Jen Swanson, CEO of Tuckpoint Advisory Group, specializes in helping organizations adopt product-led operating models. In this conversation, she unveils why many transformations fail, emphasizing the need for intentionality and genuine leadership involvement. Swanson warns against 'transformation theater' and stresses the necessity of honest self-assessment. She also highlights the importance of creating a psychologically safe environment for team members to learn and adapt, ensuring that transformation is a sustainable journey rather than a temporary fix.
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Intentional Transformation Needs Orientation
Successful transformation requires knowing your current state and your targeted future state clearly.
Intentionality in the transformation process ensures meaningful progress, not accidental change.
insights INSIGHT
Transformation Theater Illusion
Transformation theater is pretending to change while everything stays the same.
It reinforces legacy problems instead of fixing them, frustrating front-line employees seeking real progress.
volunteer_activism ADVICE
Necessity of Executive Leadership
Executive commitment and active leadership are essential to drive real transformation.
Communication must be relentless and inclusive to overcome resistance throughout the organization.
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Transformations are hard, and too often, they fail to deliver on their promise. In this episode of The Product Experience, Lily and Randy speak with Jen Swanson, CEO of Tuckpoint Advisory Group, to unpack why transformation initiatives falter and what it truly takes to succeed.
Key Takeaways — Transformation requires intentionality: Real transformation isn't accidental or surface-level; it must be deliberate, comprehensive, and backed by leadership. — Avoid ‘transformation theatre’: Pretending to change—without restructuring ownership, processes, or collaboration—is worse than doing nothing at all. — Start with honest orientation: Knowing your starting point is essential before plotting a path forward. — Executive involvement is non-negotiable: Transformations can’t be delegated. Leadership must model the change and communicate relentlessly. — Product-led is about mindset, not just teams: Everyone should operate within the product model, but not all need to be on product teams. — Pace matters: Organisations must assess their capacity for change and determine the right balance between ambition and sustainability. — Give grace for the learning curve: People need space to be bad at new things before they get good—psychological safety is essential.
Chapters 0:00 – Introduction & the myth of sneaky transformations 1:01 – Jen’s background and path into product 2:53 – What transformation really means 5:53 – Defining honest orientation 8:00 – What is transformation theatre? 12:09 – When real change feels fake 13:04 – The importance of executive commitment 16:04 – Why transformations fail 19:11 – Common catalysts for transformation 22:06 – Product-led vs product thinking 25:00 – Who’s in the op
Our Hosts Lily Smith enjoys working as a consultant product manager with early-stage and growing startups and as a mentor to other product managers. She’s currently Chief Product Officer at BBC Maestro, and has spent 13 years in the tech industry working with startups in the SaaS and mobile space. She’s worked on a diverse range of products – leading the product teams through discovery, prototyping, testing and delivery. Lily also founded ProductTank Bristol and runs ProductCamp in Bristol and Bath.
Randy Silver is a Leadership & Product Coach and Consultant. He gets teams unstuck, helping you to supercharge your results. Randy's held interim CPO and Leadership roles at scale-ups and SMEs, advised start-ups, and been Head of Product at HSBC and Sainsbury’s. He participated in Silicon Valley Product Group’s Coaching the Coaches forum, and speaks frequently at conferences and events. You can join one of communities he runs for CPOs (CPO Circles), Product Managers (Product In the {A}ether) and Product Coaches. He’s the author of What Do We Do Now? A Product Manager’s Guide to Strategy in the Time of COVID-19. A recovering music journalist and editor, Randy also launched Amazon’s music stores in the US & UK.
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