“What's the biggest problem you're dealing with here and how can I help you?”
- Sheryl Sandberg (attributed)
Start Interviews with Clear Alignment Questions
by Chip Conley on August 3, 2025
This question cuts through the noise to establish immediate value and alignment in any professional interaction.
Core Meaning
- Problem-first orientation: Prioritizes understanding challenges before offering solutions
- Service mindset: Positions you as a collaborator rather than just a job-seeker or vendor
- Practical empathy: Shows you care about their actual struggles, not just abstract concepts
- Value proposition: Immediately frames the conversation around how you can be useful
Why This Matters In Product
- Customer-centricity: Mirrors the ideal product development approach of solving real problems
- Stakeholder alignment: Creates shared understanding of priorities before diving into solutions
- Resource allocation: Helps focus limited time and energy on what matters most
- Trust building: Demonstrates you're interested in solving their problems, not just pushing your agenda
How To Apply
For product leaders:
- Use this question in stakeholder meetings to cut through politics and focus on impact
- Ask it of your team members to understand their blockers and provide meaningful support
- Frame product strategy discussions around solving the biggest problems first
For individual contributors:
- Begin user research sessions with this question to get to meaningful insights faster
- Start cross-functional collaborations by understanding what's blocking your partners
- Use it in career conversations to demonstrate your value-add mindset
This simple question transforms interactions from transactional to collaborative, creating space for meaningful problem-solving rather than performative conversations.