Choosing people to be in charge of your finances or your health should you become incapacitated or even pass away is an enormous decision. How can you know for certain you can put that level of trust in someone? Even someone you like and trust now might not make the same decisions you would when it comes to such matters.
One expert recommends testing the waters with heirs to find possible trustees and executors. To go the trial and error route, you have to begin estate planning early enough. You can set up small trusts or managed accounts for specific purposes, such as to pay for a business endeavor, begin investments or cover educational expenses.
Provide access to the trust or account in a managerial capacity to one of your heirs. Explain what you are doing and what your expectations are regarding the account or assets, but let him or her manage the assets. Don't step in constantly to redirect him or her or keep him or her from making what you think are mistakes -- this is supposed to be a learning opportunity. How someone reacts can also give you information about how he or she might function if you did make him or her a trustee or executor of your estate.
Working with heirs early also lets you create guidance for them. Once the experiment is done -- or even during the experiment after the heir has had a chance to do things his or her way a while -- you can step in and provide feedback. This type of communication and working together fosters increasing levels of trust and helps you identify heirs that you feel will try to protect both the spirit and letter of your wishes later. Because setting up such accounts and trusts can be complex, consider working with your estate planning professional to create trial runs that integrate well into your overall estate plans.
Source: Forbes, "Why Giving Your Heirs A Test Run With Your Money Makes Sense," Brian Luster and Steven Abernathy, accessed Jan. 01, 2016