I watched a rep lose a $500K deal because our battlecard missed the most important competitive technique: the landmine.
The deal was ours to lose. We had the better product, stronger ROI, and the champion loved us. But the competitor—a legacy player we typically beat—planted a single question in the CTO's mind during their final presentation: "Have you asked them about their data residency options for EU customers?"
We had EU data residency. It was in our docs. But our battlecard focused on feature comparisons and objection handling. It never taught reps to preemptively address technical requirements that competitors weaponize in late-stage deals.
The CTO asked us about EU data residency. Our rep, caught off guard, said "let me check with engineering." That two-day delay created just enough doubt. The competitor positioned it as a "concerning gap in their enterprise readiness." We lost the deal.
The competitor didn't win because they had better EU data residency. They won because they planted a landmine—a question designed to create doubt, trigger delays, and expose perceived weaknesses, even when those weaknesses don't exist.
Most battlecards are defensive weapons. They teach reps how to respond when competitors attack. But the most sophisticated competitive selling isn't about defense—it's about psychological warfare. It's about planting traps that make competitors disqualify themselves while making your product look inevitable.
I spent three years studying deals we lost to "inferior" competitors. The pattern was clear: we lost because competitors understood something we didn't. Competitive deals aren't won by having better answers. They're won by asking better questions.
The Difference Between Objection Handling and Psychological Traps
Traditional battlecards teach objection handling: "When the competitor says X, you say Y."
Competitor says: "We have more integrations."
You say: "Yes, but our integrations are deeper and actually certified by the vendors."
This works in straightforward competitive scenarios. But it's reactive. You're responding to their narrative, which means they control the conversation.
Advanced competitive selling flips this dynamic. Instead of responding to competitor claims, you plant questions that force competitors to respond to doubts you've created.
Here's the same scenario with a psychological trap:
You say (early in the process): "When you evaluate integration vendors, make sure you ask whether their integrations are certified by the actual software vendors or just built using public APIs. We learned the hard way that uncertified integrations break constantly when vendors update their systems."
Now when the competitor shows up and touts their "200+ integrations," the prospect is primed to ask: "Are these vendor-certified or just API connections?"
Most competitors can't say "vendor-certified" because certification is expensive and time-consuming. The competitor suddenly has to defend their integration strategy instead of attacking yours.
Same integration weakness. But instead of defending your smaller integration count, you've made them defend their larger one. That's a psychological trap.
The Anatomy of a Competitive Landmine
The best competitive landmines share four characteristics. Miss any of these and you're just asking random questions that create noise instead of strategic doubt.
First, they target real buying criteria that matter late in deals. Security, compliance, implementation timelines, support SLAs, data ownership—these are decision factors that surface in final evaluations. Planting early questions about these criteria creates filters that eliminate competitors before finals.
I watched a rep use this perfectly in an enterprise healthcare deal. During discovery, she asked: "What's your process for vendor security reviews? We typically go through SOC2, HIPAA, and penetration test validations. How long does your security team usually take to approve new vendors?"
The prospect said 4-6 weeks. The rep nodded and said: "That aligns with what we see. Make sure when you're evaluating vendors, you ask for their current SOC2 report and HIPAA attestation upfront. We've seen deals get killed at the end when security finds out a vendor doesn't have proper compliance documentation."
That single conversation planted a landmine. When two competitors showed up without current SOC2 reports, they were eliminated before technical evaluations. The rep didn't have to compete against them—she made the prospect's security team do it for her.
Second, they expose truths competitors can't fake. The landmine has to be something verifiable that your competitor genuinely struggles with. You can't bluff.
Bad landmine: "Ask them how many customers they have in your industry." (They'll just inflate the number)
Good landmine: "Ask them for three customer references in your industry who are using the specific features you need, and ask those references how long implementation took." (Much harder to fake)
The reference request forces competitors to either produce real customers (who might give honest feedback about problems) or admit they don't have relevant case studies. Either outcome helps you.
Third, they're planted early, not during competitive combat. Landmines work because they set evaluation criteria before competitors arrive. If you wait until you're head-to-head with a competitor to plant these questions, it looks like you're playing games. Plant them during discovery and needs analysis, and they look like you're being consultative.
I coached a rep who was competing against a well-funded startup with aggressive pricing. Instead of fighting on price during the competitive phase, he planted cost questions during discovery:
"Walk me through your budget approval process. Is this a one-time purchase or does it need to fit into a recurring budget line? The reason I ask is that some of our customers have gotten burned by vendors who offer low year-one pricing but have aggressive price increases in year two. Your CFO might want to see a three-year cost projection, not just year-one pricing."
