The 1 Brutal Question That Will Make Any Leader Instantly More Effective 

We’ve all heard about the power of positive thinking, but what about the power of negative thinking? 

Steve Jobs famously stayed motivated by reminding himself of his own death every day, author Tim Ferriss has argued that thinking through the worst case scenario in any situation can help you get anxiety under control and prepare for all eventualities, and studies have shown that a healthy amount of negativity makes entrepreneurs more successful. 

In short, while an excess of pessimism will paralyze you, not enough makes you flabby and complacent. So how do you get the right dose of anxiety and doom to propel you to your greatest potential? 

Former Google exec turned Upstart co-founder Dave Girouard offered a brilliant suggestion as part of First Round Capital’s round up of the best entrepreneurial advice of 2020. It comes in the form of a simple but powerful question. 

As the former Google exec in charge of the company’s billion-dollar enterprise apps business, Girouard is clearly not a slacker to start with. But even a striver like him sometimes needs to kick himself in the pants, he told First Round. 

“While I’m doing some things okay,” he says of his current gig as a first time CEO, “I can be lulled into a place of feeling good about myself when I’m probably not doing some other things very well.”

He uses a simple but harsh mental trick to continually push himself harder: “thinking about what would happen if tomorrow my board got together and fired me.”  

“What if they said, ‘Dave, thank you for playing. You’re done. We are recruiting a new CEO for Upstart.’ And they went out and found the very best CEO in the world, one who would just make me look like a fool. And if they bring her in and she starts at Upstart — what would she do differently than what I’m doing?” he forces himself to ponder. “I think about that for a while, and then I tell myself, ‘Why the hell aren’t you doing those things?'” 

This can’t be a very comfortable exercise. No one likes to focus on their deficiencies. Nor is it particularly nice to take a long hard look at how your performance rates against your stiffest competitors. But what this trick lacks in enjoyment, it makes up for in motivation and fresh ideas. 

Girouard’s star replacement is entirely imaginary, but his idea of focusing on someone else who is doing your job better than you reminded me of Simon Sinek’s writing on the power of rivals. 

In his latest book, Sinek confesses to being sick with envy for the accomplishments of star Wharton professor and best-selling author Adam Grant. Comparing himself to Grant makes Sinek feel a little queasy, but it also drives him to examine his own strengths and weaknesses and take action to improve in areas where he isn’t measuring up. Everyone who values excellence should have a worthy work rival, Sinek concludes. 

Just like Girouard imagining losing his job to some other rock star leader, Sinek is pushing himself to level up with a clear-eyed comparison between himself and someone excelling in a similar role. Both are asking of their rival (whether imagined or real): What skills does this person have that I lack? What are they better at than me?