So, I work with a lot of different "managers" / "bosses" at work. Maybe I can be of some assistance. Here are some tips that I've developed after breaking out of my new-guy phase... (based on what I see a lot of "new guys" doing wrong as well).

• Don't apologize for every little thing that goes wrong. No manager should feel like they need an apology for virtually any reason and apologizing for stuff makes you look spineless.

• Along the same lines, when it comes to delays in the project don't provide unnecessary explanation about what is going on, nor should you point the blame at anyone or anything else. Most often, what they care about is when the next task will be done. So, if you can, open with "it should be done by ______". If they need an explanation of why it's taking so long, then tell them in a brief format and let them know you're doing whatever you can to move things along.

• Speak less and listen more.

• When delivering work product, use minimal but effective explanation where necessary (i.e. don't be overly wordy if it's not necessary). Focus on the results and the impact from the results.

• If something isn't going right with the project and you need to let a manager know things aren't going to work out, before you go running to them, think about some potential options for keeping the project moving forward. This kind of thinking and action is the kind of behavior that managers get from their top performers and tends to lead to good things for employees who master it.

• Don't assume the manager has read your email, ever, unless they have responded to it.

• You interact with managers like any coworker but respect their time. If you need to talk to them, open with "is now a good time" etc. If they never have a minute to talk to you, then let them know you need to schedule something with them.

• Boundaries seem to come into play most often when it comes to Employee X wants to leave work at a reasonable time and Manager Y needs something done ASAP. Well, to be honest, I guess I am not very good with boundaries. I typically do whatever it takes to get tasks done, but if you can't then the key is to be able to provide options for what can be done (and/or who can do it) in your absence.

• IMO the best way to deal with notoriously DIFFICULT bosses who have difficult requests is to be reasonable and responsive to their seemingly insane requests. For example, they give you a task that takes a week and they want it done TODAY. Don't open with how it cannot be done. Focus on what deliverable work product you can produce in one day, package it nicely and send it off to them. This is being both reasonable and responsive. Provide what next steps need to be done to achieve their ridiculous request. Usually, once they see some work product, they have an idea how to proceed and will come to their own conclusion that either (a) they want to proceed along the same lines, or (b) they want you to stop working on it. If they should get frustrated that it is not done within the day, you can let them know that after digging further into the issue, you have determined that it will require more resources and possibly more people to get the task done.

• The best way to get what you want is, simple as it seems, be assertive and be able to respectfully justify yourself in an adversarial setting. If you want a raise you should have a good justification for why your work product was valuable in the past 12 months. If they don't agree and you feel like you're stagnating, it's time to find a new job. If you want training then provide them with a value proposition, tell them how much it will cost in terms of money and time and why this cost is worthwhile to the company.

• Remember managers are humans too, and they have their own strengths and weaknesses. A good team member like yourself can be a better team player if you help compensate for their weaknesses and make the most of your managers' strengths.