Describe a time when you advocated for a technical investment that had long-term business value.
Why This Is Asked
Interviewers want to see that you can champion important but non-urgent work—making the business case for technical investments that don't have immediate ROI. They're looking for persuasion skills, persistence, and the ability to translate technical needs into business language.
Key Points to Cover
- The specific investment and why it mattered for the business long-term
- How you built the case and presented it to decision-makers
- How you addressed skepticism or competing priorities
- The outcome—did you get buy-in? What was the impact?
STAR Method Answer Template
Describe the context - what was happening, what team/company, what was at stake
What was your specific responsibility or challenge?
What specific steps did you take? Be detailed about YOUR actions
What was the outcome? Use metrics where possible. What did you learn?
💡 Tips
- Choose an example where you successfully influenced the decision—or where you learned from not getting buy-in
- Emphasize how you framed the investment in business terms (risk reduction, future velocity, cost avoidance)
✍️ Example Response
STAR formatSituation: At a Series B startup, our monolith was becoming a bottleneck. Deployments took 45 minutes, and a single bug could take down the entire platform. I believed we needed to invest in a service decomposition and CI/CD overhaul, but the CEO was focused on growth and saw it as "engineering wanting to rewrite everything." The CFO was skeptical of any project without immediate revenue impact.
Task: I had to make the business case for a six-month technical investment that wouldn't show customer-facing results until the end.
Action: I built a cost-of-inaction analysis. I quantified: average of 2 production incidents per month, each costing roughly 4 engineer-hours in firefighting and an estimated 3% churn risk during outages. I projected that over 18 months, the status quo would cost more in lost productivity and risk than the investment. I also framed it as "unlocking velocity"—after the migration, we could ship features 2–3x faster. I presented this to the leadership team with a phased plan: Phase 1 (CI/CD and observability) would show results in 8 weeks. I offered to tie my team's OKRs to both the migration milestones and feature delivery, so we'd be accountable for both. I found an ally in the VP of Product, who was frustrated by our slow release cycle.
Result: We got approval for Phase 1, delivered it on time, and used the improved deployment metrics to secure buy-in for the full migration. Within a year, we'd reduced deployment time to under 10 minutes and cut production incidents by 60%. I learned that technical investments need to be framed in business language—risk, cost, and future capability—and that early wins build credibility for larger bets.
🏢 Companies Known to Ask This
| Company | Variation / Focus |
|---|---|
| Amazon | Think Big, Frugality — "Tell me about a time you convinced leadership to invest in something non-obvious" |
| Stripe | Infrastructure investment, technical judgment |
| Microsoft | Growth mindset |
| Netflix | Freedom & Responsibility, judgment |
| Apple | Long-term thinking, excellence |
| Uber | Ownership, entrepreneurship |