Handling multiple bosses can feel overwhelming—especially when they don’t communicate well with each other. But this tricky dual-reporting situation is also an opportunity to sharpen skills like communication and prioritization. Here’s how to navigate the challenges and get everyone on the same page.

Spot the sneaky signs of disconnection. Notice subtle misalignments, like conflicting updates or inconsistent project names. These early warning signs can help you prevent minor misunderstandings from turning into major issues down the road.

Get ahead of conflicts. Proactively ask your bosses how they’d prefer to handle competing priorities or conflicting directions. Questions like “When I’m getting different directions, would you prefer I flag that in our one-on-ones first, or should I suggest a three-way conversation right away?” can set expectations up front.

Bring visibility to decision-making. Document priorities in a shared location to track tasks and decisions. Review it in one-on-ones to highlight conflicts—for example, “Should I adjust this deliverable to accommodate the new task?”

Be the bridge. Schedule monthly or quarterly check-ins to align your bosses. Frame them as time-savers by saying something like, “Let’s reduce back-and-forth by touching base quickly.” When conflicts arise, take the lead in organizing a joint discussion.

Highlight the impact. Explain how misalignment affects outcomes, like delays or rework: “We spent hours redoing tasks last week. Clearer coordination up front could prevent this.” Keep the tone constructive and solution-focused.
This tip is adapted from “When You Have Two Bosses—and They Don’t Talk to Each Other,” by Melody Wilding.
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