A Guide to Thought-Provoking Insurance Conversations

By Broc Buckles

I didn’t plan on getting into insurance. My introduction to the industry felt more like walking into a sales boiler room than a financial planning firm. Everything was transactional, not relational. Each day, I had to schedule a set number of meetings, starting with a list of 200 contacts, mostly friends, family, and old classmates, and follow a one-size-fits-all script. The message was simple: smile, dial, repeat. Asking thoughtful questions wasn’t part of the playbook; closing was the goal. 

To be completely transparent, I entered the financial world as a bright-eyed young person with plenty of ambition but not much understanding of how the industry actually worked. Even the concept of Fee-Only financial planning was totally foreign to me. I assumed everyone who gave financial advice did it in the best interest of the client. That assumption didn’t last long. 

That early role taught me what not to do. I was pushed to prioritize products over people, often talking about insurance before understanding someone’s needs. It wasn’t insurance that was the issue. It was the way it was sold. 

Today, I co-own an insurance brokerage that partners exclusively with Fee-Only financial planners. We work with the advisor first. When appropriate, we help implement insurance strategies for their clients. Our goal is to make insurance a seamless, thoughtful part of financial planning. After thousands of conversations with advisors, one thing is clear: insurance is often the topic planners least enjoy discussing. Growth projections, retirement modeling, tax strategies—these come naturally. Discussions about death, disability, or long-term care are often avoided. 

Yet, avoiding risk doesn’t eliminate it. Silence unintentionally suggests to clients that protection isn't important. It potentially leaves them vulnerable when life takes an unexpected turn. The goal of this article is to help financial planners feel more comfortable addressing insurance and to understand why these conversations often get avoided in the first place. 

The Elephant in the Room

Fee-Only planners have shared with me that they often hesitate to talk about insurance for understandable reasons. Cringeworthy social media influencers only add to the problem, creating confusion by promoting insurance products in a misleading manner. You've likely seen videos featuring some "insurance bro" next to a rented Lamborghini, pitching a "Roth IRA on steroids." Rarely do these influencers reveal they're actually selling life insurance. They seldom discuss the true benefits and trade-offs involved. Real planners do not want to be perceived this way, which often leads them to avoid addressing it head-on. 

The complexity of regulations, stacks of paperwork, and underwriting requirements can also feel overwhelming. That causes planners to prioritize topics they're more comfortable discussing. The emotional difficulty of conversations about death, disability, or long-term care further complicates matters. These conversations are essential. They directly protect clients' financial goals and the well-being of their families. Framing insurance discussions around safeguarding the client's priorities can shift these talks from uncomfortable to crucial. 

Leaving these conversations out of the planning process doesn’t mean clients will avoid them. It just means they may explore them alone or with someone who doesn’t understand the full picture. 

Real People, Real Plans, Real Lessons

The Disability Surprise 

One advisor shared how a conversation with their client uncovered a major oversight. The client believed they had solid disability coverage through work, citing a 60% income replacement. During the meeting, the advisor asked a few clarifying questions and discovered the employer paid the premiums, making the benefit taxable. That meant the actual payout would be closer to 40–45% of their salary. It was a moment of surprise for the client, who admitted 60% already felt tight. Suddenly, it was clear how underprepared they were if they ever became unable to work. According to the Social Security Administration, one in four of today's 20-year-olds will experience a long-term disability before retirement, making these conversations not just helpful but necessary. 

The LTC Premium Panic 

Another advisor told me their client panicked after receiving a letter stating their long-term care premiums were increasing by 30%. The client was ready to cancel the policy. Then they reviewed the details and realized it offered a lifetime benefit and a generous monthly payout, far better than anything they could qualify for at their current age and health. Given that 70% of retirees will require some form of long-term care, a sudden and uncalculated cancellation could have had serious consequences. 

