Independent insurance agents often seek ways to increase sales with their existing clients. The straightforward answer, though sometimes uncomfortable, is simple: just ask! It may sound easier than it actually is in practice, but it’s just a matter of adding to your skill set and practicing daily.
We Encounter Upselling Frequently
In our daily lives, we constantly encounter businesses that ask for additional business. Consider what happens when you go to a sit-down restaurant. You may be planning to simply order dinner, but the waitstaff begins by asking if you’d like a beverage or an appetizer.
While you may almost always decline, occasionally, the suggestion sparks interest and sounds particularly appealing. The upsell doesn’t usually stop there; when you’ve finished your meal, you’re almost always asked if you’d like to look at a dessert menu. Flourless chocolate cake? Crème brûlée? Depending on the day and restaurant, and perhaps the friendliness of the person asking, you decide to go for it.
The same thing happens when women go to salons for a haircut. “Do you need any product?” they ask after the service. They’ll also tell you about new services they offer, and ask if you’d like to schedule highlights or some version of a new look. Do you feel exploited when asked? Probably not. You’re glad they asked because they may have presented something you didn’t know you wanted or needed.
These simple interactions just outlined offer two crucial lessons applicable to insurance professionals:
- Asking can directly lead to additional purchases
- Being asked doesn’t make clients feel exploited or inclined to take their business elsewhere.
Given how pervasive and effective this sales approach is, it’s worth considering why insurance professionals might be hesitant to adopt this straightforward method of upselling.
Why Insurance Agents Don’t Upsell
Independent insurance agents often hesitate to upsell additional insurance products for a variety of psychological, practical, and relational reasons. Here are some of the most common:
1 – Fear of Seeming Pushy or Salesy
Many agents pride themselves on being trusted advisors, not aggressive salespeople. However, there’s a distinct difference between presenting products with an intense, high-pressure tone suggesting immediate disaster without them, and simply proposing them as potential solutions to cover other financial risks.
It’s not the act of asking itself that alienates clients, but rather the intensity behind the sales approach.
2 – Concern About Cost Sensitivity
Agents often assume clients can’t afford more coverage or will reject additional premiums, especially in tough economic times. This may come from past experiences of rate shopping or losing business over small price differences.
3 – Lack of Confidence or Product Knowledge
If the agent doesn’t fully understand the product’s benefits or how to communicate its value, they may avoid bringing it up. This can especially apply to more specialized coverages (e.g., umbrella policies, E&S market options, cyber liability).
4 – Time Constraints and Workflow Pressures
Many agents are busy servicing existing clients, chasing leads, or managing renewals. Upselling requires extra time and attention. If the agency lacks a structured process for cross-selling, these opportunities may get overlooked.
5 – No Incentive or Weak Compensation Structure
In some agencies, compensation for cross-selling is low or non-existent, reducing motivation to push extra products. If commissions are delayed or unclear, agents may focus on quick wins instead.
6 – Lack of Marketing Materials or Support
Without good scripts, brochures, or email templates, it’s harder to bring up additional products in a natural, value-driven way. Agents may not know how to frame the conversation as risk management instead of a sales pitch.
7 – Belief the Client “Already Has It” or “Doesn’t Need It”
Agents sometimes assume existing clients have other policies elsewhere or won’t want to consolidate coverage. Without asking or reviewing the full risk profile, they might miss clear opportunities to fill coverage gaps.
How to Overcome These Hesitations
Consider these 5 ways to overcome upselling hesitations:
- Reframe “upselling” as protecting the client more thoroughly (risk mitigation, not extra sales).
- Train agents with client-friendly scripts and objection-handling strategies.
- Use account reviews as natural touchpoints to recommend added coverage.
- Automate follow-ups and use CRM tools to suggest products based on life changes or industry.
- Incentivize cross-selling through bonuses, gamification, or commissions.
Then you’re looking at upselling as helpful, easy, and even fun.
A Classic Book to Consider Reading
Frank Bettger’s book, How I Raised Myself from Failure to Success in Selling, is a classic sales book that combines personal anecdotes with practical strategies. Bettger shares his personal transformation from a struggling insurance salesman to a top performer. Here are the book’s key principles:
1 – Cultivate Enthusiasm
Bettger discovered that acting enthusiastic could lead to genuine enthusiasm, which, in turn, positively influenced his sales performance. He believed that enthusiasm is contagious and can overcome fear and hesitation. By consciously practicing it, he significantly increased his income and success rate.
2 – Understand and Address Customer Needs
Rather than focusing solely on the product, Bettger emphasized the importance of understanding what the customer truly wants. By asking open-ended questions and actively listening, salespeople can tailor their approach to meet each client’s needs and desires.
3 – Build Confidence Through Knowledge
Confidence in sales comes from a thorough knowledge of the product and the industry. Bettger advocates for continuous learning and self-improvement to build credibility and trust with clients.
4 – Develop Strong Relationships
Building genuine relationships with clients is crucial. Bettger suggested remembering names, showing sincere interest, and maintaining regular follow-ups to foster trust and loyalty.
5 – Practice Persistence and Resilience
Rejection is a natural part of sales. Bettger encouraged salespeople to view setbacks as learning opportunities and to pursue their goals despite challenges.
6. Organize and Plan Effectively
Time management and organization are key to sales success. Bettger recommended setting clear goals, planning daily activities, and keeping detailed records to stay focused and efficient.
7. Embrace Continuous Learning
Staying updated with industry trends and continuously refining sales techniques are essential for long-term success. Bettger believed that a commitment to learning keeps salespeople adaptable and competitive.
This book remains a valuable resource for insurance professionals and is as practical and applicable today as it was in 1940.
Final Thoughts
Upselling doesn’t have to feel uncomfortable, manipulative, or forced. At its core, it’s about offering solutions your clients may genuinely need but haven’t yet considered. Like a server who suggests dessert or a stylist recommending highlights, your role is simply to offer what’s available—clearly, confidently, and kindly. When you do this consistently, you’re not just increasing revenue; you’re increasing client satisfaction, retention, and protection. The more you practice, the more natural it becomes—and the more your clients (and your bottom line) will thank you.