Tigers, Caves, and Bets - a Product Strategy Conversation with Coach Andrew Skotzko

In this insightful episode of the Product Rising Podcast, host Cassie welcomes Andrew Skotzko – a product leadership coach and strategic advisor. Andrew shares his unconventional journey into product management, starting from growth hacking and transitioning into engineering, before finally becoming a product leadership coach. He emphasizes the critical difference between strategy and planning, introducing the concept of a strategy as a series of bets rather than a rigid plan. Andrew discusses the importance of ongoing strategy development and the avoidance of the 'strategy cave' mentality, preparing listeners for the challenges of strategic planning and product leadership. Throughout the episode, Andrew provides practical advice for product leaders on when and how to hire a coach, the creative and iterative nature of strategy, and how to effectively align product strategy with business goals. His comprehensive approach offers valuable insights for product leaders aiming to elevate their strategic game and navigate the complexities of product development.00:00 Welcome to the Product Rising Podcast00:48 Meet Andrew Skotzko: From Growth Hacking to Product Leadership03:14 The Journey to Becoming a Product Leadership Coach04:41 The Value of Customized Coaching06:43 A Success Story: Coaching a CPO in the Energy Sector10:22 The Challenges and Rewards of Strategy Development17:15 When to Hire a Product Leadership Coach23:10 Funding and Frameworks for Coaching26:09 Writing a Book on Product Strategy28:50 The Illusion of Control in Business Strategy31:15 The Concept of Bets in Strategy32:23 Differentiating Product and Business Strategy36:30 The Importance of Continuous Strategy Development38:32 Navigating Strategic Planning and Execution41:59 Collaborative Strategy Formation48:06 Avoiding the Strategy Cave Trap52:35 Final Thoughts and Practical Advice📚Resources:Andrew’s Strategy Self Diagnostic ToolAndrew’s Product Strategy Book Interest FormInspired: How to Create Tech Products Customers Love (Silicon Valley Product Group) by Marty CaganGood Strategy Bad Strategy by Michard RumeltUnderstanding Michael Porter: The Essential Guide to Competition and Strategy by Joan MagrettaPlaying to Win by Roger Martin✨Where to find Andrew:On LinkedInAndrew’s Leadership Nudges SubstackAndrew’s Make Things that Matter Podcast💫 Where to find Cassie:On LinkedIn At Cassie Camp - Learn more about product leadership coaching and fractional product leadership🙋🏻‍♀️Where to find Women in Product:On LinkedIn Website https://womenpm.org/Join the Community https://womenpm.org/wip-community/

In this insightful episode, we welcome Coco Brown, a multi-time entrepreneur and CEO of Athena Alliance. Coco shares her journey in Silicon Valley, her experience in HR and IT, and her mission to support women in leadership roles. She discusses the importance of career care, the power of coaching, and offers valuable advice for leaders navigating challenging times. With a focus on women in product roles, Coco emphasizes the opportunities for growth and diversification in their careers. She also shares her views on improving executive team dynamics and leveraging coaching for personal and professional development.00:00 Introduction and Guest Welcome01:01 Cocoa Brown's Career Journey05:50 The Power of Coaching06:20 Leadership Traits in Challenging Times09:49 The Role of Coaching in Leadership18:18 Women Investing in Career Care23:11 Paths for Product Leaders30:45 Executive Team Development36:30 Conclusion and Farewell📚Resources:Radical Candor by Kim Scott✨Where to find Coco Brown:On LinkedInExecutive Edge - Women in Product & Athena AllianceAthena Alliance💫 Where to find Cassie:On LinkedIn At Cassie Camp - Learn more about product leadership coaching and fractional product leadership🙋🏻‍♀️Where to find Women in Product:On LinkedIn Website https://womenpm.org/Join the Community https://womenpm.org/wip-community/

