Transformation Regrets

Marty Cagan reflects on his personal regrets from coaching companies through product transformations, prompted by a reader's question about whether every transformation in the book TRANSFORMED succeeded. He admits that early on he was not tough enough about serious problems, while at other times he pushed too hard and overwhelmed product leaders. He also regrets agreeing to scope transformations as mere PM training, failing to call out leaders who avoid tough decisions, and struggling when the product leader themselves is the core obstacle. The piece matters because it candidly shows that transformation success depends as much on judgment, honesty and leadership willingness as on frameworks.

01Key takeaways

• Build experience-based judgment to tell which transformation problems are critical and which can be safely deprioritized.
• Make sure leaders understand concretely what transformation requires before they commit, not just that they need it.
• Treat product management training as one part of a transformation; designers, engineers and product leaders must change too.
• Name the hard decisions leaders try to avoid, such as unfocused scope, resistant executives or people unable to change roles.
• When a product leader resists change, prioritize building trust and sharing concrete evidence of problematic behaviors before pushing further.
• Be willing to tell a company honestly when it is unlikely to commit to what transformation requires, saving them time and cost.

02Key sections

Not being tough enough

Early in his career Cagan saw real problems but lacked the experience to judge which were serious enough to derail a transformation. Experience helps distinguish critical battles from ignorable ones.

Being too tough

Once he understood what transformation required, he sometimes overwhelmed leaders who had not grasped the scale of change. Leaders often say they need to transform without understanding or accepting what that entails.

Agreeing to only PM training

Companies often equate the product model with product management training, but training alone never proved sufficient. Designers, engineers and product leaders must also change how they work together.

When the company avoids tough calls

Transformations force hard decisions about focus, leadership change and people's roles. Cagan regrets not calling out moments when leaders avoided these issues, since such moments make or break the effort.

When the product leader is the problem

Product leaders who see themselves as exempt from change, or feel threatened by coaching, are hard to help because trust is required first. Options include building the relationship, sharing evidence, involving the CEO, or stepping back.

03From the post

“A partnership dedicated to teaching best practices to product teams and product leaders”

Summary and takeaways written by PM Atlas; quotes are short excerpts. © the original author.