1. The late Stephen Covey, a legendary author and speaker, advocated planning by “starting with the end at the beginning.” Before sitting down for the planned conversation, very carefully consider and decide what you hope to accomplish. Be very specific. Then, pen in hand, list the most important aspects of a desired outcome.

2. Next, envision the setting where this conversation could take place. Consider a location where its content can remain confidential, yet also is comfortable and unthreatening.

3. Decide who should be present. Will you ask only those other family members required to execute the decision in question or limit participation to a close group whose input and opinions you value? Do you wish to include every family member with a possible stake in the decision’s outcome or that it may affect? Additionally, given those who will be involved and the matters to address, imagine the ideal timing of your family discussion.

4. With the “who, where and when” in mind, consider the “how” part of the conversation. Are you, the family leader, the best person to lead the discussion? Perhaps a trusted financial advisor might be a better “meeting leader” in some instances.

5. With the big picture in mind, write down a first draft of an agenda or outline. Use it as a guide for the conversation that you (or your meeting leader) will have with your family member(s). Prepare to discuss not only what needs to be accomplished, but also why it is important. I have heard family heads explain why a given decision was theirs to make, but also why it was important to them that family members agree.

6. Set the stage for a successful meeting by introducing the conversation topic in advance (and individually, if several people are involved) and by offering a personal “invitation” to each impacted family member.

7. Review your initial agenda, editing and amending as necessary. Practice the delivery of your most important, core message. Consider a trial run-through with a trusted financial advisor, your attorney or your CPA.

8. On the appointed day, be prepared for emotions that could range from acceptance, acquiescence, approval and gratitude to sadness, disappointment, anger and resentment. There may not be immediate acceptance of the message or your choices. Consider how you will react to the various possibilities. If your plan and thinking have been thoroughly prepared and developed, stick to your final agenda with confidence. Remember that being a caring family leader and financial decision-maker doesn’t mean you cannot be firm in your resolve to achieve the best outcome for your family and its future.

Serious family financial conversations are rarely easy. Strong bonds, good relationships and family members committed to each other’s happiness and well-being don’t always make a difficult discussion easier. Indeed, some conversations can be even more challenging in those circumstances. If you have experience with making serious presentations and you are comfortable with your ability to take the steps I’ve outlined, set forth putting your plan together.

On the other hand, many people would feel uncomfortable, intimidated even, developing and leading such an interaction with their loved ones. A trusted, fiduciary financial advisor can be instrumental in helping to formulate the topic and effectively deliver the desired message. I know that I’m honored to be involved when asked.


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