The following are some examples of the types of deep dive discussion questions you can ask. Hopefully you’ll get a response that’s just as open and honest as you’re willing to be. If not, it may help to get the ball rolling by sharing your own answer first. Because believe it or not, people really do want to go beyond the small talk and engage in something more meaningful.
* “How are you doing, really?” *
This is a question many of us ask just to be polite, so what if we cared about the answer? We can ease into the process by using this question to set the tone. Once they see we’re actually interested, a deeper discussion can begin.
* “When was the last time you (laughed, cried, felt like a kid, etc.)?” *
These types of questions are perfect for when you want to dig a little deeper and peel back the layers. Since we aren’t asked these questions often, we don’t have a conditioned response. Thus the answer you’ll get is genuine. You should also choose a topic that you have a personal connection to in order to build mutual trust.
* “Where do you want to be in 5, 10, or 25 years?” *
Questions about the future tend to catch people off guard because either they haven’t really thought about it, or they don’t want to because they don’t think their life will change. So if you ask this question, come from a place of curiosity and encourage them to dream big. Perhaps you’ll light the spark that reignites their own curiosity, thus challenging them to confront their dashed dreams.