Shakespeare Blog: View from the Lake

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Generational Wealth Planning:

Where Rubber Meets the Road

Written By: Kevin Reardon, CFP®

Oak Tree

Building on our Generational Wealth Planning blog written in 2021, we wanted to add to the conversation about what Generational Wealth Planning (GWP) really is and provide structure on how to begin the family discussion. GWP isn’t just for the ultra-rich, but for everyone looking to positively influence the next generation. So what is GWP and how do you do it?

Annual Family Meeting

At the heart of generational planning is a formal meeting you conduct at least once a year with your family. It is critically important you commit to doing this annual meeting, setting both the expectation and the avenue for ongoing discussions on important family matters, including money.

Expectations & Confidentiality

Set expectations at the beginning by explaining WHY you’re having the meeting. Once people understand the heart of the matter, it’s easier to talk about the various discussion points. You should stress the importance of confidentiality and keeping what is shared within the family. For those organizing the meeting, you’ll want to bring an extra allotment of patience and tolerance as you allow your next generation to voice opinions you may not agree with or make statements that could be counter to what you believe. The point of GWP is to open the avenue of communication within the family and keep it open. Through time and communication, you’ll have a chance to work on your differences.


You can host the family meeting at any location that allows the family to have dedicated conversations. This could be in your home, a hotel conference room, or destination resort. If you have young children or grandchildren, hire a babysitter and let the parents know you need their undivided attention. Encourage the family to turn off cellphones and look at them only on scheduled breaks. Frequently the matriarch and patriarch will lead the meeting, but Shakespeare can also be called on as a moderator. Typically, families will have their son or daughter in-laws join the meeting as this keeps the entire family on the same page. It’s better for your in-laws to hear about an issue from the horse’s mouth, and give them the opportunity to share their thoughts directly with the entire family.

Discussion Topics

You will want to have a formal written agenda for every family meeting, laying out topics and issues you want to discuss. Typical agenda items include:

– Financial Overview: Review your net-worth statement, including a list of financial assets (brokerage, retirement, bank accounts, etc.), debts (mortgages, consumer debt, notes, etc.), insurance policies, real estate, business interests, and more. The goal is to provide an overview to the next generation pertaining to WHERE your assets are. You do NOT have to list asset values if you do not wish. For clients with children who are 40+, it’s typical for parents to start sharing important financial data to give more context to the conversation. Remember, your children will eventually know everything about your finances and inherit some or all of it. The sooner you start coaching them on how to handle this wealth, the better off everyone will be.

– Estate Planning: Give an overview of your estate plan including a discussion of who your Health and Financial Powers of Attorney are, as well as your Executor and/or successor trustees. It’s important to discuss your end-of-life wishes, so the family understands it’s the agent’s job to follow your wishes, rather than operating on their own intuitions. It’s also important for adult children to hear directly from the source (Mom and Dad) why certain people were selected as agents or trustees. If there is an objection, it is better the conflict be between you and the child, rather than between siblings years after you’re gone.

– End-of-Life Care: As part of your discussion about your Healthcare Power of Attorney, talk about what type of care you would like if you become sick and can’t care for yourself.

– Last Wishes: Similar to above, it’s important to talk about your specific intentions when you die. This can include a discussion about cremation vs burial, preferences for a funeral or celebration of life, etc.

– Family Cabin or Legacy Real Estate: If there is a family cabin or legacy asset that will be passed to the next generation, have a conversation about your intentions and issues surrounding the asset. Buckle your seat belt, as this conversation is likely to be emotion driven and could derail the meeting if it’s not handled properly.

– Family Values: Many families will take time to define their core values, which can serve as a guidepost for the children as they progress forward in life. These will become even more meaningful once you’re gone, helping them navigate through difficult situations without your direct consultation.

– Expectations for Inheritance: Your children will eventually inherit assets when you pass away and how they spend and invest will be entirely up to them (presuming you don’t have rigid guidelines built into a succeeding trust). The annual family meeting is the best medium for discussing your expectations for their newfound wealth. Frequently families will role play through various scenarios as a means of coaching the next generation on how to make future decisions. The dominant theme we hear from clients is for the kids to use these assets wisely, with the primary goal of benefiting both their family and society at large.

– Second Marriages and Blended Families: The concept of a family meeting is even more critical for blended families. In instances where you may have ‘his kids’, ‘her kids’ and possibly even ‘our kids’, it’s important for the entire family to understand your intentions, both while you’re alive and when you pass away.

– Other: As you progress through your first few family meetings, you’ll have many other discussion topics you can add, including a review of your family tree, family health history, family dynamics, conversations about faith and more. When a family issue comes up, add it to the next GWP agenda to discuss.


Generational Wealth Planning is about creating an avenue to have important family discussions that will impact your children and grandchildren the rest of their lives. Once you’ve started the GWP process, you’ll find these important conversations will continue throughout the year, whether that’s at Uncle Harry’s funeral, a holiday celebration, or on a random phone call home to discuss something they recently heard about. Embrace each discussion as an opportunity to influence your most precious asset – your family. For further discussion on beginning the GWP process with your family, contact your Shakespeare Advisor.