Leadership is less about authority and more about judgment, communication, and the willingness to hold difficult truths. I've managed teams at startups and at Meta, facilitated executive workshops, and coached leaders through high-stakes decisions. These articles reflect what I've learned about the craft of leading well.
Good leadership isn't flashy — it's about making sound calls under pressure, creating clarity for your team, and building systems that don't depend on heroics.
Judgment & Decision-Making
- Evaluating Judgment — A framework for assessing the quality of your own decisions and others'
- Making Gut Calls — Strengthen your intuition by learning when to trust it and when to override it
- There Is No Best Choice — Stop searching for the perfect option and start making better tradeoffs
- Threshold Checkpoint Goalsetting — A structured framework for making decisions when the future is genuinely uncertain
Communication & Influence
- Fraught Conversations — Navigate emotionally charged disagreements without losing the relationship or the point
- The World Needs Difficult People — Harness constructive dissent to prevent groupthink on your team
- Analogies Are OP — Use analogies as a precision tool for communication and persuasion
- How to Facilitate a Great Workshop — Run workshops that produce real outcomes instead of polite nodding
Managing People & Teams
- The Conformity Trap — Identify when your team is agreeing too easily and intervene before it costs you
- Manager Initiative [Ask Jason] — Direct answers to common management dilemmas from real coaching scenarios
- Validation Over Love — Give people what they actually need — recognition for their competence, not just warmth
- The Document Arms Race — Recognize when documentation culture becomes performative and refocus on clarity
Sustaining High Performance
- Process Over Outcome — Anchor your team's morale to the quality of their process, not the randomness of results
- Rest as Hard as You Work — Model sustainable performance by treating recovery as part of the job
- Productivity Judo — Rotate tactics strategically instead of grinding on a single productivity system
- Silent Failures Are Deadly — Build systems that surface hidden problems before they become visible crises
- Timeless Wisdom — Draw on enduring principles that outlast management fads and frameworks
I coach founders and executives through the leadership transitions that matter most. Learn more about working together at jasonshen.com/coaching.