How to Handle "We've Tried This Before and It Didn't Work" in Insurance & Risk Management Sales
Expert framework for overcoming the "We've Tried This Before and It Didn't Work" objection in Insurance & Risk Management. Proven scripts and industry-specific techniques.
ScriptFly AI Team
Expert Sales Trainers
Overcoming the "We've Tried This Before and It Didn't Work" Objection in Insurance Sales
Every insurance and risk management sales professional knows this moment: You're mid-pitch, presenting your cutting-edge solution, when the prospect drops the conversation-stopping line: "We've tried something like this before, and it didn't work."
This isn't just an objection. It's a psychological barrier built on past disappointment.
Why This Objection is Unique in Insurance Sales
In the world of risk management and insurance technology, past failures carry extra weight. Unlike other industries, insurance solutions directly impact:
- Financial protection
- Regulatory compliance
- Claims processing efficiency
- Actuarial risk assessment
A previous unsuccessful implementation doesn't just represent a budget loss—it represents potential operational disruption and compliance risks.
The 3-Step Framework for Crushing This Objection
Step 1: Acknowledge the Experience
Your first move is genuine empathy. Never dismiss their previous experience.Example responses:
- "I appreciate you sharing that. Past disappointments are frustrating, especially in our complex industry."
- "It sounds like you've invested time and resources into a solution that didn't deliver as promised."
Step 2: Reframe the Narrative
Transform their past failure from a roadblock into a learning opportunity.Key Reframing Techniques:
- Highlight how their previous experience makes them more sophisticated buyers
- Position their past attempt as valuable market research
- Demonstrate how your solution addresses specific gaps they encountered
Step 3: Ask Diagnostic Questions
Use strategic questions to uncover the root of their previous implementation's failure.Powerful Diagnostic Questions:
- "What specific aspects of the previous solution fell short?"
- "Can you walk me through the key performance indicators that weren't met?"
- "How did that implementation process differ from what you initially expected?"
5 Precise Response Scripts for Past Failure Objections
Script 1: The Empathetic Technical Expert
"I completely understand. At InsureEdge Solutions, we've actually designed our platform by studying dozens of failed implementation cases in risk management. Our current architecture addresses the exact pain points that typically derail insurance technology projects."Script 2: The Comparative Analysis
"Many of our clients, like [Fictional Insurance Client], initially approached us after disappointing experiences. By focusing on granular actuarial data integration and seamless claims workflow automation, we've transformed their perspective on insurance management platforms."Script 3: The Learning Opportunity Framing
"Your previous experience isn't a failure—it's market intelligence. Each unsuccessful implementation provides crucial insights. Our solution is engineered specifically to overcome the challenges you've already identified."Script 4: The Compliance-Focused Approach
"In regulated industries like insurance, technology implementations require precision. We don't just offer a software solution—we provide a comprehensive compliance and risk mitigation strategy tailored to your specific operational ecosystem."Script 5: The Transparent Challenge
"I'm glad you've been transparent about past challenges. Would you be open to a diagnostic assessment where we can pinpoint exactly what went wrong and demonstrate how our approach fundamentally differs?"Critical Success Factors in Overcoming Implementation Objections
Technical Credibility
- Showcase specific technological improvements
- Provide concrete case studies
- Demonstrate deep understanding of insurance technology landscapes
Risk Mitigation Evidence
- Highlight robust implementation methodologies
- Offer phased rollout strategies
- Provide comprehensive support and training frameworks
Measurable Outcome Guarantees
- Present clear, quantifiable performance metrics
- Offer pilot program options
- Create low-risk evaluation pathways
The Psychology of Overcoming Past Failure Objections
Remember: This objection is rarely about your specific solution. It's about:
- Organizational trust
- Fear of repeated investment failures
- Protecting professional reputation
Your job is to transform their skepticism into curiosity and potential partnership.
Closing Thoughts: Turning Objections into Opportunities
Past failures in insurance technology implementations aren't dead ends—they're refined roadmaps to success.
By approaching objections with empathy, technical expertise, and strategic questioning, you position yourself not just as a vendor, but as a trusted risk management partner.
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Common Questions About This Objection
When is the best time to use this objection response?
Use this response immediately when you hear the objection. The key is to acknowledge their concern authentically before reframing it. Timing matters—respond too quickly and you seem dismissive, wait too long and you lose momentum.
What if this script doesn't work for my specific situation?
Every prospect is different. Use these scripts as frameworks, not word-for-word responses. Adapt the language to match your industry, product, and the prospect's communication style. The underlying psychology remains the same.
How do I practice these responses effectively?
Role-play with a colleague or record yourself. Focus on tone and delivery—confidence matters as much as the words. Practice until it feels natural, not scripted. The goal is to internalize the framework, not memorize lines.
Can I combine this with other objection handling techniques?
Absolutely. These responses work well with techniques like the "Feel, Felt, Found" method or the "Boomerang" technique. Layer multiple approaches for complex objections, but keep it conversational—never sound like you're running through a checklist.
How many times should I try before moving on?
If you've addressed the same objection 2-3 times using different angles and they're still not budging, it's likely not a real objection—it's a polite way of saying no. Know when to pivot or disqualify the prospect to focus on better opportunities.
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