“Just ask more questions.”
It’s classic leadership advice — but what if it doesn’t land the way you think?
In this episode, we unpack a tension that’s come up again and again, especially with younger Millennials and Gen Z:
Questions can build trust, open doors, and deepen connection — but when they feel forced, transactional, or performative, they do the opposite.
We’ll explore:
Why the best leaders still ask great questions — but never to manipulate.
What younger employees are really pushing back on when they say, “Don’t interrogate me.”
Four practical ways to make your questions feel authentic, not artificial.
How to match your curiosity to the moment — whether you’re building rapport, coaching, or holding someone accountable.
A simple gut-check to make sure you’re asking to connect, not control.
Closing challenge:
Before you ask your next big question, ask yourself: Do I really want to know the answer?
Then pick one relationship this week and ask a better, braver question — and actually listen to what comes next.
