Leading Sales into the AI-Powered Future: Fluency Over Fear

So I chose Queen and David Bowie's song Pressure Pushing down on Me, because that's what I hear from people. People talk about AI And I don't think that AI is going to take the pressure away. I think AI is turning up the pressure. And for those of us sales leaders who lean in, we're going to thrive. And for those of us that don't, we're going to be replaced by somebody that does. And so that's what we're going to talk about today is how do we lean in and how do we deal with AI in the future with AI fluency, not fear. What I'd like you to do is do me a favor. Drop in the chat. How many new AI tools do you think are being released every single week? How many new AI tools are being released every single week? Let me just see it in the chat here. In reality, there are somewhere between 1 to 2. Somebody put. I usually hear 5 to 6, 5, 1200. I hope not. Well, actually, it's. It's more than that. Every day, there are somewhere between 50 and 250 new AI tools released every single day. That means as a sales leader, we have somewhere between 500 and 3,000 every week that are landing on our desk. That means in an hour, you're having five to ten new AI tools that you. That will land on your desk. There's no way that we can stay on top of it. So I kind of chuckled when Gearhart said, things have changed since February. No, things have changed since yesterday. So I'm going to challenge you to reframe how you think about AI and let's think about a fluency. And instead of tools. And what I mean by AI fluency is think about a time when you studied a foreign language. And for me, it was Spanish. And when you became fluent, you had confidence and clarity. And what I mean by that, you thought you were confident enough to speak the language if you traveled and you had a chance to speak it and you were clear enough that people understood you. And that's what we're striving for with AI Fluency. And the framework that I've come up with to help you look at AI Fluency is the sale into the future S A I L. And it's skills, amplifying, brilliance, integrate, and leadership. And that's what we're going to spend the next 20 minutes or so talking about. So the first thing I want to do is I want to talk to you about what Harvard calls the 30% rule. You are considered an AI fluent leader. If you can get your team, everybody on your team to score at least 30% of on an AI assessment at the end of this, my presentation today, I'll put up a QR code and the AI assessment is out there. You can take it, you can share it with your team members and your goal is to try to get everybody on your team up to 30%. If you can do that, you're considered an AI fluent leader. And that's our goal. Once you become AI fluent, you won't be overwhelmed if every day you read here is, here's a new AI tool that's going to totally transform what you're doing with sales. So the S stands for skills. And I'm going to share with you some takeaways that you can do right now, starting tomorrow with your team to help them build their fluency and help you build your fluency. So we're going to talk about scales, we're going to talk about amplifying your brilliance, how to get better at what you're doing, how do you integrate AI into your entitled entire sales funnel? And the final one is what are leaders doing today with, with AI? So remember, the goal is a 30% rule. You want to take the assessment, share the assessment with your team. And the goal is to try to get everybody to score at least 30% on that assessment. I'm going to share and I move quickly and I will share lots of tips with you. My slides will be available. There's a handout for everything that I talk about. So all of the details, you can share them with your team. My goal is to amplify and elevate everybody. And, and so what I challenge you to do is take out a piece of paper, draw a line down the middle and write, test and tweak. Because I'm going to come up with some new ideas, things you may not have heard. I want you to test and then I want you to be able to tweak things about where you know, things that you say. Sherlyn, I'm already doing that, but how can I tweak it? Okay, so we're going to look at skills. When I talk to sales leaders, what I hear over and over again is they want their team members to prompt like a pro. They want their team members to prompt better. So here are two frameworks to help your team prompt like a pro. The first one is I like to say if you give your AI tool a gift, it will give you greatness. And the gift is gift. When you write prompts, always put in a goal. And this is the easy one, you know, what do you want it to solve for? Begin at the end. If this was a great, if this was great. This is a script. This is a voicemail message. This is an email. I stands for the intended audience. Not only do you want the audience there, a quick tip for you is go into LinkedIn, look up the the person you're sending it to, click on more and it says download the PDF, download that PDF and upload that to your AI tool and have it write the script, the email, whatever, directly for that person. And it will do a much better job than you trying to summarize who the person is. The next one is a format. Are you sending an email? Are you sending a script? What is it that you, what is the format you want? And the most important one where I find so many salespeople miss is the tone. And not just confident, casual and consultative, but you want a tone that is, do you want it written at a sixth grade level? Do you want it written at a third grade level? And people always shudder when I say that. But research has shown that the most opened inmail messages and email messages are written at about a third or fourth grade level. I had a client that she was reaching out to to auto dealers because her company gathered data and she works for one of the top credit bureaus and nobody was opening the emails. And I challenged her, I said do an AB test, rewrite them at the third grade level. And her open rate went over 42% and she all of a sudden shot to the top of the leaderboard just because her emails were being open. So do an AB test and do that. So remember, if you want to prompt like a pro, give your your generative AI a gift and and it will give you greatness. The second way to prompt like a pro is to triangulate. And what I mean by that is we don't think linearly. So train your AI tools to think like you do. Think in threes. Here are three things I want you to consider. And the simplest ones for me are industry, company and person. Industry upload an industry snapshot that your company may have. If your company doesn't provide them, you can get them free on value line. Every library has value line. You can even ask AI to provide you with some industry insights. The second one you want to do is information about the company. My favorite one is a 10k. A 10k is a your form. 10k is that 200 page document that every publicly traded company submits to the security and exchange commission. I pull the 10k, I pull the value line, industry analysis