When the competitor showed up with a lowball year-one price and 40% annual increases, the CFO rejected it without our rep having to say a word. The landmine was planted weeks before the competitor ever entered the deal.
Fourth, they align with your natural strengths. Don't plant landmines around criteria where you're weak. That's just creating problems for yourself. Plant them where you're strong and competitors are structurally weak.
We had phenomenal customer support—live chat, 99.5% uptime, 2-hour response SLAs. Our main competitor outsourced support to a third-party firm with 24-hour response times.
Our trap question: "What are your requirements for customer support? How quickly do you need responses when something breaks? Some of our customers require support SLAs in writing because they've been burned by vendors who promise great support but can't commit to actual response times."
Suddenly support SLAs became a documented requirement. Our competitor couldn't commit to our response times, so they either had to admit their support was slower (bad) or overpromise and risk breaching the contract (worse).
We turned our strength into an evaluation criterion that automatically disqualified competitors.
The Three Types of Landmines That Win Enterprise Deals
Not all landmines work in all deals. I've categorized them into three types based on what they exploit: structural weaknesses, messaging contradictions, and silent killers.
Structural Weakness Landmines
These expose gaps that competitors can't fix quickly—organizational limitations, technical architecture decisions, or business model constraints.
Example: I worked with a company competing against a platform that required customers to use the vendor's proprietary database. We used standard PostgreSQL, which meant customers could use their existing database infrastructure.
The landmine: "How important is it that you maintain control of your data architecture? Some platforms require you to use their proprietary database, which can create vendor lock-in and data migration challenges if you ever want to switch. Do you have policies about database portability?"
Most enterprises have strong opinions about database control once you ask. The competitor couldn't suddenly switch to supporting PostgreSQL—their entire architecture was built on their proprietary system. We made their technical decision into a disqualifying weakness.
Messaging Contradiction Landmines
These exploit gaps between what competitors say in marketing and what they actually deliver. Competitors often make broad claims that sound great but fall apart under scrutiny.
One competitor positioned heavily on "AI-powered automation." Their marketing was full of machine learning and intelligent workflow buzzwords.
The landmine: "When you evaluate AI features, make sure you ask vendors to show you what the AI actually automates versus what still requires manual configuration. We've seen a lot of 'AI-powered' tools that are really just rule-based automation with AI branding."
During the demo, the prospect asked the competitor to show their AI in action. The competitor's demo showed a rules engine that required manual configuration. The prospect said: "This looks like if-then rules, not AI. Can you show me the machine learning component?"
The competitor fumbled. Their "AI-powered" messaging collapsed under basic scrutiny. We didn't have to attack their AI claims—we just made the prospect curious enough to ask questions the competitor couldn't answer well.
Silent Killer Landmines
These target requirements that prospects don't think about until you mention them—and then they become mandatory evaluation criteria.
Security and compliance are obvious examples, but the best silent killers are operational factors that don't surface until after purchase.
Example: "Have you thought about how you'll handle user offboarding when employees leave? We've seen companies get into trouble when they can't quickly revoke access for terminated employees. Make sure any platform you evaluate has automated deprovisioning and audit logs for compliance."
Most competitors have basic user management, but automated deprovisioning with audit trails is often an afterthought. Once the security team hears about this requirement, it becomes mandatory. Competitors who built basic user management suddenly have to explain why they don't have enterprise-grade offboarding workflows.
We made an overlooked feature into a deal requirement that eliminated three competitors who couldn't demonstrate it.
When Landmines Backfire (And How to Avoid It)
I've seen reps get too aggressive with competitive landmines and blow up deals. The line between strategic questioning and manipulative games is thin.
A rep once planted a landmine about implementation timelines: "Make sure you ask vendors for documented proof of their average implementation time with customers your size. Some vendors claim quick implementations but their actual average is 6-9 months."
The problem: our average implementation time was actually 4-5 months, but we had one customer who went live in 6 weeks, and the rep was using that outlier as our "proof."
The competitor asked to see our implementation data. When we showed one case study instead of aggregate data, we looked like we were playing the same game we'd accused them of. The prospect lost trust in both vendors.
The lesson: landmines only work when you can deliver on the criteria you're creating. If you're planting questions you can't answer yourself, you're not setting traps—you're setting yourself up to fail.
