“I’ll Finish It This Week” and Other Lies

A+C is probably the most common where I'm at (enterprise SaaS), though its usually with management's knowledge/understanding. We wind up rushing something out to meet the client's direct need to hit their deadline, then figure out generalisation afterwards (which admittedly does drag out and has its own issues).

As a genuine question, is this approach abnormal or bad?

I'm on the technical management side of the whole thing - am I screwing my staff by encouraging this?

We want to shorten that generalisation process but that (internal) pressure to just close it out seems like the lesser of two evils when compared to the sorts of pressure that clients paying significant $$$ apply

When your manager (never say "boss", because you are your own boss, they are the manager) says "2 weeks", at that point it's their responsibility. So as long as you don't say "I can do it in 2 weeks", it remains their responsibility.

So an easy way to respond is "I'll do my best", or "I'll see what I can do". In your head, you say "YOU said 2 weeks, NOT me. So if it takes longer, it's YOUR fault, not MINE". And then you work on the project like any other project. It's not about you being bad at your job, it's about the person being a bad manager. Keep the manager up to date on the progress.

Next step is to educate your manager. Don't fall in the trap of making estimates in 5 seconds on the spot. In this case, you could respond "2 weeks? I don't know, I haven't made an estimate on that." This way you indicate that YOU are the person who should do the estimate, not them. You could follow up with "Do you want me to make a detailed estimate?". If no, then indicate "ok, I'll see what I can do" as above. If yes, make a realistic deadline (NOT estimate, see below).

Bad managers come with all kinds of tricks to pressure you, like for example "The customer expects this to be ready in 2 weeks". At that point, you really need to educate them and show how reality works:

"Wow, I hope for your sake that you made a correct estimate. I didn't estimate the work, so I have no clue if this is possible. But you might be in a lot of trouble when you made the wrong call here". See what I did here? Managers try to push problems on you, don't let this happen. Always make it clear that the responsibility is always in their camp as long as you didn't make the estimate. If the 2 week deadline is not met, it's their fault of not asking you for a proper estimate in the first place, secondly for making a wrong estimate themselves, and never because you are bad at your job and should work overtime. Don't let bad management be your fault, because it isn't.

So when you can make estimates yourself, make sure you know the difference between an estimate and a deadline. Most managers think it's the same.

An estimate is "I think it takes around 4 weeks", which basically means "Best case it takes 3 (which it never will), and something might go wrong so it could be 6 weeks". A deadline always has a buffer built in. It's a worst case scenario. Your manager will ask for an "estimate", but 99% of the time it will be a deadline. So make sure your "estimate"=deadline includes a buffer of worst case scenario. If you estimate 4 weeks, they will promise it to the customer in 4 weeks. This is wrong of course, since there is no buffer. So say 6.

And this is how you keep your sanity as a developer. Educate your managers, because a lot of them are not really knowledgeable and experienced in dealing with proper software development.

I wouldn't recommend doing this on purpose, but if you say something that forces the whole room to stop and consider, you can often break the conversational flow and leave a meeting of managers dead in the water.

You can also do something that wipes an individual manager's mental cache and they'll spend days trying to remember what everyone is up to and what's happening.

I think your final sentence is close, but I'd rephrase it: for managers, those disruptions and conversations in your schedule are them dealing with things that require intense concentration. I think most of them understand what disruption feels like, they just don't associate sitting at the computer typing with that focus because it's not the mechanics of their role -- their focus manifests differently.

My managers only rudely interrupt me when they, themselves, are clearly still processing something their boss said to them and they need my input to unblock that process. Or some kind of thing I need to do now, again to unblock whatever they have going on.