Herding Squirrels Ep 13
w Oliver Gray
Director of Engineering, Trustpilot
Oliver Gray, Director of Engineering at Trustpilot, shares his journey of transforming underperforming engineering teams into high-performing, self-directed powerhouses. Through hands-on LEGO models, Oliver reveals the power of bottom-up mission development, the pitfalls of fixed-price consulting projects, and why the best thing you can do as a leader is make your team stop needing you. From navigating AI adoption to creating psychological safety in hybrid environments, this conversation offers tactical wisdom for anyone leading technical teams through uncertainty.
Timestamps
00:00 - 01:50 - Introduction & Personal Build
Oliver introduces himself and builds a model showing his life outside work: cooking with leftovers, playing squash, and hitting the occasional EDM event.
01:51 - 04:02 - Best Team Experience
Oliver builds a journey model showing how he took a team from dealing with inherited code chaos and demotivation to becoming high-performing through clarified mission, increased ownership, and self-direction.
04:03 - 09:08 - Nightmare Team Scenario
The cautionary tale of a fixed-price consulting project gone wrong, complete with requirements gaps, access restrictions, and fundamental logic flaws that taught Oliver valuable lessons about software project structure.
09:09 - 13:13 - Leading Through Uncertainty
Oliver builds a model showing leadership as spinning between looking forward and looking back, emphasizing transparency, celebrating wins, and empathizing with team members through change. Discussion includes navigating AI adoption and the importance of product-focused engineers.
13:14 - 19:22 - Team Dynamics & Influence
Exploring psychological safety, the value of hybrid bonding moments, water cooler conversations, and how to create self-sufficient teams that don’t need constant management oversight.
19:23 - 22:25 - Final Build: Advice for New Leaders
Oliver’s final model emphasizes maintaining prioritized task lists, keeping eyes in all directions (up to leadership, sideways to peers, down to team), and building relationships across the company as gifts that inform better decisions.
22:26 - 22:47 - Wrap-Up & Where to Find Oliver
Notable Quotes
On Mission Development:
“By developing the bottom-up and saying, this is what we think we should be doing. This is how we want to move that metric. This is what we think we’re good at, what we’re skilled at. That was how we managed to change the direction.”
On Fixed-Price Projects:
“If you’re ever going to do a fixed price project, then it has to be a fairly simple project with very well-known requirements, which in software is quite unusual.”
On Empowering Teams:
“I spoke to them about, I’d helped them sort of set the mission, but now I wanted the team to take over and be their own bosses. The team could be more nimble if they were driving what they were doing as a team themselves.”
On Leadership Transition:
“One of my engineers in the past joked that I was like their work counselor. The conversations I had with him were often like, you know, he would share his frustrations and I would empathize, sometimes provide ways out or alternatives, other times just say, yeah, that sucks.”
On Self-Sufficient Teams:
“Making your team become self-sufficient without you, right? So that you only have to spend a minimum amount of time with them, like helping them unblock things or when a project’s really important at the start of it or planning. But like the more self-sufficient they are, the more power you’ve given them, the better for you to look externally or from the balcony view.”
On AI and Engineering:
“What I told my engineers was that, you know, we all need to be using it, experimenting with it, seeing what it’s good for, potentially what it’s not good for. But from their perspective, if they’re product focused, which is a big thing for me, then that will definitely sort of ensure them for longer because it will take longer for AI to be both product focused and writing code.”
Where to Find Oliver
You can connect with Oliver Gray on LinkedIn, where he occasionally shares thoughts and ideas about engineering leadership and team building. Oliver is currently exploring new opportunities, so reach out if you have a great role for a leader who knows how to build self-directed, high-performing engineering teams.
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Herding Squirrels is your podcast about modern teams, uncovering the nuts and bolts of what makes teams work. Recorded in NYC
Other Episodes:
Herding Squirrels Ep 12 w Louie Celiberti
Herding Squirrels Ep 11 w Nicole Tibaldi
