Kara Brothers spent 10 years as a strategist at Google and built a people ops function from scratch for Grid AI’s distributed team. Later, she scaled Starface World to 20,000 retail locations, growing revenue from ~$5M to ~$90M over 5 years. Here’s her field guide on how to build a productive workplace culture - and why that starts with joy.
Can a workplace be both fun and optimally productive at the same time? It’s a culture question that first-time and experienced founders alike often trip over in the early stages.
For Kara Brothers, fun vs. productive is a false binary. In fact, she says, “if you build a culture centered on joy and discipline, it’s very likely you’ll end up with productivity as a result.”
It feels counterintuitive, but Brothers explains why it's actually pure logic: “There's this inherent misconception that joy is just loafing off on the beach - but think about it, when you’re enjoying yourself, how many more ideas flow freely to you? And as a result, how much more productive are you? Being in a good mood doesn’t just make you feel better, it also makes you think better.”
But that lightness doesn’t flow from just anywhere; the conditions have to be right. “There’s a saying that ‘discipline creates joy’ - and that’s the strongest guiding principle. The act of creating something, of being disciplined in your practice, creates a profound sense of joy.”
To help other founders who are building culture from scratch, Brothers offers her field guide on how to establish a joyful foundation.
Part one: Build on what you’re already good at
There was a time when Brothers thought that to lead effectively, she had to fit the archetype of a boss lady: tough, direct, and formal in every interaction.
But she wasn’t having a whole lot of fun, and it was reflecting in the culture growing around her. It was only when she decided to introspect about what her strengths were, and the conditions where she produced her best work, that things began to change for the better.
“I learned that I’m way more productive and pleasant when I’m having a good time. I also started leading with more curiosity, and asking way more questions,” she says. Right away, she could tell people were more receptive to her. They felt more comfortable to say what was on their mind, and started bringing her more ideas and productive problem solving.
“Strong leadership and authentic culture only emerge when a founder takes the time to understand the leadership style that is inherent to them - and builds out from there. The worst thing a founder can do is go against their innate mode of leadership, because that signals to the rest of the organisation that they also need to play pretend.”
To figure out and develop that inherent leadership style, Brothers advises “leaning into what you do best, and hiring around your weaknesses to create a stronger, more balanced culture.”
Part two: On manufacturing joy
At Starface World, Brothers established resilience, joy, and transparency as core values. But how can an organisation realistically build abstract, aspirational principles into day-to-day operations?
For a fully remote business, it came down to one single question: how do people
interact with each other?
Brothers started by looking at all the communication touchpoints across the business. For the Starface team, these included Slack, all-hands, and one-on-one meetings. Brothers wanted to make sure that every one had the same human texture, calibrated to each specific medium.
The three simple tactics she used to create a culture that allowed room for play:
- Talk like humans: “In the mornings on Wednesday our HR leader would say, ‘What are you guys having for breakfast?’ Or they’d ask a fun would-you-rather question - something that disarms people and invites them into conversation that isn’t work-related.”
- Add fun to the details: “For something formal, like an all-hands meeting where you have the department heads presenting - it can feel, at worst, boring, and at best, very serious. So, while we prided ourselves on having this very polished visual language, our all-hands deck was a little bit looser - we made sure that the actual visuals of the deck were very playful, very silly. That made it much easier for people to engage.”
- Be transparent: “Filtering information according to hierarchy can create a culture of fear - and it’s very hard to feel joy in that environment. So, whenever I had information to share about big topics, like profits, or something negative about our product, I’d make sure everyone heard firsthand at the same time in the all-hands. This avoids that toxic culture of gossip.”
Every tactic may not land the first time, and some may not land at all. For Brothers, this is a normal part of the process. “When you're building a culture, you need to remember it's a living, breathing ecosystem - kind of an organism. So for me, building a culture needs to be iterative.”
Emergency procedure: Bringing the fun back in times of crisis
When Starface World was about to launch Star Balm - their first ever product outside of pimple patches - Brothers helped the team navigate some dizzying highs and heart-thumping lows.
“The team was so excited when we were planning it: designing the packaging, designing the flavors, talking to the retailers and getting them on board. But as it got closer and closer to launch, of course, we all were like, ‘holy crap, how is this going to do?’”
All the fun of creating the product turned into panic. For Brothers, this was a mission-critical issue. “I encouraged the team to bring the same level of playful problem solving to the launch process as we did to creating the product.”
