When interviews and references leave you with ambiguity about a candidate, move beyond conversation. Invite them to analyze or work on a live investment or project. Observing their thought process and how they "underwrite" a decision provides unparalleled clarity on their actual abilities.

After probing a candidate's past, 'flip the table' and present them with a current, real-world problem your company faces. This reveals their curiosity, analytical skills, and ability to engage with a new challenge on the spot, shifting from their prepared stories to raw problem-solving.

Candidates complete an exhaustive "friction logging" exercise, documenting pain points and user experience issues within a product. This practical test is a primary tool for evaluating a candidate's product sense and problem-identification skills, valued almost as much as the interview itself.

With AI tools enabling anyone to ship code, all team members directly impact the user experience. Floto.ai now includes traditional PM-style product thinking questions in interviews for engineers and growth roles to ensure everyone builds with strong user empathy and business context.

A common hiring mistake is prioritizing a conversational 'vibe check' over assessing actual skills. A much better approach is to give candidates a project that simulates the job's core responsibilities, providing a direct and clean signal of their capabilities.

To avoid hypothetical interview questions, Zipline makes its hiring process as applied as possible. This includes pair programming, collaborative design sessions, and even offering paid 1-2 week work trials. This "work together" approach quickly reveals a candidate's true fit and capabilities.

Instead of asking hypothetical questions, present senior candidates with a real, complex problem your business is currently facing. The worst case is free consulting; the best case is finding someone who can implement the solution they devise.

To get beyond polished portfolios, Wealthsimple's hiring process includes an interview where candidates do a live critique of an app like Spotify. This reveals how they think on their feet and their raw product sense, providing a more accurate signal of their day-to-day abilities.

For high-level leadership roles, skip hypothetical case studies. Instead, present candidates with your company's actual, current problems. The worst-case scenario is free, high-quality consulting. The best case is finding someone who can not only devise a solution but also implement it, making the interview process far more valuable.