What Would Your Replacement Do?

Michelle Woo
Published in
2 min readJan 28, 2021

Credit: Westend61/Getty Images

Once you’ve been at a job for a while, it becomes tougher to see your role with fresh eyes. You’ve settled into your routines, developed a rhythm with your usual contacts, and generally figured out how to get the work done. So how can you find ways to grow when a comfortable groove starts to feel like stagnation?

Ask yourself this question: What would my replacement do?

The prompt, which is somewhat unsettling but strangely clarifying, comes from Dave Girouard, the CEO of the tech startup Upstart. He tells First Round Review that as a mental exercise, he thinks about what would happen if his board got together and fired him:

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? I think about that for a while, and then I tell myself, ‘Why the hell aren’t you doing those things?’ It’s just this weird game I play to get myself to recognize that while I’m doing some things okay, I can be lulled into a place of feeling good about myself when I’m probably not doing some other things very well.

Sure, you might be annoyed at this imaginary star performer at first. What a showoff! But ultimately, you can learn from them—and, in time, become them.

Michelle Woo
Writer for

Author of Horizontal Parenting: How to Entertain Your Kid While Lying Down (Chronicle Books)