Ever wonder how to tell if a product leader is actually good—or just good in interviews? In this episode, we talk through what strong product leadership really looks like, how to spot warning signs, and what to do if you’re not getting the support you need. We also cover the questions you should be asking when you're interviewing for a new role and how to make the most of a good leader when you have one.
If you’re thinking about your next move—or just want to get better at working with your current boss—this one’s for you.
Transcript: Episode 21 - Before You Say Yes: Interviewing your Next Boss
Introduction
[0:00] Welcome Back – Kicking off the episode with a hill metaphor and the big question: what makes a great product leader?
[2:00] A Tough Early Experience – A story of receiving poor leadership advice and the fallout with IT.
Weak vs. Strong Leadership
[4:36] Leadership Is Influence – Highlighting the power of cross-functional trust and respect.
[6:00] What Great Leaders Do – Traits that matter: trust, vision, honesty, listening, decisiveness, and more.
[8:26] Anti-Patterns – Indecisiveness, pass-through behavior, and leaders who don’t push back.
When Your Boss Isn’t a Great Leader
[9:25] Taking the Right First Steps – The value of seeking out learning and acting independently.
[11:08] Pushing Change Without Buy-In – The mistake of skipping the “why” when introducing new ways of working.
[13:01] The Importance of Positioning – How to position yourself well when you have a weak leader
[14:09] Show Your Work – Tips for demonstrating your impact in a way your leader will understand and support.
External Pressures on Leaders
[16:00] How Strong Leaders Can Become Weak – How organizational pressure can derail even the strongest leaders.
[18:45] Why It All Matters – Weak leadership affects career growth, team success, and even headcount.
Taking Control of Your Narrative
[20:34] What You Can Control – Focus on your communication, relationships, and personal brand.
[21:37] What Not to Do – Avoid sabotage, complaints, and repeating broken patterns.
[22:08] Find Support Elsewhere – You don’t have to rely on your manager for growth and mentorship.
How to Identify a Strong Leader in an Interview (Role Play)
[22:30] Role Play: Product Launch – A side-by-side of strong vs. weak leadership responses.
[25:23] Spotting the Difference – Look for accountability, clarity, and thoughtful process.
[27:01] Role Play: Talent Development – Coaching vs. control and the risk of "mini-me" management.
[29:30] Interpreting the Signals – What good answers sound like—and what they reveal.
[30:26] Ask About Vision – Great leaders can clearly explain product and team direction.
[32:20] Accepting Risk – Not every role is perfect, but know what matters most to you.
Selecting a Leader Based on your Career Goals
[34:32] Know What You Need – What motivates you may change over time.
[35:25] Setting Criteria – Define what you want from a company, role, and manager.
[36:04] Learning by Example – Good senior leaders model behaviors worth following.
Getting the Most from a Strong Leader
[37:03] Soak It Up – Watch how they respond and model their soft skills.
[38:03] Be Curious – Ask questions to uncover the thinking behind their actions.
[39:39] Ask for Feedback – Strong leaders will invest in you—if you’re ready for it.
[40:18] Show Initiative – Be proactive and bring your A-game.
[40:52] Values and Fit – Great leaders aren’t always a perfect fit—know what you need.
Final Thoughts
[41:44] No One Is Perfect – Take ownership and learn from what’s in front of you.
[42:29] Don’t Take Great Leaders for Granted – The right leader is worth more than just a salary bump.
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Jun 24 202543 mins