and their LinkedIn profile. I pull them together and I ask AI to triangulate this and, and then write my message, then help me build my presentation, then help me write my point of view. If you don't like those three, pick one that you like. Here are other topics that you can triangulate with. You can do market or economic or political scans, landscape. You can add competitors to it. You can talk about role based. You can say here are LinkedIn profiles from 10 CROs in this industry. Write it generally to CROs. You can talk about how important their tech stack is and where they are in their text that you, maybe you have some notes that you've taken from a previous meeting. The more, the more information that you give generative AI, the better your output is going to be. And so if you just remember two things, one gift, G I F T goals, intended audience format and tone. And then the final one is always triangulate and add three things and ask it to triangulate these three things you will learn to prompt like a pro. And this is a skill that I teach to everybody from the students at Harvard down to SDRs and BDRs that I coach. Here's an example of a really strong prompt. Can you analyze or triangulate the industry trends? Here's the company's 10k letter and the CE, the 10k form, 10k and the CEO letter. And also here's a PDF from their LinkedIn profile. Another thing that I do, just a real quick tip is what I've learned is that there are people on your team who barely use one AI tool and there are other people on your team who are building AI bots and agents. Break them up into four groups so that they have a comfort level. If you try to just build skills with your whole team, you're going to alienate those on either side. So what I always do is I, I have people stand up and I say, okay, how many of you really have never logged into AI before or you're struggling? Okay, you're in one group and I break them up and then I challenge my, my fourth group, those that are building agents and bots to do that. So when you're going to build skills, this is just a quick tip. A training tip that I use is give them different exercises. I look, I write my slides just like this and this is what I do. I want new coverage to try a new tool. Here's a simple prompt I want you to use Group two, I want you to compare two different tools together. Group three, I want you to come up with a multi step workflow for something that we're working on. In group four, I'm always asking them build us an agent. Build us an agent for this class. Build an agent for this issue, this project. Build an agent that I can use tomorrow with my team. That's just a tip that I use. We've talked about building skills and, and that is so important. The a in fluency for sailing into the future is amplifying your brilliance. You may not realize this, but Harvard did a study and they realized that women are using AI tools somewhere between 10 and 40% less than men. I was blown away when I read that. And as I read further, what they shared was that women feel like using AI is cheating. And I started talking to sellers and sales leaders. I even had a chief revenue officer that I'm coaching and she manages over $400 million and she also thought AI was cheating. And so I encourage people to reframe it and that rather than looking at AI as cheating, look at as a way to elevate or amplify your brilliance. Here are three quick tips that you can use to help your team amplify their brilliance so that they become more AI fluent. 1. The first one is I always ask people what are your superpowers? I asked one of my clients at a couple weeks ago and she said that she's a songwriter and she sings and I had no idea but she's a great singer, she's an amazing songwriter. Songs come to her very quickly. And so she used AI to start writing jingles for her clients and she's posted a couple of them online. She was able to secure an appointment with a top airline that she'd been trying to get in the door with as well as a major retailer just by writing jingles and, and sending them out to the teams in these organizations that she was never been able to get in the door with. So ask your team members or you to step back. What is one of your superpowers and how can AI help you amplify that? And if you spend 15 minutes every morning just getting better at telling stories, asking questions, being strategic, amplify, analyzing data, data you will elevate and amplify your brilliance. The next one that I have talked about before, but it still blows everyone away is I challenge my clients and my the teams that I work with to spend 15 minutes every morning reflecting here's what I'm working on today. Help me Figure out how to do it bigger, better, simpler, faster. And one of my clients who's in the C suite at Amazon, when she got back on her coaching call the next week, she was washed down in tears. And I said, what's? And she said, sherilyn, for the first time in two years, I got my weekends back just by doing this 15 minute exercise and asking AI to help her figure out how to get better. And every day, if you're getting a little bit better, that's what will happen. And the final one to amplify it is I challenge you as sales leaders to model curiosity, share with your team every day or every week or one thing that you're doing to elevate yourself. A great exercise that I do, I do it now with every group that I'm training is teach me something AI in five minutes. Imagine if on your team's agenda every week, somebody from your team had to spend five minutes teaching the rest of the team their favorite AI hack or their favorite AI idea. At the end of the year, you would have over 50 new AI insights that everybody in your team will have learned. So amplify your brilliance with AI. The next one is integrate. And what I mean by that is you want to integrate AI into your entire sales funnel. And so here's how I look at it. Is everything from social proof and credibility all the way down to advocacy and evangelism. How can you incorporate AI everywhere? And what I would challenge you to do is pick your weakest link, because we all know that when you look at that sales funnel, there's one spot where, where you're losing your prospects. Go to that one spot and challenge yourself and challenge your team. How can you use AI to close that gap? And, and so I'm going to start with the one that I do a lot of coaching and training around, and that is just building top of the funnel with social proof and credibility. And so one of the things that I, I do with everybody is social proof. Today is one of the top skills. AI is important. Social proof is important. And the third one is building trust and connecting with people. Those are the three top skills that are helping sellers accelerate and hit quota. And so have your team optimize their LinkedIn profile because people are looking. People are using LinkedIn profiles with AI. And so there's a checklist here. The checklist is also downloadable with the resources and I'll give you the QR code here shortly. There's three things that I think are really