Master Now, Lead Now, Watch Now: A Sales Leader's Playbook for the AI Era

So I wanna start by asking people to drop in the chat the number of AI tools that your team is currently using. So how many AI tools is your team currently using? Is your sales team using 1? Are you using 5? Are you using 15? Let me know, Tricia, what are you seeing? What, what are we, what are we seeing here?

Well, first of all, Marie Diane, Houdon, I believe, It says that you are the best career coach out there. So thank you. Trip says 3.

Okay.

Marty says 3. Amanda says 1.

Okay.

I can't even count how many I'm using.

At least 6.

Yeah.

Okay.

Marie Diane, 2.

Okay. All right.

And I have nightmares about how many my team is using because then the— what gets, what gets delivered is different depending on how you've educated the different tools as well. So when I say, please put it in my voice, I'm educating it constantly. When my team says put it in my voice, it's going to be a different thing.

Right. And I'm going to— Tricia, I'm going to give you a hit, a tip on that too, as we move through here about how to put it in your voice and make it a little simpler. And so the problem— so here's the problem. The world will spend $2.52 trillion on AI in 2026, this year alone. And the problem is, is that 95% of organizations are getting zero ROI when they pilot their AI. Zero. 95% of companies are not seeing a return rate. And so the mistake is not about learning all the tools. And so what I'm gonna talk about in the next 30 minutes is what you can do. I'm gonna give you a framework on what to master now, what to lead now, and what to simply watch. You can't do it all. So I'm gonna show you how to sort it. Okay. So first of all, remember, let's remember how big this number is, Tricia. $252 trillion will be spent on AI in 2026. 95% of companies are not seeing an ROI. Um, email response rates are down 50%. Connection rates are down over 60%. So according to MIT reports, Gartner and Bain, they all come up with the same diagnosis. So often companies are using AI on a broken process. So instead of elevating and amplifying, they're just making the, the, the problem bigger. And so instead of focusing on that, what we wanna do is build judgment. And so the fix isn't more AI, it's knowing where to put it. And, and so that's what I wanna focus on today is the right strategy is judgment. And what does that look like? So here's what we're gonna talk about today is 3 rings. I want you to think about where do you put it? So when a new idea, a salesperson comes to your office, you get an email, one of your team members says, here's a really cool tool. Every day I wake up and somebody's on my calendar with a new tool they want me to see.. And so here's what I do. Do I put it in ring 1, something I need to master? And your master now should be augmenting and automating. Ring 2, your second level, is what you should be leading is agentic AI. And what you should be watching is that agent-to-agent commerce, that robotic-to-agent commerce. And that's where you wanna be. So what I, if you could walk away from here with just one thing, that is think of AI as 3 rings and where are you putting it? Do you need to master it? Is it augmenting and automating? Is it leading or is it watching? I want you to learn how to sort it. So I've talked about AI and I've mentioned the 3 A's. And if you could only do one thing that I want you to stop doing is I want you to just stop clumping together AI all as one because it's 3 things. It is automating. It is rule-based. When this happens, do X. For me, it is when a client is on my calendar and signs up for coaching, they automatically get a welcome package. It has been automated. It's something that used to take me an hour to do. I would send my welcome packet. It is automated. Augmentation is getting better. It is what I talked about last time as amplifying or elevating ourselves with AI. So this is where it assists me. I wrote this email, make it better, frame it, make it more technical, make it more, um, um, center, you know, more focused on current trends, make it, um, augmented and, um, make it, you know, for a driver or an analytic or an expressive. That's what augmentation is. And then agentic AI is when you have AI operating on its own, book 3 qualified appointments. And the reason is, is because according to the research by, you know, AI SDRs are up 284% this year. We all know SDRs and BDRs are out of a job. And by 2028, sales, B2B sales leaders will have 10 agents that they're working with. So that's something that you want to focus on is you want to start building these agents around your sales leaders. And that's where the focus, where we want to focus. So remember, it's moving from, you know, agents are using, you're using 1 or 2 agents right now. By 2028, as a B2B salesperson, every one of them will be using 10 agents to do something specifically towards a goal. All right. Now that we know when we're talking about AI, I'm going to be talking about automation. Augmentation, and Agentic. Let's talk about ring number 1. What do I want you to master now? Again, you don't have to learn it all, just which ring to put it in. So the first one is, what do I want you to master? Every single sales leader should be automating a task. If you haven't automated a task, that's my challenge. I want you to automate a task this week. And if you have, I want you to find another one to automate. Pick one item from your sales funnel. One area that you have that is, that your, your team is repeating or you're repeating. It can be research and call. Tell it to write an AI brief before every buyer. Throw in their LinkedIn Live, I'm saying, show them their LinkedIn profile, throw in your agenda, your product, and say, put this brief together before the meeting. And you should have an, a way to automate that, that it just pulls that and does it for you. It could be emails, it could be proposals. For me, I have an automated system set up so that it writes my proposals for me. And it can be any busy work that you're doing, data entry, anything that's busy that you're doing over and over again. And remember, judgment is important. So know when the human is, is important, and your human has to be able to override. So I want you to take your most repeated task, the thing you hate to do that has to be done over and over again, and automate it. And this is how you do it. So I used to tell people the best way to learn AI is once a day and take 15 minutes in the morning and go in. And my favorite prompt was, help me do this better. Help me do this simpler. What am I missing? Now I tell it, how do I automate or augment this? And then I tell it what I want to do. And I'll share with you in a second a story of what I've done recently that just blew me away.. And so, um, one, um, I want you to just drop one word in the chat for me. And if you think about one area that is repetitive that you could focus on that you would automate this week, what is that? Let me just, um, um, just drop that in the chat for me. Tricia, what are you saying? What's one word?

