In this episode of Selling the Cloud, Cherilynn Castleman, enterprise sales leader turned strategic coach and Harvard instructor, joins Mark Petruzzi and KK Anderson to break down what AI fluency really means for modern sales teams.
Rather than treating AI as a shortcut or replacement, Cherilynn reframes it as an amplifier of human strengths like perspective, empathy, and trust. She shares practical, Monday-ready routines that help sellers show up with stronger points of view, deeper buyer relevance, and clearer deal strategy.
This conversation also dives into the science of trust in a noisy, AI-saturated world. Cherilynn explains how the questions we ask and how we listen directly influence buyer confidence, especially inside complex buying committees. From discovery to prospecting to executive conversations, this episode focuses on how sellers and leaders can create credibility without adding more noise.
What You’ll Learn:
- AI as a Daily Sales Discipline: How a simple 15 minute daily AI prep routine helps sellers develop POVs, anticipate change, and continuously improve.
- POV Development at Scale: A repeatable framework for triangulating industry, company, and persona insights using AI.
- Making AI Revenue Relevant: Why leaders should evaluate AI through insights, context, and business impact instead of activity metrics.
- Trust in the Age of AI Noise: How better questions and deeper listening create credibility when buyers are overwhelmed with automation.
- High Connection Discovery Questions: How to use AI to reframe discovery questions that trigger trust, openness, and buyer engagement.
- Prospecting Without Pitching: Why offering value through insights, case studies, and tools beats asking for meetings.
- Navigating Modern Buying Groups: How to adapt when new stakeholders like CFOs enter late-stage conversations.
- Financial Fluency for Sellers: Why precise numbers, not rounded estimates, matter when speaking with executive buyers.
Key Topics:
- AI fluency as a mindset, not a toolset
- Daily AI routines for sellers and managers
- POV creation using LinkedIn profiles, 10Ks, and industry analysis
- Relationship selling and the science of trust
- Discovery questions that increase buyer confidence
- Avoiding buyer defensiveness and ethical AI use
- Executive conversations and CFO expectations
- Financial storytelling with insight, context, and impact
Guest Spotlight: Cherilynn Castleman
Cherilynn Castleman is an enterprise sales leader, strategic coach, and Harvard instructor focused on helping sellers become trusted advisors through AI fluency and relationship-driven selling. She is the creator of highly rated AI and sales programs available on Udemy Business and leads large learning communities through weekly live sessions and workshops.
Cherilynn is on a mission to equip one million women in sales and leadership with the confidence, fluency, and playbooks needed to thrive in modern go-to-market roles.
Resources & Mentions:
- Course: Smart Tips Sales – Master Relationship Driven Selling via AI
- Book: Post-Pandemic Selling
- Research Reference: Dr. Jane Dutton on High Quality Connections
- Concepts: AI fluency, POV selling, high connection discovery, financial storytelling
🎧 Listen now and follow Selling the Cloud for more insights on modern sales leadership, AI-driven GTM strategy, and building trust at scale.
Mark (00:31)
to Selling the Cloud. Our guest today is Cheryl Lynn Castleman, an enterprise sales leader turned strategic coach and Harvard instructor as well. She helps teams become trusted advisors with practical AI fluency and relationship skills. She also builds accessible learning at scale as a new to me creator. Her course, Smart Tips, Sales,
Master Relationships Driven Selling Via AI is super highly rated and available versus a via Udemy business. Her programs focus on outcomes you can see on Monday morning. Better discovery, cleaner deal strategy, clear next steps. She has coached thousands of sellers and leaders, lifted promotion rates through hands-on coaching.
and built a large learning community through weekly live sessions and workshops. She teaches simple operating rhythms that free time for customer conversations rather than adding more dashboards. And she's on a mission to equip 1 million women in sales and leadership with the fluency, confidence and playbooks to thrive. Here are three topics we'll cover today. AI fluency as a daily mindset.
