Most management conversations occur in an ad hoc manner -- during group meetings (even if many of the people present don’t need to be part of the conversation), in sudden emails and voicemails, in passing, or when a big problem desperately needs attention.
I call this phenomenon “management on-the-fly” or “management by special occasion.” There is no logic to the timing of most management conversations. In fact they are usually random, incomplete, and often too late to head off a problem or solve it before it grows large.
The only alternative to being subjected to “management on-the-fly” and “management by special occasion” is for you to get in the habit of having regular one-on-one management conversations with every boss you answer to.
How often you should meet with your boss (or bosses) depends on a range of factors. In an ideal world, maybe you would talk with every boss -- reviewing your work and getting set up for success that day -- every day. However, that may not always be possible. Every situation is different, but almost always, you should be meeting one-on-one with each boss more often than you are now.
If you are working with a boss for the first time, you should meet more often. If you are working with a boss on a new project, you should meet more often. If you are working with a boss on a project with especially high stakes, you should meet more often. If you are working with a boss on a project where there is a lot of uncertainty, then you should meet more often.
The last thing in the world you want to do is make bad use of a boss’s time by meeting more often than necessary or wasting time during those meetings. Keep your management conversations brief, straightforward and to the point. As long as you conduct these one-on-one conversations regularly, there is no reason they should be long and convoluted. The goal is to make these conversations focused, efficient, brief and simple. Prepare in advance so you can move the conversation along swiftly.
Once you’ve gotten into a routine with each boss, 15 minutes every week or every other week should be all you need. Like everything else, it’s a moving target. Over time, you’ll be able to gauge how much time you need to spend with each boss.
The fundamental goal of one-on-one meetings is communicating with your boss about the work you are doing for him. With each boss, decide what to focus on at each meeting. Before your meetings, ask yourself the following: Are there problems that haven’t been spotted yet? Problems that need to be solved? Resources that need to be obtained? Are any instructions or goals not clear? Has anything happened since we last talked that the boss should know about? Are there questions the boss needs to answer?
At the very least, in these one-one-ones, you should receive updates on your progress. Get input from your boss while you have the chance. And think about what input you should be providing to the boss based on what you are learning on the front line. Strategize together. Try to get a little advice, support, motivation and even inspiration once in awhile.