were, only to be told to… Read more »

Erik Dietrich
9 years ago
Reply to  Matt Keen

First of all, that’s a refreshing and awesome outcome. It’s really nice to hear because so frequently situations like that end in exodus and departments and companies going off the rails. And. it’s also a great follow up to the post, since this is an excellent example of the broad umbrella I mean with an “exit strategy.” Getting the tyrant ousted is an excellent exit strategy if you can pull it off.

9 years ago

Nice post. I just finished executing an “exit” strategy myself, where the plan was of the “find a new job fast” variety. In this case my nemesis was 2 levels of management above me, but he was very much into micromanaging, so his presence was still acutely felt at my level. I have found that it in these situations it really helps to know your worth as a developer. Even with a fair amount of effort in keeping your skills up to date, and just a small network of connections, you can usually find a job within a couple weeks.… Read more »

Erik Dietrich
9 years ago
Reply to  Brian

I bet it was hard, on the way out, to resist the temptation to say, “I don’t like death marches — where was that door, again?” 🙂

David S
David S
9 years ago

This is something I’ve vaguely felt, but you might be the first person I’ve read who’s managed to articulate it. Bravo! It seems like when you are deeply unhappy with a job is the time when you have the LEAST energy and social leverage to effect change in the group. I think all those platitudes might have their use in defusing a bad situation while it is still just an irritation, but by the time you are googling “How can I cope with a bad boss”, it is much too late. And the market for developers is vibrant enough now… Read more »

Erik Dietrich
9 years ago
Reply to  David S

Glad if it resonated with you, and I think you make an excellent point that you’re least likely to cheerily try to make nice with someone when you’re deeply unhappy. By that point, it’s usually avoidance, anger, and fatalism.