"Whatever happens in an interview, times it by 10": Teresa Lilly on hiring, culture, and the hard calls startups avoid

Teresa Lilly didn't plan a career in HR. She was living in Boston, took a people role at a startup, and something clicked.

"It wasn't something that I sought out. It found me," she says. "I really enjoyed it and have been in it ever since."

Watch the full interview with Rudy Crous above.

That startup became the first in a long line. From seed stage to Series D, Teresa has spent her career inside companies at the point where everything is moving fast and nothing is quite built yet. She's now the founder of Culture Pilot Co, a consulting business that works with startups at their most critical growth point, and one of the HR Influence Awards Top 12 for 2026. She also serves as Strategic Advisor to Hoogly, an AI-powered team connection platform.

The judges described her as "exactly the kind of practitioner-turned-founder the profession needs more of. She has seen what breaks in high-growth companies and is now working upstream of those problems, with real evidence to back it up."

From French teacher to pub manager to people leader

Teresa's path to HR was anything but linear. She holds a bachelor's degree in French, has managed a pub at Harvard, and once ran karaoke nights every Friday.

"I was always interested in other languages and cultures," she says. "By learning another language, it changes your worldview and the things that you kind of assume are our standard or everyone thinks the same way. You actually can go into another culture in another language and it's totally different."

She sees a thread running through all of it. The French degree was about understanding how different people think. The pub was about bringing people together. The karaoke was about getting over yourself and building connection.

"What better engagement than karaoke?" she says, laughing. "I had to get over it and get myself on stage."

When she eventually landed in HR, the fit made sense. "People are inherently interesting and all my roles previously have always been around people and their behaviours. And so it's just a different way to apply those learned skills."

Scaling a fintech 60% in a year

Before founding Culture Pilot Co, Teresa led the people function at GROW Inc, an Airtree-backed Series D fintech. The company grew its headcount 60% in a single year, reaching 470 employees. She also designed a full-company ESOP covering every single employee.

She's honest about what that kind of growth actually feels like from the inside.

"To be honest, I think that kind of growth is really hard. I don't know of anybody who does it really well, because you're in this influx of onboarding and new people and always in this state of change."

One pattern she saw clearly: rapid hiring creates a split. The people who've been there a while and the new arrivals start to feel like two separate companies.

"There tends to be quite a divide between the old timers and your new hires. Often it can feel like two different companies. There's the old way of doing things, the new way of doing things."

At GROW, the pace didn't leave much room to manage that divide carefully. "We didn't have the luxury of being intentional around that because we were building to take on the largest client to date. Everything was focused on that ramp up."

She's now applying those lessons with her consulting clients. One current client, a distributed scale-up that's been through similar growth, is trying a different approach: pairing people up for coffees through Donut, funding culture committees, giving teams autonomy to build connection organically while also orchestrating some of it deliberately.

"There's an element of orchestration and enablement that needs to happen to really build that culture, but also acknowledging that it is probably going to be uncomfortable for a little while," she says. "You might have some attrition because the old timers will say, I don't recognise this company anymore. And that is kind of the natural part of growing."

The frosting of culture

Ask Teresa what culture actually means and she won't talk about ping pong tables or Friday drinks.

"It's how things are done here. It's how decisions are made. It's how people are treated," she says. "You can say all the nice things, but if you promote somebody who treats people poorly - that is part of your culture. If people get special opportunities because of their relationships with certain individuals, that's your culture."

She finds it telling that when she interviews people about what they want to see in their workplace culture, they often talk about events.

"It's the frosting of culture. But ultimately, it's really around decision making. It's promotions. It's who you hire. It's who you don't hire. That's your culture. And that's how it shows up."

When culture and strategy fall out of alignment, she says the signal is usually straightforward: you're not getting the results you need. The diagnostic from there often leads back to leadership behaviours, hiring misalignment, or a lack of ownership.

"Oftentimes what it is, is you don't have the right skills or right behaviours in your leadership. That's often a key thing that's happening. Or you haven't hired properly. And so you have people who maybe what they thought the role would be and what it actually is, is not aligned."

Making the hard calls faster

Teresa says the work she's most proud of is helping founders make difficult decisions sooner rather than later.

"I think a lot of the work I do is holding up the mirror and speaking the uncomfortable truths to the leaders around what's maybe not working," she says. One founder told her directly: "I don't think I would have come to this point as fast if you hadn't been here to kind of reflect back. And I can't unsee what you shared."

Her approach leans on pattern matching. Having worked across so many companies at different stages, she says she has a reliable sense of how things tend to play out. But she frames her observations carefully.

"I usually don't say anything that I am not 80% or more confident is the right thing," she says. "But I think there's that caveat of, I might not have all the information. You might know more about this than I do."

She frames recommendations as hypotheses rather than gospel. "This is something that I suspect is an issue. And so I approach it as a little bit of fact finding. I'm going to share this as a point of view, but it's never gospel. And I would also say I am always happy to have my mind changed."

The decision, she's clear, always sits with the founder. "These things are not an HR decision oftentimes. It's really helping them come to that decision in a better way, but they have to own it."

The interview red flag rule

Teresa admits she's made a bad hire. It taught her something she now shares with everyone.

"Whatever happens in an interview process, and that can be not only the interview but the communication in between and showing up on time, whatever is happening, times it by 10 and that's the person you're going to get. Because they are on their best behaviour right now."

She continues. "So if they are talking over you, or they don't ask you a single question, they are never going to do that when you're working with them."

The bad hire in her own career came down to bias. "I really wanted a certain profile of a person for the role and I ignored any other warning signs that maybe that wasn't the right fit for the business." The impact was significant. Her takeaway: listen to the signals, check your own preferences, and when you do recognise the mistake, act quickly.

Assume you don't know

When it comes to working with diverse personalities, Teresa keeps coming back to one piece of advice a CEO gave her: "Assume you don't know what's going on."

"If you bring a lot more curiosity, you tend to have less frustration and a greater understanding," she says. "You also have a greater opportunity to get to a good place with that person."

She's practical about the limits of adaptability, though. "You have to decide how much you want to adapt how you are working, how you're speaking to the people. Some things can be a minor tweak, but some things can actually be quite taxing for you personally if you have to dramatically alter how you're working with different individuals."

What fills the cup

Teresa's advice to her younger self comes down to two things (and a bonus).

First, the serenity prayer. "Understanding what can you change and what can't you change and understanding the difference. In HR, we touch so much of the organisation, but oftentimes things are not in our direct control."

Second, protect what gives you energy. "HR can be exhausting depending on what's going on. So it's really coming back to what fills your cup, what gives you energy. And that can be work but it also can be outside of work."

And the bonus: "Your time is finite. Trying to do it all is never getting you ahead. And so just letting that go a bit."

She moved from Boston to Australia. She went from running karaoke nights to designing ESOPs for hundreds of people. The thread connecting all of it is the same one she identified back in that first startup: people are interesting, their behaviours matter, and if you pay close enough attention, you can usually see what's coming before it arrives.

Teresa Lilly is the Founder of Culture Pilot Co, Sydney. She is a 2026 HR Influence Awards Top 12 ANZ, B&T Best People & Culture Leaders 2024, and Strategic Advisor to Hoogly. Connect with her on LinkedIn.

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The HR Influence Awards 2026 Top 12 ANZ are presented by Compono.
Full details at hrinfluenceawards.com.au.