Lev’s promotion to senior project manager came with an unexpected challenge. Although he continued to report to his functional boss, Gina, the head of product development, he now also answered to a project-specific boss, Navin, the leader of a critical new software implementation. This dual reporting structure was meant to speed up delivery, but Lev soon noticed that his two bosses hardly talked to each other. He often found himself relaying information between them, trying to align conflicting priorities and navigate different directives. Situations like Lev’s aren’t just frustrating — they’re becoming increasingly common. Gallup data finds that over 72% of U.S. employees work in a matrixed organization to some extent, giving way to org charts with dual reporting lines. The rise of cross-functional and project-based work means workers may also answer to project leaders, regional heads, or client partners in addition to their official managers. Keeping one boss happy is tough enough. Add a second to the mix and suddenly your job description includes extra, unanticipated coordination and influencing. There’s no question that managing up to multiple bosses isn’t easy. But the very things that make it challenging — navigating different communication styles, negotiating workloads , building consensus — are exactly the skills that will set you apart in your career now and in the future if you play it right. So, what do you do when you’re caught between two leaders who don’t talk? The answer isn’t cc’ing each of them on every email or throwing up your hands and saying, “Both of you figure this out!” Here’s how to create alignment while also getting the support and clarity you need. Spot the Sneaky Signs of Disconnection Sure, it’s obvious your bosses aren’t communicating enough when they schedule you for two different meetings at the same time. But there are often subtler signs that go unnoticed until they create headaches. For instance, do you find yourself explaining (and reexplaining) basic context in every meeting? Do you notice your functional manager still refers to an initiative as “Project X” while other collaborators started calling it something else weeks ago? Look out for mixed messages around timelines and resources as well. Maybe one boss casually mentions you’ll be working with Mariana from operations next quarter, while your other boss already knows Mariana is being transferred to a different department. You may also notice that each leader has a distinctly different view of what “high priority” means for your deliverables. These small disconnects are like early warning signals. Catch them early and you can prevent minor misunderstandings from spiraling into major problems. Get Ahead of Conflicts Be upfront with both bosses and acknowledge that disagreements and communication breakdowns will happen. It’s not a matter of if, but when. Bringing this up could sound like: “I’m excited about working with both you and David. Can we talk about the best way to share information between us?” “I’ve learned matrix structures work best when we’re intentional about our communication. Since I’ll be reporting to both teams, what’s your preferred way to handle competing priorities when they come up?” “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?” Some leaders might push back with “We’ll figure it out as we go” or “It won’t be an issue.” Try role-playing with a concrete example: “Next month we have both X and Y due. How do you want to allocate resources?” Show you’re thinking about how to make this arrangement work for everyone. Bring Visibility to the Decision-Making Process Don’t simply hope your bosses will somehow sync up. Create a master priorities document that’s shared with both managers, along with which leader decided what and when. Review this log in your one-on-ones with each boss, asking for corrections or additions. This keeps each leader informed and highlights any conflicts. Plus, when one boss adds something urgent, you can calmly refer to this list and say, “Looking at my current priorities list, I’m scheduled to deliver the audit to Vicky tomorrow and the vendor review to you on Thursday. Which of these should I deprioritize to make room for this new task?” Be the Bridge Sometimes you need to get everyone in the same room (even if it’s a Zoom room ). While your bosses might resist “yet another meeting,” frame it as eliminating time-wasting back-and-forth. A monthly or quarterly touch-base can head off dozens of issues before they start. When urgent miscommunications do arise, take the lead to schedule an ad-hoc session. For example, “Instead of me playing messenger, let’s hop on a quick call with the three of us to sort this out. I’ll grab 30 minutes in everyone’s calendar.” In these meetings, present concrete options your bosses can decide on: “If we push out the donor outreach campaign, we can focus on the grant. But if we want to focus on donor outreach now, we’ll need to request a grant extension. Here’s how either choice affects our fundraising targets…” Make the Costs Clear Your bosses may not realize how much their lack of communication is affecting you or others. You have a responsibility to highlight the impact — not to complain, but to justify why better coordination matters. Keep the tone constructive and solution-focused and when possible, tie it to metrics they track: delayed launches, duplicated expenses, missed opportunities, or team burnout. For example, “We spent five hours last week redoing work because we had different interpretations of the requirements from each department. If we could get on the same page upfront, we’d save a lot of time and resources.” Humans are highly motivated to avoid losses , which is why showing what’s at stake can often provide the push they need to change. While challenging, managing multiple bosses who don’t communicate is a skill you can master — and it’s one that will serve you as you grow in your career.