Five quick questions for better strategy

Overview
This Substack post by Jeff presents a concise framework of five quick questions that technical leaders can use to assess the quality and relevance of their strategy. The questions are designed to surface hidden assumptions, clarify objectives, and identify gaps in execution without requiring a lengthy analysis.

Key Takeaways

• Simple, repeatable questions help keep strategy grounded in reality.
• Regularly revisiting these questions prevents drift and misalignment.
• The framework encourages rapid feedback loops between leaders and teams.
• It can be applied to product roadmaps, engineering initiatives, or organizational direction.
• Asking the right questions early saves time and resources.

Who Would Benefit

• Engineering managers looking to align team work with company goals.
• Technical founders needing a quick sanity-check on strategic decisions.
• Senior leaders who want a lightweight tool for strategic reviews.
• Product owners responsible for roadmap prioritization.
• Anyone in a leadership role who wants to improve strategic clarity.

Frameworks and Methodologies

• None specific, but the questions complement OKR and Lean principles.