Her solution? Change the environment and maximise for joy. “Ahead of the launch, we planned an offsite to offset that high-pressure moment. This always works, because you’re taking people away from their day-to-day, away from that routine that’s stressing them out, in order to inspire new thoughts.”
“My go-to is always renting a house on the beach - somewhere peaceful and beautiful. It’s also important not to over-program it. I allow a lot of downtime, a lot of free space, because these people have back-to-back Zoom meetings all the time. By the end of it, you’ll feel how much lighter everything is - and it made a world of difference.”
Part three: Hiring for joy
While culture may start at the top, the leader is not in every single room and is not making every decision (hopefully). Every hire is an extension of the culture, which means they need to have some degree of personal alignment with the organisation’s culture.
“It doesn't matter what level you’re hiring for. You have to be conscious of the attitude each person is bringing into the ecosystem - even the intern managing the mailroom has an impact on carrying the culture. You need to ask whether they’re adding or subtracting to the culture.”
In many cases, the most resilient employees are also the most joyful. They are not easily derailed by the normal challenges of doing something very hard, Brothers explains. “People who are joyful in their work are generally less likely to be derailed by sudden changes. If the work excites them, they’re going to be more open to the unknowns and they can allow that to be awesome - versus someone who is stressed out by unknowns.”
#1 Swap interviews for genuine conversation
“We can all be tricked in the interview process” says Brothers. “That’s why I don’t spend too much time on standard interview questions.”
In place of the static, stuffy job interview that most people are familiar with, Brothers prefers to engage in free-flowing, get-to-know-you type conversation - with questions coming from both sides.
“It helps you pick up the right people, because during a more casual conversation, it's hard for a non-emotionally-intelligent person to just keep throwing practiced tropes at you. It requires real engagement, off-the-cuff thinking, and curiosity from their side.”
#2 Look for imperfections
For Brothers, the biggest red flag in a candidate is when they try to hide their imperfections. “They are putting in time and effort to cover up weaknesses, instead of using that same time and energy to improve. If someone acknowledges imperfections upfront and says how they manage them, it’s a strong signal of self-awareness.”
If she had to ask a conventional interview question, Brothers would ask ‘what are your weaknesses?’ - but with a twist: “I’d rather ask ‘what makes you nervous about accepting this role?’ or, ‘what would the closest person to you say is something that drives them nuts about you?’ Something that uncovers the thing they might not want to share in the interview, only because it exposes a bit of a vulnerability.”
“If I feel like their answer is not a trope - not a perfectly rehearsed answer - then for me, that signals an understanding that we're all human beings with imperfections that don't make or break us.”
And if things aren’t working out, Brothers says, “with some warning and some proper guidance, I do believe in firing fast. We make mistakes hiring. And even as a candidate looking for a job, you make a mistake entering into a culture that's just not a right fit for you. You're doing both of you a disservice by allowing that to fester. The best thing for both parties is a clean and fair cut.”
#3 Trust your gut (even though everyone says not to)
“I'll be honest - a lot of this is instinct. I'm a really fast decision-maker, and it’s based on intuition,” says Brothers. “While it's not always seen as valid in business, I believe that it should be.”
Having a sound gut reaction isn’t something that just naturally arises - it’s the result of built-in pattern recognition developed from experience, not just vibes. Where it comes in handy the most is when a decision needs to be made without much information to go on.
“It’s being able to be decisive in the face of complete uncertainty, and being okay with being wrong - while knowing that a decision was necessary. That's probably the number one most natural skill set that's helped me."
The big takeaway: “Build it how you want it to feel”
“It takes resilience to regularly bring joy to your work,” Brothers says. It can be a difficult thing to hold onto when the pressure is on - a big funding round coming up or the launch of a product that may not be 100% ready yet.
With her latest venture, New Juice Studios, Brothers once again finds herself in the position of building culture from scratch. “It’s exciting and daunting. I keep thinking that how I build this is how it will feel to work here.”
Her final piece of advice is directly for founders who are in the weeds and feel the walls closing in “When you’re feeling overwhelmed, take a breath and remember what it feels like without all the fear and the doubt. Remember what you initially set out to do and how you wanted it to feel. Ask yourself: What is this vision without any fear and without any doubt? It’s a simple question that can bring you back into the right state of mind - and help you find joy again.”