How to use AI to amplify strengths and turn prep into a repeatable routine that shows up every day in results. Relationship selling and the science of trust, the questions and behaviors that build credibility fast with modern buying groups, and leading as a CRO in a time of extremely rapid change. How to focus to team, communicate change, improve impact without adding any additional noise.
Sherlyn, we're so happy and proud to have you here. Welcome to Selling the Cloud.
Cherilynn Castleman (02:13)
Thank you, Mark. Thanks, KK. I'm thrilled to be here today.
Mark (02:16)
All right, we're gonna take you right into our first topic. And our first question is, you frame AI as an amplifier for what sellers already do well. If a CRO asks you to install AI fluency in 30 days, what would reps and managers need to do each day and each week? And what early results would you expect by say week four?
Cherilynn Castleman (02:38)
So first of all, I would start with a 15-minute AI prep session for every rep. I would have them spend 15 minutes asking AI, first of all, one, to develop a POV, a point of view, which I know we're going to talk about a little bit later, for each of their clients. It's something they can do very quickly to triangulate and develop their opinion, because as you know, state of sales reports from LinkedIn and Salesforce told us that 87 percent of
B2B buyers expect us to show up as trusted advisors, meaning we have to have a POV. So use AI to develop your POV. Second of all, spend five minutes using it to look around the corner. Where is my industry going? Where is my product going? Where is my company going? If you ask those questions every morning, you're going to get insights. And the final thing is, what can I do better? What can I, what am I missing? How can I, so for example, I'll say,
How can I be a better coach? How can I connect better with my audience? What is a new training insight I can try? What's a new engagement I can use on Zoom? I am every day getting better. They spend 15 minutes every day amplifying what they already do. They're going to accelerate deals. Number two, I would encourage managers to add to their weekly minutes, teach me something in five minutes. Have every rep teach something to the rest of the team.
once a week. That means by the end of four weeks your team has learned five AI insights. Over the course of a year they will learn 50 AI insights. And I had a client who was in the middle of the pack as a manager for a Fortune 100 fintech company and she became the number one sales manager of the year within six months just by doing that one exercise. That will free up
And what you will see is you will see about 30 minutes a day freed up from your reps. That 30 minutes, if you have 50 reps and they're doing about $100,000 per deal and they're doing one deal a month, if you take that math out, that will give you an additional $4.5 million in new revenue that and no additional headcount.
KK Anderson (04:44)
Wow, it's really fascinating when you put it that way and you break it into numbers.
Cherilynn Castleman (04:47)
Yeah, and that is one of the biggest takeaways, I think, that sales leaders and chief revenue officers can look at is when we first started using AI, people were talking about how to use it for email and how to ⁓ sound better. And what the most recent research is coming out is you have to ⁓ apply what I call ICB, insights, context, business impact. How is it driving revenue?
How is it saving you money? How is it increasing operational efficiency? How is it increasing your ROI? Those are the questions that leaders want to start asking every single week. This is what my reps are doing. How is that making me money, making me more money, or saving me
KK Anderson (05:28)
And it's interesting because you need the leaders, the L1s and the L2s asking AI those questions and using the data to get smarter. But the sellers as well, like you said, use it to look around the corner, research your competition, your customers. And we know and have known for a long time that our customers are much smarter when they get to us. They know more about our product than we probably do.
Cherilynn Castleman (05:48)
It used to be there were a ⁓ couple of months ago we had about 79 % usage today. B2B sellers are 98 % using AI. Customers are 100 % using AI. So your customers are using AI and 100 % they know your company, they know your competitors, they know your product. They probably have done more research than you have. So that's why you have to show up.
Mark (06:02)
Thank
Cherilynn Castleman (06:12)
with a POV, you have to connect with them, you have to build trust with them. People want to do business with people they know, like, and respect. Period. And we can leverage AI to do that.
KK Anderson (06:24)
And so where I was gonna go next was, I actually, I kind of thought people were getting over this idea that AI is cheating until I was in the car with my kids of all people. And one of my daughter's friends was like, AI is cheating, I can't believe AI, it's just not fair. And it's interesting, do you hear that still in your trainings and your classes that people feel like it's a cheat?