important. The first one is use Activate, Activate the name pronunciation, LinkedIn is your handshake. And so if you pronounce your name, at least somebody gets to connect with you and hear your voice. I don't care if your name is Joe Smith, how you say, hi, I'm Joe Smith. It still lets people connect with you. It's like that handshake. So make sure you pronounce your name on LinkedIn. The other thing that is so important, and I shared this with two of the, my co professors at Harvard, they weren't doing this, is when you write your about statement, make your about statement, an I statement and talk about who you are. And, and so it's a very personal. So when somebody reads it, they want to meet you. And then at the bottom of the abouts section put ask me about and then write in 25 keywords. Now how do you get the T. The keywords is you go to AI and say, what are the 25 keywords that I can use for people to find me and my services? And you put that in there. When both of the professors that I work with did this, one of them got a brand new client and a keynote presentation and the other one got two clients in the first week just by adding the keywords and updating their I statement. It's very powerful. And so these are some tips for you if you want to build the top of your funnel and the first social proof and the first phase of your funnel. So just like I focused on that, you can pick any of these and ask AI to focus on that and use that to close your gaps. The other thing is I talk about social proof. Social proof, I think is one of the most powerful tools that we have as sellers today. There's so much noise out there with AI. Anybody can put up a profile and say, I know how to coach and train, I know how to instruct. But if you can't prove it on social media, if you can't prove it on LinkedIn, then it doesn't mean anything. Share your case studies, share your wins, talk about how you lead your team. Talk about the difference that you make for your clients. You can prove what you're doing on LinkedIn and that will separate you from, from your competitors. Now here's a guide, just very simply that helps you and your company figure out some things that you might want to do. So if you have great engagement, okay, I know that I have about 20,000 people that follow me, so it's a decent amount. So I'm focused on conversion. So, so if I'm focused on Conversion. I post thought leadership. I'm always posting about AI, the things that I've discovered in AI, the things that I discover at teaching. I talk about the products that I offer and the services and I am constantly offering case studies. When you connect with people on LinkedIn, always offer a value. Don't offer the don't, don't say let's meet. Offer case studies, offer thought leadership, offer checklists. Those have the best conversion. If you don't have a lot of people that you're converting and you want to grow, these are the things that you can grow. Again, thought leadership works. Industry insights work. Customer case studies are great for growth. If you're just trying to reach more people, personal stories are one of the best and and talk about yourself. Talk about a personal story and connect it to business. Employer branding works. Case studies always works behind the scenes. People love behind the scenes. I recently launched a course on Udemy and I and I took videos of me behind the cameras and with hair and makeup because people love it and it works for reach. You see, engagement is really hard and so I tell people, don't chase algorithms. Don't worry about engagement. Talk to your community. Talk to one person. When I write a pro a post, I write it for one person and that will help you build your social proof. The next thing that the final thing I want to talk about is leadership. What are you doing to build your leadership? And there's three things that you can do with AI for leadership. The first one is you can leverage AI to help you see around the corners we used to talk about in sales. Go to where the the hockey puck is going, not where it is. How do we know where the hockey puck is going? You leverage AI every week input for your forecast trends and and start asking AI to help you see around the corner. See around the corner for where your industry going. See around the corner for where your clients are going. See around the corner for where leadership is going or where your company is going. Constantly challenge AI to help you be more strategic. See around the corner. The second one is use it for innovation. How do you free up what you're thinking about? Test new bold ideas. Come up with check for once a week. Find the signal and think of one bold idea and go out and try it. Like I said, my client, she was so nervous about posting these jingles but it was a bold idea and she did it and it worked and she's going to continue to do it. And the other one is normalize these rituals. Talk about the AI wins of the week, ask your team, what did you do? What did what, when, what worked? Make being bold with AI very normal. And ask yourself what's one trend that you're seeing that you haven't acted on? And so what I'd like you to do as, as we're closing here is think of one signal that you have seen today and one bold step that you can do to move forward. I know there's been tons of ideas and I don't know if it was be something that I mentioned or something that one of my other somebody else on the platform has shared with you, but I know that you've seen one signal and ask yourself, what's one bold step? And if not, go into AI and say, what's one bold step that I can do so that I can move forward, so that I am. I become fluent. So remember the 30% rule. It's about building your skills. Teach your team to prompt like a pro, amplify their brilliance. How do you help them elevate their superpowers, elevate what they're already doing better. Figure out how to integrate AI into every single stage of your funnel and, and finally leverage it as a leader. Build curiosity, look around the corner, think about innovation, take bold steps and build the type of team that you want to lead. I'm going to, so I'm going to ask you again, what's one thing that you're going to test or tweak? And if you point your camera at this QR code, you will, you will be able to download the slides that I've shared today. There is the AI assessment you can, that you can take and it will immediately tell you where you scored and where your team scored. All of this is free. You can enroll in my certificate course with Udemy. You can get my newsletter or follow me on LinkedIn. This QR code will take you to all of that. There is a handout for how to write great prompts. There's handouts about how to build better your LinkedIn profile. There's a handout about amplifying your brilliance with LinkedIn. And there is. And so or if you want to work with me, it also you can also jump on my calendar. I want to thank you for joining us today. It has been absolutely my pleasure to share this information with you and at this point, Gearhart, I'd love to open it up for questions.