The Shiny Object Trap 

I've had several advisors tell me their clients had purchased insurance policies without their knowledge. That mostly happened simply because they never discussed insurance. Sometimes, clients were drawn in by something they saw on social media, like a shiny product in an Instagram reel or TikTok. That product promised a better deal or seemed to offer something their plan was lacking. They either made the purchase outright or brought it to their advisor only at the last minute. 

Often, these policies duplicated existing coverage, conflicted with the clients' financial plans, or included unnecessary and costly features. A straightforward conversation at the right time could have prevented these issues. 

That underscores a key point: When planners proactively discuss insurance, clients benefit from an integrated approach to their financial planning. When they don't, clients might turn elsewhere. That risks incomplete or conflicting advice. 

Even when clients loop you in, assuming their insurance needs based on surface-level facts can still lead to misalignment. It’s not just about what they have. It’s about what they value. 

How to Have the Conversation (Without Sounding Pushy) 

These conversations aren’t easy. Period. Advisors regularly talk with clients about debt, spending, and taxes. Those topics aren’t always fun, but they’re manageable. Talking about dying, becoming disabled, or needing care in old age can feel far more uncomfortable. 

However, clients deserve the full conversation. Their goals are more than just numbers on a spreadsheet. They’re built on relationships, health, and a sense of purpose. 

Start by acknowledging the discomfort. Let clients know you understand talking about death or disability isn’t enjoyable but it’s an important part of making sure their plan holds up under stress. 

Use open-ended questions that keep the focus on the client’s life, not the insurance itself: 

• What’s something in your life you’d want to protect no matter what? 
• If you couldn’t work for six months or a year, how would that impact your plan? 
• Who would step in if you needed care long term? 
• Has anyone in your family ever gone through something that changed their financial picture overnight? 
• How do you want decisions to be made if something unexpected happens? 

These are not sales questions. They are planning questions. They are meant to help the client think more deeply about their own values and priorities. The answers often lead naturally into meaningful conversations about insurance strategies. 

You don’t need to be an expert in every product or process. You just need to be willing to have the conversation, listen closely, and bring in the right partners when needed.

From Theory to Real Life 

Insurance isn’t always the fun part of planning. It’s often the part that matters most when life doesn’t go as planned. Being proactive doesn’t mean being pushy. It means showing clients you care enough to prepare them for the moments they hope never happen. 

These conversations won’t always be easy but they can be incredibly meaningful. They enable clients to feel seen, heard, and supported in a way that goes beyond numbers. When you make space for the hard topics, you help ensure the rest of the plan can stand strong in the face of uncertainty. 

Clients may not remember every number you show them. They will remember whether you brought up the uncomfortable stuff, helped them navigate it with confidence, and gave them peace of mind. That peace of mind is not theoretical. It’s something they carry with them. 

When insurance is approached with care, clarity, and collaboration, it becomes more than a policy. It becomes a critical part of a thoughtful financial life. 

Recently, our team reviewed a few of our active long-term disability income claims. These aren’t just names on a spreadsheet. They are real people dealing with real illnesses and injuries that have disrupted their lives and livelihoods. Most of them weren’t eager to have conversations about being unable to work for an extended period of time. These discussions weren’t fun to initiate or navigate. The process took time. Their benefits weren’t cheap. Today, their families are covered. Their plans are protected. Their peace of mind is real. 

This isn’t a billboard for insurance. It’s a reflection of what happens when the uncomfortable conversations actually happen. Insurance, when implemented thoughtfully, changes lives. It keeps people in their homes, kids in their schools, and families afloat when everything else feels like it’s falling apart. 

These are the moments that remind me why these conversations matter so much. It all starts with the willingness to have them. 

You don’t have to be perfect. You just have to be present. Showing up for these conversations—even when they’re difficult—can make all the difference. Your clients are counting on you to help them see the full picture. With the right approach, you can turn one of the hardest parts of planning into one of the most meaningful. 

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Broc Buckles is the co-founder of BC Brokerage.

image credit: Adobe Stock Images