Retirement Investor

Top 3 Tips for a Family Money Meeting


Have you ever considered or wondered how your loved ones will utilize their inheritance? Will these financial resources unite or divide your family? Have you done a good job in communicating your “money values”? Have you provided a framework to allow your loved one’s success in your absence? If you have answered yes to any of these questions, rest assured you are not alone.   

The HBO series “Succession” has turned many heads to the inheritance discussion. “Succession” dramatizes many of your worst fears of power and family challenges as it relates to the wealth transfer conversation. Misunderstandings, conflicts and faulty assumptions could be alleviated with communication. Surprisingly, few wealthy families take the time to address these concerns. Why is that? Perhaps it’s not knowing where to start or it’s the sensitivity of the subject that leads to procrastination. 

Having a conversation or family meeting to discuss money in general may simply be out of your comfort zone and this is understandable. Most people simply do not know where to begin. Money is a complicated subject with the ability to overwhelm emotions and potentially cause angst, conflict, and expectations. Despite how uncomfortable this subject may be its best to talk to your family about inheritance early and often. Should the discussion be approached with a formal or informal agenda? Who should attend? Should the conversation happen in a public place?  

At our firm we have been watching the narrative unfold for 25+ years. As our clientele has gotten older through the years, we have found that conversations are morphing into new concerns, questions and perspectives. Take a deep breath and consider a different perspective. The following three tips will help you to overcome these challenges:

The conversation starter. If you find yourself in a position where the conversation is warranted but you do not want to have it directly, consider an outsider to assist. Financial advisors, estate planning attorneys, or family office staff members can be a starting point in creating an agenda. Activities such as setting the agenda, taking notes, and keeping track of items that require follow up can all be handled by this person. 

  • What attributes are important to you in choosing this person? 
  • Is this person going to create a good energy for your meeting? 
  • Will this person come prepared? 
  • Will this person keep to the agenda but also be sensitive enough to take time for off-topic conversations? 

Location, location, location. As we have all gotten used to during the pandemic, new capabilities with technology now exist that people didn’t embrace a few years back. Technology can certainly help but, we have found that face to face interactions work best due to the importance and complexity of the conversations. 

  • Would your attendance be best at a travel destination such as a beach house or ski resort? 
  • When is the next family event where everyone will be coming home?  
  • What is the family’s favorite local spot?

Situations may present themselves where technology may be the only way. Should that be the case, albeit not ideal, go with it.      

What is your expected outcome of the meeting? As with anything in life, having well defined goals leads to superior outcomes.  The key is setting the stage for best outcomes and getting best outcomes always centers on communication. 

  • How will the meeting foster open communication among family members? 
  • What are the rules to allow people a safe place to think and feel as decisions and problems require solving? 
  • What are the number of agenda items to tackle at each meeting? 
  • Who is going to debrief and summarize what was discussed, note decisions which were made, and list appropriate action items?    

Like planning for retirement, it was scary at the time, but you gained new knowledge, new capabilities, new confidence, and as time passed it was not as bad as you may have thought. Finding a perfect window of time, an ideal location, and a trusted moderator for the inheritance conversation may never seem to present itself. The words of French poet, Alfred de Musset, puts it best “Perfection does not exist; to understand it is the triumph of human intelligence; to expect to possess it is the most dangerous kind of madness.”  

For the most part, in our experience, due to the respect for the family member broaching the topic, conversations such as these are very well received. Painting a picture of expectations by the patriarch of the family is treated with the utmost respect and honor. At CG Capital, we have found that the very conversation provides a meaningful roadmap to the family and those that are leaving their wealth feel as though a weight has been lifted off of their shoulders as artificial expectations dissipate with meaningful conversations. Horror stories exist on all levels. Do not let these outlier events/family members or HBO series prevent you from having a heartfelt conversation with those whom you love.

Dennis Coughlin

Since 1996, Dennis has been helping individuals and business owners make informed decisions about their finances, enabling them to protect and maintain their quality of life while creating a sound legacy. His singular professional focus is to serve as a financial advocate for his clients by ensuring they understand the financial strategies they have implemented — strategies designed to give them the confidence and comfort that comes from knowing their financial lives are in order.

Dennis is a CERTIFIED FINANCIAL PLANNER™ professional and has earned the Accredited Investment Fiduciary® (AIF®) designation. He’s passionate about educating people on the wide variety of financial topics in which he is well versed, so he is a frequent speaker at numerous schools, colleges, and private corporations regarding the importance of effective financial planning. He enjoys writing, and has been published in several local media outlets as well as by Kiplinger,, OnWallStreet, and, and he is frequently quoted in the media.

Dennis graduated from the State University of New York with a degree in finance that included a concentration in accounting. He later continued his education at the Wharton School of Finance at the University of Pennsylvania, earning a certificate in retirement planning, and participated in a roundtable discussion on behavioral finance and modern portfolio theory at the Harvard Faculty Club.

On a personal note, Dennis has a deep passion for his family, his wife, Jennifer, and their two beautiful children, Allie and Jake. They’re residents of Whitesboro, New York, where Dennis loves to be outside, golfing, fishing, biking, and swimming. You can also often find him in the kitchen, cooking up a tried-and-true favorite or experimenting with a new edible creation for family and friends.

Fun Fact about Dennis: He loves the outdoors so much that he obtained his NYS Guide license, so he can help others enjoy it, too.

Qualities I Admire in People: Humility, Honesty, Gratitude, and Sense of Humor

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