Cherilynn Castleman (06:47)
And with a lot of women, Harvard did it. There was an article that was recently said how AI is impacting women's career. And they discovered that women use AI in business 10 to 40 % less than men. And when they asked them what was the real reason, women said, because it's cheating. And so I tell people, just reframe it. I said, take what you already do well.
What is your superpower? What is the one thing that you're better at that AI will never replace? AI will never replace your authenticity, your ability to care, ⁓ your ability to connect with people and ask AI to help you elevate that, to amplify that. Take 15 minutes in the morning and say, I'm a great listener. How can I be better?
I ask great discovery questions. How can I do better? I'm meeting with this client. We don't seem to connect. How can I connect better with this type of client? My client's very analytical, very amiable, very expressive. A trick that I tell people is write a simple email and then ask AI, rewrite this for an analytic, rewrite this for an expressive, rewrite this for a driver, and rewrite this for an amiable. They're different as night and day. That alone will help you connect.
with your clients, just reframing that. Another example is if you go to LinkedIn, go to the three dots, and it says PDF this profile. PDF the profile, attach it to the AI tool that you're using, and say reframe this email specifically for this person. And it will say, they're very innovative. They're very amiable. They're very analytical. And it will reframe it. You will connect with them. That's the power of AI and connecting with people.
Mark (08:24)
All right, well, that's very cool. So please help us to make this a little more Monday ready. Let's say a rep has a discovery call this afternoon with a new account. Walk through the 15-minute AI assisted prep that produces in your mind the most useful point of view for the call and how you coach them. How do you coach them to bring that into the conversation? We've discussed a little bit
this here, but take us a little deeper if you would.
Cherilynn Castleman (08:51)
Absolutely. So what I always coach my clients to do is to triangulate your POV. It's something that AI, generative AI tool does so well. So first of all, research your client. Pull down their LinkedIn profile. If they're an executive, pull their bio and that's number one. So you want to triangulate. want three things, industry, company, person or persona. So if you can't find the person, do a persona.
Pull down several CFOs in that industry. Pull down, if they're a Gen Z, pull down Gen Zs in that industry in that job role. So the better you can micro-segment, if you can't do the person, do the persona. That's number one. Number two is company. My favorite company document for publicly traded companies is a 10K. The Form 10K, as your listeners know, I'm sure, comes from the Security Exchange Commission. You can get it on
the investors page of any publicly traded company, and the third one is an industry analysis. My favorite place to get it is Value Line. Value Line is free on every public library. If you work for a large enterprise company, they have this information for you. They have an industry analysis. They have company analysis. Pull it in and ask AI to triangulate this for you.
and it will pull the three together and develop a POV. And then you just say to somebody, Mark, if I said to you, I have an idea I want to run by you, what would you say? People say, yeah, nobody's going say no to an idea. And that's all it is is an idea. Even if you're wrong, you get credibility because you showed up with an idea. So show up with an idea. This takes 15 minutes. This used to be an eight-hour workshop that I did on how
Mark (10:15)
Yeah.
Cherilynn Castleman (10:31)
to research and how to read a 10K. Value Line has the ratios in there, so it can pull it and it has the ratios in there for three years. It will do a financial analysis POV, it will do an expressive one, any way that you want it. Fifteen minutes.
KK Anderson (10:46)
And then you take that information and you turn it into a value hypothesis for what outcomes your customer wants to achieve and what's going to get in the way and how you can help.
Cherilynn Castleman (10:54)
Yes.
Right. So if it's a first interview, those are the three things. If it's a second interview, I include the discovery document with it. And whether you are going into a meeting and saying, have an idea to run by you, and you're starting your meeting that way, or you're sending a follow-up email, or you're going into your solutioning, or you're doing a demo, it doesn't matter. You always want to show up with your opinion. I'm the trusted advisor. I have an opinion.
