How to Ask for Payment Details During a Medicare Supplement Presentation — Without Feeling Awkward

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How to Ask for Payment Details During a Medicare Supplement Presentation — Without Feeling Awkward

Written by Glen Shelton

Glen Shelton launched Lead Heroes in 2015 after noticing a lack of quality and service among telemarketed lead providers in the insurance industry. As president of Lead Heroes, Glen actively manages a call center with real people generating quality insurance leads. With processes designed to improve efficiency and lower costs, Glen helps maximize ROI for agents selling Final Expense life insurance and Medicare Supplements to seniors.

October 18, 2025

Let’s be real — asking for payment details can feel uncomfortable, even for seasoned agents.

You’ve done all the work: built rapport, presented the plan, answered every question… but when it’s time to collect the bank info, something shifts. The confidence drops, the tone changes, and suddenly the client says, “Let me think about it.”

Sound familiar?

Here’s the truth:
If you make asking for payment sound like a big deal, your client will feel it too. But if you handle it smoothly and confidently, it becomes a natural next step in the process — not a roadblock.

Ask Premium

Step 1: Build Value Before You Ask for Payment

Before you even mention the word “premium,” make sure your client clearly sees the value of their Medicare Supplement plan.

Start by contrasting Med Supp with Medicare Advantage:

Explain what they gain: No referrals, no network limits, no surprise bills.
Position Med Supp as peace of mind: “You can see any doctor who accepts Medicare — anywhere in the country.”
Paint the emotional payoff: “Once you have this plan, you won’t have to worry about unexpected hospital bills again.”

Once your client understands why Med Supp is the top-tier option, payment becomes just another step toward that peace of mind.

Step 2: Normalize the Payment Conversation

When you get to the point of collecting payment, don’t hesitate — just transition naturally.

Say something like:

“Alright Mrs. Jones, to get your plan activated, we just need to set up your monthly premium. Most clients prefer automatic withdrawal from their checking account — what bank do you use?”

Notice that you didn’t ask permission to collect payment — you simply moved the conversation forward.

The key is tone. Keep it calm, confident, and conversational.
If you’re casual and comfortable, your client will be too.

Remember: confidence transfers.
If you treat the payment step like a normal part of enrollment, your client won’t think twice about it.

Step 3: Think Beyond the First Sale — Cross-Sell Smart

Here’s where top agents separate themselves from average ones.

Once a client buys a Medicare Supplement plan, they’ve shown two key things:
1️⃣ They have disposable income.
2️⃣ They trust you.

That’s your cue to start a cross-selling conversation.

From that single Med Supp sale, you can easily open doors to:

  • Final Expense coverage

  • Cancer or Heart Attack policies

  • Hospital indemnity plans

  • Annuities or Life insurance

Smart cross-selling doesn’t just boost your commissions — it helps your clients get complete protection.

If you’re already helping them with healthcare coverage, you’ve earned the right to ask,

“Would you like me to also make sure your loved ones are financially protected if something happens to you?”

That’s how you multiply every Med Supp sale into a long-term relationship.

Med Supp Leads

Exclusive Medicare Supplement Leads

For agents focused on growing their Medicare Supplement book, we offer exclusive, call-verified Med Supp leads at our standard rate.

 100% exclusive — never resold
 Call-verified interest in Medicare Supplement plans
 Minimum order: 10 leads
 Delivered in as little as 7 business days

If you’re looking to consistently write Med Supp business and keep your pipeline full year-round, these leads give you a reliable, predictable flow of prospects who pick up the phone and are ready to talk coverage.

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