Sometimes Your Job is to Get in the Way

A VP of Engineering at Slack recounts how a CTO's directive during a high-profile outage triggered a complete overhaul of the development pipeline, turning an eight-hour emergency meeting into five working groups that eliminated chronic downtime over three months. The story is framed around a leadership tension: knowing when to stay out of the way versus when to step in and draw a hard line. Using the film Get Shorty as a metaphor, the author argues that the harder and riskier skill is recognizing which moment you're in — intervening too late lets systems fail, but intervening unnecessarily can undermine team trust and sell people a 'Cadillac of minivans.'