How to ask deeper questions
Start with an easy question and move to the thoughtful ones once people are relaxed. These work best in pairs or groups of up to five: mentoring, a new team, or a leadership offsite.
Always let people pass, and answer first yourself so they can see how much to share. Questions tagged More personal are skipped by the picker unless you turn off Work-safe only.
For a group too big to talk it through, use a word cloud question such as “Name one value you try to live by.” In a few seconds the room sees what it has in common.