Back tostdlib
Blog Post

TBM 217: Why Are You Doing This? (Wrong Answers Only)

Leaders should constantly question whether a task is the highest-impact use of effort, using a checklist of why, metric relevance, sunk cost, and customer value to avoid blind commitment.

Leaders who want to keep their teams focused need a simple habit: before any commitment, ask why the work matters right now. The article offers a checklist that starts with the basic question of what you are working on and why it is the most important thing. It then forces you to examine the metric you hope to move, the customer impact, and whether the effort aligns with long-term outcomes. By treating each decision as a hypothesis, you create space to reconsider when conditions change.

The piece walks through real-world triggers that should cause a pause: a metric that looks good but isn't tied to customer value, sunk-cost thinking that blinds you to better options, a CEO's favorite idea that may not be the best path, or a competitor's move that isn't a strategic fit. It also highlights the danger of treating past successes as guarantees and the temptation to use learning new skills as a reason to start work. Each scenario is paired with a question that pushes leaders to weigh short-term wins against sustainable growth.

By embedding these questions into meetings and planning sessions, a leader builds a culture where respectful pushback is normal and decisions are constantly re-evaluated. The result is fewer wasted efforts, better alignment with customer needs, and a team that feels empowered to surface better alternatives instead of blindly following the first plan.

Source: cutlefish.substack.com
#leadership#product management#decision making#strategy#engineering management

Problems this helps solve:

Decision-makingCross-functional alignment

Explore more resources

Check out the full stdlib collection for more frameworks, templates, and guides to accelerate your technical leadership journey.