One word. Everybody's getting, everybody's thinking.

Okay. Um, that would be what is repetitive that if you could automate one thing, what would you automate?

One thing that we would automate that's, you know, one thing I just got today is everything that's in my calendar is now in a preview at the end of the day and also set up for the next morning and the prep notes I need because that's every day.

Cool. That's, that's a great one. Thank you.

Thank you, Jerry. Jerry is saying scheduling.

Okay.

That's, that's a great one. And so you would be surprised if you, whatever AI told you, you using. If you just every morning say, how do I automate scheduling? How can I automate scheduling? And just, and just work on this and build on this until it's automated. It will happen. And, and, and so instead of just saying—

meeting is another one.

What's another one?

Prospecting.

Prospecting.

Slide deck for QBRs. Email scheduling.

So slide decks are an easy one. There's so many tools out there that will automate slide decks. It is unbelievable. I, you know, I build my slides now in about 2 minutes. My, my AI tool build these slides for me in 2 minutes. So, and it's all branded and I, I didn't have to touch them. So absolutely, that's not mastered that yet.

I get the, like, you know, this is the slide content and then I get ugly slides and need to work on that.

Okay. And I'm, so I'm just gonna share with you, Tricia, I'm just gonna stop here for a second and share with you one tip. And this goes back to what you write. So I tell people, create a brief. So I took 20 documents that I had written and blogs prior to AI, dropped it into AI, and I said, write out my guidelines for how I write, how I speak. Now, what are the top 100 words that AI use that I don't use? Now put these in, in the rules. What are the top 20 phrases that AI uses that I don't phrase? Now put these in here. I also added, I told her to add do not ever write with the African American vernacular because I never say yo sis. And a couple times AI had said this, started a letter like that, and I was like, I never speak that way. And so I have a 9-page document that talks about here are Sherrilyn's rules for when she writes. So I don't have to prompt. I just load that tool up. I just load that Word document up and it automatically does that for my posts, for my emails, for my articles, for my blog. It knows that I have one for training. So I've taken all the trainings that I did, all of my philosophies, everything that I think is important for training and adult learning. And I built a 12-page training philosophy. And now that's a document. So when I'm building out my slides, when I'm building out a training, I upload that first and then I just dictate into Word, here's what I want this training to do. And literally that's what I did. And it built this deck for me. And so I said, I have a, you know, Sales 3.0 Masterclass Assistant training. It's 30 minutes. It has my guidelines and here's the 3 things that I wanna teach and it will do that for you. So build those guides. It does take a little time to build 'em and once you build them and they're built right, you're no longer prompting like a pro. And I used to teach people how to prompt like a pro. No more. Build a couple guides. Build a prospecting guide. Build your writing guide. Build your training guide. Whatever guide you have, take the time to build that document. Um, tweak it, see what you missed. Where the gaps is, try it until it works and it will work. Does that work for you?