Rules for avoiding backfire:
Only plant landmines where you have clean proof. If you're questioning competitor security practices, you better have SOC2, penetration test results, and compliance certifications ready to share.
Plant early and subtly. If you wait until you're head-to-head with a competitor, landmine questions look like competitive attacks. Plant them during discovery when you're still building trust, and frame them as helpful buying criteria, not weapons.
Let the prospect discover the gap. Don't say "Competitor X doesn't have this feature." Say "Make sure you ask all vendors about this capability" and let the prospect discover who has it and who doesn't.
Be prepared for the landmine to hit you. Sometimes prospects apply your criteria more strictly than you expected. Have proof ready that you meet the standards you're setting.
The Competitive Trap I Use in Every Enterprise Deal
There's one landmine I plant in nearly every complex B2B deal because it exploits a weakness that almost all competitors have: the gap between promised functionality and actual customer usage.
The setup is simple. During discovery, I ask: "When you evaluate solutions, would it be helpful to talk to customers who are using the specific features you care about, not just general reference calls?"
Every prospect says yes. This sounds like helpful, consultative selling.
Then I deliver: "I'll set up calls with three customers who are actively using [specific feature you need]. I'll ask them to show you how they've implemented it and share what results they're seeing. Would it be useful if they walked through their actual dashboards and workflows, not just talked about it?"
This creates a new evaluation standard: show, don't tell. Prospects now expect to see real customer implementations, not just hear testimonials.
Most competitors can't deliver this. They'll provide reference calls where customers say nice things, but they can't show real implementations because:
- The features are too new and no customers are live yet
- Customers are using basic features, not advanced ones
- Implementations are messy and not "demo-ready"
- They don't have customers in the prospect's industry using the specific capabilities
I've won deals where our product was more expensive and had fewer features, simply because we could show three customers using our platform for the prospect's exact use case, and the competitor couldn't.
The beauty of this landmine is that it doesn't feel like a competitive attack. It feels like exceptional customer service. But it creates an evaluation bar that eliminates competitors who rely on demos and marketing instead of proven customer outcomes.
Building Landmines Into Your Battlecard
Traditional battlecards have a "Competitive Positioning" section that says things like "When they say X, you say Y."
Advanced battlecards have a "Strategic Questions" section that lists landmines to plant during discovery, before competitors even show up.
Here's what that section looks like for a competitor who positions on breadth of features:
Strategic Questions to Plant Early:
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"How will you evaluate whether vendors' features are actually production-ready versus beta functionality that's not fully supported yet? We've seen buyers get excited about feature lists only to discover half the features aren't ready for their use case."
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"Do you need to see customer proof-of-concepts for the specific features you're evaluating, or are you comfortable with roadmap commitments?"
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"What's your process for validating that features actually deliver the ROI vendors claim? Some of our customers ask for documented case studies with metrics, not just testimonials."
Each question is designed to expose a weakness in the "more features" positioning:
- Many features are beta/not production-ready
- Features exist but no customers are using them
- Features are built but don't deliver measurable value
Your rep plants these questions during discovery. Two weeks later when the competitor shows up with their feature list, the prospect is primed to ask: "Which of these features are production-ready? Can I talk to customers using them? What ROI have they seen?"
The competitor has to either admit features are vaporware or scramble to find proof they don't have.
You didn't attack the competitor. You helped the prospect develop better evaluation criteria. Criteria that happen to disqualify your competitor's core positioning.
That's advanced competitive selling.
The Uncomfortable Truth About Competitive Landmines
Psychological traps work because most competitors are lazy. They use the same positioning, the same demos, and the same objection responses in every deal.
When you plant landmines that expose structural weaknesses or messaging gaps, you're not being manipulative—you're forcing competitors to defend claims they shouldn't be making.
If a competitor claims "AI-powered" but it's really rules-based automation, asking them to demonstrate the AI isn't a dirty trick. It's basic due diligence.
If a competitor claims fast implementation but their average is 6 months, asking for proof isn't playing games. It's protecting the buyer from overpromises.
The discomfort comes from being proactive about exposing these gaps instead of waiting for competitors to get away with exaggerated claims.
Most PMMs teach reps to be reactive—respond to competitive threats with better answers. I teach reps to be strategic—set evaluation criteria that make weak competitors eliminate themselves.
The deals you win aren't always the ones where you have the best product. They're the ones where you ask the best questions.