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Manage Your Boss Every Day – The Basics of One-on-One Meetings [part 2]

By Bruce Tulgan, excerpted from Its Okay to Manage Your Boss

This is part two in the It’s Okay to Manage Your Boss series. You can find part one here.

Are you spending too much time dealing with your bosses? It might seem like that. But the reality is exactly the opposite: The problem is not that you are spending too much time with bosses, but rather, you are not spending enough time dealing with them in the right way. Most managers and non-managers alike are so busy juggling their various responsibilities that they don’t usually make time for regular management conversations. Instead, most management conversations occur ad hoc: Maybe during group meetings – even if many of the people present at the meeting don’t need to be part of that conversation – in sudden emails and voicemails; in passing; or when there is a big problem that desperately needs attention.

I call this phenomenon “management on-the-fly” or “management by special occasion.” In this scenario, there is no systematic logic to the timing of management conversations, in fact they are random; incomplete; and often too late to avoid a problem or solve one 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. The hard part is actually getting in the habit of making time every day to manage your bosses. New behaviors, no matter how good they are, often don’t feel comfortable until they become habits. It will take time to get used to the new behaviors, not just for you, but also for the bosses you are going to manage more closely.

So take the initiative. Schedule regular one-on-one management meetings with your bosses.

When, How Often and for How Long?

How often you should meet with your boss or bosses depends partly on the nature of the work you are engaged in with each of them. How often you should meet with a particular manager will also be determined by his or her particular style and preferences and also by what works for you. In an ideal world, maybe YOU would talk with every single boss— reviewing your work and getting set up for success that day—every single day. Some bosses need more attention than others. Talking to every boss every day is not always possible and may not be the ideal. In fact, every situation is different, but most of the time the short answer is that you should be meeting one-on-one with each boss more often than you are currently.

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-one-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 that you can move the conversation along swiftly. Once you’ve gotten into a routine with each boss, fifteen minutes every week or every other week should be all you need. Like everything else, it’s a moving target. Over time, you’ll have to gauge how much time you need to spend with each boss.


What Should You Talk About in One-On-Ones?

The fundamental goal of one-on-one meetings is communicating with your boss about the work you are doing for him or her. Over time, you and your boss will use your growing knowledge of each other to guide YOU during each conversation. But in general, you’ll talk about the work that is going well, poorly, or just fine. Maintain an ongoing dialogue with every boss about the four management basics:

  • What is expected of you.
  • The resources you need to meet those expectations.
  • Honest feedback on your performance and guidance on how to adjust it as necessary.
  • What credit and reward you will earn for your hard work.

At the very least, in these one-one-ones, you need to 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, yes, even inspiration once in a while.

If You or Your Boss Work in a Remote Location?

Some bosses are harder to stalk than others. These days it is increasingly likely that you or your boss might work from home, an office across town, or a client location across the world. I’ve heard countless stories from very determined boss-managers who’ve had to stalk their bosses from remote locations, calling every fifteen minutes until the boss finally answers. Or texting. Or faxing. Or Facebook messaging. Scheduling two-way web-cam conferences. Even showing up on-site at the boss’s location to try to get some one-on-one time.

I hope you are not in that situation.

The best situation is for you and your boss to work out a protocol for a regular schedule of one-on-one meetings whenever you can. Here are some best practices that you can apply if you don’t work in the same location as your boss:

  • Keep each other informed about when you’ll both be at a central location, such as the organization’s headquarters, so you can schedule in-person one-on-one time.
  • Schedule occasional in-person meetings when it is convenient for you to visit your boss in his or her remote location or when it is convenient for your boss to visit you where you work.
  • If you have access to web-cams, schedule a regular one-on-one meeting via the web.


In the absence of in-person meetings and two-way web-cams, make good use of regular telephone conferences and email. Unfortunately, too often when people communicate primarily via telephone and email, they neglect scheduling regular one-on-one conversations and, as a result, their communications tend to be disorganized, incomplete, and random. Here are some best practices for using telephone and email to communicate regularly with your boss:

  • Schedule regular one-on-one telephone calls, then honor them.
  • Prepare in advance of the one-on-one call. Send your boss an email recapping what you’ve done since your last one-on-one and the steps that you followed to get those things done, and any lingering questions or issues you have about those actions. Then outline what you plan to accomplish next, the steps you plan to follow, and any questions you may have about these upcoming actions.
  • Ask your boss to respond to your email in advance of your one-on-one conversation to help you prepare even further, for example, by including any other items in the agenda that he or she would like to cover.
  • Send your boss a reminder via email or text message 30 or 60 minutes before the scheduled one-on-one.
  • Immediately following the call, send your boss an email recapping what you both agreed on in your conversation: the actions you need to take, the steps you plan to follow, the date and time of your next scheduled phone call, and the promise to send an agenda prior to the next meeting.

I know you are busy. Your bosses are busy. Nobody has enough time. That means you don’t have time not to manage your bosses. Dedicate time every day to manage your bosses, make it a rigorous habit, and it will start to pay off almost immediately!

About the Author

Bruce Tulgan is an adviser to business leaders all over the world and a sought-after keynote speaker and seminar leader. He is the founder and CEO of RainmakerThinking, Inc., a management research and training firm, as well as RainmakerThinking.Training, an online training company. Bruce is the best-selling author of numerous books including Not Everyone Gets a Trophy (Revised & Updated, 2016), Bridging the Soft Skills Gap (2015), The 27 Challenges Managers Face (2014), and It’s Okay to be the Boss (2007). He has written for the New York Times, the Harvard Business Review, HR Magazine, Training Magazine, and the Huffington Post. Bruce can be reached by e-mail at, you can follow him on Twitter @BruceTulgan, or visit his website