In this episode, Cassie welcomes Bosky Mukherjee, the prolific founder of PM Dojo and SheTrailblazes, and a veteran product advisor, leadership coach, and trainer. Bosky discusses her journey into product leadership, the formation of PM Dojo, and her mission to support women in product management. The conversation delves into the nuances of product management training versus coaching, the impact of AI on the industry, and strategies for driving cultural shifts within organizations. Bosky also shares insights on balancing humility with confidence and offers practical advice on leveraging coaching to unlock business potential and personal growth.More about Bosky:Bosky Mukherjee, an executive tech leader with over 22 years of global experience—spanning early-stage startups to high-growth companies like Atlassian.She’s the founder of SheTrailblazes and a powerful force for change in how women succeed, thrive, and rise to the top. Through her flagship program, Leadership Edge, Bosky equips women to lead with strategic visibility and executive communication—fast-tracking their path to promotion, all the way to the C-suite, and when the time is right, into entrepreneurship.Her work isn’t just about career growth. It’s about power, parity, and making sure women aren’t just at the table—but driving the agenda.Bosky is also the founder of PMDojo, where she helps companies build stronger, more strategic innovation teams—equipping product and technology talent to drive bigger business impact and communicate with executive fluency.00:00 Introduction and Guest Welcome00:49 Bosky's Journey into Product Leadership01:36 Challenges and Realizations in the Executive Room03:05 Founding PM Dojo and Its Mission04:50 AI in Product Management09:41 Training vs. Product Leadership Coaching11:05 Coaching Styles and Skills Development15:03 Working with Companies and Teams18:56 Driving Cultural Shifts in Organizations23:19 Assigning Dollar Value to Business Transformation23:33 Navigating Product Leadership Challenges24:38 Implementing Small Shifts for Big Changes25:25 Facilitating Business Conversations26:47 Success Stories and Skill Development28:39 Working It Out: Lessons from School30:26 Confidence, Humility, and Curiosity31:55 Hiring a Coach: When and Why34:53 Building Community and Networking38:18 Creative Budget Solutions for Product Teams44:10 Conclusion and Final Thoughts📚Resources:✨Where to find Bosky Mukherjee:On LinkedInSheTrailblazesPMDojo💫 Where to find Cassie:On LinkedIn At Cassie Camp - Learn more about product leadership coaching and fractional product leadership🙋🏻‍♀️Where to find Women in Product:On LinkedIn Website https://womenpm.org/Join the Community https://womenpm.org/wip-community/

Welcome to the podcast featuring Hope Gurion, an esteemed product leadership coach. She is recommended by Marty Cagan in his book, Transformed, has moderated product leadership councils with Phyl Terry’s Collaborative Gain, and works with Teresa Torres in training teams on Continuous Discovery Habits. In this episode, Hope delves into her extensive background in product management, sharing insights from over 25 years in the tech industry, her roles as Chief Product Officer, and SVP of Product. She discusses her transition from consulting to coaching, offering valuable guidance on becoming outcome-oriented and enhancing team effectiveness. Hope covers the challenges of finding the right company fit, the nuances between training and coaching, and key strategies for cross-functional collaboration. Tune in for actionable advice on elevating your product management career.00:00 Introduction and Welcome00:39 Hope Gurion's Background01:54 Transition to Coaching03:37 Challenges in Product Leadership04:55 Coaching and Training Approach07:25 Importance of Discovery in Product Management09:47 Balancing Training and Coaching15:57 Selecting the Right Coach18:51 Defining Success in Product Leadership21:33 Peer-Based Coaching vs. One-on-One Coaching28:23 Transformation in Organizations39:57 Podcast Origin Story and Conclusion📚Resources:Fearless Product Podcast & Mentioned episodes:S2 Ep. 2: How Do You Balance Investing in Tech Debt vs Customer Value?S1 Ep. 8: How Do You Say No to the CEO?Transformed by Marty Cagan - Hope is profiled as an exemplary product coachCollaborative Gain with Phyl Terry - Hope is a moderator for product leader peer councilsContinuous Discovery Habits at Product Talk with Teresa Torres - Hope trains teams✨Where to find Hope Gurion:On LinkedInHope’s Website - https://fearless-product.com/ 💫 Where to find Cassie:On LinkedIn At Cassie Camp - Learn more about product leadership coaching and fractional product leadership🙋🏻‍♀️Where to find Women in Product:On LinkedIn Website https://womenpm.org/Join the Community https://womenpm.org/wip-community/

