Using Case Studies in Interviews with Jessica Wolf

Intro: Welcome to The Daily Bolster. Each day, we welcome transformational executives to share their real- world experiences and practical advice about scaling yourself, your team, and your business.

Matt Blumberg: Welcome to The Daily Bolster. I'm Matt Blumberg, co- founder and CEO of Bolster, and I'm here today with Jessica Wolf, who is the co- founder and CEO of Skye, which is spelled S- K- Y- E. Skye is a platform for accelerating professional goals with one- to- one coaching. Jessica, good to see you.

Jessica Wolf: Thanks. Thanks for having me back.

Matt Blumberg: So the last time we spoke, we spoke about how to pick a coach and interviewing coach candidates.

Jessica Wolf: Sure.

Matt Blumberg: And what I wanted to talk about today was actually when you interview people to join the team at Skye, preferably senior people, what do you look for? How do you approach those interviews? And I know one of the things that you said you do, when we were talking before, was that you do case studies with every interview, and that's a little different than some of the other things that other guests on the show have said to me. So I'd love to understand what that means. What does a case study look like? What are you looking for? How do you design them? How do you evaluate candidates against them?

Jessica Wolf: Sure. So my co- founders and I met at Columbia Business School, which of course is all about the case study. And as we were embarking on this entrepreneurial journey together, we realized we hadn't hired anyone for our own businesses before. We'd only hired internally. And so we recognized that we might have some blind spots in hiring and costly potential mistakes, so we were trying to mitigate against bias and just asserting for cultural fit or whether you liked someone versus their actual skill set. We decided to introduce case studies to all of our interviews, and this is not just for senior executives. It's for every person on the team. And they're very much dependent on your field. So for technical leaders, I think they almost always have a case study in which you have to do live tech problem solving, so our CTO will lead that. But for product, we of course look at their portfolio, and then we actually have them work through a problem and problem solving so we can assess their analytical skills, their ability to think both creatively and from that left brain too. What else? For go- to- market, we have sales leaders put together a plan of how they would approach outbound sales in their first 90 days. So there's a few different ways in which you can design a case study that really helps you understand how that person thinks and how they like to work and how they could contribute in that first three months.

Matt Blumberg: So it's almost like an audition or an assignment as opposed to you giving them a specific case to read and react to it.

Jessica Wolf: It's an assignment.

Matt Blumberg: Yeah.

Jessica Wolf: And it can be live or you can have time to prepare before.

Matt Blumberg: Which do you like better?

Jessica Wolf: I always feel bad so I like to give them time to prepare for it because I know I would really struggle with a live case. But my co- founders do live cases. We just did one for our CSM role and I thought it was really hard. They had to, in under 10 minutes, take a series of coaches, a series of leaders, and match them based on key criteria, and then create an onboarding plan. In under 10 minutes, that's really fast.

Matt Blumberg: That is pretty fast. Do you give them feedback in the moment? Like they produce an onboarding plan in 10 minutes, do you challenge them on it? Do you ask them questions about it? Do you give them feedback or do you sort of say, " Well, thanks for the interview and we'll get back to you"?

Jessica Wolf: It depends. So our CT, Gabe, gives feedback. He actually jumps in and will help solve a technical problem if a person is struggling, so we'll give him a few tips and then see how they do with the extra support. I think our chief product officer, at the end, he'll kind of say, " Hey, this is how we might have gone about it," so he does a review. I don't. I just say thank you. And then if that person wants to speak later and review, I'm happy to go through it with them.

Matt Blumberg: Have you ever gotten a great idea out of one of those but didn't end up hiring the person?

Jessica Wolf: No. That's amazing. That would be really good.

Matt Blumberg: You get a great idea and you're like, " All right, that's my person."

Jessica Wolf: I should look for that.

Matt Blumberg: Yeah. All right, the art of the case study in interviews. Jessica Wolf from Skye, thank you so much for joining me.

Jessica Wolf: Of course.