Sparking Powerful Conversations in the Family Business


Laine Jordan (LJ): You call yourselves Wealth Whisperers ™. Can you tell us more about how you define a wealth whisperer?

Jamie Weiner (JW): I think advisors recognize that business owners have an added level of complexity in their lives — this holds true for wealth-holding families as well. This complexity is just a natural part of the system. Challenges arise, in part, because when families own a business or manage wealth together there is an additional need to find consensus, which is a critical component of moving things forward in families. We as advisors, however, typically find that reaching consensus is a struggle.

Clients struggle to hear each other, and the advisor is often in the midst of this noise and can lose track of what the issues are truly about. So, advisors can benefit from figuring out how to quiet the noise that is taking place in the family.

For example, sometimes family members approach us regarding their vacation properties. Surprisingly, vacation homes, usually created to allow families to enjoy time together and to bring generations closer, can become a major issue. One family member says that he or she has bad memories from childhood and thinks, “This home is worth a lot more money; let’s sell it.” Another family member feels that this is “home,” saying “I have memories of my parents — they are no longer alive so we should hold on to it.” The third family wants to use the home this summer. We see this type of conflict all the time.

LJ: As advisors, how can we better assist families in their communication efforts?

Carolyn Friend (CF): The first thing is for the advisor to realize that this is normal. We call this normalizing. It is commonplace for people who own something together to have different ideas about it and to experience conflict. An advisor might be tempted to say, “You are in the middle of the swamp, and there is no way out, no common ground.” The family can’t come to an agreement and the advisor is stuck. Everyone’s emotions seem to take control.

Whereas when people quiet down and take a step back, we’ve often found that the family and the advisor can say together, “Let’s meet in the middle — let’s try this for now and then move to something else.” We use the example of the vacation home because in the past year we have been approached at least a half dozen times with this issue. Advisors are constantly being approached by families regarding the transition of something, typically regarding the transition of power — who is in control and who is getting control. Our goal is to help advisors understand that there are all these things going on behind the money.

LJ: What does it mean exactly to “get behind the money?”

JW: I believe people intuitively understand the key communication and conflict issues. However, we have gotten very specific. We’ve developed a list of eight pain points that we have repeatedly found in families, and we have never put this list in front of a family and had the family state that it doesn’t share any of these issues!

For example, in addition to things like the transition of power, an obvious issue can be divvying things up. Who is going to get what assets? That can be about ownership or dividends. There are a lot of issues that come up that all boil down to divvying things up. Sometimes the issue isn’t just about the money — it can be about who is favored and the types of relationships people have with each other and the meanings behind these relationships. There are issues that typically aren’t discussed by advisors such as who is marrying into the family. Others may be, is everyone going to succeed, and what is the standard of success to this family?

LJ: What are the pitfalls advisors encounter regarding these issues?

CF: The biggest pitfall is viewing it as a psychological issue, that there is something wrong with someone who wants something that the other person has — and therefore there is no solution. That is the complexity of business-owning families. People have different roles that they play within the family, but these roles can change within the business. And then there are the roles, on top of family and business roles, with regard to the ownership structure and the shareholders. Advisors need to be able to say to families, “Let’s step back. Of course, you have these feelings. Is there a way for us to use the word compromise? Is there a way to recognize that there is a solution, and it doesn’t have to be a solution where someone is made out to be bad?”

JW: I think it’s also important to understand that, as advisors, we may have our own set of glasses and biases. That certain professional advisors want to create technical solutions to problems. Family business consultants have a different perspective, but we all come to the table wanting to solve what is presented –that is the technical problem that is in front of us. We may want to create an estate plan and come to a decision. We sometimes don’t take the time to have conversations that go underneath all these issues and get to the reasons that people are struggling with some of these technical issues.

CF: This is where people get stuck. They look for technical solutions rather than recognizing that there is a common-sense solution to the issue.

LJ: Please share your parting advice regarding assisting families in better communication.

JW: The first piece of advice I share with advisors is to have fun! Ensure that working with families is fun for you as an advisor. People naturally come to family meetings with apprehension. We want to alleviate their apprehension and have them relax and engage in conversations that become natural. We developed a deck of cards, called the Inheriting Wisdom Conversation Starters, to help families begin communicating and having fun prior to a family meeting. It has become our opening exercise at dinner the night before the meeting.

CF: My favorite card is If you were blindfolded for a day, pick a family member who will act as your guide. We use this with our own family as a focus group. It did cause a bit of conflict in the family as I chose our youngest daughter instead of my husband. My reasoning is she knows more, she’s more technical, she can understand me better.

JW: Another example is my favorite card which asks what unhealthy item is in your grocery cart. Family members always enjoy thinking about what little cheat they enjoy most.

LJ: Thank you, Carolyn and Jamie.

About the contributors

Carolyn Friend, CFBA, is co-founder of Inheriting Wisdom in Chicago. She is dedicated to helping families identify their pain points in a strategic and structured manner, work through their road blocks and get everyone back to business even sooner. Carolyn can be reached at [email protected].



 Jamie Weiner, CFBA, ACFWA, is co-founder of Inheriting Wisdom. He is focused on helping families garner meaningful communication between generations and provide solutions to sustaining wealth and strengthening family legacies. Jamie is a member of the FFI board of directors and co-chair of The Practitioner editorial committee. He can be reached at [email protected].



If you are searching for a tool to help families to better communication and would like a complimentary deck of Conversation Starter Cards, please visit,