Boss management is in important work skill. The need to communicate a particular item through a face-to-face meeting can fall into three general categories:
- Urgent information he must know as soon as possible
- Things that need to be resolved today
- Things that can wait until a good time
Each of these needs to be handled slightly differntly.
If it can wait until he has some free time, simply send him a meeting request using the first available free moment you see in his calendar. Make sure to specify the topic. If there is some infomation he needs to see in prepartion for the meeting attach it to the meeting request or send and email with the attchments or links to where the information can be found.
Things that need to be resolved today require a bolder approach. First, know how you boss likes to communicate. When he is in meetings or on calls, does he read his emails or use IM? If so send him a quick note describing the situation and why it needs to be discussed today and asking him to make a time to squeeze you in. The magic words to use are: "If this doesn't get resolved today, we may not be able to meet the deadline." Do not however use those words unless they are true. No one listens to the boy who cried wolf.
If he doesn't checks his emails or IM during a meeting, you may need to get a bit more creative about finding out when the meeting will end and conveniently being near the conference room when it does, so you can ask him when he can give you the time you need. Make sure to tell him how much time you need in your request. If I need only five minutes or less, my boss will often go to the next meeting just a little late.
Finally there are genuinely urgent issues. These are typically only involving either issues concerning things already in production or upset clients. I make it a rule to never let my boss get blindsided by urgent issues that he hears about from someone higher in the organization than he is. So if he is on the phone, knock on his door anyway and go in and say, "I'm sorry to disturb you but such and such has come up." Sometimes I write those words down, so the call isn't disrupted if he is on speaker phone. I don't often know what his call is about or how urgent it is, so I then let him determine if the call or my issue is more critical. Normally my boss will either tell the call that something has come up that he has to deal with and set the meeting to be completed later or he tells me something like, "This call will be done in five minutes, I'll come get you when I'm off." In the second case, I leave until he can get back to me.
Same thing if he is in a meeting. I will knock on the door, open it slightly and say, I need to talk to _. Usually the manager then comes to the door and I tell him the problem and the urgency and he decides to leave the meeting or not. The key to this is not disrupting the meeting unless the issue is genuinely urgent. The server room is on fire is urgent. You have to leave right now because your spouse died is urgent. The CEO is going to want to talk to you about why client XYZ is upset as soon as you are free is usually urgent. I need a decision on XYZ that isn't due to production for three weeks is not.
If you are having trouble connecting well with your boss, it is possible that you and he have different ideas about the urgency of the issues you want to discuss with him. Perhaps you need to have a meeting to discuss how he would prefer to be contacted and what issues he would see as urgent enough to interrupt him.