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Created: October 23, 2020
Modified: June 6, 2023

Podcast Episode 171: How to Have Those Awkward Financial Conversations

What You’ll Learn:
Financial planning isn’t always an easy process. We often need to address situations that can be awkward for the client. Today we’ll tell you about six of these challenging conversations and how we approach them. Don’t let these awkward planning topics keep you from opening up and taking them head-on.

Talking about money can be difficult for many people. Throw in a situation that makes you uncomfortable and it can turn into a very awkward conversation for a client.

But we don’t see it that way. There aren’t many topics we haven’t worked through with clients through the years so we understand the challenges and concerns.

In this episode of the Money Wisdom podcast, we want to bring some of those conversations to the forefront and help you understand what we do to make things easier for the people we work with.

Removing a Child as a Beneficiary

Families should be consistently evaluating their beneficiaries and making changes as life events happen or needs evolve. You’d be surprised how common this situation is for many of our clients because we work with a lot of people in their 60s who have adult children. They might be a little embarrassed to come into our office to address a situation within their family, but we ease their minds very quickly. You don’t have to split everything equally.


When a couple decides to split, rarely do they both continue to work with the same financial advisor. We can think of a couple of times where both spouses stayed on with us but more often the person that’s not as actively involved decides to go somewhere else. We often get referrals from divorce attorneys whose client is looking for a fresh start. But whatever your wishes are, we’ll make sure they are met.


Financial stress can really push you emotionally. That means that we will sometimes break down. We can think of many instances where people lost a loved one or experienced a major life event and cried in our office. Our job is to listen and support them because many people don’t feel comfortable having these financial conversations with friends. This gives them an outlet to release that stress and get relief.

Embarrassing Financial Decisions

The reality of life is that we’ll all make bad financial decisions at least once in our life. Sometimes those are more embarrassing than others. Maybe you’ve been scammed out of money or faced drug or alcohol abuse that impacted you financially. We are there to help build a plan that can help them rebound and regain optimism for the future, and this is something we’ve seen from a number of people.

Sibling Squabbles

Family drama occurs in all of our lives, but it can escalate when there are money and assets at stake. The most common thing we see is when siblings argue or fight over pieces of an estate. Maybe one sibling was much more involved than the others or the will or trust didn’t layout things like the family expected. Whatever the issue is, we are there to listen. We follow the law. And oftentimes, we’re just de-escalating the situation.

Wanting to Change Advisors

Whether you are leaving another financial advisor or wanting to leave us, we work to make this transition as easy as possible. If you’ve gotten to the point where you want to make this change, this is something you’ve thought about for a long time. We won’t work to change your mind because we realize it’s your money. Too often advisors forget that.

Whether you’re dealing with any of these awkward conversations or not, remember that it’s not a reason to run away from the financial planning process. You just need the right person guiding you through these challenges and we do that every day with our Money Map process. Feel free to reach out to learn more.

[0:37] – The loss of Eddie Van Halen

[2:32] – Removing a child as a beneficiary on an account.

[4:30] – Working with both spouses during a divorce.

[6:12] – When a client cries in the office.

[7:35] – Client that’s made an embarrassing financial decision.

[9:27] – Siblings that are arguing over finances.

[12:08] – Client that needs to make a change with their financial advisor.

[13:58] – A good way to begin addressing these awkward conversations. 

Thanks for listening to this episode. We’ll be back again next week for another show.

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