Building a Strong Culture with Jailany Thiaw
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: Hi, welcome to The Daily Bolster. I'm Matt Blumberg, the co- founder and CEO of Bolster, and with me today is Jailany Thiaw, the founder and CEO of Upskill. Welcome to The Daily Bolster.
Jailany Thiaw: Hey, Matt. How's it going? Thanks for having me.
Matt Blumberg: Good, good to see you. Tell everyone real quickly first, what are you doing at Upskill?
Jailany Thiaw: Absolutely. Upskill is a pre- seed company and we build software to improve the candidate experience for the next generation of job seekers, so Gen Z going out and applying for their first big job.
Matt Blumberg: Very cool. Well, it is probably a daunting environment for most kids coming out of college right now to find their first job.
Jailany Thiaw: At the very least.
Matt Blumberg: All right. What's on your mind today?
Jailany Thiaw: Awesome. As I mentioned, we're an early stage company. We're a team of five based mostly in the greater New York area, and I'm thinking about expanding our team. Top of mind for me is who I'm bringing into the company, and particularly the sort of places that we're sourcing them from, how I think about building company culture. If I'm bringing on engineers that might be in other parts of the country, might be in other parts of the world, how do I think of building and maintaining a strong company culture that is productive, that is positive, that people feel welcomed in. If we're going to be virtual first or hybrid at best?
Matt Blumberg: Yeah, it's a great question and it's one that every startup is facing right now, quite frankly, every company is facing. I think it's interesting, at the beginning of the pandemic when everyone moved to Zoom, every company said, oh, this is great. We're never going to go back into the office again. We're never going to need to spend money on RAD or see each other. I think people have figured out now that it doesn't quite work like that. It was easy to shift an existing culture onto Zoom for a little while than it is to create one when you're not in person. I would say for me, there are kind of a couple of things about this. The first one is to make sure you're being really, really intentional about documenting the company's values and the kind of culture that you want to have. That's advice that you should do, whether you're in person or remote or hybrid. But I think it's even more important. There are a lot of companies that gloss over that in the very early stages because they're like, ah, we all sit in a room together all day, it doesn't matter. But when you're not in a room together all day, it's even more important to get you as the founder and then get the team's assistance or buy- in around, what are the principles by which we want to operate? What do we want this place to be like and feel like? I think that's the first thing. For me, the second thing is I think you have to do some in- person work. When everyone's scattered across the country, it's hard. When everyone's scattered across the globe, it's even harder. I don't think you necessarily have to get people together more than once a year, although you benefit from doing twice a year or even four times a year, or maybe it's once a year for everybody, and two or four times a year for a leadership group as the organization gets bigger. But there's just no substitute for actually being together in person to build relationships. We found at Bolster, which is still an early stage company, we're only 30 or 35 people ourselves, that once a year with everybody and then a couple other times with leadership is a really good cadence. We use that time together. We really guard it fiercely because there's not that much of it, and we use it very intentionally to do things that are better to do in person. We try not to just co- work when we're all together. We try to do things like feedback or professional development. Things that require collaboration, things that drive community, social events, doing service work in the community. Just things that get everybody mixing together and getting to know each other as humans. Even if you're scattered across the globe, figure out how to cost effectively do that once a year, and I think there's some real benefits you get from it. Then the third thing I would say is be intentional about using online, which you're going to be like if you're hybrid, most of the minutes are going to be online. Figure out ways of using online channels to mix business, collaboration and social things. I don't know that there's a formula for this. A lot of companies do games with everybody online once in a while, a end of the work week Jackbox TV- type game. Or if you Google online scavenger hunt for teams, you're going to find 72 options. They're not very expensive. Pay someone a hundred bucks to facilitate a game show or an online scavenger hunt. Those things aren't the same as doing them in person, but that doesn't mean that you shouldn't do them. But we've found some other things that I think are pretty helpful as well. For example, we live in Slack, which most startups do, and we have a couple of geek bots set up in Slack that ask a given channel, which could be the all- hands channel, or it could be a group. Every week you get a ping of a few questions, highlight of your weekend, lowlight of your weekend, top goal for the week. Are you red, yellow, or green today? Just keeping some kind of baseline momentum of conversation going in Slack, we found to be really helpful. Another thing we've done that's pretty fun is we've changed the way we do all- hands meetings. Old school, all- hands meetings where like CEO- founder gets up and talks the whole time. Now what we do is we actually have a rotating chair every week. Every week it's literally a different person in the company and that person hands off the baton to the next person, and they're responsible for facilitating the all- hands meeting that week. They have to go do the work to figure out what's gone on in the company. Some of it's automated that pops into a Trello board using Slack and Zapier, but some of it's also like they have to pull themselves up out of their day- to- day and connect with the business and connect with people in the business. I think if you figure out how to weave those things in, being intentional about values and culture, leveraging in person when you can do it, and then figuring out how to rethink some traditional patterns of work online to reinforce. Hopefully, some of that does the job.
Jailany Thiaw: Awesome. Thanks a lot. I appreciate that.
Matt Blumberg: Absolutely. Hope it was helpful and good to see you. Thanks for joining.
Jailany Thiaw: You as well. Take care.
Joining Matt on today’s Ask Bolster episode is Jailany Thiaw, founder and CEO of UPskill, a future-of-work startup automating feedback in entry-level hiring pipelines.
Jailany and Matt discuss the best ways to get company buy-in as you build and maintain a strong and welcoming culture—especially in an early stage or remote environment.