My startup hiring interview hack: Why? Why? Why?

Hiring people for your startup is hard. There’s no way around that. Whether you’re a little unknown startup nobody ever heard of, or a hotshot rocketship making headlines in the techpress, figuring out which candidates to hire is really difficult.

How can you assess which applicants would add the most value to your startup? (And whom you should avoid like the plague?)

Conducting a hiring interview

I have an unorthodox opinion on the topic of job interviews. Interviewing people isn’t my primary way of judging whether someone is a good fit for our company.

Beware of "job interview experts"

I’ve learned from experience that some of the best interviewees make the worst employees, and some of the best employees are the worst interviewees.

Making a good impression during a job interview is a skill that can be learned and some people invest a great amount of time and effort into developing their job interview skills.

Time and effort they could have invested into developing the skills they’re actually hired for. You don't want to hire this kind of people, because they tend to be the ones who are also good at playing office politics and claiming credit for other people's achievements.

But even if you take these extreme cases aside ...

Every job applicant packages himself favorably

Many founders fail to look beyond the packaging. They see the big bold letters on the box, and the shiny colors and make a judgment call: “Oh, this candidate looks good!” Or “No way am I going to hire this person!”

If they think it’s a good one, they’ll remind themselves: “Do your due diligence. This is an important decision!”

So they turn the package around and carefully study the fine print on the side. “Well, this still looks good! I’ll hire this guy!”

The problem is: they haven’t actually opened up the box and looked at what’s inside.

To get insights into what’s in the box, you need to get through the superficial layer of bullshit and have a real interaction.

If that sounds like a lot of work, don’t worry. You don’t need a PhD in psychology. There’s a super simple hiring hack for this.

How to interview someone so they reveal their real self

Ask them whatever questions you need to ask them. There are no standard “great interview questions”. It really depends on your startup’s needs, and you just have to do your homework and figure out what the best questions to ask are.

So come up with a list of questions you want to ask, and then follow up on each of their answers by asking "why" three times in a row.

Interviewer asks initial question.
Interviewee: “That’s a great question, and I’m happy to share with you that blablabla [insert a couple of bullshit phrases here that make a great-sounding answer]."
Interviewer: “That’s good! Why?”
Interviewee: “Because I really blablabla [insert more bullshit].”
Interviewer: “Oh, interesting. Why do you think that is?”
Interviewee: “Well, hm ...“ [at this point you can often see the wheels inside their head turning, and the answers aren’t as slick and polished anymore] “so blablabla [still contains a good percentage of bullshit]”
Interviewer: “Oh, this is good. Why?”
Interviewee: “Uh, oh, well …” [Some serious mental processing is going on. They might be a little less articulate, and more introspective. That’s a good sign!] “Ok, so I think this ... [Depending upon where the conversation went, they demonstrate their level of expertise, or reveal how their thought process works, or what drives them, or they bring up formative experiences that made lasting impressions on them.]”

Getting real

Now these are the insights you’re looking for. You’ve opened the box and got a glimpse of what’s inside.

These deeper insights provide a better foundation to build your judgment on than the slick answers you’ll get with standard interview questions.

What if, after three why's, you're still not getting "real" answers?

Some really smooth interviewees will try to circumvent the answer. They'll tell you something like, "Well, that's a really good question, let me think about it, I don't really know, but let me get back to you later on that."

Here's how you respond to those people: "Take a guess. If you had to guess an answer, what would be your first guess?"

Don't let them off the hook. Push until you move the conversation beyond the level of "things people say at job interviews".

Want to see an example?

When I interview someone for a job, I want to know a) what they want from life, and b) why they want it.

So I ask the candidate this question, and follow up with "why" until they get real.

You can see how such a conversation develops during an interview:

Now that I've shared all this advice on conducting hiring interviews with you, it's important that you ...

Don’t weigh interviews too heavily!

The interview shouldn't be the deciding factor in your hiring decision.

In a startup, it’s all about performance. What can each team member contribute to the company?

I like to bring up the example of a basketball team, because in sports, it's all about performing. A coach who wants to bring a new player into the team would first and foremost want to see how they perform on the field. What they actually do matters more than what they say they do.

This is why you want to place them in a situation where they demonstrate their abilities as quickly as possible. If you're hiring a salesperson, make them pick up the phone and pitch!

If you think hiring is hard, try firing …

Hiring is largely hard because mistakes are painful to fix. But mistakes will happen. It’s unavoidable. The important thing is to fix your mistakes quickly.

When you’ve made a bad hire, fire them quickly. Don’t give them the opportunity to drag the whole team’s performance down.

Be respectful when firing someone, and try to help them transition into a position at another company that suits them better. After all, it was you who made the mistake of hiring them! But by all means, do not delay the decision because you feel bad about it.

"The way to be a great at hiring, is to be unafraid of firing."—Gary Vaynerchuck