The short version here is that experience matters for some roles and not for others. When you're hiring someone that is going to run a large part of your organization experience probably matters a lot. Most of the best hires that I've made in my entire life have never done that thing before. So it's really worth thinking, is this a role where I care about experience or not. There are three things I look for in a hire. Are they smart? Do they get things done? Do I want to spend a lot of time around them? And if I get an answer, if I can say yes to all three of these, I never regret it, it's almost always worked out.
You can learn a lot about all three of these things in an interview but the very best way is working together, so ideally someone you've worked together with in the past and in that case you probably don't even need an interview.
If you haven't, then I think it's way better to work with someone on a project for a day or two before hiring them. You'll both learn a lot they will too and most first-time founders are very bad interviewers but very good at evaluating someone after they've worked together.
Silicon Valley: A Reality Check | Slate Star Codex
So one of the pieces of advice that we give at YC is try to work on a project together instead of an interview. If you are going to interview, which you probably will, you should ask specifically about projects that someone worked on in the past. You'll learn a lot more than you will with brainteasers.
For some reason, young technical cofounders love to ask brainteasers rather than just ask what someone has done.
Really dig in to projects people have worked on. And call references. That is another thing that first time founders like to skip. You want to call some people that these people have worked with in the past. And when you do, you don't just want to ask, How was so-and-so, you really want to dig in. Is this person in the top five percent of people you've ever worked with?
What specifically did they do? Would you hire them again? Why aren't you trying to hire them again? You really have to press on these reference calls. Another thing that I have noticed from talking to YC companies is that good communication skills tend to correlate with hires that work out. I used to not pay attention to this. If someone is difficult to talk to, if someone cannot communicate clearly, it's a real problem in terms of their likelihood to work out. You generally get this, otherwise they wouldn't be interested in a startup, but now that startups are sort of more in fashion, you want people that actually sort of like a little bit of risk.
If someone is choosing between joining McKinsey or your startup it's very unlikely they're going to work out at the startup. You also want people who are maniacally determined and that is slightly different than having a risk tolerant attitude. So you really should be looking for both.
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By the way, people are welcome to interrupt me with questions as stuff comes up. There is a famous test from Paul Graham called the animal test. The idea here is that you should be able to describe any employee as an animal at what they do. I don't think that translates out of English very well but you need unstoppable people.
You want people that are just going to get it done. Founders who usually end up being very happy with their early hires usually end up describing these people as the very best in the world at what they do. Mark Zuckerberg once said that he tries to hire people that A. This strikes me as a very good framework. You don't have to be friends with everybody, but you should at least enjoy working with them.
And if you don't have that, you should at least deeply respect them. But again, if you don't want to spend a lot of time around people you should trust your instincts about that. While I'm on this topic of hiring, I want to talk about employee equity.
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Founders screw this up all the time. I think as a rough estimate, you should aim to give about ten percent of the company to the first ten employees.
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They have to earn it over four years anyway, and if they're successful, they're going to contribute way more than that. They're going to increase the value of the company way more than that, and if they don't then they won't be around anyway.