Interview questions Duncan is ready to dig into. Copy them, tweak them, or bring your own.
1When you look at how most people become managers, where do you think organizations get it wrong from the very beginning?
2You’ve worked in environments where the usual playbook stopped working fast. What did those moments reveal to you about the difference between authority and actual leadership?
3A lot of workplaces say they want innovation and adaptability, but people often still feel tightly managed. What does that contradiction do to a team over time?
4What have you seen happen when someone is promoted because they’re excellent at the work, but not necessarily prepared to lead other people?
5During the financial crisis and later during COVID, what stood out to you about how leaders responded once control started slipping away?
6Why do you think so many organizations still fall back on command-and-control habits, even when the work now depends on trust, judgment, and initiative?
7There are a lot of conversations right now about AI changing the workplace. What do you think it exposes about a company that was already struggling to keep people engaged?
8What does it actually look like for someone at work to feel like they matter, and how can a leader tell when that feeling is missing?
9When a company says it wants a healthier culture, where do you think the real work begins if they want that change to last?
10As work keeps changing, what do you think leaders will need to unlearn first if they want to build organizations that stay effective without losing their humanity?