I am blown away. It is such a pleasure to follow your presentation because it is scientifically correct and it's totally practical. You have a way of Phrasing things that it is hard to be simple and. And eloquent. And what, what comes to my mind when I think about what. What you said today is. Fear paralyzes cells, but fluency propels them. And the future is reserved for those who are fluent in AI and absolutely. I happen to speak three languages, German, French and English. And what came to my mind when I listened to you is that we all need to learn AI, which is a new way of expressing yourself. And I think that AI is a creative challenge, not just a thinking challenge, where we need to look at the world through the lens of AI and see what comes. What do we see? And the beautiful thing is that this is a lens that not only goes down to the micro like a microscope and analyzes more and more in granular levels, but it zooms out to the universe and brings all the stars closer to us and gives us all the details that we normally are not exposed to.

Absolutely. And, and I love that you talked about the language and you. And I'm sure that you remember that point where it just clicked and you're like, I'm confident and I'm clear. People understand me. And if you look at AI that I want to build my skills, I want to use leadership, I want to amplify and get better, and I want to use it everywhere in my sales funnel. Then you won't be overwhelmed when every day you're getting emails about, here's a new tool, here's a new tool, here's new as a tool. I mean, you don't get overwhelmed. You just say, I'm fluent, I got this.

Absolutely. Perry, what was your takeaway from shellyn?

Oh, I gotta say, rich, rich content. There's so much there.

Thank you.

Yeah, I really, I loved a lot of it. And I think, you know, the one that I think is really practical and easy to implement instantly is the idea of just getting the team to share what are your AI wins this week. I think that's just a very simple, easy one to execute immediately.

Yeah, it is. And the teach me something in five minutes. I mean, very short, very simple. Every week somebody teaches. Can you imagine at the end of the year, everybody's learned 50 AI hacks. It just, it just one of my clients did this and she went from being just a middle of the pack manager to manager of the year. She got manager of the year and the only thing she implemented was teach me something in five minutes. And that amplified her team and. And she ended up going to president's club with the majority of her team and outperformed every manager. And she works for a very large Fortune 500 company.

