Make Working With Multiple Managers Easier

Every boss comes to work with a unique background, personality, style, way of communicating, level 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. And some bosses are not formal managers or supervisors, but rather temporary project leaders or a lateral colleague from another team.

Regardless of their formal level of authority, to create the best working relationship with each boss—and therefore the best working conditions for you—understand how each boss works and customize your interactions accordingly.

This does not mean catering to the personal whims of each boss or accepting 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. The only way to learn what works and doesn’t is through routine, one-on-one conversations. As you meet individually with each boss, the differences between them will jump right at you.

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

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 to this boss?
6. When should you talk to this boss?

Together, these six questions can help create a focalizing lens through which to better understand the working relationships you have with supervisors and leaders.

1. Who Is This Boss at Work?

Don’t worry: You don’t need to ask yourself who this boss is deep inside. In fact, you shouldn’t try. All you need to find out is who this boss is when it comes to work and management.

Consider who they are at work so that you can adjust your approach accordingly:

• What is their position and reputation, and what are their responsibilities and other relationships?
• Where does this boss fall in the organizational hierarchy?
• Does the boss handle very important work?
• Does the boss work alone most of the time, or are they involved in various task forces or teams?
• Are coworkers fond of this boss, or have you heard them badmouthed by others?

This information will allow you to set expectations about your boss’s overall time and energy, and to strategize the best way (e.g., how, when, and for how long you should conduct your ongoing management conversations) to craft a strong, valuable relationship.

2. Why Do You Need to Manage This Boss?

The key to answering this question is to have a clear understanding of your goals for managing each boss and of what you need from that boss. Ask yourself:

• Do you need to clarify expectations?
• Do you want to learn about the larger context in which your work fits into the overall mission of your organization?
• Do you need to get more concrete schedules for your deliverables?
• Do you want a comprehensive work plan or step-by-step instructions for achieving your tasks?
• Do you need a better understanding of the resources necessary and available to you to do your job?
• Do you need feedback on your progress?
• Do you need to make course corrections in your performance?
• Do you want credit for your hard work or negotiate a special award, like extra time off, in exchange for delivering more or faster on your projects?

3. What Do You Need to Talk About With This Boss?

With every boss, you need to talk about the work. But when it comes to details, what you talk about with any boss ultimately should be determined by what you need to accomplish in the immediate future. For example, if you want help clarifying short-term priorities, then walk through your to-do list with that boss. If you want help improving your overall productivity, then talk about the number of items on your to-do list each day and ask for more assignments.

4. How Should You Talk with This Boss?

Some bosses respond best if you take an even-measured tone and stick to the facts. Some bosses respond best if you pepper them with leading questions. Some bosses respond best to effusive enthusiasm. Some bosses respond best to worry, fear, and urgency. If you pay attention, you’ll see that different bosses are more or less responsive to different manners and means of communication.

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5. Where Should You Talk to This Boss?

Whether it’s your boss’s office or some other obvious place to meet, it’s best to choose a place that is convenient for both of you, and then make a habit of meeting there every time. That space will become the physical scene in which your management relationship with that boss will develop.

Wherever you get in the habit of meeting, be sure to bring along an effective notetaking method to record the details of every conversation.

6. When Should You Talk to This Boss?

When considering what days and times to meet each boss, you are often limited by that boss’s schedule and your own. Sometimes, the time you meet is dictated completely by logistics. For example, if you work a different shift than your boss does, you may need to come in a little early or stay a little later to meet with them.

Maybe you have a boss who gets a slow start in the morning (or maybe you get a slow start), and so you decide it’s best to meet with that boss just before lunch instead of first thing in the morning.

Continue asking and answering these six questions about every single boss and stay tuned to that boss as each of you grows and develops. Keep in mind that the answers to these questions are going to change with time.