Asking Tough Questions

Following a recent talk, someone posed a question about discovery you may have asked. “Is asking questions about a client’s life, family, family-of-origin issues, work, money, health, and fears going too far?” In other words, are we asking questions that are “too personal.”

Is there a line we can cross when doing deep discovery?

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, well, rather leave there. Others add that our work centers on business, so why probe into the soft, tender, nervy tissues of personal, business, family, or mental health issues better left alone. Do we really need to know all that “stuff” most people keep buried like an old bone?

My answer was a bit surprising. “Start,” I said, “by asking expected, open-ended, even easy personal, family, and work questions. Listen carefully with ears and eyes for phrases, sentences, or body language 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 create a conversational space where the prospect or client feels safe to take us where he/she needs to go.

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 them have a better grasp on why knowing as much as you can about clients opens so many doors to serve them better. Stop for a moment and look over your life’s shoulder. Where did the road take a sharp turn and toss you out shaken, bruised, and 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?

This wonderful work in which we find ourselves requires a depth of knowledge across so many disciplines. The givens are obvious to one’s unique profession. But 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, parents’ in decline, and the list keeps going.

Here’s the take away: Ask easy questions and then follow up with others nested in the initial responses. The other person will take you where you need to go, offering information about so many specifics if you will but let him or her talk and keep talking.  You do not have to probe. The other person will answer the tough questions readily if you are a warm, open, caring, understanding listener. Then handle all the knowledge you glean with sensitivity and compassion while forging a deeper relationship in which you can offer your best counsel.

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