How NOT to transform

Aakash Gupta
2 min readMay 19, 2024

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There’s so many ways orgs mess up transforming the product team away from the feature factory.

Here’s the top one’s:

1. Understanding and commitment

It’s not enough to just have engineering, product, and design on board for transformation.

Transformation has vast impacts for marketing, sales, customer success, finance, and the rest of the business.

You need to drive top-down alignment from the CEO and Senior Leadership Team to bring all these diverse functions along.

2. Shifting culture

Cultural shift is often the hardest element of a transformation:

• Sales is still used to promising features
• Marketing is still used to dates on when features will arrive
• Customer support is used to having a direct hand in the roadmap

All of these things take time. The mistake people make is to gloss over the real tensions for the sake of meeting a pre-planned schedule.

Things may take longer than you think.

3. Co-create selected processes

Process is generally seen as the problem in transformation, so the point isn’t to add in massive amounts of process.

But it’s impossible to have no process. You’ll still need a way to lock in what features the team is building, say, next quarter.

You want to co-create these bottoms-up with the teams and functions in the org, and adjust as necessary. No one wants a book’s interpretation of processes. They want something they created for the specific needs of your org.

4. Building capabilities

As you align on processes and shift the culture, there’s still going to be capability gaps. Don’t assume the game is quite over yet.

This is where a lot of teams go wrong. They don’t build the capabilities to win the trust of executives and other functions like sales and marketing, because:

• PMs lack domain expertise
• Designers are under-hired relative to engineering
• Product leaders lack experience in truly empowered product environments

All sorts of capability gaps like these prevent success. You have to be ready to invest to upskill the org, and pay for experienced talent where needed.

This means buying the reforge subscription, paying for the newsletter, hiring the coaches and experts…

5. Sustaining and scaling

There’s still the possibility that your CEO seizes back control, or Sales begins to take over more as it drives more of the new revenue.

The way to stop these things is building mechanisms to sustain at scale. You need feedback loops. You need talent who can flag it before it becomes pervasive.

These things are possible for most. You can’t just move into discovery in the new world without acknowledging the journey to get there.

It requires sustained effort and focus.

Ready to go further on how to transform?

Check out my deep dive with Paweł Huryn, and a feature from Marty Cagan.

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Aakash Gupta

Helping PMs, product leaders, and product aspirants succeed