Career Ladders and Rewarding Zero-to-One Work

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How do you disagree with your CEO, especially a visionary founder, without putting your job or credibility at risk?

In this episode of Supra Insider, Marc and Ben sit down with Elena Luneva (CPO, advisor, and executive coach) to unpack one of the most common, emotionally fraught challenges in product leadership: what to do when your CEO wants to change direction based on a gut instinct, and you disagree?

Drawing from Elena’s coaching experience and her own time leading product at high-growth companies, the conversation explores how to navigate power dynamics, set boundaries without losing trust, and protect team momentum amid constant change. They also share tactical frameworks for managing roadmap pivots, setting expectations with execs, and negotiating trade-offs when the team is already stretched thin.

Whether you’re a PM, product leader, or founder, you’ll walk away with practical strategies for navigating tough conversations, advocating for your team, and growing your influence, without losing your job or your sanity.

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Interviewing at Uber, Figma, or Stripe?

Exciting news! If you’re a PM preparing for interviews at Uber, Figma, or Stripe… we think you’re going to love Insider Loops. You can read about it in Ben’s LI post, Marc’s LI post or check out the site directly below.

In this episode, we covered the following topics:

* (00:35) Why this question resonates so deeply: “How do I manage a CEO who drives the roadmap by gut?”

* (05:20) The challenge of re-underwriting your mental narrative every time the CEO shifts direction

* (07:38) Why these moments can feel personal, even when they’re not?

* (12:28) Why your executive team, not just your builders, becomes your “first team” as a product leader

* (14:10) A playbook for responding to surprise roadmap changes: Listen, calibrate, and triage

* (19:54) Advice for CEOs: How to share ideas without shutting down your team

* (27:08) Using the Horizons framework to evaluate bets—and defuse emotional debates

* (34:31) The hidden costs of failed bets—and why many great PMs leave big companies to do risky work elsewhere

* (44:09) Giving CEOs the menu: options, trade-offs, and sunk costs

* (54:18) Why great product leaders should also validate gut instincts with market truths

* And more!

Links:

* Elena’s Course on AI Powered Executive Communication

* Elena’s Course on How to Develop CPO-Level Skills

* The Substack post that inspired this conversation: Your CEO Just Got Back From a Conference. Now What?

* Elena’s Letters: https://elenasletters.substack.com

* Elena’s LinkedIn: https://www.linkedin.com/in/elenaluneva/

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

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

If you’re a new subscriber, we encourage you to check out some of the recent episodes you might have missed:

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* 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 Meta-style PM interviews? Ben's course for Product Sense and Analytical Thinking PM interviews has been selected by Lenny Rachitsky as a Top Course in Product on Maven 🔥. Enrollment for the 10th and final cohort of Ben’s course closes TONIGHT (Oct 13) and kicks of Oct 14. Ben’s popular AI Copilot for interview practice is available here.

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