The Ultimate Cold Calling Cheat Sheet for Insurance Agents in 2025

Let’s be honest for a second.
Cold calling sucks, especially when you’re new.

Back in 2019, I started selling insurance and my manager handed me a phone book (yes, they still exist) and said, “Start dialing.” I was ready to quit by the end of the week.

Fast forward six years, and cold calling now pays my mortgage.
Last month alone, I made more from phone calls than most people make in three months. Not bragging, just being real about what’s possible when you figure this out.

If you’re just getting started or struggling with calls, this guide’s for you. I’ll show you what worked (and what didn’t), how I talk to people on the phone, and how I stopped dreading it.

Why Cold Calling Remains Effective in Modern Insurance Sales

Everyone says cold calling is dead. "Nobody picks up anymore," they say. And yes, it's tougher now than it used to be. But here's the truth:

When someone is worried about protecting their family, business, or health, they’re open to talking, if you reach them at the right time and say the right thing.

Example: I called a landscaping business owner in Ohio. He’d been robbed a month earlier and never had business insurance. I explained what he needed. He listened. Three days later, he bought a policy.

It’s not magic. It’s just reaching out at the right time.

Cold Calling Cheat Sheet for Insurance Agents, people don't buy insurance when everything's perfect. They buy it when they're scared something bad might happen, or when something bad has already happened to someone they know.

Essential Mindset and Preparation for Cold Calling

Why Cold Calling Remains Effective in Modern Insurance Sales:

This is huge, and most people don’t talk about it.

If you think you’re bothering people when you call, you’ll sound like you’re bothering them. I used to start every call with, “Sorry to bother you…” and guess what? People hung up on me.

Now I remind myself:

I might be helping this person avoid a financial disaster.

That’s not annoying, that’s useful.

Also:

• I stand up while calling. It helps me sound more energetic.
• I remind myself rejection isn’t personal. They’re not saying “no” to me. They’re saying “not right now” to a random call.

Pre-Call Research Strategies for Better Results

Before I call someone, I spend 60–90 seconds looking them up, usually on LinkedIn.

If they just started a business, I know they probably need insurance.
If they work for a big company, I skip the health insurance pitch, they likely already have it.

I’m not stalking them—I’m just trying to make the call feel more relevant and less like a cold pitch.

Proven Cold Calling Scripts for Insurance Products

Forget cheesy sales scripts. I talk like a real person.

Here are the actual openers I use:

For business insurance:

“Hey John, this is Mike from Midwest Insurance. I help small business owners figure out their insurance situation. Are you handling that yourself right now or working with someone?”

For life insurance:

“Hi Sarah, Mike from Midwest Insurance. I help families make sure their life insurance still fits their situation today. A lot of people bought something years ago and never looked at it again. Sound familiar?”

For health insurance (especially for self-employed folks):

“Hey David, Mike here. I work with self-employed folks to find health insurance that doesn’t cost a fortune. Are you dealing with that headache right now?”

Why this works:

• It’s short and clear
• It ends with a simple question
• It sounds like a real conversation, not a sales pitch

Professional Objection Handling Techniques

Most people aren’t excited to get a cold call. That’s fine.
But don’t give up right away. A lot of "no’s" just mean "not yet."

Here’s how I reply:

“I’m not interested.”

“Totally understand. Can I ask, do you already have coverage, or is it just not a priority right now?”

“I don’t have time.”

“No problem. Would later this week or next week be better for a quick chat?”

“Just send me info.”

“Sure thing, what exactly would you like to know, so I can send the right stuff?”

“It’s too expensive.”

“Yeah, I hear that a lot. Most people are surprised by what’s available now. Want me to show you a few options?”

Notice I’m never arguing, I’m just being helpful and curious.

Building Trust and Credibility Over the Phone

This is probably the hardest part. Someone who doesn't know you from Adam has to decide whether to trust you with something as important as their family's financial security, build trust and credibility on cold calls.

This part is tricky. You're a stranger calling about something personal. Why should they trust you?

Here's what I do:

• I match their energy. If they talk fast, I speed up. If they’re calm, I slow down.
• I ask real questions. And I actually listen to the answers.
• I repeat what they care about. If they say “I want to protect my kids,” I bring that up again later in the call.

People trust you more when they feel heard, not sold to.

Strategic Follow-Up Systems That Convert Prospects

Most sales don't happen on the first call. I follow up with people three times over about two weeks, then leave them alone for six months.

The first follow-up is usually sending them quotes or information they asked for. Second is calling to see if they have questions about what I sent. Third is checking if they're ready to move forward or if they need more time, follow-up system that closes insurance leads.

I don’t expect to sell anything on the first call. Most people need time to think.

Here’s my system:

1. First follow-up: Send them what they asked for (quotes, info, etc.)
2. Second follow-up: Call 2–3 days later to answer questions
3. Third follow-up: A week later, check if they’re ready or need more time

If nothing happens, I wait a few months and try again. People’s lives change. One “not now” could become a “let’s talk” after a wedding, baby, or price hike.

