How to Prospect for Life Insurance Clients

Most advisors make the mistake of leading with spreadsheets - that no one cares about. Nobody makes life-changing financial decisions because of a probability chart. People take action when they feel something—fear of running out of money, excitement for a dream retirement, or the urgency of protecting their legacy. Stop bombarding clients with data.  Start telling their story.  Show them what’s at stake. Paint a picture of their future—both the dream scenario and the nightmare they want to avoid. 5 Ways to Connect with Clients on a Deeper Level: 1️⃣ Ask "What keeps you up at night?" - Don’t assume you know their biggest concerns. Let them tell you. 2️⃣ Use real-life stories - Share examples of clients who faced similar situations and how they overcame them. 3️⃣ Speak in dollars, not percentages - "You have a 70% chance of success" is meaningless. "You could run out of money by 82" hits home. 4️⃣ Frame every decision in terms of impact - How will this affect their kids, their lifestyle, their legacy? Make it personal. 5️⃣ Repeat their words back to them - People trust you more when they feel heard. Mirror their language to show you truly understand. Logic informs.  Emotion drives action. Learn the difference, and you’ll close bigger deals faster.

You don't need to cold email 10,000 prospects. Instead, use The Dream 100 Strategy by Chet Holmes. This approach focuses on creating relationships with a carefully selected list of high-value prospects, typically called the “Dream 100.” The idea is to identify the top 100 prospects or clients who, if they become customers, would most impact your business. Rather than spreading efforts thinly, you concentrate on winning these accounts with persistent, personalized outreach. I can attest to testing this strategy dozens of times; it works! It's also much more fun because you can avoid being a dirty, rotten spammer. Here’s how you do it on this platform: 1. Pick 100 companies (think about it). 2. Build a list of all the critical stakeholders on SalesNav. 3. This will end up being about 300 people. 4. Do research on all those people. 5. Read the CEO's memos and what the company puts out. 6. Figure out what each company's top 3 goals are. 7. Enrich that list using tools like Apollo. 8. Add that list to your CRM. 9. Upload that list to LI ads to get a matched audience. 10. Monitor their LI for when they post (daily), ' like,' and 'comment' on their content. 11. Create short-form content that stakeholders are going to care about. 12. Sponsor your content to that micro-audience so that every time they log into this platform, they see you adding value. 13. Write a personalized connection request. 14. Set up a monthly LI event (long-form content) about solving problems those Dream 100 customers care about. 15. Invite them to the monthly event. 16. If they attend, ask if they saw it; if not, send them the replay (most busy executives watch the replays). DO NOT: - Machine gun them pitches - Be weird in the DMs - Tag them on your content - Gate your content Do this for 12 months; I'd be surprised if you don't close a good chunk of them. Be so good and helpful, they can't ignore you. PS - Most are too lazy to do all this. You can use this to your advantage.

Cross-selling life, health, and supplemental insurance products effectively requires a client-focused, data-driven, and trust-based approach. Here are the best strategies: 1. Leverage Existing Relationships and Trust • Personalized Reviews: Schedule annual policy reviews to evaluate needs and introduce relevant add-ons (e.g., critical illness with life insurance). • Educate, Don’t Just Sell: Use these reviews to explain why additional coverage matters—health risks, income protection, rising healthcare costs, etc. 2. Segment and Target Strategically • Profile by Life Stage & Risk Exposure: • Young families: Life + health + accidental death. • Empty nesters: Life + critical illness + LTC or cancer policies. • Seniors: Medicare Supplement + final expense. • Use Data and CRM Tools: Identify clients with only one product and predict next-best offers. 3. Bundle for Value • Create Packages: Offer bundled pricing or incentives (discounts, simplified underwriting). • Simplify Messaging: Position bundles around peace of mind, not just price (e.g., “Complete Family Protection Plan”). 4. Train Your Team in Needs-Based Selling • Not product-pushing: Cross-selling should solve problems, not push policies. • Use fact-finding tools or risk assessments to reveal gaps. • Train reps to ask open-ended questions like: • “If something happened to you tomorrow, how would your family manage financially?” • “Have you thought about how you’d pay your bills if you couldn’t work for 3+ months?” 5. Use Trigger-Based Campaigns • Set up automated emails or call reminders triggered by: • Policy anniversaries • Claims made • Milestones (turning 26, 50, retirement) • New product launches 6. Educate Through Multiple Channels • Email newsletters, webinars, or short videos that break down: • Why life and supplemental policies matter • Real-life scenarios (client stories or testimonials) • Offer free resources like “Insurance Checklists” or “Protection Gap Calculators.” 7. Make Enrollment Simple • Pre-fill application forms when possible • Offer e-signatures and virtual meetings • Use simplified issue products where underwriting is minimal 8. Track & Measure • Monitor which cross-sell campaigns work best • Track metrics like: • Policy-per-client ratio • Retention rates • Uptake on specific bundles

"I don't believe in life insurance." When a prospect says this, most agents start arguing. Big mistake. Here's what they're really saying: "I have a deeply held belief about money, security, and what matters in life." Fighting that belief = instant resistance. Instead... Ask them about their values: • What matters most to them? • Who depends on them? • What legacy they want to leave? I had a client once adamantly against insurance. But when we talked about his daughter's college dreams... His perspective shifted completely. Because it wasn't about insurance anymore. It was about love. About protection. About ensuring promises get kept, even if he couldn't be there. Remember: People don't buy insurance. They buy peace of mind for the people they love. That's the conversation worth having.