And that's what it is. And you could say, how does this land with you? Or this is what I'm discovering in the industry. How does this resonate with you? You're asking their opinion, but you're showing up with somewhere to start other than just with open-ended questions.
KK Anderson (11:35)
So let's, we could stay on this topic forever. Let's move on to the second topic though, relationship selling and the science of trust. And what's interesting is I was listening to a podcast just this morning about how, thanks to AI, right? And if you, I mean, you see it every day, you scroll LinkedIn and it's like emojis and dashes and it's just a bunch of chatty-bitty trash, noise. Let's call it noise. I wouldn't say all of it is trash, right?
And so, and people are used to seeing that now. And so it's like the trust continuum is getting longer than it used to be. Like it used to be, like if you had a really slick website, you know somebody dropped 10 grand to build a really slick website or way more than that, right? You you used to be, and now an AI tool can turn that on and you know, 30 seconds flat. And so it's harder for people out there to know who they can trust and what's real and what's not real. And so,
you teach that trust shows up in what we ask and in how we listen. you know, AI is making that harder. Like how, like, how do you balance that? Like how have you added that whole dynamic and that change into your teachings and your coaching?
Cherilynn Castleman (12:41)
So the first thing that I do is I ask my clients to pause for a second and tell me what is it about their client that they really care about. You have to give a damn about your client. There's no AI tool out there that's ever going to do that. And that's where you start. So if you really care about your client and you pause and say, what is it you care about? What is it that's important to them? And if you don't know, that's the first place you start, because that's what you have to start from.
is you have to care about your client and what's important to them. Once you care about them, you can craft discovery questions that are high connection questions. And for example, and AI can help you do this. again, it's a tool to amplify and elevate you. So Dr. Jane Dutton at the University of Michigan has done a lot of research on high quality connections, HCQ. If you go in and ask AI,
to reframe your discovery questions as high quality connection questions, what you're gonna do is you're gonna trigger what I like to call the love hormones. It is the oxytocin. It triggers the hormones that makes clients trust you, like you, want to do business with you. For example, I had a client who was in the financial services industry.
And she used to ask her clients, tell me about your insurance policies or your insurance that you have. you how you feel when somebody asks you that. Her second appointment rate was around 17%. When she asked AI to refrain that, the question was, what is it about insurance that scares you? Can you see that just that little switch there makes somebody connect with you? I have another client, she's a career coach, and she used to say, tell me where you want to be in three to five years.
And she was coaching women and AI suggested that she ask, when was the last time you cried at work? Because if you're a woman and you're going to look for a coach, it's probably because something is upsetting you to tears. And so you can ask little questions that just connect with people. have a client that she sells ⁓ data to, she sells data and
All of her clients are data scientists. And she said, Sherrilyn, data scientists don't have feelings. I can't ask you questions. And I said, hear me. Just for one week, let's just try it. She came back, and her clients now know her as a data therapist. Because she started asking them, what does it feel like when your company asks you to change the algorithm real quickly to come up with something? And this frustrates and angers, and they don't have the right data. And so her solution helps.
resolve this and she's like now all my clients want to start with how they feel every time we meet. So she connects with them. She was able to renew more accounts than she ever has just by starting asking those types of questions. ask better discovery questions. Two of my favorite ones are either first or finance. What was it like for your first podcast, KK? Can you remember your very first podcast?
KK Anderson (15:38)
Yeah, the instant emotions, instant
Cherilynn Castleman (15:39)
Okay,
you see the emotion, you see what happens? Versus telling me about what's it like to have a podcast as a first question. Or if I asked you, Mark, what was your finest podcast? So first and finest questions are great connections to connect with people. You can make these very technical, very financial, very industry specific, but an AI can help you do that.
KK Anderson (16:01)
And I know Mark's gonna jump in here, but I gotta ask one more question. That's brilliant, by the way. I absolutely love that, first and finest. What about in prospecting, when you're trying to get the meeting? How are you breaking through the AI noise and building trust?
