The Insight Lever: How Cherilynn Castleman uses AI to ask better questions without outsourcing trust

AI can research the buyer, identify patterns and rewrite a sales question. But it cannot decide what deserves to be asked, when to remain silent or how to earn another person’s trust.

That boundary is central to how Cherilynn Castleman brings together more than three decades of sales experience and her daily use of AI.

Cherilynn does not treat AI as a replacement salesperson. She uses it to improve what happens before and around a human conversation: the preparation, the context, the quality of the question and the discipline to listen properly to the answer.

That is why I see Insight as the primary Business Lever in her story.

The commercial mechanism is not more AI-generated outreach.

It is better preparation creating the conditions for a better question—and a better question revealing something commercially useful that a conventional sales script might never reach.

The problem with asking questions you could have answered yourself

Relationship-first selling does not mean avoiding the commercial purpose of the conversation. It means refusing to treat another person as a route to a target.

Cherilynn’s starting point is simple: people want to feel seen, heard and understood.

Yet many sales conversations open with questions whose answers were already available on a company website, a LinkedIn profile or a public filing. The salesperson may believe she is gathering information. To the buyer, it can feel like an interrogation—or evidence that the salesperson did not prepare.

AI changes the preparation available to us.

It can bring together information from a LinkedIn profile, company materials and financial documents. It can identify themes and patterns a person may not notice immediately. It can also take a familiar discovery question and help reshape it into something more specific and emotionally meaningful.

But access to more information does not automatically produce a better conversation.

As Cherilynn put it:

“AI masters patterns… What it can’t do is it can’t give you the judgement.”

AI can find the pattern. The seller still has to decide whether using it would be relevant, respectful and useful.

That distinction matters because the goal is not to manufacture intimacy. It is to enter the conversation well prepared enough to ask a question worth answering.

Better questions can change commercial outcomes

Cherilynn described two examples from her coaching practice.

One client in financial services routinely asked prospects to describe the insurance they already had. Cherilynn encouraged her to use AI to turn that conventional information-gathering question into a higher-quality connection question.

The alternative was:

“What is it that scares you about insurance?”

According to Cherilynn, the client’s second-appointment rate moved from 11% to 42% after changing the question.

Another client, a career coach, had been asking women where they wanted to be in three to five years. The revised question was much closer to the current problem:

“When was the last time you cried at work?”

Cherilynn reports that the coach’s conversion moved to almost 90%.

The original questions invited prepared, rational answers. The revised questions invited the prospect to talk about the problem as she was actually experiencing it.

The commercial value did not come from AI having an answer.

It came from AI helping the seller reconsider the question.

This is where Insight can move Revenue downstream. Better insight into the person and the problem improves the conditions for a useful commercial conversation. It does not guarantee a sale, but it can make the conversation more relevant, differentiated and honest.

The four seconds AI cannot use for you

The question is only half of Cherilynn’s method.

After asking it, she advises the salesperson to wait.

Four seconds.

Long enough for the other person to decide whether to continue.

If they do not, she offers three short prompts:

• Tell me more.
• How do you mean?
• And…?

Then she returns to silence.

This is not a minor conversational technique. It exposes the human work that remains after AI has helped with the preparation.

AI can suggest the question. It cannot sit in the discomfort of the pause for you. It cannot notice the shift in someone’s expression, decide whether to continue or recognise when a line of enquiry has become intrusive.

The seller holds that responsibility.

Cherilynn’s test is direct:

“Only humans can build trust. Only humans can care. Only humans can have judgement.”

That is the boundary.

AI can extend what the founder sees. The founder decides what to do with what she has seen.

Fluency is not the same as frequent use

Cherilynn makes another distinction: using AI every day does not automatically make someone AI fluent.

She compares it with practising the piano badly—repeating the same wrong note until the mistake becomes familiar.

A founder can use AI constantly and still send inaccurate emails, accept hallucinated information or reproduce generic work without examining it. Frequency alone does not improve judgement.

Cherilynn recommends deliberate practice: 15 minutes each day, at the time when your mind is sharpest, spent becoming more capable rather than merely producing more.

Her suggested progression is practical:

• move from isolated prompts to reusable briefs;
• move from disconnected chats to defined workflows;
• ask what is missing rather than accepting the first output;
• give each AI tool a clear job;
• review the work before it reaches another person.

