Talking to Your Manager
There exists tons of academic material about managing, and specifically about managing technical employees, but there's hardly anything to help the employees deal with managers. It's a "learning to work with others" skill, sure, but there are some aspects to working in an IT environment that make it a difficult skill to learn.
Here are some helpful hints to aid technically minded IT staffers in their struggle to coexist with managers.
Techies must be honest with their managers, and they must also learn to communicate in a manner that works for their specific situation. Some managers enjoy confrontation; they see it as an opportunity to learn. Most however become defensive. Gently, yet bluntly, is the name of the game.
Be Nice, Be Candid
Your manager needs to know what you think, about everything. Immediately saying "that's stupid" or undermining a manager's orders isn't helpful. Bringing up your concerns—now that's completely different. There are no magical words to help people understand why others view them as confrontational or difficult to work with. The best piece of advice, as was given to myself by a mentor, is to read Dale Carnegie's "How to Win Friends and Influence People." The book has a slightly sales-oriented slant, and was written in the 1930's, but it certainly has stood the test of time and is capable of helping in every aspect of your life.
Giving your manager honest feedback is essential. In order to help your manager guide the IT organization as a whole, he needs to be given a small amount of credence. Managers aren't stupid; they understand things about the IT business that you've never considered. They don't really even need to know how it all works; they just need to be your bridge to executive management.
Line managers should have a bit of technical knowledge, and if they don't, then it's your job to bring them up to speed. They may not be interested, but when something requires a technical explanation, be sure to provide all the background information necessary for the manager to understand the issue at hand. Even if they don't quite parse everything you say, at least they're given all the information they need.
When a manager gets promoted, he usually stops worrying about the details of what's happening within IT. His concerns may begin to shift from enforcing Change Management to ensuring regulation compliance, for example. Managers will be more focused on budgets and the like, so your cries may go unheard. This may make zero sense in some smaller or micromanaged organizations, but I bring it up because we need to understand the importance of reaching out to higher-level management.
Your current manager is your direct link to the people who make money decisions. If you're unable to give your manager ammo for the higher-ups, he may be unable to acquire you more gear or people when the need arises. Said ammo is the elusive "business case." This isn't rocket science (like rocket science is hard anyway, pshaw!); just begin thinking about how to spin a proposal to make it look beneficial from a financial standpoint. Bam! You're thinking like a manager now. It also helps to pay attention in meetings when your manager drifts to talking about the business itself.
Not the Enemy
Your manager is your boss, not your friend. It's probably painfully clear already, but it needs to be said. However, the term "boss" does not imply "enemy" by any stretch of the imagination. You should never belittle your boss, especially in front of your coworkers. That kind of mojo spreads like a virus, and it never turns out well. Conversely, you shouldn't just support everything your boss says if you know it's incorrect. You need to come out and explain why "there may be a better way" or that "I understood that differently." It's all in the wording, as the previously mentioned book will teach you.
There are other aspects to working well in an IT environment aside from simply coercing your boss.
A manager needs to know what's going on. I mean: really. For some strange reason IT people like to keep secrets about their progress, their technical problems, and their plans. It's likely that they simply want to avoid hearing their boss's suggestions, or that they don't want to appear inadequate. As long as important problems are brought to your boss accompanied with a plan, he will be grateful. Snags happen, more often than not, and managers understand that. They need to know when an impasse has been reached, so they can plan accordingly. A technical issue that you've known about should never be able to surprise your manager.
When you open up to your manager, he will return the favor. You may be mystified about the reasons behind a certain past decision, but once a trusted channel of communication has opened up, you'll find that things get a lot clearer. You may even get a bit more decision-making power in the process. Give a little, get a little.
In a peachy world where everyone cares about other people, this could actually be some useful advice. But everyone knows that some people are just plain… difficult. If your manager refuses to understand the reasons behind a problem, and continually blames you for all problems, there are two possible causes. Either you really are doing things wrong, or your manager is worthless. If the latter is true, don't hesitate to confront him in private. Don't do this unprepared, though. Read the Carnegie book mentioned earlier! When all else fails, go above the manager's head, but be prepared with documentation and examples. It helps to be able to show how the manager has cost your company money as well.
Hopefully most of us are in a situation that's somewhat less dramatic. For most people, simply opening a channel of (effective) communication will solve a surprising amount of problems. That often requires swallowing a bit of pride, and also admitting that your manager is, well, your manager.