Cherilynn Castleman (16:15)
So just bottom line, offer value, offer value. Offer case studies, offer assessments, offer checklists. People are doing research. People want knowledge. And so I say leverage social proof. AI, anybody can go out in AI and say, I am a great coach, or I am a great podcaster, or I'm a great ⁓ strategist. Use.
LinkedIn or whatever platform you use or emails or whatever, however you're doing your outbound to demonstrate that you can prove you do this. So offer social proof. Here's a case study where I helped a client like you do this. Here's a checklist that I use with my clients. Here's an assessment that you and your team might want to take. I have an AI assessment tool that I give out and I'm constantly saying, do you want to see where your team is for AI fluency? Take this AI fluency assessment. It is just a free tool.
Here's a handout on how to prompt like a pro. Give value. Once you give the value, then I always say, if you have more questions about this, jump on my calendar. People know how to book meetings today. You don't have to book them. You can wake up every day with new clients on your calendar by offering value and insights. I ended up with ⁓ a huge client from a major retailer who said,
KK Anderson (17:19)
Yeah.
Cherilynn Castleman (17:27)
She just, she used all my free resources for six months and finally she's like, okay, now we gotta bring Sherrilyn in.
And she just got on my calendar, so we want to hire you. It's just that quickly. so what it is. The trust is there. Here, give value, give value. Stop saying, hi, I read your post and let's have a meeting. never, don't ask for meetings. Just give value. And again, if you can't think of what to give away, AI can help you come up with tools, resources. You have case studies. I've got clients who've gotten job offers.
and ended up earning six figures more than they ever had just by posting case studies on LinkedIn. Here's what I did with a client anonymously. Here's what I did with the top 10 airline. Here's how I helped them and the percentage I helped them did the case study. And I had a woman, the chief revenue officer called her and said, I want you to come in and be my head of sales ⁓ and went around HR and didn't even look at a resume. It's like, whatever you did with that client, I want you to do that for us.
Because it's proof, it's a social proof, a lot helps you do that.
Mark (18:29)
Right on. Sherilyn, that's so you've taken us through some of the things that you want to say and things that add value to the full discussion early on. Let's talk a little bit about things that that you want to make sure you don't say or things that could actually trigger things like buyer defensiveness. And in general, like what two behaviors that do you see that
you know, that you can then do the lower that threat and increase that openness right away.
Cherilynn Castleman (19:01)
So one of things that I call is don't be cringy, okay? There's so much information out there. It is so easy to take someone's information and abuse it. Don't do that. Just treat people the way you want to be treated. So number one is don't be cringy. Don't take the data, don't share somebody's information. Be respectful, be kind if given a choice between
You know, right and kind, choose kindness, just always be kind. I always say a fool with a tool is still a fool. There are fools out there with AI. Just because you have AI doesn't mean that you have to abuse it. Be ethical, stop and think about does this make sense? Is this ethical? The other thing is you will know if you're not triggering the trust and the love hormones, you're triggering their amygdala. And what happens when you trigger their amygdala
is you see fight, flight, fawn, or freeze. If you're seeing any of those with your clients, they're fighting with you, they're arguing with you, they are freezing, they are not showing up, they are stalled, they are fawning. You ever ask a client a question and they sit there and they look at you? Well, they are fawning. just, you know, that's where they are. Or they just ghost you. Any of those say, okay, I've done this, it's time to stop, and AI is a great tool. I tell people,
open a Word document, dictate just in your own voice what happened and ask AI to help you analyze it and say, what did I do wrong? What could I have done better? What made my client freeze? And learn from it. Another thing I see is that you mentioned it. So people try to sound ⁓ more intelligent or more technical. And how do you feel when you're around people with pretense? How do you feel when you go to that Thanksgiving or holiday meal
and your in-laws or somebody has a girlfriend or boyfriend with them and they're just putting on airs. Everybody knows it. They can't stand it. Well, we don't want to do business with people like that. So the best way to be authentic and have your authentic voice come through is to just dictate. I use Word because it's not intimidating. I tell people just go into Word, hit the dictate and just dictate the email. Dictate the script. Dictate what you want to do and then drop it in. AI will use your words.
they will use your intonations and you will sound like who you are. So those are a couple ways to avoid triggering the amygdala and have somebody go into fight flight freezer form for you.
