Tips to Make Difficult Financial Conversations Easier

Whether it’s talking to kids about affording college, aging parents about ongoing care, or to our bankers, financial planners, or partners and spouses about a host of money-related issues, handling a difficult financial conversation can be a major stressor.

Which makes sense. Money is a big, emotional topic, touching on our sense of safety, security, control, and worthiness.

Facing up to challenging financial situations and having candid conversations with the important people in our lives is an essential part of a healthy relationship with money and having a good financial plan. But often we avoid these conversations with a mix of fear, shame, and plain old procrastination.

As financial advisors, we spend years refining not just our money skills, but the people skills we need to help have the conversations that build relationships and help us be as productive and engaged as possible with our clients. Building trust, listening, asking questions, handling strong emotions, and introducing difficult topics are all part of the job description—and ultimately lead to the vulnerability, honesty, and empowerment that help clients create and fulfill their visions for their lives and financial futures.

Here are some pro tips to help you through difficult financial conversations.


When you know you’ve got important money matters on your mind, it’s important to figure out a time and a place to sit down with your loved one. Know when and where you’d most like to be—preferably somewhere comfortable and private where you won’t be interrupted. Set a time when neither of you will feel stressed or rushed. And it’s okay to do a little prep and have talking points, in case you feel

Stick to one topic.

It’s tempting to want to tackle “everything about our finances that’s freaking me out” in a big financial conversation, but that will set you or your conversation partner either on a path to overwhelm, defensiveness, or both. For example, if you need your teen to understand that their dream college isn’t affordable for the family, resist the urge to talk about their spending habits, summer job, allowances, or other related issues. That kind of conversational pile-on can lead to people shutting down or becoming defensive. Keep your focus on the single issue at hand and the financial facts you are both facing.

Start with curiosity.

This is a mindset opportunity: Having a firm agenda to persuade the other side that you are right can result in fear and pushback. When you approach the conversation with an open attitude and a genuine desire to learn, that respect and vulnerability tend to encourage more of the same.

Be ready to deal with negative reactions.

What you have to share may provide feelings of disappointment, anxiety, disbelief, or fear—be prepared for all of them, but don’t take them personally. Instead, ask questions. If they disagree with the facts you’ve shared, ask them why. If they are frustrated, ask them to share what’s causing that, and listen openly without interjecting or getting defensive. Try using the phrase “I hear you,” which shows empathy lets someone know that you are listening and have heard what they are sharing, even if you don’t necessarily agree.

End with acknowledging that you both did a hard thing.

Talking about money can be hard, but gets easier with practice. Simply by facing up to some difficult facts or topics, you’ve taken a positive step in your relationship not just with money, but with those close to you whom it impacts. Thank them for listening, and acknowledge all the good things that came from the conversation.

If you need help facing difficult financial realities or with having a hard conversation, Aspen Wealth Strategies advisors are ready to help you take that first step and get you on the road to greater financial peace.

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