Jennifer Dulski is President and COO at Change.org. She cites research by Tom Gilovich on regret: Namely, we are more likely to regret what we didn't do or say (omission) than what we did do or say (commission). Dulski draws on this research to help her make decisions.
Katharine Frase is Vice President and CTO at IBM Public Sector. Her adviser from graduate school acknowledged the importance of doing good science, but emphasized that communicating it to others - executives, colleagues, customers or family - was more important.
Nancy Tellem is President at Microsoft entertainment and digital media. Two job offers arrived on her desk: a promotion within her legal organization, and a step-down to a business creative post. An executive friend in entertainment suggested that she follow her heart and grab the latter.
Travis Kalanick is Co-Founder and CEO of Uber. He has a sense for the people whom he asks for advice, and the best comes from the stories they share with him.
Karenann Terrell is Executive VP and CIO at Wal-Mart. The chief engineer she used to work for described her as a mediocre engineer, as she related her desire to move to the top of the food chain in her profession. Instead, he steered her to jobs that she was strong in and that made her stronger yet. Seeing any feedback as a gift inoculated her from criticism and paved good headway in her career.
Ben Lerer is Co-Founder and CEO of Thrillist Media Group. His father gave him all sorts of advice, but it all boiled down to have fun.
Brian Chesky is Founder and CEO of Airbnb. Paul Graham of Y Combinator advised him to do things that don't scale. It prompted him to focus on creating an amazing experience for one person. Once he's achieved that, then he can figure out how to scale.
David Kenny is the Chairman and CEO of The Weather Channel. The advice he found to be the best was to hire for where the company was going to be three or four years down the road, not necessarily for the job at hand. So it meant over-hiring for his executive and management team, and this has always served him well.
Steve Shannon is General Manager of Content and Services at Roku. The most consistent advice he has had was on risk-taking. Bud Colligan of Macromedia pointed out that he had created his own luck, in light of his business success. Shannon saw the need to play offense (i.e., take chances), not just defense.
John Collison is Founder of Stripe. He draws on the same adviser as Chesky above, that is, Graham, and on the notion of unscalable strategy for user acquisition. This helps maximize what a small and nimble company can do.
Thank you for reading, and let me know what you think!
Ron Villejo, PhD