What do you do when you’re suddenly in charge… and totally unprepared?

In this episode, I speak with Gillian Davis, leadership strategist and founder of Overtime Leader, who’s spent the last decade helping scaleups grow their leadership and culture as they move from scrappy startup to mature company.

Gillian’s journey started with crisis: she took over her family’s business when her father fell ill. She later left corporate “with a vengeance,” and found herself dropped into a high-growth tech company with zero systems, zero onboarding, and a ton to figure out.

Since then, she’s served as VP of People at WeTransfer, co-authored the book First-Time Leader with George Bradt, and worked with leadership teams to help them scale intentionally — before chaos sets in.

In this conversation, we talk about:

* The intern confrontation that reshaped her leadership style

* Why she quit corporate without a plan — and what she found instead

* How product thinking changed how she does organisational design

* Common mistakes founders make when hiring senior leaders

* Why fast growth doesn’t mean rushing leadership

Whether you’re a founder, a first-time VP, or just someone trying to lead through uncertainty — this one’s packed with stories and insights you’ll want to remember.

🔗 Guest Links

* Gillian’s website: OvertimeLeader.com

* Gillian on LinkedIn: linkedin.com/in/davisgillian

* Her book: First-Time Leader (with George Bradt)

🗂️ Timestamps

* 00:00 – Intro & Gillian’s origin story

* 05:30 – Leading through crisis with no playbook

* 15:00 – The intern confrontation that changed everything

* 22:00 – Leaving corporate with no plan

* 26:00 – Joining a tech startup with no systems

* 32:00 – Product thinking meets leadership

* 45:00 – Helping founders build leadership post-Series A

* 59:00 – The importance of brave, long-term leadership

What happens when you go from designing or building things yourself… to leading a team of 100+? And what if your career didn’t follow the standard product ladder to get there?

In this candid and funny conversation, Lidia Oshlyansky shares her journey from social worker to backend engineer to product and UX leader at companies like Google, Spotify, and fast-moving startups.

We explore the invisible work of leadership, the emotional challenges of management, and what it really takes to drive change in complex organisations—without losing your humanity.

Whether you’re navigating scale, burnout, tough cross-functional relationships, or wondering if you’re still contributing anything at all… this episode will resonate.

🧠 In this episode, we cover:

* Why Lidia left social work to become a backend engineer—and how she discovered product along the way

* The existential doubt of managing managers (“What am I even doing?”)

* A mindset shift: empowering others is the work

* How to build better relationships between product, design, and engineering

* What to do when collaboration breaks down—and why sometimes, the right move is to stop trying

* How to approach transformation in legacy organisations without arrogance

* The difference between startup chaos and corporate resistance—and how to lead through both

💬 Favourite moment:

“I like that creative innovation chaos—and I like being able to harness it.”

👤 About Lidia:

Lidia Oshlyansky is a veteran product, UX, and design leader with global experience across big tech (Google, Spotify), publishing, and startups. She’s currently Chief Product Officerat Gillion, a Stockholm-based fintech. You can find her on LinkedIn (her only public presence—by design!).

🎯 For:

* Product leaders navigating growth or career transitions

* Managers stepping into more abstract leadership roles

* Anyone wrestling with cross-functional dynamics, change, or self-doubt

We often think great leadership is about having all the answers and staying composed under pressure. But what if the real key to leading a high-performing team is being open about your mistakes?

In this episode, Kim Wylie reflects on two decades of leadership experience at Google, Farfetch, and scale-ups—sharing what actually builds trust and performance when you’re stepping into a new team.

We talk about:

• Why trying to be the perfect manager backfires

• How Kim built psychological safety in a team that didn’t trust her at first

• How to handle resistance to new ways of working in distributed teams

• The team rituals she uses to foster connection, even across regions

• What to do when your team gives you negative feedback

• The neuroscience of why solving everyone’s problems is not good leadership

• And how even senior leaders still struggle with imposter syndrome

This is a masterclass in human-centred leadership—with practical tools, real stories, and the kind of honest reflection most leaders wish they heard more often.

🧠 Some Takeaways

“If you’re a manager and you’re always solving everyone’s problems, you’re robbing them of that dopamine hit.”

“One of the biggest lessons I learned is that being vulnerable builds trust—and trust drives performance.”

“People need to see that how you show up on day one is how you’re going to keep showing up.”

🔗 Links & Resources

Follow Kim on LinkedIn

Watch the full video interview on YouTube

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