Career Chess: Andrew Stockwell on Hiring for Character, Trust, and the Flood of AI Applications

Great leadership isn't about having all the answers. It's about knowing which questions to ask. Andrew Stockwell spent 20 years in market research, at Forrester and elsewhere, before an unexpected pivot into HR changed the direction of his career entirely. He started in the sailboat industry, moved through financial services, got laid off during the dot-com bust, and eventually built a career helping senior executives make complex technology decisions. Then, during the pandemic, while working as a strategic advisor reporting to a CFO, the head of HR resigned and he was asked to fill in on an interim basis. That "interim" role became permanent, and Andrew found the calling he didn't know he was looking for. He's now a people leader with two decades of market research experience behind him, most recently VP of People at Vendr. On this episode of Career Chess, Andrew talks about the difference between fostering trust and fostering fear, why he hires for character and trains for skill, how the flood of AI generated job applications is changing the way companies and candidates find each other, and what he's learned from the hardest parts of the job: layoffs, tough calls, and leading people through them with dignity. Tune in for a conversation about building trust, embracing discomfort, and the real cost of leading with fear instead of curiosity. Read more about his work and ask him questions here: https://thetrove.io/u/andrew-stockwell