Rippling's Tough PM Case Study Evaluates Problem-Solving Depth

When I first started working in the product organization at Rippling, I was introduced to an interview framework I hadn't used much in my career. Every product person at every seniority level is given the same extraordinarily difficult case study. It requires thinking about many dimensions simultaneously - data propagation issues, technical considerations - it's comprehensive and deliberately challenging.

What's counterintuitive is that the same impossible task is given to everyone from entry-level PMs to VPs. The rubric we use evaluates what an entry-level PM looks like versus junior, mid-career, senior, or executive PM. Everyone comes away feeling like they failed, while on our side, we're evaluating how far they got - "Wow, that person saw around three or four corners in a really impressive way." There were ten corners they didn't see around, but they spotted four of the hardest ones.

We're not just looking at technical solutions but human interaction patterns: Were they defensive when given new information that challenged their solution? Did they interrupt us to ask more questions? Our recruiting team sometimes feels we eliminate people too aggressively at this stage, but I've found wisdom in it.

The approach reveals how candidates handle impossible problems - not whether they can get all the way through the concrete wall, but how far they can drill with the bit we've handed them. Some get a millimeter in, others an inch. Nobody gets through completely, but you learn a tremendous amount about how they think and operate under pressure.

This method works because product management requires polymathic skills - you need to be good at working with others, communication, project management, and technical understanding. By giving everyone the same challenge, we can more accurately assess their relative capabilities across these dimensions rather than trying to calibrate across different problems.