The key is to make sure that your boss knows your goals. So, tell him your goals and dreams. Don't be shy, but don't sound like a broken record. Once a year you should discuss, in a private one-on-one meeting, where you want your career to go. I remember the day I walked into Les Lloyd's office and said, "Les, I may be a freshman now, but someday I want to be one of the student managers here at the computer center." He thought for a moment and told me what accomplishments I needed to have under my belt before he would consider me for the position. I worked my ass off that summer and soon he announced my promotion. I have had similar experiences at jobs after graduation.
Upward delegate only when it leverages your boss's authority
Upward delegation means giving an action item to your boss. The key is to know when to do it and when not to. If you try to give your boss an action item when it isn't appropriate, it looks like you are avoiding doing your work.
Here's an appropriate case: you are having trouble convincing a customer that her department has to pay for a server. Either she wants your IT team to pay for it, or she doesn't feel that the server is needed. Asking your boss to help explain the situation to her is appropriate because it leverages his authority. He has the authority to speak to the business issues involved, while your credentials are relevant to technical aspects. Your boss's authority also leverages his knowledge of the political power structure of your organization. He may know that it is a lost cause, or whether it would be appropriate to go over the customer's head.
Solve Problems at the Right Level
Don't debate technical issues with vice presidents, and don't solve a political issue with technology.
Managers usually want to speak to people at their level. Vice presidents generally communicate with other vice presidents. Directors generally communicate best with other directors. If you need to cross this line, communicate to the peer who reports to the person you want to speak with, or go through your boss, who is much more able to navigate the organizational structure.
To clarify this point, let's look at a situation where it would not be appropriate to upward delegate. The server has been purchased and is waiting to be installed. Would it be appropriate to ask your boss to install it? Generally, the answer is no. Such a task does not leverage his authority. If he is technical, he may have more experience and be able to install the server faster than you, but if he has delegated it to you, trying to push it back up to him simply looks like you are shirking your responsibility.
On the other hand, if you do not know how to install such a server, asking for help is appropriate. In that case, you are not asking for your boss to do the task, you are asking for training. It is leveraging his authority to ask for training. A manager's primary responsibility is to allocate resources. He can decide whether it is appropriate to train you personally or delegate the task to a coworker. By asking him for training, you are making a request that is appropriate because you are asking for the allocation of training resources.
Understand and help accomplish your boss's goals
If you want your manager to help you, you have to help him. "But why? It's his job to do things like career management, right?" Well, technically yes, but you get more flies with honey than vinegar. Your manager will spend more energy making you a success if it's obvious that you spend time making him a success.
More specifically, success in this case means meeting your boss's goals. Earlier I wrote that you shouldn't expect your boss to have ESP and be able to guess your career goals. Likewise, don't try to use your ESP to guess your boss's goals. More experienced coworkers might have a good understanding of what motivates your boss, and you should listen to them for guidelines. However, nothing beats talking directly to your boss.
I've had a number of bosses who surprised me when, privately, I asked them what their goals were and how I could help them meet those goals. The way I phrased my query was something like: "What metrics does your boss use to evaluate your performance? If I know how you are measured, I can contribute to the team more effectively by keeping those goals in mind."
In one case, my boss explained to me the specific technical projects he wanted to see completed that year. He had "sold" these projects to management, and they were expecting them to be completed. I soon realized that much of the work I did had little to do with those projects, and I redirected my priorities to make my boss a success. He noticed, and I benefited.
Another time, I was told the criteria that determined whether my boss got a bonus at the end of the year. It sounded greedy at first, but then I realized, who am I to judge? So I redirected my priorities to make sure that those criteria were met. My goal was, essentially, to make sure my boss's bonus was maximized. That would put me in the best position to get what I wanted, whether it was a raise, a promotion, or just a super-duper cool new computer on my desk. Is this unethical? Certainly not (as long as I didn't do anything unethical to meet those goals, of course).
This brings up an interesting conundrum. What if my boss had said the criteria he was measured by was something that I felt wasn't good for the company? For example, if I felt that what the company needed most was to strive for technical excellence, but he was being measured by growth metrics? You have to trust the judgment of the superiors who set up your boss's criteria. Or, strive for both goals. Sound difficult? Well, if you're smart enough to know more about what's right for your company than your boss's boss, it shouldn't be very difficult to find a way to meet both goals at the same time.
I don't think it's cynical to give higher management exactly what they ask for. However, sometimes your boss is measured in a way that unintentionally promotes bad behavior. For example, I once visited an IT helpdesk whose manager was rewarded based on whether he was able to decrease the average initial response time to customer requests. (You can see where this is going, right?) Soon, everyone he managed was answering calls on the first ring (or very soon after receiving an electronic trouble ticket) and putting the caller on hold. Service wasn't getting any better, but they were meeting their metrics. The following year, management started measuring performance based on average time to resolution. As you can guess, tickets were closed very quickly whether or not the issue was really resolved. The statement, "I'll close this ticket; you reopen it if my suggestion didn't fix your problem" became commonplace. Again, customer satisfaction didn't improve.