How to Handle "We've Tried This Before and It Didn't Work" in Software as a Service Sales
Expert framework for overcoming the "We've Tried This Before and It Didn't Work" objection in SaaS sales. Proven 3-step method with industry-specific examples.
ScriptFly AI Team
Expert Sales Trainers
How to Handle "We've Tried This Before and It Didn't Work" in Software as a Service Sales
Every SaaS sales rep knows that sinking feeling when a prospect throws down the "we've already tried something like this" card. It's the conversation killer that can derail even the most promising sales opportunity, turning potential game-changing solutions into forgotten pitches.
Why SaaS Prospects Say "We've Tried This Before and It Didn't Work"
In the world of enterprise software, past failures aren't just memories—they're battle scars. Each unsuccessful implementation represents lost time, wasted budget, and damaged credibility for decision-makers. When a prospect says they've "tried this before," they're really revealing deep-seated frustration and protective instincts.
The Real Reasons Behind This Objection:
- Fear of repeating previous technological disappointments
- Budget constraints from prior unsuccessful investments
- Organizational trauma from complex implementation failures
- Skepticism about promised ROI and actual delivered value
- Desire to appear experienced and discerning
The Wrong Way to Respond (That Most Reps Do)
Most sales reps panic and immediately go into defensive mode, which only reinforces the prospect's skepticism. They desperately try to prove their solution is different without understanding the underlying concerns.
Don't:
- ❌ Argue or dismiss their previous experience
- ❌ Immediately launch into a product feature dump
- ❌ Sound desperate to prove yourself right
- ❌ Ignore the emotional context of their past failure
The 3-Step Framework That Actually Works
Step 1: Acknowledge Without Agreeing
Validation is your first weapon. You're not saying they're right—you're showing you understand their perspective.Example Response:
"I completely understand. Sounds like you've been through a challenging implementation that didn't deliver what was promised. Most of our clients felt exactly the same way before working with us."
Step 2: Reframe the Conversation
Transform their past failure from a roadblock into a learning opportunity.Example Response:
"What specifically didn't work in your previous solution? Those exact pain points might be precisely why our approach is fundamentally different."
Step 3: Ask a Diagnostic Question
Questions shift control and reveal deeper insights.Power Questions to Ask:
- "What would have made that previous implementation successful?"
- "If you could redesign that past solution, what would you change?"
- "What specific outcomes were you hoping to achieve that didn't materialize?"
Real-World Example: CloudFlow Analytics
When CloudFlow Analytics was selling their enterprise project management platform to a mid-sized tech company, they encountered a classic objection. The prospect, a seasoned IT director, had been burned by two previous software implementations.
What Happened: The CloudFlow rep used the 3-step framework. By deeply understanding the previous failures and reframing them as valuable insights, they transformed a potential "no" into a $180,000 annual contract.
Key Takeaway: Empathy and strategic questioning beat feature lists every single time.
Industry-Specific Considerations for Software as a Service
SaaS sales have unique dynamics that amplify the "we've tried this before" objection. Technical evaluations, security concerns, and complex integration requirements make prospects more cautious.
- Implementation Complexity: Each failed project increases skepticism exponentially
- Average Deal Size ($25,000): Higher stakes mean more rigorous due diligence
- Typical Objection Triggers: Previous vendor promises, complex onboarding, unclear ROI metrics
5 Variations You Can Use Tomorrow
Variation 1: The Empathy Reframe "I hear you. Sounds like your last implementation was more frustrating than helpful. Let's explore how we're different."
Variation 2: The Social Proof Angle "Companies in your exact industry have seen 200% faster implementation with our approach. Want to hear how?"
Variation 3: The Risk Reversal "We're so confident in our solution that we'll provide a full implementation guarantee. Zero risk to you."
Variation 4: The Future-Pace "Imagine if your next software rollout actually exceeded expectations. What would that mean for your team?"
Variation 5: The Direct Challenge "Most teams stick with familiar failure. Are you ready to try a genuinely different approach?"
Common Follow-Up Objections (And How to Handle Them)
"We're not ready to try again" → Validate their caution while gently challenging their current status quo.
"Your solution looks too similar" → Immediately highlight 2-3 unique differentiators with concrete examples.
"We can't afford another mistake" → Offer a low-risk pilot or phased implementation strategy.
The Bottom Line
Handling the "we've tried this before" objection isn't about winning an argument—it's about understanding, empathizing, and strategically repositioning your solution. Master this, and you'll transform objections into opportunities.
Quick Win: Record your next sales call and analyze your objection handling. Self-awareness is your fastest path to improvement.
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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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