Following a presentation I made to a class of new advisors, a member of that class of 75 came to me in the hall with a question about discovery. “Are asking questions about a client’s life story, family, family-of-origin issues around work, money, investments, health, and fears about a host of things going too far?” In other words, is there a line we can cross when doing deep discovery? Are we asking questions that are too personal?

I’ve heard the too personal question many times. It is not only a great question, but reveals an insecurity that is universal. Some would say it is a fear that another may know things in our past we would rather leave there. Others add that our work is financial in nature. So why probe into the soft, tender, nervy tissue of personal, business, family, or mental health issues better left alone. Do we really need to know all that stuff some people wish would go away?

My answer to my new friend in the class was a bit surprising. “Start,” I said, “by asking expected, open-ended, even easy personal, family, money, and work questions. Listen carefully with ears and eyes for phrases or sentences that send a signal saying, ‘there is more.’ Then, depending on those hints here and there, ask, ‘Could you tell me more about __________ (your brother who has special needs, your dad’s disability, the friend who died in the Iraqi war, etc.)?’” 

The idea is not that we go places uninvited, but rather we simply respond to what we are hearing, inviting the other to take us where they need to go. 

Frankly, asking tough questions hinges on our willingness to face those same tough questions in our own lives. Advisors who know their story—good, bad, ugly—and have learned how life has shaped who they are transition to those tough questions easier and more effectively. Where did life’s road take a sharp turn and toss you out shaken, bruised, confused? What does money mean to you? What have you learned when things have not gone your way? Are you stronger in the broken places?

Knowing our clients’ lives beyond the numbers is vital if we hope to have meaningful, transformative engagement with them across multiple years. It matters that we know a client’s family-of-origin went through a horrific handful of years because the chief breadwinner was disabled. We must know about special needs children, work history challenges, chronic health issues, and parents in decline. 

Here’s the takeaway. Ask easy questions and then follow up with others nested in the initial response. The other person will take you where you need to go IF you will but let them talk and keep them talking. You do not have to probe. They will answer the tough questions readily if we will be a warm, open, caring, understanding listener. Then handle the knowledge you glean with sensitivity and compassion and watch as your relationship grows and how much more they will tell you.