KK Anderson (21:27)
I'm a big follower of Rory Vadin. I don't know if you know him. He runs Brand Builders Group and he wrote the book, Take the Stairs. And he says, my gosh, I feel like I've been quoting this every day. He says that in today's age, your humanness is now your uniqueness because everything else is,
Cherilynn Castleman (21:34)
Okay?
KK Anderson (21:46)
AI generated, like you have to leverage your humanness as your uniqueness. That's, that authenticity is still, is now even more than ever, you know, paramount. So buying groups are larger, they're complex. Very often, in these times, leaders who used to have decision-making authority now have to get the CFO involved and, and, and they're.
Cherilynn Castleman (21:51)
Yeah.
It is.
KK Anderson (22:09)
more constrained than they've ever been. And so how are like, on this theme of building trust and authenticity and triggering the love hormones, I love that by the way, how do you do that when you've got like a buying group that's constantly changing? Like you're halfway through your sales process, you're on a, you have a meeting to negotiate or talk about terms of something and then next thing you know, boom, the CFO is there and you've never met him before. Like what are your kind of tips on that?
Cherilynn Castleman (22:36)
So a couple things. So first of all, I always ask at the beginning of any meeting, whoever's there, because like you said, buying committees are much larger. They used to be three to five people. Today they can be 12 to 18 people on a buying committee. Regardless of how large the buying committee is, at the very beginning, always go into the meeting asking each and every one, if you could get one thing out of this meeting, what do you want out of this meeting? Because...
That may change the direction of the meeting. So you don't want to guess where the CFO, the CFO could be there because they're looking for operational efficiency, cost savings. They could be there because they're looking to drive revenue. They could be looking to improve the pipeline. You don't know why they're there. And so ask, and so I always ask, even if there are 15 people in the room, I'll take 15 minutes and say, real quickly, what's one thing you want at this meeting? And I note those down. Now I have the direction of the meeting. That's number one. Number two.
Do your homework and do like I said, so do a POV for the chief marketing officer, do a POV for the CFO, do a POV so that you have those. So you're not changing the agenda, you're just changing the lens. And number three, executives want to talk about numbers. Develop your financial fluency. Understand what the key numbers are. Are they interested in what's driving revenue?
and be able to tell stories. And the stories, again, is the insight, what is the number, what does this number mean, and where is this number going? How will it impact us in the future? So is it the cost of acquisition? Is it the cost, is it the life, the cost, the client life cost of, you know, of maintaining the lifetime value of that client? So.
Know those numbers and be able to speak to them. And one other tip I always tell people when a CFO is in the room, take your numbers out three digits. Never say 50 million. Say 47.2 million. Know your numbers by three digits. CFOs will dismiss you if you round your numbers as a salesperson. So know your numbers. I'm sorry, what? Yeah, if you talk to CFOs, they'll tell you, I hate it when somebody says 15%.
KK Anderson (24:33)
That's a good tip.
So that's a good tip.
Cherilynn Castleman (24:42)
Because nothing is exactly 15%. It's 14.7 or 15.2. So know your numbers, know them out three digits, know your numbers and tell financial stories with them where you can talk about the insight from the numbers, the context, and what it means to the business. And be able and have a financial point of view in your back pocket so that you're just changing the lens, you're not changing your agenda.
Mark (25:07)
Well, you know, Cheryl Lynn, that is also it's like speaking with someone who's bilingual and, you know, speaking in the language that they may be struggle with the whole time and maybe touching it for a second. You know, CFOs, are they are bilingual. And one of the items is numbers. It has to be. So that makes a lot of sense.
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