Can you describe a time when your pitch to leadership was unsuccessful?

Question

Can you describe an experience where you attempted to present an idea or proposal to leadership, but it did not go as planned? Please include details about the situation, your approach, the challenges you faced, and the lessons you learned from the experience.

Accepted Answer

Certainly! Presenting to leadership can be a challenging endeavor, especially when the outcome is not as expected. Here's an experience that illustrates such a scenario:

**Situation:**
I was working as a product manager at Uber, focusing on improving user experience for our app. We identified a potential feature that could streamline the ride-hailing process by utilizing machine learning to predict user destinations based on previous trips and current location context. I believed this feature could enhance user satisfaction and potentially increase ride frequency.

**Approach:**
I thoroughly researched and prepared a detailed proposal, showcasing data-backed projections of increased user engagement and highlighting technical feasibility. I arranged a meeting with the leadership team, including the head of product and several senior executives, to pitch the idea.

**Challenges Faced:**
During the presentation, I faced several unexpected challenges. Firstly, I underestimated the leadership's focus on current operational priorities, as they were more concerned with immediate operational metrics rather than long-term enhancements. Secondly, some executives had concerns regarding user privacy and data security, which I hadn't addressed comprehensively in my presentation, thus shaking their confidence. Lastly, the discussion revealed that a similar concept had been attempted in the past but hadn't taken off due to technical limitations at the time, a historical context I wasn't fully aware of.

**Lessons Learned:**
From this experience, I learned the importance of aligning my proposals with the company's current strategic objectives and being thoroughly prepared to address potential concerns, particularly around security and privacy, which are paramount at Uber. Additionally, I realized the value of understanding past initiatives thoroughly to ensure my proposals are informed by previous learnings. I now place greater emphasis on engaging stakeholders from different departments early in the proposal process to gather diverse perspectives and preemptively address potential challenges. This experience ultimately enhanced my ability to tailor pitches to different audiences and anticipate questions more effectively, which has led to more successful presentations in subsequent attempts.

Can you describe a time when your pitch to leadership was unsuccessful?

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