I love it. This is the canonical, canonical document. It's sometimes referred to as, right, the essentially the Bible of your presence or your brand or your IP, whatever it might be.

Yeah. And so, and so take the time to do that. We used to spend— used to— I used to tell people, learn how to prompt like a pro, do this. Do this, do this. I don't prompt anymore. I just attach it and say, build me a training deck. Write me a blog, or here's what I'm writing about. Now fix this blog. And it automatically, and it will come back and say, these are your rules. You just have violated them. Which way do you want me to go? So just, just a thought for you. Okay. So that's how, that's how you automate is creating a document that you can use and keep asking it to automate. So that's where we want to go. And here's my Automate. Okay. So the next one is that the next one is lead. What do you want to lead on? And this is a big one. If you have never been an agent, build an agent. I want you to build your first agent. It can be, it can be scary. But it literally doesn't take very long, usually about 10 or 15 minutes to build an agent. The basics are there. Every AI tool out there will build an agent for you. And if you have built an agent, I'm going to challenge you to build another one. And so I want you to run at least one additional agent for your team this month. Because again, go-to-market engineers is the future of where AI sales roles are. There have been multiple papers written about it and articles. I'm sure you've had people talk about it. They're saying that a go-to-market engineer will be— will earn somewhere between $200,000 and $300,000. And what they will be doing is this is your B2B salesperson, person, and they will have 10 agents. So if you're going to lead, then lead by adding agents to your team. And if you build one a month or build one every 6 months, by 2028 you will have had— you will have your 10 agents that your team will need. Give it a real goal, you know, say, you know, book 3 qualified demos and work with that agent until they can do that. Send out 100 emails. I, I guess that I know, I know people who build agents that, that work on LinkedIn, or they sent, they build agents that work with their calendar or build agents. Um, you know, about a year and a half ago, we were talking about teaching salespeople to code. It's now click. You don't have to code anything. All you have to do is click. So build agents, get your team building agents. You got really smart people on your team. Ask them to spend 1 hour a month and come back and build an agent and share it with you. Make sure you design, you design a handoff. So is that where the agent starts and stops? You're not replacing everybody, you're just replacing one, one small section or one small task. Make sure that you look at where the human layer comes in. Are you making sure that you're maintaining that trust and that relationship? Because that's one thing that AI will never replace is trust. And again, a lot of agents fail because you have bad data or weak personalization, or it's already a broken process. You can't fix a process with an AI agent. Once you have a process that is working, you can build an agent to run it. And remember to coach it like a rep, set expectations, keep giving it feedback, making it better. And if it keeps underperforming, scrap it and start over again. And most importantly, which is something that so many sales leaders forget, is you have to score this just like you're scoring your, your, your reps. What is the revenue? What is the ROI? Is it saving time? Is it driving more leads? Are you getting an ROI on it? If you're not, scrap it and start again. So the second ring that I want you to do is lead with an agent. And the third ring that's important is, um, what do you want to watch? And so what's coming down the pipeline, and this is robotics and agent-to-agent commerce, and I want you to be literate in this. I want you to be aware of it. But this is where you have to have some discipline with restraint. I'm challenging my clients and my students to just pause with this. You don't want to be the first one. You don't want to be an early adopter with this one. This is very, very early. And so what you want to do is you want to watch it. You know, they say by 2028, um, that 90% of all B2B sales, over $15 trillion, will be happening between agents. We're not there yet. And so, um, what you want to do is I want you to read at least one report a