What to do when your non-technical boss is just plain wrong

This can't be the most efficient way of doing things. I think it's also a strong argument for having a management and executive team that is actually technical.

Note: I find myself in this exact situation at my current job - multiple non-technical managers that don't realize how much they don't know and constantly make asinine requirements or timelines and reject advice from more technical experts.

The best game to play in this instance is to gain favour with their boss and anybody actively competing with them while passively disagreeing with them. You must passively disagree with them because the aim is to form a situation where you re-inforce their political opponents while appearing to be neutral - eventually they will come to you for support, and at this point they will be pliable. Something which will also help you gain authority is giving certain good ideas to other people whose interests will be in fighting your battles, however this is dangerous and you must make sure that they feel indebted to you.

If you don't want to kowtow to an idiot or beat them at their own game then simply quit and leave them to their mediocrity. There are likely to be a few places around where people will listen and use advice.

Edit: I obviously prefer just joining somewhere else without these kinds of insecure personalities, but my point was that political battles shouldn't be played in the light. You need to wear a cloak, you need to gather forces, and you need to resist the urge to slide the dagger in until others ask you to.

Find someone who will translate your technical point into something that your boss will understand. Or improve your capacity to convince non-technical people.

In my first job, I had to convince a boss of how to fix some performances issues in database. He did not understood anything and organized a small meeting with someone he trusted a lot and who was more technical. This third person was really helpful to answer all the questions of the boss because I had difficulties to explain what was obvious for me.

This is really the key to any interaction with another human being whether we're talking about speaking to an overseas technical support person, your boss, your mom, or your partner.

0. Realize your non-technical boss isn't some cartoonish, mustache-twirling villian with a fetish for poor technical solutions. He or she is picking them for a reason, possibly a misguided reason.

1. Figure out their motivations. Tricky, because most people are unwilling or unable to articulate what they want, even to themselves. Generally, your boss probably just wants things to run smoothly, make money, and look good to their boss. If they're choosing poor technical solutions, it's because they (correctly or mistakenly) believe those poor technical solutions are the best way to get to #2.

2. Figure out how both your goals and theirs can be met.

3. Communicate #2 to them.

None of those steps are easy, even though there are any a few of them. But it can be done. I'm not always successful at it, but here's an example of a time I did it right.

My boss employed ahem, "affordable" contractors who were basically "Dreamweaver jockeys" - they constantly sent us tangled 1990s-style HTML that I essentially had to re-write from scratch, taking me longer than it would than if I'd simply done it from scratch.

Instead of just telling him how that was a poor technical idea, I took the time to sit with him and show him (in a text editor) the difference between modern HTML5 and the horrible Dreamweaver spew, and how much more quickly I could change the modern code in order to respond to client requests. His eyes lit up at that point, because I was solving a real challenge he had - being responsive to change requests.

The icing on the cake was when I showed him some of the online galleries where we could purchase pre-made, high-quality HTML templates. Not only were they better-designed than the crap our contractors were sending us, they were easy to work with and were a fraction of the cost.

So I didn't just say, "Dreamweaver sucks! Everybody knows that!"[1] I demonstrated the wins a technically cleaner solution would give him.

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[1] I realize it's probably possible to just use Dreamweaver in a disciplined way, and create very clean markup with it if you wish. No offense to anybody making good stuff with it.

Unfortunately, as a functioning adult, you have to take other people's feelings into account, even when they are (GASP!) wrong. The reality is even if you are completely 1000% correct, if you don't give the other person a way to save face, they will fuck you over given the chance. The solution is simple - be nice.