Every entrepreneur has regrets, or at least things they would do differently if they had it all to do again. And apparently that includes even wildly successful ones like Patrick Collison, who founded super successful payments company Stripe with his brother and made himself a billionaire at the ripe old age of 31. 

As part of a long and fascinating fireside chat with fellow entrepreneurs recently, LinkedIn founder Reid Hoffman, the host of the event, asked Collison to reflect on choices that made Stripe into the powerhouse that it is today. 

Humbly, Collison pointed out that decisions that seen momentous in hindsight are generally completely unglamorous in the moment, but when pushed by Hoffman he allowed that, though it's not exactly flashy, hiring the right people for leadership positions made a huge difference. And that he wished he'd put even more thought into finding the right people even earlier.  

"With a lot of our products," Collison says, "if we hadn't done it at that moment, hopefully, by being customer-centric, a year later we would have realized we should do it. I think the things that counterfactually really mattered are hires."

So how do you identify those hires those leaders who will move your business from good to extraordinary? Collison offers founders three handy rules of thumb to ask about every potential hire. 

1. Is this person so good that you would happily work for them? 

This is a solid old standby but it's a classic for a reason. If you wouldn't work for a potential hire, why would you put a significant chunk of your business and employees in their hands? 

2. Can this person get you where you need to be way faster than any reasonable person could? 

Jeff Bezos, in his first job ad for Amazon 25 years ago, famously requested engineers who could build complex systems in "in about one-third the time most competent people think possible." Collison is apparently of the same school. 

"Are they capable of getting where you need to be in four years in two years?" he tells Hoffman he asks of potential leadership hires. "That's a very high bar, and a lot of fabulous people will not be capable of that, but you're really short-changing your organization by not insisting on that." So go ahead and insist on the borderline unreasonable.  

3. When this person disagrees with you, do you think it will be as likely you are wrong as they are wrong? 

"You're probably pretty disagreeable people," Collison says to laughs from the entrepreneurs in the audience. "You wouldn't have become entrepreneurs if you weren't, and so you're necessarily the kind of person who, when people disagree with you--maybe you've learned to be nice and polite and smile, but inwardly you're thinking, no." (Science, as a side note, backs him up that this is a common part of the entrepreneurial character.) 

Being headstrong might be essential for getting an innovative new business off the ground, but Collison insists you still need at least a small circle of leaders whom you trust enough to let them to interrogate your ideas, sniff out your mistakes, and teach you things. 

Hoffman agrees, asking, "If you're not going to learn from a hire, then how is the acceleration going to happen?"

The rest of the chat is equally fascinating. If you're interested, check it out in full here: 

Published on: Nov 19, 2019
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