No, I do not mean a traditional gift for the holiday season (in fact, I don’t think holiday gifts are appropriate for most workplaces or corporate cultures but that is a topic for another post). I mean something that will be much more valuable for them – learn when to ask your boss for help. And a closely related corollary – know when to inform your boss. An underutilized value an employee can bring to their manager and their company is knowing when to ask for help. This seems fairly simple on the surface but in reality it is quite complex and subtle. The reason it is important is somewhat obvious. The more often you go to your manager then the more of her time you take up, decreasing both your efficiency and hers. Generally companies do not actually care about what you accomplish but rather they care what you accomplish per-unit-time. Efficiency is critical. Of course, if you don’t go to your manager often enough then your work product suffers, some work needs to be redone, and again, you generate inefficiencies. You may also make your manager look bad up the chain of command; never a great idea. So why do I assert that this is a complex and subtle issue?
First, every manager is different in what they “want to know”. Some of them want more detail and want to give more input than others. So right away you need to be able to judge your managers state of mind and needs. Even more subtle, these needs can vary depending on the project, the other activities your manager is involved in, and perhaps the phase of the moon! In addition, your manager is likely to be too busy, with multiple demands on his time and looming deadlines so even if you know it is a good idea to connect, it may take significant effort. It is easy to interpret this as an indication that your manager does not want to be informed or does need to have input. However, when the project does bubble up to the top of their to-do list, it will not matter how busy they were when you did not inform them of a problem or ask for their help when it was needed.
This issue is also subtle because there is rarely a clear “right answer”. You must have the confidence to know when consulting your manager is not necessary and the humility to know when it is. There is simply a large grey area so the decision is dependent on your skills, your self-awareness, and even your managers personality. I have seen that many times very good employees need too much handholding from their managers and I have seen average employees try to go-it alone too often. Thus, as with many issues of performance and becoming a leader, self-awareness and awareness of others, your boss in particular, is crucial.
So how do you strike the right balance? Improve your powers of observation and your powers of inquiry without going overboard. Initially, ask your manager at the end of your consultations if they would have preferred that you had gone further on your tasks before checking in. But be aware that even your managers may give you a less-than-direct answer. Perhaps they are not sure about their answer or do not want to diminish your performance. You need to read their body language, their tone, and the outcome of your actions on the project. Independent assessments from a trusted advisor or mentor can be very beneficial in this regard.
In summary, always consider the need to take up your managers time. Their need to be informed and your need to get advice are both important. Constantly ask yourself if your awareness of self and others is accurate. And in the end, be sure to learn from every interaction.
"Engineering Management Thought of the Week" Jeff Glass 
Dr. Glass, I think this is an important point to make. I have seen several people suffer because they either asked too much or didn’t ask enough.
I think you hit the major important points. As an employee, you need to read and understand your manager’s expectations and how much they want from you. Thinking of two managers I have had in particular, one was particularly hands-off and let me manage myself, for the most part, while another expected me to constantly keep him updated. Though I preferred one over the other, I learned a lot from both.
There are also at least two reasons to ask questions of a manager. One is to establish expectations, especially during discussions and discussions of tasks. In these situations, I always try to ask my manager, for example, when he expects something to be completed.
The other reason I ask questions of my manager is to learn. I have only been in this industry for 6.5 years, and in my role for a little over a year, so I know there’s a lot I don’t know. Especially as a result of my experience as a project manager, I have learned how to use the strengths of those around me, and even those above me. On the other hand, ask too much and it appears you don’t have the knowledge or skill for a role.
Jordan, Thanks for the insights and examples. Great point that understanding expectations is a key reason for these discussions. Managing those expectations can be an important goal too.