Your SOC 2 report doesn't really close deals. Neither does your questionnaire answers. The document that took your team far too many hours (or far too few minutes with an LLM) to assemble gets skimmed in ten minutes and set aside. The actual evaluation is a 45-minute call where an enterprise security team watches you talk — and decides within the first few answers whether you're real.
Calibration, Not Interrogation
Enterprise security teams already know what good answers look like. When they ask how you encrypt data, they're not learning something. They're watching whether you say "AES-256 at rest, TLS 1.3 in transit, all buckets encrypted with customer managed key support on the roadmap" without hesitating, or whether you reach for "industry best practices" like a life raft.
"Industry best practices" is the security equivalent of "I'm a people person" in a job interview. It communicates nothing except that you've heard the question before.
The follow-up lands immediately: "Walk us through the algorithms and your key management approach." Now you're either answering from experience or performing confidence you don't have. Buyers have sat through these calls before. They can tell.
IAM architecture, data isolation, operator and CICD maturity, pen testing methodology, subprocessor inventory, data residency — each question is a depth check. Not "do you have an answer" but "how far down does your answer go before it runs out."
Where Vendors Break
Technical questions establish a floor. Scenario questions find the ceiling.
"A key engineer leaves on bad terms. Walk me through offboarding."
"Critical vulnerability, Saturday night. What happens?"
"Your subprocessor gets breached. When do we hear about it?"
These aren't hypothetical to the person asking. They've been the one making the 2 AM phone call. They've written the board memo. They're listening for whether you've also been there or whether you're theorizing.
One vendor I spoke with handled this by describing my concerns before I asked about them: you're probably concerned how your data is protected from our staff and a cloud breach; here's how we've thought through those events and our controls in place. They weren't reading off a script. No hedging, just operational memory.
The vendors who falter start every answer with "Well, we would..." and never reach a specific noun, date, or number.
The Person on the Call Is the Message
Ninety percent of Fortune 1000 companies have dedicated security leadership. They expect to see their counterpart. Perhaps not a a CISO or VP of Security in title, but someone whose experience matches the conversation.
Smaller companies get a pass on the title. They don't get a pass on the depth. A technical founder who built the architecture and can speak to specific controls, specific tradeoffs, specific decisions — that person outperforms a polished exec reading talking points. Buyers respect ownership over credentials.
If nobody on your team can go deep on a security call, that's not a hiring problem for later. It's a revenue problem now. A fractional CISO who joins customer calls and handles these conversations isn't overhead. It's the difference between a stalled pipeline and a signed contract.
Ways to Lose in Real Time
These can lose the confidence of your prospective buyer's cybersecurity approval.
Lying about where you are. Enterprise security officers cross-reference your claims against your SOC 2, your architecture diagrams, your public docs. Getting caught doesn't lose one deal. It loses every deal that buyer would have referred. Everyone knows if you used an LLM to come up with your answers.
Three vague answers in a row. One gets a pass — nerves happen. Two shifts the note-taking. Three and the evaluation is functionally over.
Treating the review as beneath you. Some vendors radiate impatience, as if the buyer should just trust the product. This tells the buyer exactly how you'll behave during a real incident: dismissive until forced to care.
Deferring everything. "I'll get back to you" works once. If every answer requires a follow-up email, the buyer starts wondering who at your company actually knows how the system works.
What Readiness Looks Like
The vendors who pass aren't flawless. They're prepared in a way that makes preparation invisible.
Documentation arrives before anyone asks. Trust center, architecture diagrams, pen test summaries, scenarios and threat modeling — not as a performance, but as a default. Security isn't a fire drill for these teams. It's just a way of operating.
They're specific without being rigid. Confident without being defensive. And when they hit a gap, they say so: "We don't have that today. Here's the roadmap, here's the priority, here's what we do in the meantime." That answer builds more trust than a clean scorecard, because every buyer on that call has been lied to before. Honesty in a sales process is disorienting — in a good way.
The buyer on the phone isn't necessarily evaluating your product's risk profile. They're evaluating whether recommending you will make them look competent or foolish. Every answer you give on a security call is really answering one question: "Can I stake my reputation on this vendor?"
Make it easy.