Brilliant. Love it.

Awesome.

But it goes to show that bright people become. Get brighter.

Yes.

Yes. And that's why I always tell people, look at it as amplifying your brilliance. It's not. It's not cheating. And. And I tell people, don't, don't. I don't go into AI and say, write this email for me. What I say is, I wrote this email. Now here's who I was writing it for. Here's what my goal is. Here's what my objective is. Here's the 10k. Here's the value line industry. How do I make it better? What am I missing? I am amplifying who I am, not just telling it. Do my work for me.

Yeah. And also, you want to do it intentionally. And I remember, Perry, you were talking about this morning, sales leaders who adopt AI with intention. They're turned inside into impact. Data without execution is just noise. Yeah.

Yes.

It is experimentation.

Absolutely. Well, Gearhart, thank you again for giving me the opportunity to amplify my voice. You know, I'm on a mission to empower a million women by 2030. And anytime that I get a chance to amplify my voice, I appreciate it. I appreciate you. I appreciate your audience. And I can't thank you enough for letting me share what I've learned about AI and how I'm approaching it with my students and my. And my clients.

Beautiful. And your little bit of research that you shared about women use AI less than men. I think that's an important one for us to keep in mind as leaders as well.

Yeah. It's a May 2025 Harvard Business Review article. You can pull it up. Just look up women in AI and I was blown away. 10 to 40% less than in business and career.

That hesitation to embrace it. Something that comes from upbringing, from that maybe I'm not good enough.

No, Women. Women. Women are very ethical, and they work hard, and. And so we're used to, you know, I mean, I. You know, I was a working mom, and I had a career, and I was a wife. And. And you're doing all this, and so it's immediately you think, oh, it's cheating. I want to do it right. I want to be. I want to be the best. And so it is. So it's just. You just have to change your parents.

Where does the cheating come from?

It's just that. It's just. I don't know. Perry, what are you thinking?

I think as women, it's a shortcut and where we like to do things thoroughly. And so I can see, you know, shifting in the mindset for women.

Yeah, yeah, it is. I was surprised. I thought that women would embrace it and say, oh, here I can. Now I can do more.

Okay, yeah, I can save time.

Yeah, I can save time. And so it is. I. I spend a lot of time challenging women. Just do one thing to amplify your brains. And once they do, it changes their life. But I was fascinated with the article because it said women think it's cheating. And. And so it has nothing to do with socioeconomic or upbringing. It's just women generally, their values are. I'm going to be honest. I have integrity. I want to do it the right way. I want excellence. And I was like, AI will help you do that.

Do you think it has to do with the idea to be authentic 100% of the time?

It's. It's important. That's one of the reasons why women outsell men almost 2 to 1. Sales leaders and women, because women are authentic. And in a day of AI, in a day of when everything is zoom, one of the biggest things that we can come to the table with is our authenticity. And AI can help you be more authentic. So don't ask it. Like I said, don't ask it to write. Ask it to make you better. And so that way you can be authentic. And like I said, this, this woman who started singing these jingles talk about authenticity. That's. That's who she is. And it worked. And, and so that's it. So no, it helps you be more authentic. Allow yourself to be vulnerable.

By the way, there's a new book out, how to be inauthentic. The author claims that being authentic is not going to get you to a level of effectiveness. Did you get if you adopt your behavior to each situation, so you adapt to each situation.

Well, I will, I will challenge that because when you. Everything that you see net today, sales, the salesforce did a study. It said 87% of B2B buyers want us to show up as trusted advisor. Have you ever trusted anybody who was inauthentic? Think about it. The people that you trust are authentic. And so if 87% of buyers expect us to show up as trusted advisors, all you can do is build their trust by being authentic.

And that's been our theme all day. Is about.

I know, I.

You know, it's turning up. And every single one. Which is great.

Exactly. It is. It is wonderful when you have people like you, Sherlyn, and Perry, to, you know, all the other speakers, to teach us the way they see the world. So when we look at the aggregate, we can identify where we need to go, and we can realize where do we stand? And there's so much potential out there. And I think that's the wonderful, noble mission you have, Sherilyn. To lead a million women to a place of greater performance, greater satisfaction, greater happiness, and better.

Absolutely. Absolutely. And thank you again for helping me amplify my voice. I appreciate you, Gearhart. Nice meeting you, Perry.

Nice meeting you, too, Sherry Lynn.