My Favorite Interview Question for New Hires

What’s up, everybody? Welcome back to the podcast. Today I want to share with you one of the best interviewing hacks I’ve ever come across for hiring rock stars. I find hiring to be very, very difficult, and I think most entrepreneurs do. And the reason is you only have a limited amount of time with a human to make a judgment about how they’re going to be on a day to day basis to actually work with. You don’t have a ton of information to go off. You have your initial gut feeling, a quick conversation, maybe two, 3 hours worth of interviews with multiple people on the team. But that’s not a lot to go with. And especially in a world where it’s one thing to show up and talk and interview and answer all the right questions, it’s another thing to see how somebody actually works day to day.

And because the consequences of hiring the wrong person is so high, not just from a monetary perspective, but also from the damage that it can do to the team, morale is so critical that we hire rock stars, and if they’re not rock stars, we get them off the team very, very quickly. Now, we’re not going to talk about how to do that per se today. What I want to talk about, though, is just one question that I found to serve me very well in an interview context, because a lot of times there’s only so many questions you can ask in an interview that people haven’t heard before to get them off their game. For the most part, everybody has wrote answers they’ve already rehearsed and practiced million different times. And so you want to get people off their scripts and get them talking or authentically about who they are, so you can get beyond the professional mask that they’re trying to project and see, you know, to the person that is behind them. And that’s not to say that they’re, they’re doing anything nefarious or weird or wrong even. It’s just that we all do that. We want to put our best self forward.

We want to say all the right things in the right way. And so we practice, we rehearse for this. Right? So how do we get somebody out of that flow zone and into the unknown, murky territories where they’re actually answering questions, questions for the very first time and thinking through things so you can get a sense for who is this person, really? Well, here’s a question I really like. It’s actually three questions. So the question itself is, what’s the biggest obstacle you’ve ever had to overcome? Or what’s the biggest struggle you’ve had in your life? What’s the moment in your life that you were tried the most? Some question that gets them to think about when things were hard. Now, a lot of people, they’ve thought about this question before. They already have an answer for this. Like, ah.

The thing that I’ve struggled with most in the past was this relationship with my boss. I had a difficult time communicating, and here’s what I learned from it. Cool. Now, the, the second question in this equation is when the magic starts to happen, you say, cool.
What else?
Can you give me another instance of an, of, you know, what’s the second biggest obstacle in your life that you’ve had to overcome? What was the second biggest struggle right. Now, they might have had the first answer pre prepared. Now, the second time, they probably have another answer, somewhat pre prepared. Some other thing that obviously jumps out to them that they can present and they can tell you about it, right? And you sit and you listen, you go, cool, cool, cool, cool, cool. And by the time they finish that, and then you ask them the third question, which is awesome.

What else?

What’s another time, what’s another one of the biggest obstacles? Like, what’s the third biggest obstacle you’ve ever had to overcome? Right. You keep asking the same question three times, maybe even more four times. If, depending on how quickly they generate the answers, you can tell how much they’ve thought about it, how much they’ve pre rehearsed it, and you want to keep going until you get them to go. Hmm. Let me think. What else was it? Oh, this other thing, actually, I haven’t thought about this in a while. Let me walk you through this. And now, once you get to that answer, you know that they haven’t pre prepared it.

So you’re going to get a very authentic view into how they viewed the problem, how they thought through the problem, what the solution was. Right. You’re going to start to see them. And the way that I discovered this question was actually in talking to GPS. I was working with a lot of limited partners. So these are private investors who invest large sums of money into private equity deals. And I was working with these LP’s to help them navigate the nuances of interviewing respective operators and partners. And that’s difficult because, again, you don’t have a lot of information to go off of when it comes to interviewing somebody and then making the decision, do I want to give them $100,000 to invest? Right.

And so there’s a certain type of individual that wants to do this type of investing, and they tend to be very detail oriented and they want to have all their ducks lined up and they want to ask all the right questions. Right. And so I would sit down with these lP’s and do a little bit of coaching with them and say, okay, so we’re going to ask this question. This question. Here’s what we’re looking for. Here’s the answers that we’re trying to get to. And the problem is when you’re, say you’re an LP and you’re coming to interview with me because you’re interested in investing with us at Invictus Capital. Well, the problem that I realized pretty quickly is that I have already heard every question you could possibly ask me.

And I’ve sat and I’ve rehearsed countless times the stories and how I’m going to tell them and where I’m going to pause and how I’m going to deliver it. Right. And so when somebody comes and they’re like, what’s the biggest lesson or the biggest failure that you’ve had in your business? I already have the answer. This isn’t the first time I’m hearing that. I’m ready to tell you my story. And I had an LP once who just kept asking me, cool, what else? What’s another time? What’s another time? He just kept asking after, like, five, six, seven times. And by, like, number six and seven, I was, like, having to go pretty deep into my memory to be like, all right, what else do we got here? Well, what else can I think about, right? Like, I got out of my rehearsal and into fresh territory, and that is where he got to really see my thought process. And so I’ve taken that from that particular interview, and I teach it to my lp’s to ask their gps.

And then I’ve used this in hiring now, and it’s been a very powerful question because most people, they probably have two stories two times in their life. Something went terribly wrong that they’ve kind of prepared for in the interview. Most don’t have three and most certainly don’t have five, right. And so if you just keep sitting there and just look back at them and say, that’s great.

What else?

Tell me another time. And you just keep asking the same question over and over and over and you get to some really interesting answers. Another example of this, when somebody, when you ask them, like, what’s your biggest weakness? And somebody, I work too hard. Cool.
What else?

You know, I care too much about what other people think.

Awesome. What else?

Oh, you know, sometimes I’m a little bit messy.

Oh, interesting. What else?

Yeah, sometimes I miss deadlines because I’m a little bit messy and blah, blah, blah. Right now you’re getting to the real stuff. Before, you were just getting the answers that they rehearsed. But as you keep asking the same question over and over, it makes them keep digging. So take that question, run with it. When you’re doing hiring, if you’re going to invest with somebody, if you’re thinking about partnering with somebody, just keep asking the same question over and over and over, and you will start to uncover deeper and deeper levels of answer that you weren’t going to get otherwise. So hope this brings a little bit of value. Good luck out there.

Hiring is tough. I believe in you. Don’t give up. Keep doing it. Just ask better questions. Get better answers.