Manage Each Boss Differently

The best way to fine-tune your approach to each boss is to continually ask yourself six key questions about each one.

You answer to so many people at work on a daily basis that sometimes it’s hard to say exactly who your actual “boss” is. In many ways, clients and customers are your bosses. Colleagues in other departments who need things from you—so called “internal clients and customers”—are also your bosses. And there are plenty of big shots at work, who may or may not interact with you daily, but are obviously among your bosses: managers above you or your boss’ bosses; bosses on other shifts; bosses in and outside your areas; and bosses on your and other teams. Ultimately, you answer to all of these bosses.

Indeed, it helps to think of your relationships at work as customer relationships and, therefore, as relationships in which you answer to them as if they were your bosses. After all, work is a transactional relationship. You are getting paid with a salary and maybe non-financial rewards such as vacation or flexibility in your schedule in exchange for your time and effort. If you are trying to do a “great job” at work every day, then you answer to everybody and try to please them all. When you do that, it inevitably results in competing—maybe conflicting—needs, expectations, requests, and demands on your time. You probably already have too much work on your plate from too many bosses all the time. Plus, you need to keep straight the different work standards and management practices of each “boss.” That’s a lot to balance and coordinate day after day.

No matter how many bosses—formal and informal—you answer to, your goal should be to maintain a high-quality management relationship with every one of them.

Establish a Regular, Well-Functioning One-On-One Dialogue with Every Boss

Because every boss is different and has his or her own style, preferences, and habits when it comes to managing, the best way to maintain a high-quality relationship with him or her is by establishing ground rules up front. At the outset of your relationship, have a conversation outlining how you are going to work together. There are probably some corporate or organizational policies in place that already define some aspects of your working relationship. Clarify exactly where, when, and how you are going to observe and practice those policies whenever you are working on any tasks or project. Make a commitment to follow these practices and then take responsibility for following through on them.

You also need to discuss up front some of the broader goals you have for working together, such as maintaining certain levels of productivity and quality standards, making a valuable contribution, and achieving measurable results. You might even discuss subtle rules of conduct that are expected of you, such as work hours, attitude, attire, making personal calls at work, etc.

But the most important thing you need to agree upon from the get-go is how you plan to communicate with each other. Make sure you discuss scheduling regular ongoing conversations about work and confirm the following goals for every conversation:

  • Walking away with a mutual understanding of what the goals of an assignment are
  • Spelling out guidelines and parameters
  • Specifying a clear timeline of deliverables

Suggest that you make a habit of asking each other clarifying questions and discussing step-by-step instructions for any new task. Finally, try to agree that you will each take notes and check at the end of each conversation that you are on the same page.

Customize Your Approach to Every Boss

Your various bosses come to work with different backgrounds, personalities, styles, ways of communicating, work habits, motivations, levels of ability and skill, and accomplishment. Some of them are more engaged than others. One boss wants to spell out every detail for you, while another boss expects you to figure out everything on your own. In order to create the best working relationship with each boss, you learn and understand how each boss works and customize your approach for each of them accordingly.

I’m not suggesting you cater to the whims of each boss or go happily along with downright bad management practices. But understanding their whims and management weaknesses is not all bad. When you know the whims and management weaknesses of a boss, then you have more tools in your arsenal of solutions with that manager. The only way to learn what works and doesn’t with each boss is through those one-one-one management conversations. As you meet individually with each boss, the differences between them will jump right at you. Over time, you’ll be able to tune in to that boss and adjust your approach as needed. The best way to fine-tune your approach to each boss is to continually ask yourself six key questions about each one:

  1. Who is this boss at work?
  2. Why do you need to manage this boss?
  3. What do you need to talk about with this boss?
  4. How should you communicate with this boss?
  5. Where should you talk with this boss?
  6. When should you talk with this boss?

Together, these six questions make up a powerful tool for customizing your approach to each boss. I call it the “customizing lens.” If you become obsessed with asking and answering these questions, you won’t be able to avoid customizing your approach with each boss.

Bruce Tulgan is an adviser to business leaders all over the world and a 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. Tulgan is the best-selling author of numerous books, including “Not Everyone Gets a Trophy” (revised and updated, 2016), “Bridging the Soft Skills Gap” (2015), “The 27 Challenges Managers Face” (2014), and “It’s Okay to be the Boss” (revised and updated, 2014). He has written for The New York Times, the Harvard Business Review, HR Magazine, Training magazine, and the Huffington Post. Tulgan can be reached by e-mail at; followed on Twitter @BruceTulgan; or via his Website,



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