Mastering the Art of Working for Multiple Bosses

Jan 24, 2019

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In the midst of catering to many masters, your work must get done.

If this sounds familiar, plan to take an hour out of your busy day to get some sound advice, practical tips and proven techniques to help make handling your job seem almost effortless.

This Webcast focuses on how to deal with more than one boss by helping you manage your workload, different personalities and expectations and your sanity while getting results on the job.

Attend and you'll hear:

  • Strategies for handling specific boss types
  • Ways to identify, acknowledge and accommodate boss preferences and differences
  • Tips for managing virtual bosses
  • Guidelines for chunking and clustering your tasks to maximize your productivity
  • How to initiate discussions with your bosses to clarify your role and manage their expectations on an ongoing basis

Question & Answer Session

Due to the overwhelming number of questions received during the Webcast Q&A session, Jennifer Kahnweiler graciously agreed to answer a number of additional questions following the Webcast.

1. How should people handle their bosses who don't agree on a process and you're caught in the middle?

I would try approaching them individually and telling them specifically how the different interpretations of the process are creating problems for you. Be Specific. Ask them to talk with each other to reach agreement and communicate their direction to you in writing. If this doesn't work then I would suggest scheduling a meeting ASAP with the three of you (face to face is ideal) where you can clear up confusion and get back on track.

2. How do I get other people to submit time sensitive information on time? I have deadlines and when I have not received their information it puts me behind in submitting my work load. I've done meeting markers, reminders and it still does not help.

It sounds like they feel no sense of urgency to comply. Are there any consequences for not complying ( i.e. name is listed publicly, boss is sent at e-mail, etc)? Do they understand the critical importance of providing it? If not, they will tend to see the task as a low priority and act accordingly. I suggest you talk to the late responders and find out what is preventing them for meeting these deadlines. Be prepared to make a persuasive case and emphasize their critical role in the outcome. Ask how you can support them. As a backup, ask your boss to send out a strong statement clarifying your role and emphasizing compliance with these deadlines.

3. Regarding a flex schedule ...what does one do to match the work style of a manager that is a procrastinator?

You can use this info to your advantage. If her procrastination is causing a problem for you by last minute requests let her know you need more lead time. Prepare a calendar of due dates and use this as a guide to keep her on track in advance of deadlines. This is true quadrant 2 activity (highly important and low urgency) that will keep you from living in quadrant I (highly important and high urgency).

4. My Boss is able to keep three to four things going on in his mind at one time. We may be talking about one subject and he tasks me with something then five minutes later asking questions—I assume it's on the same topic and often times its on a totally unrelated topic. How do I let him know we aren't on the same page?

This sounds like a style difference. You have learned that assuming you are on the same topic doesn't work. Ask him what topic he is addressing when you are not sure.
In your regular meetings take the time to offer him feedback about this behavior. We all have blindspots. Unless he is first aware of his behavior, he has little incentive to change. Try the "AEIOU" approach to bring up your request in a nonthreatening way.

Here is an example of what it might sound like:
Acknowledge— " I know you have lots of ideas and topics to share with me"
Express— " I want to make sure I support you in the best way possible. In our conversations, it is often hard for me to know when you have switched topics."
Identify (your proposal)—It would be easier if you could let me know when you have changed and switched to a new subject.
Outcome(benefits)—I believe this will help me to stay on task as we plan together.
Understanding—How does this sound?

5. Of all of my managers—six in all—five have never had an assistant. How do I teach them how to utilize me correctly?

Schedule time with each one to better understand their priorities. This will help you suggest tasks you can take on to make their lives easier. You can suggest they keep a running log of any jobs they can't stand doing. Training your bosses on how to leverage your talents is a learning process for both of you and will evolve as you produce concrete results.

6. I often am the "Go to" person for others in our office that I do not support. It often disrupts my schedule making it difficult to accomplish the things I need to do for my direct manager. Our office environment is open, so I can't close my door. How would you recommend I handle the others that are coming to me with questions or needing information?

Being the "Go To" person is a mixed blessing as you have discovered. While you gain visibility and help others your real work can suffer. Some suggestions: try facing your chair away from the line of sight. Using headphones or a phone headset can also send a message that you are busy and people will seek answers elsewhere. Preparing a sheet of faqs that you send out can prevent some questions and sending people to others for answers can help. Though it may be against your nature, you have to start protecting your time or the important work for your boss will not get done and then you will need your own go to person.



Jennifer Kahnweiler, PhD, is a global speaker and author based in Atlanta, GA, who is known as the “Champion of Introverts.” Her bestselling books The Introverted LeaderQuiet Influence and The Genius of Opposites have been translated into 16 languages.

Jennifer has spoken at hundreds of organizations, including GE, NASA and the U.S. Embassy in Vietnam. She is a highly regarded faculty member of the American Management Association and was the “Madrina” (Godmother) speaker at the Universidad Americana’s Commencement in Paraguay. Dr. Kahnweiler has been featured in the Wall Street Journal, the New York Times and Time magazine.