Tips for Interviewing Senior Leaders with Jenny Lawton

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 my friend Jenny Lawton. Jenny is a Bolster alum and someone I've worked very closely with over the years. She's also a very experienced senior operating executive within the tech and startup worlds. Besides Bolster, she has worked at Techstars, at LittleBits, at MakerBot. She is an advisor and board member and coach and mentor extraordinaire, particularly for early stage founders. Jenny, good to see you.

Jenny Lawton: Nice to see you too.

Matt Blumberg: All right, I want to talk today about interviewing. You have interviewed and hired dozens and dozens and dozens of senior executives, maybe in the hundreds at some point. What is your interview process or what do you think is unique about your interview process for senior execs?

Jenny Lawton: I have a pretty basic interview process and I often think in grid. So I have a four- square process that I look at for understanding people and helping people understand themselves. And it has... In the upper right corner, there is a good at, like box where you put things that you're good at and you like doing. In the lower right corner is this box that's things that you're good at and don't like doing. In the upper left box are things that you like doing but you're bad at. And the lower left box you just shouldn't even touch you're bad at, you shouldn't even be there. And so I used to actually have people fill it out in the interview. I would give them a sheet of paper, fold it in four and say, " Now, you need to fill this out. We'll talk about what's in there." That was actually... I found people saying, " Can I take it home and then come back to you? So that really wasn't a very efficient process. So I've just jumped to asking people if they could share with me something that they're good at doing but don't like doing. And what I'm doing there...

Matt Blumberg: Okay, so you're picking one box.

Jenny Lawton: I'm picking one box. Tell me something you're good at but don't like doing. And the red flag that I'm looking for there is if what they tell me is a core part of their job, that's saying to me that it's most likely not the right job for them because I think people are most dissatisfied when they end up spending their time doing things that they're good at and don't like doing. It's drudgery. You really want people very squarely in that good at/ like space.

Matt Blumberg: Right.

Jenny Lawton: The only time when I find that it's okay that it's there, and I'll have a follow on question as well, if that's a core part of the job. If they're in a management position and they're going to hire people who are going to do that work that they don't like doing, but they are good at and like, I ask them, " How are you going to handle that because this is a core part of your job?" And if they come back with the answer that they would have other people who are good at it doing it, then we can have a conversation about it. But, very telling question.

Matt Blumberg: Well, that's a good second layer question underneath it too. So let me ask you real quickly, what about the other corner of, I guess it would be, I love it, but I'm not very good at it. I get the other two corners. One, you don't touch, one, you amplify. But what do you do with that one of, I love it but I'm not very good at it. What happens when that comes up in an interview process?

Jenny Lawton: So it depends on the job. For an executive it's probably not the right fit, but for a mid- level person, it might be good that you're hiring someone that they love it and they're not good at it. If you feel like they're able to move over into that box, it's actually... I think that there's a lot of growth potential with that person.

Matt Blumberg: Or I guess if they have a roadmap for moving into that box.

Jenny Lawton: Yeah. And so it's a good conversation. But I'll tell you the good at/ like one, I asked the guy who had applied for a really very detailed financial job once. I'm like, " Could you tell me something that you're good at and like doing?" And he's like, " Anything?" And I said, " Yeah, anything." He's like, " I love playing classical piano." I was like, " I don't think this is the right job for you." So that's how I flipped to the tell me something that you're good at and don't like doing because the answers that you got on the good end, they just took it very seriously, told me what they were passionate about.

Matt Blumberg: Well, I love a good two by two matrix as much as the next person and this is one that I am going to take note of for sure. So thank you for sharing that with us today.

Jenny Lawton: Thank you.