Leah’s ProducTea: 71: John Cutler - How to structure a product organization

🚀 The Missing Piece in Tech 🚀

We’ve seen companies with “This Is How We Do Engineering” and “This Is How We Do Design” pages...but where’s the guide for product management? Here’s the catch: these product playbooks are about so much more than what to do—they’re about how to do it together.

Product teams that work well together are built on shared mental models that encourage cross-functional collaboration, not just function-specific success.

☑ Single Shared Model
▪️ Clear operating models help each function understand their own goals—but they should always fit into a larger, shared model that drives the whole team forward.
▪️ A product playbook should show how to move work across silos like engineering, design, and sales—not just create more.
▪️ A good operating model isn’t about control; it’s about alignment and making sure teams aren't duplicating efforts.

☑ Simple Guidelines that Stick
▪️ Clear boundaries work better than vague guidelines. If your team works best at 7 or fewer people, stick to it.
▪️ Measure only what counts. Rather than tracking 100 metrics, identify the top 5 metrics that drive your outcomes.
▪️ Make your rules visible and understood. Complex rules get ignored, but simple ones create accountability and real results.

☑ Embrace and Evolve
▪️ Try temporary “scaffolds” (short-term processes) to help teams when scaling gets rocky. This creates space to find what really works before committing long-term. ▪️ Don’t expect change to happen overnight. Create checkpoints every 4-6 weeks to keep teams aligned and adjust if necessary.
▪️ Make it a habit to re-evaluate every six months. An operating model shouldn’t be written in stone; it should evolve with your team’s needs.

Biggest takeaway: An aligned team is unstoppable. But alignment doesn’t just happen—it’s designed, reviewed, and consistently improved.

Product teams that work well together are built on shared mental models that encourage cross-functional collaboration, not just function-specific success

A product playbook should show how to move work across silos like engineering, design, and sales—not just create more

A good operating model isn't about control; it's about alignment and making sure teams aren't duplicating efforts

Clear boundaries work better than vague guidelines. If your team works best at 7 or fewer people, stick to it

Rather than tracking 100 metrics, identify the top 5 metrics that drive your outcomes

Make your rules visible and understood. Complex rules get ignored, but simple ones create accountability and real results

Try temporary 'scaffolds' (short-term processes) to help teams when scaling gets rocky

Create checkpoints every 4-6 weeks to keep teams aligned and adjust if necessary

Make it a habit to re-evaluate every six months. An operating model shouldn't be written in stone; it should evolve with your team's needs

An aligned team is unstoppable. But alignment doesn't just happen—it's designed, reviewed, and consistently improved

For every one of those companies that have like 'This Is How We Do Engineering at X' and 'This Is How We Do Design at X,' you don't have this sort of product management portal that says 'Do these things.'

In the companies where it works, those [functional guides] are very important ways of describing the models of like the philosophies of the individual functions, but they're subservient to a common mental model for how they work together as teams

If you haven't taken the time to figure out some set of things that are stable enough that are going to be around quarter over quarter...don't even show up at the product review

One of the least defined things often...is how you talk about things that are broken

Make clear...where does the buck stop. This is to your point on like who is writing now this operating model for a product line, for instance

The dominant approach to continuous improvement is actually: if you can't fix it yourself or around you, escalate it formally through things

If it hurts, do it more often

Make it a habit to re-evaluate every six months. An operating model shouldn't be written in stone; it should evolve with your team's needs