Navigating Conflicting Directives

In Q2 of 2022 at Dropbox, I found myself in the middle of a tension that’s common in large organizations: conflicting directives from leadership. My group was focused on collaboration within teams, spanning across the Pro SKU, Business Standard, and Enterprise. At the start of the quarter, my PM partner was advised to divest from Enterprise clients and lean toward short-term revenue. Meanwhile, my boss instructed me to go deeper into Enterprise and invest in a new admin experience. Both perspectives had merit, but they pointed us in opposite directions.

Diagnosing the Conflict

The misalignment surfaced in a team leads meeting. My PM partner and I compared notes and realized that what our respective leaders were asking us to prioritize didn’t line up. When we raised this misalignment, stakeholders asked us to demonstrate a feasible path forward rather than just flag the problem.

Digging deeper, we uncovered a few important dynamics. A senior architect was advocating for the admin opportunity and had the ear of my boss, partly through past backchannel conversations. At the same time, company goals were clearly oriented toward short-term revenue. The disconnect wasn’t just about strategy—it was also about communication breakdowns and a lack of clear roles.

Actions to Move Forward

The first step was to repair communication. I sat down with the senior architect and clarified roles and responsibilities: I would remain accountable for strategy, and he would be responsible for execution. That created much-needed clarity.

Next, I worked with my PM partner to reestablish priority. We were able to align stakeholders on the importance of short-term revenue, but there was no agreement on the right approach. To break the deadlock, I proposed a compromise: give the architect a three-week runway to see if the admin initiative could be broken into smaller pieces that might generate faster revenue. We allocated DS and PMM support for exploration, while also pushing forward with PMs and design leads on expanding paid security features, which had clearer near-term upside.

Results and Lessons

The architect ran lightweight concept testing with smaller enterprise clients, partnered with PMM for customer conversations, and collaborated with DS on data exploration. Despite the effort, we didn’t find a credible short-term revenue path. With evidence in hand, we communicated our recommendation to divest from Enterprise and refocus on nearer-term opportunities.

“Sometimes leadership isn’t about choosing a side—it’s about creating a path to test both and letting the evidence guide the decision.”

This experience reinforced a few lessons for me. First, misalignment often stems from communication gaps as much as from strategy itself. Second, defining clear roles and responsibilities helps build trust and avoids power struggles. And finally, when faced with conflicting directives, creating a structured way to test assumptions not only brings clarity, it helps stakeholders feel heard—even if their preferred path isn’t the one pursued.