I have a manager who is trying to listen and lead with empathy and compassion. He’s asking all of his employees how they are doing and he consistently gets back “ok.” How can managers check in with the people on their teams that may prompt deeper responses?

Repetitive questions like “How are you doing?” can lead to superficial answers. Instead, try:

• “What challenges are you facing today?”
• “What’s been working well for you lately, and what hasn’t?”
• “What do you enjoy most about working from home, and what do you miss?”
• “How can I better support your work?”
• “If you could improve one thing about your current work setup, what would it be?”

These specific questions encourage employees to reflect and share more meaningful insights.