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 operating model?
27:00 – What success looks like in transformation
30:05 – Balancing transformation with business as usual
33:01 – Keeping everyone aligned
35:13 – Psychological safety and learning curves
37:03 – Final words of advice
Featured Links: Follow Jen on LinkedIn | Tuckpoint Advisory Group | Buy Janice & Jason Fraser’s book 'Further Faster and Far Less Drama' | Bruce W. Tuckman's 'Using the Stages of Team Development - Forming, Norming, Storming & Performing' framework feature at MIT Human Resources
