Asking the Tough Questions

Following a recent talk I gave, a new advisor came to me in the hall with a question about discovery. “Is asking questions about a client’s life story and their family’s issues around work, money, investments, health, and fears going too far?” In other words, is there a line we can cross when we do deep discovery? Are we asking questions that are too personal?

I’ve heard the “too personal” question many times, and it 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 tissue of personal, business, family, or mental health issues better left alone. Do we need to know all that “stuff” most people wish to keep buried?

Sociologist and author Brene Brown addressed this “bridge too far” issue in her TED talk, “The Power of Vulnerability” and her bestseller, Rising Strong. Speaking wisdom to this familiar insecurity, she reminds us that being open, transparent and candid about our past takes courage. The effect, however, infuses powerful DNA into a relationship that creates, rather than diminishes trust.

My new friend was somewhat surprised at my answer. “Start,” I said, “by asking expected, open-ended, yet simple personal and work-related questions. Listen carefully with ears and eyes for phrases or sentences that send a signal saying, ‘but wait—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 bid the prospect or client to take us where he or she is most comfortable. At every turn, the other person chooses the roads down which we travel together.

Asking tough questions empowers the relationship creating both a foundation of trust and space in which we can offer our best counsel


So, how do we move through a conversation laced with potentially complex issues? How do we build a bond with another person that not only conveys information but creates an opening to offer more impactful advice and support? Rather than dodging or outright avoiding what some might claim are topics too sensitive for an advisor-client conversation, asking tough questions empowers the relationship creating both a foundation of trust and space in which we can offer our best counsel.

This seemingly bold step hinges on our willingness to face those same tough questions in our lives. Advisors who know their story—good, bad, ugly—have learned how life has shaped who they are. They have a better grasp on why knowing as much as you can about your clients opens so many doors to serve them better. Stop for a moment and look over your life’s shoulder. Where did the road turn sharply and toss you out shaken, bruised, and confused? What does money mean to you? What was learned when things did not go your way? Are you stronger in the broken places?

This wonderful advisory work in which we find ourselves requires a depth of knowledge that spans many disciplines. The givens are those things we can measure, quantify, analyze, and benchmark. 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 went through a horrific time 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 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, offering information about so many areas of their life 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 you offer them a warm and inviting presence and listening ear. Handle the knowledge you glean with sensitivity and compassion. Walk in those sacred spaces with integrity and care as you build a stronger bond between yourself and those you serve.

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