ALP 299: Hire people who understand how to solve problems

Most hiring processes obsess over the wrong things. Do they know our project management software? Are they proficient in this specific tool? Meanwhile, the one capability that actually determines whether someone will make your life easier or harder—their ability to solve problems independently—gets a cursory “are you a good problem solver?” question that everyone answers with “yes.”

In this episode, Chip and Gini break down why problem-solving ability should be the primary hiring criterion, especially as AI makes technical skills easier to acquire and offload. The conversation explores why this matters more now than ever: as AI handles tactical execution, the ability to define problems clearly, break them into components, and figure out solutions becomes the differentiator between humans who add value and humans who get replaced.

Chip and Gini discuss how problem-solving cuts across every role, even ones you don’t typically think of as problem-solving positions. Designers facing impossible deadlines, account people navigating last-minute client demands, anyone dealing with the reality that things rarely go according to plan. They all need to be able to figure out how to move forward rather than escalating every obstacle upward.

The episode tackles the mechanics of actually interviewing for this capability. You can’t just ask “are you a good problem solver?”—you need scenario-based questions that reveal how candidates think through challenges. But not hypothetical scenarios you make up; real situations that have happened in your agency. Ask them to walk through how they’ve handled compressed timelines, missing information, conflicting priorities, or last-minute changes in past roles.

Gini shares how her daughter’s school explicitly focuses on humanities and emotional intelligence rather than technical skills, anticipating that AI will reshape what jobs exist. She connects this to Anthropic’s hiring practice of seeking people with humanities degrees who can absorb information, think critically, and demonstrate emotional intelligence rather than just technical proficiency.

The episode concludes with an important reminder: if you hire problem solvers but then micromanage how they solve problems, you’ve wasted the hire. You need to let them solve things their way, even if it’s different from how you’d do it, or you’ll end up with everything back on your plate anyway. [read the transcript]

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