611: The #1 career decision product leaders get wrong – with  Ben Lamorte

Make the career decision aligned with who you are

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TLDR

I’m welcoming back Ben Lamorte, veteran OKR coach, to discuss his new book Start With You: Go Beyond Prototyping. Get Clarity Before You Commit. Our conversation centers on how product professionals can use decision analysis and introspection to shift from endlessly prototyping their lives to making bolder, more authentic career decisions reflective of their true selves. Ben shares his personal journey, lessons learned from working in OKRs, and his Identity Blueprint tool for individual career clarity.

Introduction

My guest today was on the show about two years ago, and he gave us one of the best conversations we’ve had on getting an organization clear on what actually matters. Ben Lamorte, the most experienced OKR coach and founder of OKRs.com, is back, and this time the subject isn’t your company’s goals. It’s yours.

Ben has a new book called Start With You: Go Beyond Prototyping. Get Clarity Before You Commit and it makes a contrarian argument for product professionals. We’ve built our careers on prototyping and iteration — test, learn, adjust, repeat. Ben says that’s the right way to develop a product, and the right way to run the first half of your career. But by mid-career, he argues, you’ve already gathered the data about yourself. More experiments won’t help. What you need now is the language to name what you already know, and the courage to commit to it. He’s taken the decision-analysis framework,  information, values, alternatives, that he learned from his Stanford professor Ron Howard, and applied it to the question of what you do next with your professional life. And given the pace of change hitting product people, this is a very important discussion to hear.

Summary of Concepts Discussed for Product Managers

Personal Reflection on Career

After years coaching over 200 organizations on OKRs, Ben experienced a professional slowdown, leading him to apply rigorous decision frameworks inward. When his daughter asked him, “Would you do your work tomorrow if you didn’t get paid?” he began to reflect on personal fulfillment and career direction. This catalyzed his transition from organizational OKRs to helping individuals, especially mid-career professionals, define what truly matters for themselves and make value-aligned commitments.

Ben’s New Book, Start with You

Ben’s book helps professionals identify their identity capital, which includes experiences, credentials, re