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The conversations you should have when making a will

In an effort to help you with creating your will, we spoke to someone very familiar with the process, COO and co-founder of Trust & Will, Daniel Goldstein, for his advice.

Okay, so you’re thinking about making a will. Good for you looking after your family, pets, estate and assets (yes, even that spoon collection you’ve been working on since the 2nd grade).

However, if you’ve never made a will before, there are two things you should probably know before you get started.

1. Kind of like applying for life insurance, it’s not as hard to do as you think (especially thanks to online, self-directed services like Trust & Will).

2. As you go down the path of creating your will, there are going to be a few important conversations you’ll want to have with your loved ones.

So, in an effort to help, we spoke to someone very familiar with the process, COO and co-founder of Trust & Will, Daniel Goldstein, for his advice. Here’s what he had to say.

The most sensitive conversation is probably the one to have first

“The hardest question is typically who somebody should elect as legal guardians for their kids,” Goldstein says. “There are many factors to consider when appointing a legal guardian—values, financial stability, geographic location, life circumstances, and many more.” Suffice it to say, this might include some less-than-comfortable conversations with siblings and other relatives, but it helps to keep in mind the ultimate goal of these conversations: peace of mind about what would happen to your children.

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If someone has appointed responsibilities in your will, you should go ahead and let them know

It might seem obvious, but once you’ve made the difficult decisions on who will inherit the responsibility for taking care of your loved ones, your belongings, and your finances, you need to sit down and talk with them.

“We highly recommend talking to anybody who has a future responsibility within the will—this includes your executors and guardians,” Goldstein says. ““These are responsibilities which people shouldn’t be surprised by. Plus, it gives them time to discuss the minutiae of wishes within the will, and understand the intentions in more detail.”

You should also make sure a few key people know where to find the document that outlines their responsibilities. “We always recommend talking to immediate family members to let them know how you’ve created a will and where it is stored,” he says. “This includes parents and siblings.”

The trickiest conversation is probably the one to have first

“The hardest question is typically who somebody should elect as legal guardians for their kids,” Goldstein says. “There are many factors to consider when appointing a legal guardian—values, financial stability, geographic location, life circumstances, and many more.” Suffice it to say, this might include some less-than-comfortable conversations with siblings and other relatives, but it helps to keep in mind the ultimate goal of these conversations: peace of mind about what would happen to your children.

Not every beneficiary needs to be notified

Okay, so this is probably more of a conversation that can be skipped. “It’s not necessary to notify beneficiaries unless it has a specific benefit to help explain the purpose of a specific gift,” Goldstein says. In other words, if you’re designating, say, an organization as a beneficiary, you don’t need to let them know if you don’t want to.

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Use your will as an opportunity to reconnect

Relationships (especially the lifelong ones) can be messy or complicated. Writing your will gives you a chance to address them head-on. “Honest conversations always present the opportunity for connection,” Goldstein says. “The reality of life is we all die. [Writing your will] opens up opportunities for these conversations as well. Overall, having the conversation opens up the book to other sensitive conversations such as parental health, child care, and family values.”

That all said, fair warning: Things can get intense, so you’ll want to choose an appropriate setting. “It could lead to some awkward conversations,” Goldstein says, “so people should be prepared for the sensitivity of the topic.”

Consider having a conversation with those not in your will

“It massively depends on the person and family dynamic,” Goldstein says. “Some people will benefit from conversations with beneficiaries and even to notify people who are purposely not in the will that they aren’t in the will. This can be helpful for the aftermath of fighting, but is definitely not common or pleasant.  We believe transparency and communication makes the whole industry and process better and hard conversations are better had while people are alive than between people after the person has died. Once somebody has died, context is lost and it can divide people.”

When it comes to discussing what to list in your will…anything goes

Some people wonder what’s appropriate to list in an important document like a will. Obviously, your finances and major possessions should go in there, but what about those odd mementos with limited monetary value (like your favorite backup catcher’s rookie card)? Goldstein says to go ahead and include it. After all, having a will in place helps dictate where you leave your legacy.

An estate is considered everything you own,” he says. “Most people give their estate in an aggregate way to an individual or a series of individuals. [But] some people like to call out specific assets—jewelry to their daughter, car to their grandson, etc. If there is sentimental or specific value, it’s great to give it as a specific gift. Otherwise, it’s up to the beneficiaries to determine value and divide according to the determined value.”

Now, if you’re like most people, you don’t want to take the time to list every single thing you possess, but you also want to make sure you don’t forget anything important. How should you prioritize it? “That’s a relational question,” Goldstein says. “It definitely depends on the person, marriage, family structure, etc. From a decision perspective, it’s good to divide it generally as an estate and then think about specifics afterwards.” However you proceed, it’s always a good idea to talk with your relatives about any specific items you want them to inherit. This way you can gauge their interest in what might turn out to be an unwanted gift. (“Actually, Uncle Louis, I don’t want your collection of mint condition Beanie Babies…”) If there is interest, just make sure your will backs it up in writing.

Now that you know why you need a will and what to talk about when creating a will… it seems like a pretty good time to, you know, make a will. As Goldstein says, “We strongly believe everybody should have a will or an estate plan of some sort—it makes life much easier for everybody.” Easy living, now there’s a stance anyone can get behind.

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Louis Wilson is a freelance writer whose work has appeared in a wide array of publications, both online and in print. He often writes about travel, sports, popular culture, men’s fashion and grooming, and more. He lives in Austin, Texas, where he has developed an unbridled passion for breakfast tacos, with his wife and two children.

Haven Life Insurance Agency (Haven Life) does not provide tax, legal or investment advice. This material has been prepared for informational purposes only, and is not intended to provide, and should not be relied on for, tax, legal, or investment advice. You should consult your own tax, legal, and investment advisors before engaging in any transaction. Individuals involved in the estate planning process should work with an estate planning team, including their own personal legal or tax counsel.

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About Louis Wilson

Louis Wilson is a freelance writer whose work has appeared in a wide array of publications, both online and in print. He often writes about travel, sports, popular culture, men’s fashion and grooming, and more. He lives in Austin, Texas, where he has developed an unbridled passion for breakfast tacos, with his wife and two children.

Read more by Louis Wilson

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Haven Life is a customer-centric life insurance agency that’s backed and wholly owned by Massachusetts Mutual Life Insurance Company (MassMutual). We believe navigating decisions about life insurance, your personal finances and overall wellness can be refreshingly simple.

Our editorial policy

Haven Life is a customer centric life insurance agency that’s backed and wholly owned by Massachusetts Mutual Life Insurance Company (MassMutual). We believe navigating decisions about life insurance, your personal finances and overall wellness can be refreshingly simple.

Our content is created for educational purposes only. Haven Life does not endorse the companies, products, services or strategies discussed here, but we hope they can make your life a little less hard if they are a fit for your situation.

Haven Life is not authorized to give tax, legal or investment advice. This material is not intended to provide, and should not be relied on for tax, legal, or investment advice. Individuals are encouraged to seed advice from their own tax or legal counsel.

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