99% of brokers will tell you that they prospect. Very few can explain what that actually means on a weekly basis. After coaching 4200+ brokers across the last 18 years. Here’s how I’ve noticed the top performers prospect: → They start with momentum Every day begins with inactive clients and friendly contacts. People who know you, like you, and even trust you. Have these stored in your CRM. Then create your daily list. You should know exactly who you are calling before the day starts. That block should be tight. 30 to 45 minutes maximum. Thereafter, energy drops and performance depreciates. But remember, calling alone is not a prospecting plan. Effective brokers surround their calls with immersion. Prospect letters, short videos, DM conversations, and emails. Physical and personal touches that create familiarity. By the time you call, you are not a stranger. That is why I do not believe in cold calling. What most people call cold calling is really just lazy sequencing. Warm conversations close faster, convert better, and feel more professional. Here’s your takeaway: A real prospecting plan is not about volume. It is about structure, sequencing, and disciplined daily execution. Consistency is what separates great brokers from average ones.

I’m living the dream on vacation right now, but I keep being amazed at the terrible prospecting that goes out, so I just have to share. This was Tuesday. Of this string of calls, only one voicemail was left (and it was ok…not great). Let me give some quick pointers on how to do prospecting well in today’s day and age: 1 — DO YOUR RESEARCH. Especially with AI, it is easy to do exceptional research. If I was prospecting me, this is what I would do: 1 — search recent earnings calls, website, press releases, etc. Do enough research about the company to be able to show that you know what they are going through…you know how they are growing…you know what matters to them. THEN…show that in the outreach. 2 — BUILD A RELATIONSHIP. Relationships aren’t built by calling one time, or sending an email, or connecting on LI. Relationships are built over time. Show that you care. Show that you want to build a relationship. 3 — PLAY THE LONG GAME. This goes hand in hand with number two. It is going to take time, so don’t get frustrated if you don’t get the results you want at the very beginning. 4 — make it multi channel. Email, phone, social media, carrier pigeon, direct mail, etc. Do whatever you need to do to make them notice (IF your solution is that good, solves the problems, etc). 5 — make every interaction count. Don’t use outreach that wasn’t tailored for that specific account. In the days of AI slop, it is too easy to “personalize” outreach. Make sure it really is personalized/relevant/valuable and NOT just AI slop. Now go get after it and don’t be lazy. The bar for sales right now is so low, but for those who do it the right way (using the above blueprint) the results can be exceptional.

If I could go back in time to my early days in sales, I would spend a lot less time worrying about product knowledge, and a lot more focussing on these six building blocks of success: 1. A Clear Ideal Client Profile (ICP) You don't have the time or resources to sell to “everyone”. Instead, define the characteristics of the companies you can help the most (and where you have the best chance of success). Define the characteristics of these companies in terms of technical, cultural and economic characteristics. If you focus on companies that are a long-term strategic fit, you can base your outreach and conversations on partnership instead of being pushed into justifying your service on price. 2. A Target List You can’t hit a target you can’t see. Build focussed lists of specific clients that match your ICP criteria. There have never been more sources of data to help you do this; from Linkedin, Lusha, Apollo and ZoomInfo to Clay, ChatGPT and beyond. 3. A Buyer-Focused Linkedin (& Social Media) Presence For best results, your Linkedin profile shouldn't be a CV about you and your career – it should be a shop window for potential customers to understand the services you offer. Write your profile about the problems you solve and the outcomes you deliver. Then, briefly explain the framework you use to deliver results, followed by some testimonials and case studies to back up your claims. 4. Regular, Relevant Content Publishing content on Linkedin (and other social channels) is one of the best ways to become a known expert in your industry. When someone in your sector has a problem you can solve, the goal is to be the person they think of first. In that sense, you can think of publishing content as a form of long-term prospecting. 5. A Simple Outbound Cadence Prospecting isn’t rocket science. You simply need a clear, repeatable structure for contacting potential customers by phone, email, networking, Linkedin, direct mail (or any other appropriate channel). If you can get clear on what you'll typically say in initial messages and conversations with new prospects, it makes the routine and habit of prospecting much quicker and easier. 6. A Process for Improvement Continuous refinement is what separates predictable pipelines from feast-and-famine chaos. Create a weekly and monthly habit of tracking your prospecting results so you can understand what level of activity is needed to achieve what level of results, where you can improve, and what you need to do differently. After that, it's a just a case of #RepsRepsReps! 💪💯 Good selling!

