I recently listened to Hilary Gridley on Lenny’s Podcast discussing “How to build a team that can ‘take a punch’: A playbook for building resilient, high-performing teams.” As a leader, her insights deeply resonated with me.
Here are my three key takeaways:
1. Learning to “Take a Punch”
We’ve all been there that sinking feeling in your stomach when you realise you’ve messed up in a meeting or when a situation goes completely sideways. Hilary calls these moments “taking a punch,” and her approach to handling them is refreshingly practical.
Instead of avoiding these situations or scrambling to defend yourself, Hilary teaches a more powerful strategy: take purposeful action that demonstrates who you really are. Her framework boils down to one essential question: “What’s one thing I can do that shows the opposite of what I’m afraid this person thinks of me?”
She shared a perfect example from her own experience. During a meeting about health tracking features, she accidentally laughed when her CTO suggested tracking ketamine use, thinking it was a joke. Rather than sending a long explanation or apology, she took swift action. She researched and sent her CTO information about tracking sports betting as another emerging health issue, subtly demonstrating that she does take these matters seriously.
This approach brilliantly transforms defensive energy into productive momentum. Instead of spiraling in self-justification, you take small, concrete steps that reshape the narrative through your actions, not your words.
What strikes me most is the simplicity and directness that this method reinforces. It gives me agency in situations where I might otherwise feel helpless. By reframing career missteps as opportunities that demonstrate character and build stronger relationships, I can develop my “resilience muscle”, something every leader needs in today’s complex workplace.
2. Understanding How Leaders Think, Not Just What They Think
Another powerful insight from Hilary centres on a subtle but crucial distinction that it’s far more valuable to understand how your stakeholders think rather than just what they think. This completely changes how we operate within organisations.
When you grasp the thinking patterns and mental models of strategic leaders, you unlock the ability to anticipate their concerns, understand their decision-making frameworks, and align your work accordingly. As a leader myself, I’ve realised I need to flip this around too. By making my own thinking transparent to my team, I give them the same clarity and autonomy.
Here’s where Hilary delivers a hard truth that hit home for me: we often see ourselves as the protagonist in our workplace story. But the reality is that we’re part of a larger narrative. Once we accept this and focus on understanding how key decision-makers think, everything changes. Teams naturally pull in the same direction because they’re operating from shared mental models, not just following orders.
The impact is immediate and practical. Decisions move faster because people aren’t constantly seeking approval for every detail. There’s less friction because team members can anticipate what will resonate with leadership. Most importantly, it creates genuine alignment that comes from knowing why certain decisions get made.
This insight has fundamentally changed my approach to leadership. Instead of just communicating decisions, I now share my reasoning, the context, the trade-offs I’m weighing. It’s about helping my team build accurate mental models of how I and other leaders think, giving them the tools to navigate independently and effectively.
3. Using AI to Accelerate Learning and Development
Hilary’s perspective on AI as a tool for professional development really excited me. As leaders, we’re constantly pulled in different directions and time is our scarcest resource. The idea of using AI to become better managers and help our teams grow faster is genuinely game-changing.
She’s built custom GPTs that fundamentally transform how her team learns. The one that particularly struck me was “Aristotle” – a tool that creates LSAT-style logical reasoning questions set in real PM scenarios. Instead of getting feedback on your reasoning skills maybe once a week in meetings, you can practice hundreds of times with instant feedback. That’s a complete shift in how we think about skill development.
Even more impressive, she’s created GPTs that mirror her own feedback style, available 24/7. Her team can get manager-quality feedback at 11 PM on a Sunday if they’re working on something. What traditionally takes years to develop through sporadic feedback can now be compressed into months or even weeks.
But here’s what really resonated with me: Hilary doesn’t just throw AI tools at her team and hope they stick. She applies behavioral psychology principles to drive adoption, focusing on three key elements: consistency (starting with tiny, daily actions), reducing friction (making it easier to use the tool than not to), and creating powerful reward loops (ensuring people feel great when they use these tools).
This approach brilliantly weaves together all three insights from the podcast – building resilience through rapid skill development, operating more effectively through constant feedback, and creating sustainable habits for an AI-driven future. It’s not about replacing human judgment; it’s about accelerating how quickly we develop that judgment by getting exponentially more practice.
The potential here is enormous. AI fundamentally changes how professional development works, allowing individuals to accelerate their growth in ways we’ve never seen before. If we can help our teams compress years of learning into months while giving them the autonomy to develop on their own schedule, we’re not just becoming better leaders but we’re changing how people build careers.
You can find the whole podcast episode here: https://www.lennysnewsletter.com/p/how-to-build-a-team-that-can-take-a-punch