If you had a dime for every time you found yourself asking this question, would you have retired by now? It's the catch 22 for a developer, you have tons of code to write and test, but also tons of interruptions and meetings to talk about when you'll be able to finish your work. Worse yet, they're so out of touch with technology, they offer no help if you do run into a real problem, am I right? Completely Clueless, proof positive of the Peter Principal in action.
Or are we developers missing something, blinded by our brilliant technical skills?
Early in my career my father gave this advice: "Don't dismiss anybody. They have their job for some reason, be it a skill, knowledge they hold, or a personality trait. Find out what it is they know that you don't and learn from it."
If we take a step back and apply a little logic, that clueless manager is likely higher in the food chain than you, which means that at some point they've had to impress somebody to get promoted. They get to keep that job only so long as they continue to fulfill the business's needs. These facts would contradict our original hypothesis, perhaps those clueless managers aren't so clueless after all?
The reality is a manager has to be aware of and answer to the business reality. It's never just a matter of "will it work?" but "when will it work and at what cost?". No matter how good an idea seems on paper, ultimately it's got to look good in a project plan to be worth money from a project sponsor. Businesses survive because of Profitable Success.
So a challenge to you if you are struggling with a clueless manager. For the next few months, but aside your assumptions about what your boss needs to hear and instead open up and really listen to what they are asking for. For example you can start with the following exercises:
1) Switch from a pull to a push status model. If you don't know already, ask your boss what day of the week they report the project status up the chain. Then prepare your status report to them a day earlier and send it (put the reminder in your calendar!). Be ready to clarify anything they have questions on.
I've found that after a few weeks as my boss learned to trust my report, more importantly I learned how to phrase things to get my boss's attention when needed, those annoying interruptions to explain current project state dropped off to almost nothing.
2) Use your boss's words back at them: If your boss talks in percentages report percentages, If your boss likes hours talk in hours. Whatever your internal project clock is, figure out a formula to convert to their measure and stick to it consistently.
My company requires percentages. My boss likes hours. I only trust completed test cases. My solution was a spreadsheet that tracked hours worked then subtracted that from hours estimated, generating a total hours remaining and percentage complete. If my test cases success % matched these raw numbers, I knew project was on track. When my test case % started slipping, I adjusted the raw numbers down and more importantly, communicated how I would catch up with the plan. Turns out my boss is not a complete ogre, and offered up solutions other than overtime to get things back on track. (It helps that she's being measured on keeping week to week consistency. who knew?)
3) Temper your innate optimism and supreme confidence in your god-like technical skills. Leave room for a little self-doubt. Chances are your manager has seen all kinds of ways that projects fail: technical, political, financial. Chances are also that your manager is where they are because they've survived those various disasters, and earned the credit for saving what they can. Ask your boss for war stories. Turns out while technology moves forward, the fundamental problems facing software development haven't. Your boss has likely moved through all kinds of fads, vaporware, and religions. Likely, they've survived by paying attention to some eternal truths, and not limited their career to the buzzword of the day.