A good relationship with your boss can help your job (or your thesis, if you are in grad school) and your career more than most things, and a good 1×1 is the most frequent substantive interaction most people have with their bosses.

Your 1x1s should make you comfortable with how your boss thinks about the work environment and your role in it.  If your 1x1s go well, nothing in your annual performance review, with the possible exception of how you rank versus your peer group, should be a surprise to you.  So how do you have a good 1×1?

The first step is to align your expectations.  Especially if you have not worked with your boss very long, ask what s/he wants from your 1x1s: how often s/he wants them, how long they should last, what topics s/he would like to cover.  Your boss should also ask you want you want from them, but if s/he doesn’t, you should tell your boss that, at a minimum, you want to convey what your boss needs to know about your current work to feel comfortable with your progress (which means you need to know what that is); what you should be learning about your team, your company, and your industry; and what changes or developments you should be preparing for in the short- to medium-term (say six months).

Once you have your 1x1s scheduled and your expectations aligned with your boss’s, come to your 1×1 prepared: have all the data you need to explain to him or her how your work is going, and what is going on around your work that your boss needs to know about.  Come with a brief list or set of notes about what your boss needs to know.  It’s not always possible but always helpful if you can block off the half-hour before your 1×1 to prepare for it, so you aren’t rushing from the previous meeting to your 1×1.

A common mistake many employees make is going to their boss with a problem and a request that s/he solve it.  Remember, your boss hired you to solve problems.  Sometimes you will need your boss to help out, but you should never tell your boss something for the first time and ask him or her to fix it for you.  Instead, you should be keeping your boss apprised of the problem over time and what you have already done about it:

• (first 1×1 in which the problem is called out) “I’m foreseeing a problem here; networking is overcommitted and can’t tell me when they’ll get to our project, though I have been asking for two weeks”
• (second 1×1 in which the problem is called out) “escalating the problem to the manager didn’t help, and his manager is unresponsive”
• (third 1×1 in which the problem is called out) “I’ve been talking to five different people in that group and nobody has been able to help, and we looking at a 4-week delay if this isn’t resolved: what do you recommend I do next?”

With the context of the first two interactions, the last request is the kind you should be making of your boss, who can advise you what to do and who may or may not step in.

You should also be discussing your career development with your boss, but not in every 1×1.  You should ask your boss if you can set aside some time from your 1x1s every month or six weeks – less often and you will both forget – to discuss your next steps in your career: what skills you should be learning, what you should be reading, and how you are progressing against any specific objectives from your last performance review, if you had one.  These conversations can occur as one of the agenda items in your regular 1×1 but generally are more useful if they are in dedicated conversations, when you are not both focused on the importance of delivering your current work.  You should review how you are progressing against the development objectives from your performance review, if you had one, and if you do not have objectives, you and your boss should create them together.  The way you keep track of and actually do this is to schedule career-development 1x1s via a regular calendar invitation.

Unless you work on a very small team or in a small company where you all see each other constantly, after every 1×1 in which you have been directed to do a specific thing, write a quick confirming email to your boss and cc yourself: “Thanks for your time today.  Per your advice, I’ll be escalating the situation with networking, and if I haven’t resolved it by next Friday, I’ll ask you to step in.”

Here’s another post on bad 1x1s with generally good bosses, and here’s a post on 1x1s with bad bosses.  In the meantime, you can find a lot of additional information about dealing with your boss in my book, available in paperback or ebook from Amazon and as an iBook.