Questions like this are often asked at Amazon to assess a candidate's fit with Amazon's Leadership Principles.
I will be answering the PM interview question: "Tell me about a time when you had to make a decision to make a short-term sacrifice for a long-term gain."
The Initial Situation
Let me tell you about a time when I was leading the development of a billing application, a critical part of the platform that the first enterprise customer needed to be fully onboarded into the platform. There was an ambitious launch date set for July 1st - the start of Q3. What initially seemed like a straightforward new system implementation became significantly more complex when I learned that our client planned to deprecate their existing product around the same time.
The Complexity Revealed
The billing system wasn't just about processing new transactions - it needed to handle multiple complex fee schedules:
- Monthly fees in arrears,
- Monthly fees in advance,
- Quarterly fees in arrears,
- Quarterly fees in advance.
Additionally, we now faced the unexpected challenge of migrating historical data from the client's legacy system—a requirement that hadn't been part of the original scope.
The Short-Term Sacrifice
Recognizing the potential risks, I knew I had to make a difficult choice. This meant having several challenging conversations with key stakeholders: My immediate manager, CPO The COO The customer success manager overseeing the account I had to carefully explain the different interpretations of what a "launch" could mean in this context, and why rushing to meet the July 1st deadline could lead to serious problems down the line.
The Decision and Its Implementation
Instead of rushing to meet the original deadline, I advocated for a phased approach:
- First, ensuring the accurate migration of historical data
- Then, implementing and testing the various fee calculation methods
- Running two systems in parallel until we get consistent data
- Finally, launching the complete system and deprecate the existing one only when we were confident in its reliability
The Long-Term Gains
This decision, while initially disappointing to stakeholders, led to several positive outcomes:
- A more robust and thoroughly tested billing system
- Identified issues with fee schedules that the client currently had in their existing application, saving them about 3.5% of their fees.
- Preserved data integrity from the legacy system
- Enhanced stakeholder trust through transparent communication
- Avoided potential financial errors that could have damaged client relationships
Key Lesson Learned
The most valuable lesson from this experience was that sometimes the bravest professional decision is to say "no" to an unrealistic deadline. While it's tempting to try to meet an already communicated timeline, the true measure of success lies in delivering a reliable solution that serves long-term business needs. Leadership isn't just about meeting deadlines - it's about having the courage to make difficult decisions that prioritize quality and reliability over speed when the situation demands it. This experience taught me that transparent communication about challenges and realistic timelines, though sometimes difficult in the short term, builds stronger trust and better outcomes in the long run.