March 19, 2015 / Esther Choy


A colleague recently shared a research that really opened my eyes. In October of 2013, U.S. Trust published a report entitled, “The Philanthropic Conversation: Understanding Advisors Approaches and Clients’ Expectation.” The report explores how advisors such as financial/wealth advisors, trust/estate attorneys and tax professionals/accountants promote philanthropy and discuss philanthropic opportunities with their clients.

Many research findings confirm our long held beliefs. Not this one!

Among many wonderful insights, the following three points struck me the most.

  1. Advisors don’t bring up philanthropic discussions nearly as often and early as clients would like them to.
  2. Advisors don’t have a sufficient understanding of their clients’ personal values and motivations, especially in the area of giving. Yet, clients’ perceptions of advisors depend on their ability to discuss such topics.
  3. Both advisors and clients believe that the discussion of philanthropic giving enhances relationships, and therefore, business developments for advisors.

Based on this report, it seems that a pre-requisite of wealth managers is to get to know client stories well and early. Social and professional protocols, however, can sometimes hold you back from prematurely doing a deep dive into your clients’ private worlds.

So how to you elicit stories from a client? How do you get them to share what’s important to them?

At Leadership Story Lab, we offer a module called “Aggressive Listening = Good Storytelling.

In this course, we turn our focus to asking good questions and doing aggressive listening. Our clients have found that by asking gentle and thoughtful questions during early meetings, they can shorten the formal professional distance with their clients. There are many great resources on how to ask good questions. Some of my favorites are:

Here are a few examples of some of the questions I’ve found to be most effective in getting people to share their stories:

  • Where did you grow up? What was it like to grow up there?
  • What was most important to your parents?
  • How are your children like you? Unlike you?
  • Given the choice of anyone in the world, whom would you want as a dinner guest?
  • Tell me about a serious hobby of yours. [At Leadership Story Lab, we have a workshop to help people mine their passion DNA by dissecting their hobbies!]
  • What is your greatest accomplishment in life?
  • What is your earliest and strongest memory of money?
  • Which family traditions do you continue with your own family?
  • For what in your life do you feel most grateful?
  • If you could have a wish list, what would be on it?

Of course, there are many more. Regardless of the questions you ask, the key to collecting stories while deepening your relationship with clients is to listen and adapt the question as you go based on the client.

Perhaps the biggest take away from this philanthropic research is that wealth advisors have a strong untapped potential as conduits for exponentially larger, targeted and satisfied giving. There is so much latent capacity to do well while doing good!

I would love to hear what your favorite gentle and thoughtful questions are when you are getting to know someone in a professional setting. Leave them in the comments below or send them to me at

If you need more ideas on collecting stories, Leadership Story Lab can help you develop the right approach. Also, subscribe to our resources newsletter for quick tips, free events and coaching sessions.

#storytellingculture #BusinessCommunication #LeadershipStoryLab #communicationstraining #LettheStoryDotheWork #storytelling #businessstorytelling

Esther Choy

Esther Choy founded Leadership Story Lab in 2010 to help others leverage the art of storytelling to create extraordinary opportunities.
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