You’ve heard it. You finally get a prospect on the phone… you make your bold statement… and they say the words that sound polite but mean go away: “Can you send me something?” Most producers hang up. The pros? They lean in. Here’s the truth... buyers lie. Not because they’re evil. Because they’re busy, guarded, and trained to protect themselves. And when you sound like every other agent, you trigger that defense. So what do you do? You don’t argue. You don’t pitch harder. You mirror. Repeat the last few words... with curiosity. “Send you something?” Now they have to explain. And the more they talk, the more truth you uncover. Then you label what you hear: “Sounds like you’re just slammed right now.” “Seems like you’ve had a good relationship with your broker for a while.” That tiny shift shows empathy, keeps them engaged, and turns a dead call into a conversation. These techniques come straight out of Chris Voss’ book Never Split the Difference... the same negotiation principles the FBI used to talk down hostage-takers. If they can defuse that kind of tension, you can navigate an insurance objection. Here’s your move this week: When a buyer throws a brush-off... “We’re happy with our agent,” “We just renewed,” “Send me something” ... don’t fight it. Mirror it. Label it. Then ask: “Before I hang up… can I ask you this?” You’ll be shocked how many stay on the line.  Role-play this today with your team.  List the five brush-offs you hear most and practice until these strategies roll off your tongue.

Why Most Insurance Sales Conversations Fail And What to Do Instead Let’s be honest. Many insurance sales conversations don’t fail because the product is bad… They fail because the approach is wrong. 🔹 Common mistakes in insurance sales 1. Talking too much about the product 2. Using complex, technical language 3. Leading with price instead of value 4. Rushing the client to decide 5. Ignoring the client’s real concerns When this happens, prospects don’t say “no”… They say: “I’ll think about it.” 🔹 What actually works • Start with the client, not the product Ask questions. Understand their lifestyle, income, responsibilities, and risks. • Translate features into real-life impact Don’t say “coverage.” Say: “If something happens, this keeps your business running or your family stable.” • Simplify everything If it sounds complicated, it feels risky to the client. • Address trust upfront Be transparent about claims, terms, and limitations. Confidence grows from honesty. • Focus on long-term value Insurance is not an expense it’s financial protection. 🔹 The mindset shift Stop trying to convince people. Start helping them understand their risks. A simple question that changes everything: 👉 “If something unexpected happens tomorrow, what would be the financial impact on you?” That question moves the conversation from selling… to self-realization. For insurance professionals: Your strongest tool is not your product knowledge… It’s your ability to: • Listen • Simplify • Build trust • Guide decisions Because in insurance sales, the goal isn’t just to close deals… It’s to open people’s eyes to what’s at stake. #InsuranceSales #SalesStrategy #CustomerExperience #FinancialLiteracy #RiskManagement #Insurance #GeneralInsurance #InsuranceEducation #TheInsuranceJournal #TIJ

I had a discovery call with an insurance agency prospect that reached out to me last week...asked a very simple (but, obvious) question, here's what happened next 👇 Me: "So, what's working and NOT working for you right now?" Simple. Direct. Seemingly obvious. He told me they got taken to the cleaners on the investment in conferences and trade shows this year. The ROI just wasn’t there. But when I asked what DID work for them this year... His answer was immediate: "Live" events. Specifically, seminars delivered incredible returns. Here’s what I learned... Sometimes, the answers are already in the room. You just need to ask the right questions. When we talked further, I said: “Great. Then let’s do more of what’s working. And scale it even bigger this year.” We often chase shiny objects, try new strategies, and spread ourselves too thin. Throwing sh*t against the wall to see what sticks. But success is often about doubling down on what’s already proven to work. For this prospect, it’s "Live" events (specifically, in-person seminars). Yes, IN-PERSON seminars still work great. Why? Because with the right "Live" event strategy and game plan, it ATTRACTS prospects, not repel them. Here's simplified formula WHY it works: NICHE FOCUS + VALUE (SOLVING PROBLEMS) + AUTHORITY = TRUST + RESPECT + HIGHER CONVERSIONS (per unit of time invested) →→ ROI For you, it might be webinars, workshops, or partnering with influencers in your niche who have access to your dream clients. Here’s the bottom line: → Stop wasting time pounding the phones and cold calling. → Stop chasing tactics that don’t offer value. → Focus your outbound outreach time and energy on inviting prospects to something valuable instead. The right question-based frameworks during a discovery call can extract pure gold. By obsessing over your dream client’s problems and challenges, you build trust—and help them refocus. Plus, you stop the chasing shiny object syndrome in it's tracks and/or you get them to stop doing crap that just doesn't work (like cold-calling). ❓So, what’s working for you right now? ❓And how can you scale it? P.S. Let me know if there's enough interest in learning the "how to" of planning, organizing and executing a "Live" event content strategy in 2025, and we'll throw together a workshop or bootcamp event on it in January.