The Confidence Gap: Why Many Producers Struggle with Cross-Selling (and How to Fix It)

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Cross-selling should be a natural part of a producer’s job. After all, they already know the client, understand the risks, and have a foundation of trust. Yet many producers hesitate the moment the opportunity arises. They pause. They second-guess themselves. They decide to “bring it up next time,” and next time never arrives.

It’s not because producers don’t care or don’t recognise the value. It’s usually a confidence issue—one that creeps quietly into day-to-day conversations and leaves revenue sitting untouched.

Understanding why producers hold back is the first step toward helping them move forward with more certainty and less pressure.

Cross-Selling Isn’t About Pushing More—It’s About Understanding More

Many producers think cross-selling carries a negative connotation. They imagine clients rolling their eyes or feeling pressured. They worry they’ll come across as salesy or opportunistic. And so, they avoid it entirely.

But cross-selling done well isn’t about pushing—it’s about anticipating.

Sometimes clients genuinely need additional protection. Sometimes they’re exposed to risks they don’t know exist. Sometimes they would appreciate a recommendation but don’t know what to ask for.

The hesitation often comes from producers overthinking the exchange. Cross-selling isn’t a pitch; it’s a continuation of the advisory role they already hold.

When producers reframe it that way, the conversation feels more natural, more helpful, and less like an upsell.

Producers Often Lack Clear Visibility Into Client Gaps

One of the biggest contributors to the confidence gap is uncertainty. Producers don’t always remember exactly which policies a client already has, which ones they declined, what was discussed last year, or what risk areas were flagged previously.

This isn’t a lack of discipline—it’s the reality of managing dozens or hundreds of relationships at once.

Cross-selling becomes easier when producers can clearly see coverage gaps, upcoming renewals, and missed opportunities. That’s where tools like an insurance broker crm help create clarity, not by automating conversations, but by giving producers the information needed to have the right conversations.

Confidence increases when producers don’t have to dig through emails or rely on memory.

Fear of Rejection Makes Cross-Selling Feel Riskier Than It Is

People sometimes forget that producers are human. They like positive feedback, smooth conversations, and clients who appreciate them. Introducing another product means risking a moment of rejection—or even worse, feeling like they’ve made the conversation awkward.

Most producers genuinely want to protect their relationships. To them, even a small “No thanks, I’m not interested” can feel like misstepping on a boundary.

But what they often don’t realise is that clients rarely view cross-selling as pushy when framed properly. In fact, most appreciate the guidance. Producers just need support in approaching the topic in a way that feels respectful, comfortable, and consultative.

Training Often Focuses on Product Knowledge, Not Conversation Skills

Producers spend a lot of time learning policies, coverages, carrier differences, exclusions, and risk categories. What they don’t always get is real-world practice in approaching cross-selling without feeling awkward.

Many agencies treat cross-selling like a task rather than a skill.

Yet conversation skills—timing, phrasing, curiosity, tone—are what actually make cross-selling land well. Producers benefit from coaching that teaches them:

 • How to introduce new coverage naturally
• How to read client openness
• How to avoid overwhelming them
• How to position the offer as value, not cost
• How to pivot gracefully if the client declines

A single coaching session can unlock confidence that product knowledge alone never produced.

Producers Get Stuck Thinking Every Cross-Sell Has to Be Perfectly Timed

Another trap producers fall into is waiting for the “ideal moment.” They assume they need the perfect segue, the perfect opening, or the perfect client mood.

But perfect never arrives.

The best cross-selling moments usually come from simple check-ins:

 • “Has anything changed in your business this year?”
• “How has your team grown since we last talked?”
• “Are there any assets or contracts you added recently?”

These questions naturally reveal new exposures. And when producers approach conversations through curiosity rather than sales intent, clients respond openly.

Clients Don’t Know What They Don’t Know—And They Need Producers to Speak Up

A surprising number of clients assume they’re fully protected when they’re not. They think existing coverage automatically extends to new purchases, new employees, new partnerships, or new risks.

And because they rarely read policy details closely, they rely heavily on their agent to help them stay protected.

This means producers aren’t “selling more”—they’re closing knowledge gaps. They’re preventing surprises down the road. They’re doing exactly what clients expect them to do: anticipate needs.

The confidence gap shrinks when producers realise silence is more harmful than speaking up.

Internal Culture Plays a Bigger Role Than Most People Expect

Agencies often unknowingly send mixed signals about cross-selling. Some push hard for results without offering the training or support producers need. Others avoid discussing cross-selling altogether because they fear being seen as too sales-driven.

Producers pick up on this. If cross-selling feels like an obligation rather than a natural extension of service, they avoid it.

When agencies normalise conversations about uncovering client needs—rather than “selling more products”—the atmosphere shifts. Cross-selling becomes part of the agency’s identity, not an occasional task.

The Fix Starts With Confidence, Not Pressure

Most producers don’t need motivational speeches. They need structure. They need clarity. And they need tools that support—not replace—their expertise.

Fixing the confidence gap means giving producers:

 • Simple language for introducing new products
• Clear visibility into client needs and gaps
• Training that focuses on conversations, not memorisation
• Encouragement instead of pressure
• A supportive environment that celebrates consultative selling

When producers feel confident, clients can feel it too. The conversations flow more naturally. The recommendations land softer. The trust deepens.

Cross-selling stops feeling like an obligation and starts becoming a natural part of the producer-client relationship.

Because at its core, cross-selling isn’t about squeezing more revenue out of a relationship—it’s about protecting clients more fully. And when producers have the confidence, clarity, and tools to do that well, everyone wins.