Tim Herbig Connecting the dots of Product Strategy, Product OKRs, and Product DiscoveryIn this episode, we welcome Tim Herbig, a product leadership coach with a special focus on OKRs, in addition to product strategy and discovery. Tim shares his unique journey from product management to coaching, elaborating on the complexities and nuances of implementing OKRs in various business contexts. Through his insightful discussion, Tim covers the misconceptions about OKRs, the importance of adapting them to your specific needs, and effective strategies for measuring success. He also dives into the integration of product discovery and product strategy with OKRs, offering practical advice for product leaders facing challenges with OKR implementation. Whether you're in a startup or a large enterprise, Tim's expertise provides valuable perspectives on how to make OKRs work for your team.00:00 Introduction and Guest Welcome00:48 Tim Herbig's Journey into Product Management01:52 Transition to Coaching and Consultancy03:53 Specialization in OKRs and Product Management06:50 Adapting OKRs to Different Contexts09:46 Challenges and Strategies in OKR Implementation13:58 Measuring Success and Influence in OKRs22:47 OKRs in Product vs. Broader Company Context25:38 The Role of OKRs in Strategy and Discovery27:11 Confidence and Hypotheses in Strategy29:36 OKRs in Startups vs. Large Enterprises32:07 Adapting OKRs to Fit Your Context33:47 Common Misconceptions and Best Practices40:00 Aligning OKRs Across Teams47:43 When to Bring in OKR Support50:57 Conclusion and Contact Information📚Resources:Book: Radical Focus by Christina WodtkeBook: Measure What Matters by John DoerrArticle: Zone of control vs Sphere of influenceArticle: Ravi Mehta's Narrative, Commitments, and Tasks Framework✨Where to find Tim Herbig:On LinkedInTim’s Website - https://herbig.co 💫 Where to find Cassie:On LinkedIn At Cassie Camp - Learn more about product leadership coaching and fractional product leadership🙋🏻‍♀️Where to find Women in Product:On LinkedIn Website https://womenpm.org/Join the Community https://womenpm.org/wip-community/

In this episode of the podcast, we welcome Tami Reiss, an experienced product leader, speaker, author, trainer, and coach. Tami recounts her journey into product management, becoming a CEO, and her multifaceted roles at Justworks and Insight Partners. She discusses how she transitioned into coaching, emphasizing the importance of learning, networking, and building relationships. Tami shares advice on the different types of product coaches, the value of continuous learning, and the significance of owning business metrics and strategic planning. The discussion also covers effective stakeholder management, getting buy-in, and why having a coach can be pivotal in advancing one's career. Tami offers practical tips for influencing cross-functional teams and highlights how important it is to ask the right questions to build trust and foster collaboration. Tune in to explore actionable insights for product leaders and discover why coaching is a vital tool in your professional toolkit.00:00 Introduction and Guest Welcome00:29 Tami Reiss' Journey into Product Management01:27 Life's A Pitch and Coaching Engineers01:56 Becoming a Product Leader Coach03:08 Writing a Children's Book on Product Management04:47 Networking and Career Opportunities05:22 The Importance of Long-Term Relationships11:08 Diverse Perspectives in Coaching17:14 Types of Product Coaches19:35 The Value of Coaching for Product Leaders24:29 The Role of a Sounding Board in Professional Growth25:03 Navigating Board Meetings and Strategic Decisions26:57 The Importance of Asking Questions and Building Empathy28:50 Influence Without Authority: Building Bridges31:59 Defining Success and Strategic Leadership33:28 Coaching and Professional Development36:41 Financial Language and Strategic Alignment43:12 Exploring Growth Strategies and Presenting to the Board46:11 Conclusion and Final Thoughts📚Resources:What Do Product Managers Do? A Primer for Aspiring PMs of All Ages, by Tami Reiss✨Where to find Tami Reiss:On LinkedInTami’s Website - My Leader Within (with booking link)💫 Where to find Cassie:On LinkedIn At Cassie Camp - Learn more about product leadership coaching and fractional product leadership🙋🏻‍♀️Where to find Women in Product:On LinkedIn Website https://womenpm.org/Join the Community https://womenpm.org/wip-community/

In this episode, we got some straight talk from Teresa Torres, learning how she incorporates her masters in Learning & Development from Northwestern into her design of product learning experiences. Teresa shares invaluable insights about when blogs and podcasts might be enough for your growth—and when training courses may really be what's needed to take you to the next level. Do you know if you have blind spots? Or are you navigating some unique and tricky contexts where a coach can help? This far-ranging episode explores all these concepts with the founder of Product Talk and author of 'Continuous Discovery Habits'. Teresa discusses the fundamental differences between coaching and training and highlights the importance of deliberate practice in skill development. She offers practical advice on advocating for discovery practices within organizations and provides tips for product leaders to enhance their teams' capabilities. This episode is a must-listen for anyone looking to deepen their understanding of product development and improve their practice through structured learning.00:00 Introduction to Skill Building and Coaching00:35 Sponsored Segment: SuperInterviews01:26 Welcome01:32 Guest Introduction: Teresa Torres02:36 The Journey from Coaching to Training05:06 Understanding the Difference Between Coaching and Training09:57 The Role of Deliberate Practice in Skill Building14:54 The Importance of Community and Peer Coaching21:57 Understanding Business Outcomes22:23 The Challenge of Opportunity Solution Trees23:22 Effective Discovery Practices24:57 Choosing the Right Trainer or Coach27:29 Reflective Questions for Product Teams32:50 Advocating for Discovery in Organizations36:42 The Role of Product Leadership Coaching40:31 Aligning Sales and Product Teams45:00 Conclusion and Final Thoughts📚Resources:Teresa’s website - Product TalkContinuous Discovery Habits✨Where to find Teresa:On LinkedIn💫 Where to find Cassie:On LinkedIn At Cassie Camp - Learn more about product leadership coaching and fractional product leadership🙋🏻‍♀️Where to find Women in Product:On LinkedIn Website https://womenpm.org/Join the Community https://womenpm.org/wip-community/

