Following a presentation to new advisors, I heard a question you may be asking. “Are questions about a client’s life story, their family, work, health, and fears going too far?” Put another way, can we ask questions that are too personal?

The “too personal” question has many sources. Some would say it is a fear that another may know things about our past we would rather leave there. Others that our work is financial in nature so why probe sensitive issues better left alone? Do we need to know all that “stuff” most people—even ourselves—would rather leave 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. Professor Brown reminds us that being open, transparent, and candid about our past takes courage. The effect, however, infuses powerful, trust-building DNA into a relationship.

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.’” Test the waters with expected topics. Look, listen, and absorb what you hear.

Then 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 instead, go where they took us in the first place. This is key: the other person chooses the conversational roads down which we travel.

But what if we find ourselves down an uncomfortable rabbit hole? Simple. Test the relationship by asking, “Are you okay telling me more about _______?” Doing so creates a foundation of trust on a road the other person has said is okay to travel.

There’s a catch. The freedom to ask tough questions hinges on our having faced tough questions in our own lives. Advisors who know their story—good, bad, ugly—have learned how life has shaped them. They have a better grasp of why knowing as much as possible about clients opens so many doors to serve them better. Where did the road turn sharply and toss you out shaken, bruised, and confused? What does money mean to you? What did you learn when things did not go your way?

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 engagements with them. 

Here’s the takeaway: 

• Ask easy questions and then follow up with others nested in their initial responses. They set the follow-up topics, not us!
• The other person will often tell you more, offering information about so many areas of their life if you will but let them talk and listen with care. You do not have to probe. 
• They are more likely to answer the tough questions readily if you can say with integrity, “I’ve faced something much like that myself.”
• Be non-judgmental. Handle what you hear with sensitivity and compassion. 
• Be present in those sacred spaces with integrity and care as you build a stronger bond between yourself and those you serve.

Maybe what some call “a question too far” is simply allowing what the other person is saying to shape the conversation, honoring their story, and seeing how it takes you precisely where it and the relationship need to go.