Why not asking for what you want is holding you back | Kenneth Berger (exec coach, first PM @Slack)

Lenny's Podcast episode, sponsored by Sidebar and Webflow, in which Lenny Rachitsky talks with Kenneth Berger, Slack's first product manager turned executive coach, about his career magnum opus: asking for what you want. Berger's evidence from a decade operating and seven years coaching: when you actually ask out loud, you are much more likely to get it - and the two failure camps are people pleasers who never ask and hope others read their minds, and control freaks who only order. The work starts with knowing what you want, and his compass is complaints: every complaint implies a dream, so each grievance is a draft of a request. The most important step, he argues, is hearing the response you get, because the ask is only the beginning. He also tells the story of being fired from Slack three times. PARTIAL COVERAGE: this summary highlights the core skill; the resistance work and scripts are not covered. These are Berger's own views and coaching methods, not independently verified.