Leading Through Ambiguity 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: Welcome to The Daily Bolster. 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, that's an awesome title, of Vivvi, and Vivvi is a really cool company whose mission is to make exceptional childcare and learning accessible to working families by partnering with employers to provide childcare as a benefit. Charles, welcome to The Daily Bolster.

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

Matt Blumberg: Yeah, I'm excited to talk to you about maybe a couple of different things today and a couple episodes, but the first one I wanted to talk to you about is something that you and I have discussed before, which is how you get comfortable as a CEO leading through ambiguity, which we must all do every day because the world of startups is never clear.

Charles Bonello: Yeah. Well, thanks so much for having me. It's really exciting to be here. And listen, it's the question that's on I think my mind and almost every other founder's mind all the time. For me, when I think about leading through ambiguity, there's really three components, and the first is getting comfortable with ambiguity and how do I get comfortable with ambiguity and what do I see out there? I mean, look, oftentimes when there's a fork in the road or where there's a big decision to be made or something is outside of your control, it seems like there are infinite possibilities. Well, as soon as you put those down on paper, they cease to be infinite and they start being finite. When you start mapping out the different modalities, when you start mapping out the different paths that you can take, it becomes really easy to start checking those off. All of a sudden, infinite possibilities become three possibilities become two possibilities become one that you're really confident around. You take that step further and how do you get to that point? I think it really comes down to transparency. You have to be transparent with two parties, in particular. The first is transparency with your team, and that takes two forms. The first is actually being transparent about what's on your mind, what you're working on, what's coming to you, because you've hired these people, you've brought them into your world, you've brought them into your ecosystem. To use that, they have to be fully informed to understand how to best support you and how to drive the company forward. But just as important as that is transparency around expectations. We have a thing here that we say oftentimes, ambiguity isn't a blocker to you doing your job. Ambiguity is your job, right? And your job working at-

Matt Blumberg: It's a feature, not a bug.

Charles Bonello: Yeah. It's a feature, not a bug. Right? But that's why you join an early stage company because otherwise, go join Microsoft, which is a wonderful company. They have very defined roles, very defined roles, very defined processes. Part of the joy and part of the excitement of joining a startup is having to navigate through the ambiguity and being able to put your fingerprints on it. So it's one thing if that's a surprise to everybody, but to say it early and often and on an ongoing basis empowers them to do the second part of that, which is surfacing those concerns and supporting you through that. So for me on the team side, that's most important. Set those expectations early and clearly, and then drive it home by sharing across it, because otherwise you're going to have everything on your shoulders. You're going to have everything on your shoulders anyways, but it's a good way to help lift the burden. The second party is the board. Yes, there's a very legal and formal relationship between a company and a board and the founder and the board, but really it's everybody on the same team and you have to live by that mantra of no surprises, whether they're good or bad. There's obviously a lot of temptation or sentiment that you have to be on top of everything and know everything and have confidence in everything. Look, if you've done the work of mapping out scenarios and thinking about it in thorough fashion, you'll get there, but bringing the board in early and being able to lean on them because they've seen this not only at your company, but at hundreds of others, allows you to draw on all of that experience. I think it's not surprising that a lot of founders become history buffs if for no other reason than self- preservation. In the whole scope of everybody's experience in the world, there's somebody else who's experienced something similar to you. You just happen to have people on your board who are there particularly for that reason.

Matt Blumberg: No, that's right. Actually, I think what's interesting about your three points, which it's a great formula, transparent with the team, transparent with the board, map out the options to make the infinite finite. I think what's interesting about those three as I think about the topic of leading through ambiguity, is you can do those three in any order as it best suits you. So you can be transparent with your team and your board to help you create a finite list of options or you can be transparent with one of those groups to help you create those and then chew through it with the other way around.

Charles Bonello: Yeah. And it totally depends on the stakes of it, right? If you're thinking about where to locate your office, that's a little bit different than whether you're thinking about to go into a new product direction or to shut down a product or to sell or to buy. For me, it becomes a funnel of a process. It's like, let's ingest everything that is out there so that we have the full context, and then you can start whittling it down or using that to inform strategy on how you attack.

Matt Blumberg: That's right. Okay. Charles Bonello, CEO of Vivvi. Thank you for being here today to talk about leading through ambiguity.

Charles Bonello: It is my pleasure. Thank you so much for having me.