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Manage the Maze of Multiple Bosses: 4 Strategies to Work with Multiple Bosses Successfully

At first it seemed exciting. My fellow manager, Sara and I would be reporting to two Vice Presidents in the new division. Woo Hoo! VP Marco was new to the company with a stellar reputation for innovation. VP James had been with the company many years with solid achievements. Our first meetings went well. Sara and I were asked to look over our existing plans and be ready to present our results.

That’s when the fun began.

Marco came to our joint team meeting, engaged in some get-to-know-you conversation, said he understood where we were going, and participated in a team-building game.

James met Sara and me in his office – (based on his schedule blocked out in 15-minute chunks.) He grilled us for about 10 minutes and asked us for documentation, detailed project plans, and a weekly update.

OK. Two different bosses, two different styles.

Marco might show up any time, kibitz for a while, ask what we needed from him, and look for ways to smooth the way. He often organized social events for our two teams. He wanted a weekly one-page report with a few bullet points and lots of white space. When we met with him, he wanted us to come to the point quickly.

James was only available at the appointed weekly meeting, although if you could find a blank 15 minutes you could have a quick “emergency” session. Our reports for him had to be detailed, with references, graphs, charts, and hard data. He often said something like, “In the footnote on page 34 you said X. How does that jive with what you show on the graph on page A-7?

After every meeting, Sara and I would compare notes and share our frustrations. We realized we had to adapt to Marco and James quickly in different ways.


Four strategies to first cope with then succeed with different bosses.


Identify each bosses’ work and communication styles and flex your own. Each week we prepared two reports, one high level, one detailed. In the review meetings with Marco, we hit the high points and got out. We patiently explained every point in detail and double checked any work for inaccuracies and inconsistencies for James.


Proactively develop plans, schedules, and expectations in advance and get approval. Once we had concrete plans, James was comfortable going through the detailed results and confirming next steps. Marco saw the plans and schedules as a way for us to be fast and focused as we reported highlights and next steps.


Invite discussion not challenges using aligned assertive communication. Sara and I learned to think through ways of presenting information that did not set off confrontation inadvertently. We used inclusive language (us, we, our,) aligned with their situations and objectives, and phrased open-ended questions to stimulated dialogue. We stated our points straight forwardly, using a neutral or pleasant tone. Tension dissipated as we honed these skills.


Use problem solving to resolve conflict when it arises. When Marco or James differed strongly about our results or recommendations, we invited them (tactfully) to engage in some problem solving with us. At the very least, we got them to restate the problem clearly and concisely so we could work on solutions offline.


None of this was easy and it won’t be for you either. No matter where you sit in the hierarchy, when you have more than one boss you must be both flexible and firm. Flex to match your bosses’ individual communication and work styles. Be firm in working out a plan to accommodate their needs and get agreement. Be firm in showing places where overlapping demands make success unlikely and helping them recognize consequences. Be flexible in working out solutions.


Bonus Strategy: Scan the environment to assess what you are learning from working with multiple bosses. Both James and Marco taught me many important lessons I’ve applied successfully on other assignments. Once I stopped churning the frustrations and focused on recognizing each leader’s strengths, I was open to learning and growth. My results got better too.

Whether you’re an admin, project manager, supervisor, individual contributor, team leader or manager at any level, managing multiple bosses is a learnable skill your need in today’s workplace.

(c) Rebecca Staton-Reinstein and Advantage Leadership, Inc.

For more ideas on managing and leading successfully, check out Conventional Wisdom: How Today’s Leaders Plan, Perform, and Progress Like the Founding Fathers. https://www.advantageleadership.com/successstore

If you want more information about the Flex or Aligned Assertive approaches, drop me an email at Rebecca@AdvantageLeadership.com


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