In this episode, we welcome Phyl Terry. “ Part of the reason I dress the way I do is because that's who I am. But part of the reason I dress this way is I'm trying to lead cultural change.” - mic drop! 🎤💥What does leading cultural change have to do with coaching? Phyl shares insights on the importance of asking for help and building a community for growth and development. They outline the three-tier coaching model at Collaborative Gain which features peer-to-peer coaching, concierge coaching, and CEO coaching. Phyl emphasizes the importance of mindset shifts, the collective brain, and positive politics in navigating corporate environments. Tune in for a deep dive into the evolving role of product coaches and how to leverage community and coaching for career success.00:44 Guest Introduction: Phil Terry01:18 The Importance of Community in Coaching01:57 Three Tiers of Coaching at Collaborative Gain05:45 The Intelligence Revolution and Mindset Shift06:58 The Intelligence Paradox and Human Evolution10:48 The Role of High Fidelity in Cultural Evolution13:15 The Impact of AI and the Internet on Innovation21:20 Positive Politics and Career Development29:12 The Evolution of Product Management29:48 Building Relationships and Asking for Help31:36 The Power of Vulnerability in Leadership35:01 Navigating Positive Politics41:46 The Importance of Councils and Coaching48:38 Personal Stories of Resilience and Community53:28 Conclusion and Final Thoughts📚Resources:Collaborative Gain https://collaborativegain.com/ - Learn more about Executive and Associate Councils, and Concierge Coaching Never Search Alone https://bookshop.org/p/books/never-search-alone-the-job-seeker-s-playbook-marty-cagan/18752511Checklist for Laid Off or Let Go https://www.phyl.org/checklist-for-laid-off-or-let-go ✨Where to find Phyl:On LinkedIn https://www.linkedin.com/in/phylterry/ Phyl.org 💫 Where to find Cassie:On LinkedIn https://www.linkedin.com/in/cassandracampbell/At Cassie Camp https://www.cassiecamp.com - Learn more about product leadership coaching and fractional product leadership🙋🏻‍♀️Where to find Women in Product:On LinkedIn https://www.linkedin.com/company/women-in-product/posts/ Website https://womenpm.org/Join the Community https://womenpm.org/wip-community/

Our guests for this episode are Vidya Dinamani and Heather Samarin - co-writers of Groundwork: Get Better at Making Better Products and co-founders of Product Rebels. Vidya and Heather define the "core" of great product management and then go deep on "winning hearts and minds" as an uplevel once you’ve got your core down. It’s the 1-2 punch any product leader can use.We discuss the differences between training and coaching, share a "from the field" story about a product team going from disregarded to high-impact, and 4 contexts where you might think about hiring a coach. Lastly, we touch on AI and product management. Faster horses, anyone? 00:00 Introduction and Guest Welcome00:19 Founding Product Rebels01:21 Customer-Driven Product Management05:01 Scrappy Customer Research05:32 Groundwork and Core Principles14:37 Winning Hearts and Minds20:33 Training vs. Coaching25:54 Challenges and Success Stories39:48 When to Bring in a Coach46:44 Conclusion and Farewell📚Resources: - Book: Groundwork: Get Better at Making Better Products https://www.amazon.com/Groundwork-Get-Better-Making-Products/dp/0578776324  - Product Management Team Assessment: https://productrebels.com/assessment/  ✨Where to find Vidya:On LinkedIn https://www.linkedin.com/in/vdinamani/At Product Rebels https://productrebels.com/Hosting the Product Leader Summit https://www.productleadersummit.com/how-it-started 🌟 Where to find Heather:On LinkedIn https://www.linkedin.com/in/heathersamarin/ At Product Rebels https://productrebels.com/💫 Where to find Cassie:On LinkedIn https://www.linkedin.com/in/cassandracampbell/At Cassie Camp https://www.cassiecamp.com 🙋🏻‍♀️Where to find Women in Product:On LinkedIn https://www.linkedin.com/company/women-in-product/posts/ Website https://womenpm.org/Join the Community https://womenpm.org/wip-community/

An interview with Marty Cagan kicks off our new series, The Coach's Playbook. He shares with Cassie his take on coaching, doing it right and elevating the product practice.