Managing Rejection and Maintaining Performance

Some days, you’ll make 30 calls and nothing good will happen. Other days, you’ll close three sales before lunch.

That’s how this business works. You’ve got to stay level.

If I’m in a bad mood, I don’t call. People can hear it in my voice. I’ll do admin work or take a break instead.

Rejection sucks, but it’s not personal. That’s the biggest lesson I’ve learned.

Technology Tools and Systems for Cold Calling

You don’t need a $200/month CRM to succeed.

Here’s what I use:

• A spreadsheet to track who I called
• My phone (with caller ID)
• A notebook to write down what people said
• A call recorder (for training and feedback)

I tried some auto-dialers before. Hated them. Too fast, felt robotic.

The only tool I use now that actually helps?
PowerDialer.ai – It helps me stay organized, send follow-ups automatically, and remember who to call back.

That's it. I tried one of those systems that dials multiple numbers at once, but half the time it connected me to voicemail when someone answered, or connected me when I wasn't ready. I'd rather dial myself and be prepared for each call, cold calling technology tools for insurance agents.

The one piece of technology that helps is call recording, but only for training purposes. I record myself sometimes and listen back to see what I could do better. It's painful but helpful.

Where I Actually Get My Leads

I don’t buy leads from sketchy websites anymore. Too many wrong numbers and people who don’t want to talk.

My best leads come from:

• Referrals (just ask people you help!)
• Website quote requests
• Local networking (like chamber events)

Not all leads are equal. If someone asks for a quote or is referred by someone they trust, the conversation is way easier.

Best and Worst Times to Cold Call

Here’s what I’ve noticed over the years:

Best times:

• January – New year, people want to “get their life in order”
• Tax season (March–April) – People are thinking about money

Harder times:

• Summer – People are distracted or on vacation
• Holidays – Hit or miss depending on the week

I still make calls year-round, but I go easier on myself during slow months.

Mistakes I Used to Make (So You Don’t Have To)

• Talking too much on the first call
• Sounding like I was reading
• Not asking what the next step should be
• Taking rejection personally
• Calling the same person five times even after they said no

You don’t need to be perfect, you just need to keep learning and improving.

The Only Metrics I Track

Forget call volume. That’s just noise.

I focus on:

1. How many people I talked to (real conversations)
2. How many wanted a follow-up
3. How many ended up buying

I know that if I talk to 10 real people, I’ll probably close 1–2 sales. That’s what keeps me dialing.

On a typical day, maybe one in ten people I call will have a real conversation with me. Out of those conversations, maybe two or three will be interested enough to get quotes or meet. Out of those, maybe one will buy.

So I need to talk to about thirty people to make one sale. Your numbers might be different, but that's reality for me.

I don't worry about how many calls I make per day. I'd rather have twenty good conversations than fifty bad ones.

Getting Past Gatekeepers (Without Lying)

When I call businesses, I’m usually greeted by a receptionist. Here’s what I say:

“Hi, this is Mike from Midwest Insurance. I’m calling to talk with John about business insurance. Is he available?”

Simple. Honest. Most of the time, they’ll either transfer me or tell me when to try back.

My Voicemail Strategy

Yes, I leave voicemails. They work, but only if you keep them short.

“Hi John, this is Mike from Midwest Insurance. Just wanted to share some business coverage options that might save you money. Call me back at 555-1234 if you’re interested. Thanks!”

That’s it. No pressure. No rambling. One in 20 will call back, and that’s enough.

How I Build a Connection (Fast)

People decide whether they like you within the first 30 seconds.

Here’s what I do:

• Use their name naturally
• Match how fast they talk
• Ask about their situation before I talk about myself
• Listen, and mention the things they care about

You don’t need to be slick. Just be human.

Final Thoughts: Cold Calling Works, If You Work It

Cold calling isn’t easy. But it gets easier and more profitable, the longer you stick with it.

Some days will suck. That’s normal.
Some people will be rude. That’s also normal.

But when you help a family get covered, or save a business owner money, that’s the part that feels good. And yes, it pays well when you do it right.

If you’re just getting started, give yourself six months to get good. Don’t quit after a few bad days.

Want to Make Your Cold Calls Smarter (and Easier)?

I use PowerDialer.ai to stay organized, follow up automatically, and manage my calls without a mess.

Try a free demo here.

Frequently Asked Questions About Cold Calling

How many calls should I make per day?
Around 30–40. Focus on real conversations, not just numbers.

What if I get nervous?
Totally normal. Keep practicing. It gets easier fast.

Should I use a script?
Use a loose framework, not a word-for-word script.

Is it legal to call cell phones?
Be careful, follow the rules. Use numbers people gave permission to call.

How do I know someone’s serious?
They ask questions, they mention their situation, and they don’t hang up right away.