Four out of ten. That’s how confident Sarah said she was that her business could stand up to a cyberattack. Sarah owns a 15-person firm in the UK, and she doesn’t exist. Luan Wise built her in Claude, live, on Episode 7 of The AI Social Playbook, and interviewed her for about ten minutes while I watched.
The four didn’t surprise me. What came a few minutes later did. Luan asked Sarah how likely she was now to raise cybersecurity with her IT provider. Quite likely, Sarah said – next time they spoke, not as a fire drill. Then she admitted she was nervous about that conversation, because she didn’t want the provider to think they’d done anything wrong.
Nobody in that exchange mentioned price, features, or a competitor. The thing slowing Sarah down was a relationship she didn’t want to make awkward.
The campaign that answers the wrong objection
If you market anything that replaces something – a new provider, a platform migration, a service the buyer assumes their current vendor already covers – you’ve probably built this campaign. You write the comparison chart. You build the ROI calculator. You offer a demo in every email. And the pipeline stays quieter than the traffic says it should.
I’ve worked with plenty of owners of businesses Sarah’s size. They’re focused on the day-to-day, and risk isn’t top of mind until something happens or they see it in the news. What I hadn’t put into words before this episode is what sits on top of that. For Sarah, even asking her current provider a direct question feels like an accusation. So she doesn’t ask. And a buyer who won’t ask her incumbent the question will never reach your comparison chart.
You won’t find that objection in a survey, because you’d have to know to ask about it. A buyer on a discovery call probably won’t volunteer it either, because it’s a slightly embarrassing thing to say to a stranger who’s selling to you. Luan’s role-play surfaced it in about nine minutes.
How Luan got the persona to say it
Luan never asked Sarah, “What’s your objection?” The relationship came up because of the order of her questions, and you can run that same order on your own buyer this afternoon.
- Build the persona from research you already have. Luan was explicit that she wasn’t asking Claude to invent a buyer. She brought a briefing: the size and type of business, the owner’s role, the fact that she’s responsible for security without being an expert in it, the Finance Director who’ll want a say, and what existing customers had already told her team. Her seed prompt ended with the three rules that matter most: I want to interview Sarah. Stay in character and answer from her perspective.
- Ask broad, and listen for the assumption. Her first question was deliberately wide: tell me about your business and your biggest priorities. Sarah talked about keeping the team busy and billing. Cybersecurity was on the list, not at the top. Then came the line that mattered: her IT provider handles laptops and email, and she thinks they do something around security, “but I couldn’t tell you with confidence.”That’s an assumption about an incumbent. When you hear one, stop and write it down.
- Push on the assumption, not on your product. Luan’s follow-up wasn’t about cybersecurity services. It was about the relationship: you’ve said you use an IT provider; have you asked them? Sarah said she’d only ever raised it as a side comment. Then Luan asked for a confidence score from one to ten, and got the four.
- Ask about an action that involves the incumbent. This is the step I’d tell you not to skip. Luan asked Sarah how likely she was to take a specific next step, and that step meant talking to her current provider. That’s the moment the nervousness came out, along with the line Luan flagged for every marketer watching: “I’ve realized I’ve been asking the wrong question all along.” Ask a persona about features, and you’ll get feature objections. Ask what it would have to do next, and who it would have to face, and you get the real ones.
- Switch seats and turn it into a brief. In the same chat, Luan told Claude to become the marketing lead for the cybersecurity provider and say what the conversation meant for their marketing. The answer was specific: Sarah won’t act today; she’ll act on her next call. She wants to prepare first, so she needs guides, comparison content, and “what good looks like” material, not book-a-demo offers. The tone has to be gentle, because she doesn’t want to feel accused. And the jargon has to go.That’s a different campaign from the one most of us would have written. If I were running it, I’d start with a plain-language list of questions to ask your current provider. It gives Sarah the words she said she didn’t have, and it gives her a reason to remember who handed them to her.The full seed prompt, the switch prompts, and a persona briefing template are in the Blueprint on the Episode 7 page, along with Luan’s full screen share.
Where this breaks
Sarah is a simulation. Her answers come from your briefing and from everything the model has read about people in her seat, which, as I mentioned during the episode, includes a lot of Reddit. That makes her useful, and it also makes her an easy person to believe too much. Luan put it plainly on the show: “We can’t take at face value what an AI tool is giving us.”
Three things to watch. First, the persona wants to please you, so Luan keeps asking Claude how confident it is in an answer, as a percentage, and keeps asking why until the number means something. Second, the wording changes between runs. Luan rehearsed the scenario a couple of days before we recorded, and the words were different both times while the overall picture held. Trust the pattern and treat any single quote with suspicion. Third, Claude drifts. In our run, the marketing lead’s debrief brought up the Finance Director from Luan’s original brief, when the interview never got there. Useful, but it wasn’t something Sarah had said.
And one thing we didn’t get to: we never put a real headline in front of Sarah during the session. That’s the obvious next step, and it’s the first thing I’d run after the interview. The prompt for it is in the Blueprint, marked as not run on air.
The whole exercise runs on the free version of Claude. It still takes time, because you have to think about who’s in the decision and what you already know about them. As Luan said, “It just means that you can do it from your desk.”
The objection behind the objection
Every B2B purchase that replaces something asks the buyer to admit something: that the current provider fell short, or that an earlier decision – maybe their own – needs revisiting. Marketing that ignores that asks the buyer to take a social risk and calls it a conversion step.
The persona role-play is one way to see that risk before you spend a budget guessing around it. The tool will change. Next year it may be a different model, or an agent sitting in your CRM. The question that surfaced Sarah’s objection won’t change: what would this person have to do next, and who would they have to face to do it?
Ask your persona that question this week. Then take whatever it says to a real customer on your next call, and ask them the same thing.
