Key Questions for Every Interview with Charles Bonello

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: I'm Matt Blumberg, co- founder and CEO of Bolster. And I'm here today with Charles Bonello. Charles is the co- founder, CEO, and very proud first Dad, which is a great title, of a very cool company here in New York called Vivvi. Vivvi's mission is to make exceptional care and learning accessible and affordable to working families by partnering with their employer to provide childcare as a benefit. Charles, thank you for joining me on The Daily Bolster.

Charles Bonello: Matt, thanks so much for having me. I'm really excited to be here today.

Matt Blumberg: So my question for you today is about interviewing and hiring executives, which is something we like to ask a lot of our guests. And I'm wondering if you have one or two key questions that you always ask when you're interviewing a candidate for a leadership role in the company, and why you ask them.

Charles Bonello: It's a big one, and it's really exciting when you get that opportunity to bring in a potential leader. And so for me, I always kind of come down to two, maybe two and a half questions that I ask everybody. The first big one that I always ask is, tell me about the accomplishment that you're proudest of. Listen, everybody's prepared with their resume. They've gone through the different scenarios with their colleagues, their mentors, probably other people on your team. This is a real chance to let them shine and tell you through their actions and their words what is most important to them and what their superpower is, right? And there's always the opportunity to kind of sidestep it and say, " it's my family, it's my house, it's this project." But really trying to dive into that question, saying, " Well, what about that makes you so proud? What about that did you do? What were the decisions that you made within that context that you're really proud of? And what was your process of making that decision? Or what could you have done better alongside that?" And it just becomes a really natural and flowing conversation to build a relationship because too often, whether you're talking to investors or other hires, you have to figure out in this little pressure cooker of 90 minutes whether or not you're going to get married. Building that organic discussion into it really helps.

Matt Blumberg: The thing I like about that framing of the question is you're not just asking about an achievement or accomplishment where someone's likely going to talk about the biggest result they can point to. But the thing they're most proud of could be something small or hidden, but something that sort of gives you more of an insight into them. So I love that. All right. What's question two?

Charles Bonello: Question two, I always end with what's your dream. And again, when I was asked that question when I was interviewing at the McKinseys of the world, my answer was something very canned, where in the back of my head I was saying, " I want to play center field for the Yankees, but in the meantime I can make presentations for your clients." It becomes really helpful to understand what motivates this person, what makes them tick? How does that align with your values and your mission? Because somebody might be really competent, but they don't align with mission or values, and that might not be a fit, or somebody might be on the bubble, but is really enthusiastic and passionate about what makes you tick, either directly or kind of in an adjacent manner. And you can really start using that and taking down these notes so that when they do start, you're tailoring your management style to really help support them to achieve their dreams. Because if you're able to do that, then you better believe they're going to do the same thing for you to help you achieve your dream, which is to grow your company really quickly and to hopefully exit someday. So for me, it's all about how do you get to know them better? How do you get to understand what makes them tick in a way that isn't some level of psychoanalysis and sitting on a chair, or doing the thing from Billions where you hire an office psychiatrist to deconstruct everybody.

Matt Blumberg: Right. And then you said you had a half.

Charles Bonello: Yeah. It was adjacent to the first point, and sometimes I'd say, " What is a decision that you would revisit today, or earlier in your career and why?" And sometimes that's a hiring decision. The most often thing that I hear about is a hiring decision. I would've moved sooner to-

Matt Blumberg: Yeah.

Charles Bonello: Yeah. So people will say, " I probably would've moved sooner to let somebody go from my team," or going back even further and saying, " I probably would've asked this question during my interview with this person that would've led to a different outcome on it." It's just interesting for me to understand how people dissect the decisions that have led them to that point in their life. For the most part, if they're getting to that stage, they've already taken accountability for anything good or bad in their career. They've also understood that other people play a key role in supporting them and growing them. And again, it's just like scratching under that layer of what a resume or a LinkedIn profile or a GitHub profile says about somebody.

Matt Blumberg: Yeah, absolutely. All right, Charles Bonello, interview tips for hiring CXOs. Thank you so much for joining me today.

Charles Bonello: Thanks so much, Matt. I appreciate it. Talk to you soon.