Learn how to categorize decisions by difficulty and apply the right tool-checklists, OODA loops, WRAP, or stakeholder maps-to make faster, better choices and avoid costly overanalysis.
Decision-making falls on a spectrum from trivial choices like picking a coffee shop to high-stakes strategic bets such as acquiring a competitor. The piece starts by breaking decisions into easy and hard groups, defining clear criteria, stakes, information gaps, and stakeholder involvement. It shows why mis-applying System 1 intuition to complex decisions or over-engineering simple ones wastes time and creates friction.
The core framework is a diagnostic step that maps a decision onto archetypes-routine, crisis, strategic bet, optimization, exploration, innovation, and value trade-off-and then matches each archetype to a concrete tool. Checklists and automation handle routine work, OODA loops accelerate crisis response, WRAP guides strategic bets, decision matrices and A/B tests sharpen optimization, while design thinking and lean startup methods drive exploration and innovation. Real-world examples, from security breach runbooks to portfolio thinking for innovation, illustrate how the right tool reduces cognitive bias and decision cost.
Finally, the article offers a meta-process: Diagnose the decision shape, Match it to an archetype, Simplify where possible, involve the right people, and Act & Review with a lightweight record. By documenting reasoning and iterating on feedback loops, teams build a shared language and a decision archive that makes future choices easier. Technical leaders get a practical playbook to turn vague uncertainty into structured, repeatable action.
Check out the full stdlib collection for more frameworks, templates, and guides to accelerate your technical leadership journey.