Finding Balance: The Intersection of Perfectionism and Opportunity Cost

What actually sets you apart in a world where AI can do more and more of your job? In this episode, Marc and Ben are joined by Hilary Gridley—Head of Core Product at WHOOP and instructor of the Maven course How to Be a Supermanager with AI—to unpack how great product leaders can use AI to magnify their strengths instead of dulling them.

Hilary breaks down her approach to time allocation, sharing how she dissects messy, ambiguous work into its component parts and uses AI as a thinking partner—not a crutch. They explore how to identify high-leverage tasks, when investing time is essential for clarity, and why doing something the hard way is sometimes the point. The conversation also touches on how PMs can design their roles around their superpowers, what good taste really means in product, and how managers can help their team grow by doubling down on what makes them exceptional.

If you're trying to become more intentional with how you spend your time, use AI more thoughtfully, or lead a team of PMs in this new era—this episode is for you.

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To support the podcast, please check out the links below:

* Preparing for a PM interview with tech companies like Meta and Google? Check out Ben's course for Product Sense and Analytical Thinking PM interviews (selected by Lenny Rachitsky as a Top Course in Product on Maven 🔥) and his AI Copilot for interview practice. Supra Insider listeners get 10% off the course with promo code “suprainsider”. Enrollment is now open for the next cohort starting June 17th.

* Supra has teamed up with Maven to bring you something special – courses that our own community members have personally curated. And because you're part of the Supra family, you get $100 off any of these handpicked selections with code SUPRAxMAVEN.

In this episode, we covered the following topics:

* (00:00) Hilary’s approach to identifying and doubling down on her spikes as a product leader—and how AI helps magnify them.

* (04:00) How she breaks down ambiguous product work into sub-skills to better allocate time and energy.

* (11:30) The tradeoff between leverage and clarity—and why doing something the hard way can be the right call.

* (17:00) Frameworks Hilary uses to decide when to delegate, when to coach, and when to go deep herself.

* (22:00) How she uses AI tools like Claude as thinking partners to sharpen ideas and move faster.

* (27:00) Why “taste” in product is hard to teach—but essential to develop as a PM.

* (32:30) The biggest mistake new managers make when trying to “round out” their team—and how to coach for spikes instead.

* (38:00) How to build a team with differentiated strengths that complement each other instead of copying one another.

* (44:00) What Hilary learned from teaching 100+ managers in her Maven course on using AI to lead more effectively.

* And more!

If you’d like to watch the video of our conversation, you can catch that on YouTube:

Links:

* Hilary Gridley: https://www.linkedin.com/in/hilarygridley/

* Hilary’s Substack: https://hils.substack.com/

* How to Become a Supermanager with AI: https://maven.com/hilary-gridley/ai-powered-people-management

* Hilary’s recent episode on “How I AI” with Claire Vo

* Superpowers by SYPartners: https://apps.apple.com/us/app/superpowers-by-sypartners/id1309752471

* Marc: https://www.linkedin.com/in/marcbaselga/

* Ben: https://www.linkedin.com/in/benerez/

To support the podcast, please check out the links below:

* Supra has teamed up with Maven to bring you something special – courses that our own community members have personally curated. And because you're part of the Supra family, you get $100 off any of these handpicked selections with code SUPRAxMAVEN.

* Preparing for a PM interview with tech companies like Meta and Google? Check out Ben's course for Product Sense and Analytical Thinking PM interviews (selected by Lenny Rachitsky as a Top Course in Product on Maven 🔥) and his AI Copilot for interview practice. Supra Insider listeners get 10% off the course with promo code “suprainsider”. Enrollment is now open for the next cohort starting June 17th.

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