Her own briefs are substantial. She described an instructor philosophy brief of approximately 18 pages and a communication brief of approximately 11 pages. The point is not that every founder needs documents of that length. It is that the quality of the output depends on making the relevant standards, context and boundaries visible.

Cherilynn’s analogy is useful: treat AI like an important new employee.

You would not tell a new team member to write to your most important client without explaining the product, the relationship, examples of previous communication, the words the company uses and the things it would never say.

The same standard should apply to AI.

One tool should not be asked to do every job

Cherilynn’s daily stack also reflects this discipline.

She uses Claude as a thinking and strategy partner, including for workflows. She uses ChatGPT as a place to capture and develop half-formed ideas. She uses NotebookLM for proprietary information, course development and frameworks.

The important point is not the particular brand attached to each job. It is that she does not allow the tools to become interchangeable.

Different work carries different context, privacy and judgement requirements. A tool used for casual ideation does not automatically receive access to email, folders or sensitive business information. A system designed for customer records should not be expected to become the company’s strategist.

The founder defines the job and the guardrails first.

This is another form of Insight: understanding enough about the work to decide what the tool may see, what it may do and where its output must stop.

Transparency protects the human relationship

Cherilynn is equally direct about disclosing her use of AI.

On LinkedIn, she may explain that a post was drafted by her, polished by AI and accompanied by AI-generated creative. When she uses an avatar to teach one of her frameworks, she identifies it as her avatar rather than presenting it as a live recording.

Her principle is not that AI involvement weakens the work.

Hidden authorship weakens trust.

In a feed increasingly filled with automated and synthetic material, she argues that honest, original thinking becomes more valuable. Her metaphor is clean water: when the surrounding water is dirty, clean, fresh water matters more.

Transparency helps the audience understand where the idea came from, what AI contributed and where the human remains accountable.

Visibility is not the same as virality

Cherilynn applies the same relationship-first principle to LinkedIn.

She describes LinkedIn as the modern business card: the place where a person should be able to understand who you are, what you stand for and why they might want to meet you.

But she rejects the idea that every post must perform at scale.

Her advice is:

“You want to be visible, not viral.”

Choose three subjects. Keep contributing to the community around them. Respond to the people who engage. Then post again.

The objective is not maximum attention from everyone. It is sustained relevance to the people the founder is equipped to help.

AI can assist with research, briefs, profile development and the polishing of a post. It cannot substitute for a clear point of view or a willingness to participate in the resulting conversation.

The Five Business Levers

The sequence in this story is not fixed, but one commercial pathway is visible:

Better preparation strengthens insight. Better insight produces better questions. Better questions create more useful conversations. Better conversations improve the conditions for trust and revenue.

The human remains responsible for every consequential step.

My Lever Lens takeaway

The more I considered Cherilynn’s conversation, the less I saw it as a lesson about using AI to sell.

It is a lesson about refusing to confuse information with understanding.

AI can collect the public facts, compare patterns, challenge a conventional question and help prepare a founder for a conversation. That is valuable.

But information becomes commercially useful only when someone applies judgement to it.

The founder still has to decide:

• whether the question is relevant;
• whether the information is appropriate to use;
• when to remain silent;
• what the answer actually means;
• and whether the next step serves both the person and the commercial objective.

That is why Insight is the primary lever here.

The advantage is not that AI can generate more questions.

It is that a well-prepared founder may be able to ask the one question that opens a more truthful conversation—and then remain human enough to hear the answer.

Watch. Take. Ship.

Watch

Watch Cherilynn’s full founder conversation to hear her approach to relationship-first selling, deliberate AI practice, briefs, guardrails, LinkedIn visibility and financial fluency.

Watch Episode 03 with Cherilynn Castleman →

Take

Use Cherilynn’s Three Rings to decide what you need to Master, what you need to Learn and what you are allowed to Watch rather than chase.

Take her free Master / Learn / Watch sorter →

Ship

The deeper application is Cherilynn’s LinkedIn Operating System: a guided member experience for turning your positioning, voice, proof and themes into a reusable system rather than starting every post from a blank prompt.

One question to take back to your business

Where are you using AI to produce more activity when the real opportunity is to prepare better and ask a question worth answering?

The Lever Lens is where Michelle Jones-Walker examines each AI Power Women conversation through five commercial levers: Insight, Growth, Revenue, Capacity and Delivery. Business acumen provides the lens; applied AI is the lane.