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Help users design high-performing product and engineering organizations by choosing the right reporting models, team sizes, and cross-functional partnerships. It focuses on reducing friction and maximizing ownership through structural clarity.
Passed 20 of 22 test cases with the skill, and 8 of 22 without it.
and 12 more in the full report
12 fixed8 passed either way2 still failing0 broke
Tokens, turns and time describe resource use, not a dollar price.
One of 12 test cases the skill fixed. Same model, same prompt, with and without the skill.
Our tech and product department is growing from 25 to 70 people, and we are suffering from slow delivery and blurred ownership across our feature teams. Can you analyze our situation and build a comprehensive organizational restructuring proposal? Please include a breakdown of team boundary definitions, an assessment of leadership pairing across levels, a framework for choosing structural models based on company goals, and guardrails to maintain velocity as we scale.
| Checked | Without skill | With skill |
|---|---|---|
| Recommends evaluating a General Management model for speed versus a Functional model for product cohesion. | Missed | Passed |
| Recommends structuring teams around durable customer segments or outcomes rather than temporary feature projects. | Passed | Passed |
| Recommends pairing Product and Engineering leads at every level of the organization. | Passed | Passed |
The instructions your model reads when the skill loads.
Structure your teams to maximize autonomy, speed, and strategic alignment.
Help the user with organizational design for product and engineering using insights from 27 guests and posts across Lenny's Podcast and Newsletter.
Bill Carr: "Let's create teams that can stand alone, where there's a single leader and the cross- functional resources that they need are all either directly report to them or are dedicated to them. So they don't necessarily have to be a straight line direct report. In Amazon's case, for the most part it was. There were some dotted line, but it could be all straight line, it could be all dotted line, it could be a mix of the two."
Move away from shifting resources between tasks toward a program orientation where teams own a specific customer area indefinitely. This empowers single-threaded leaders to take full ownership of long-term outcomes.
Claire Vo: "I'm using CPTO for short code of running product and engineering design functionally together. There should be no debates over what's best for product or what's best for engineering, what's best for design speed. What is best for the organization?"
Consolidating product, engineering, and design under one leader eliminates functional silos. This alignment stops internal debates and optimizes for overall organizational speed over individual department goals.
Dhanji R. Prasanna: "So all engineers report into one single team now, all designers report into one single team and there's single head of engineering, single head of design, et cetera. And so that was the big transformation that we made, and that meant we could really drive forward AI, we could drive forward platform and just technical depth generally."
Transitioning to a functional structure helps a company align on singular technical strategies. It allows for standardized engineering levels and policies that drive excellence across the entire department.
Heidi Helfand: "I really like it when there's transparency in reorgs. There's a story in my book from Christian Lima at Spotify about how they reorged a large infrastructure team. They visualized it on whiteboards and brought people over to the whiteboards to see the future team structure that the leaders wanted and they got input into the design."
Maintain transparency during reorganizations by visualizing proposed structures on public whiteboards. Involving employees early helps identify structural errors and increases engagement with the new mission.
Karri Saarinen: "We actually don't have much PMs in the company. We only have one and we can talk about more about it. One of the things I think that happens is when you build a team and you start creating these very specific roles for everything I think that often the PM can be the ones figuring things out and making decisions and guiding the team, but they're not the ones building the feature."
Eliminating dedicated PMs for every team can increase ownership among those actually building the product. Distributing management tasks to engineers and designers fosters higher attention to detail.
test cases passed, vs 8 / 22 without
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