quarter. This quarter, I recommend the Bain report. It's an incredible report about, um, B2B sales and, and what's coming with robotics. And, and so keep up on what's going. So read a report, know who's going to be, who's, who's leading the field. Are you, where are your clients in this? And, and just understand this. And when somebody comes to you and they're saying, oh, I want you to buy this and you want to be first to market with this, I think we're a little too early. It is coming. But right now, this is where I just want you to watch what's going on. And so the 3 things that we talked about again is what to master, which is automation and augmentation. What you want to lead is agentic AI. And what you want to watch is that e-commerce of agent to agent or robot to agent. And so a meta skill or a most important critical skill for 2026 is judgment. This is the ability to sit between where, where AI is, whether it's augmenting, agentic, or automating, and the human. And this is a human skill. And so you have to keep coaching your team on that and keep building this. AI will never replace the trust. AI will never replace the caring and the curiosity. That's where we have to keep building and have to keep growing. And you can't ignore it. And it's a skill that you have to keep coaching with your team. Now, I'm going to use myself as a use case here, and I promise to share with you a little bit about what I do. So every morning I was spending 15 minutes saying, how do I reach— I'm on a mission to reach 1 million women by 2030. How do I reach 1 million women? How do I become a better coach? And one of the things that I used to do is every time a client signed up, I would go and pull— I have 6 assessments that they would get, and I'd pull my 6 assessments, write a nice intro drove to them, send that to them. That took me about 30 minutes. When the assessments would come in, I would review them. And so during one of my sessions, I was saying, okay, one of my clients asked me, Sheryllyn, is there a way I can get this electronically? So I asked my AI tool to help me build out a prompt so I could drop this into, um, SurveyMonkey, one of the survey tools. And it said, why would you do that? Why wouldn't you just augment this and automate this? And I was like, okay, what would that look like? And it said, well, in 5 minutes we can do this. And literally today I have a website with 6 of my tools, 6 of my assessments on it. It took my AI tool probably 7 minutes to build it. The clients go in, they select their assessments, they complete them, they get a report right there, um, with where their gaps are. I get a report and I was like, wow, this is crazy. This is the best thing. And then it said, well, Sheryllyn, you're coaching and training this. Why don't you take it to level 2? Where's your agent? Why don't you build an agent to let them run the whole flow that I approve? So then I built an agent. So now when that comes in, it goes into an agent and the agent reads it, um, writes the assessments, writes the recommendation, and in my inbox lands, here is their coaching strategy and here's where you need to work with them. And it, it just blew me away that this is what I do. And so I, so I went from a 15-minute session to, I also do a 1-hour AI kind of mastermind that I do once a week. And this week, this is what I built. And, and so my challenge comes from real use cases. My challenge to everybody listening is, Yes, AI is moving fast. And if you just stop and say, is this ring one? Is this something I can automate or augment like I did when I built the website for my assessments? Is this something that I can build an agent for where agent can run the whole process flow? People still want me as a coach. They still come to me for my expertise. But all the pre-work of before they come, That wasn't creating value for me. And my clients actually get more value out of these reports, um, than they were getting before, because they were just sending them to me and they did not get any insights until I sent them to them. So that is, um, I think that's what I want to get across, is start thinking about 3 rings. What can I master? What can I augment? And what can I automate? Where can I build an agent is the second ring. And what do I watch? Because we're going to agent to agent or robot to agent buying commerce. And just real quickly, um, here is a quick 5-question purchase checklist for you. And again, um, you're probably getting emails and inmail messages every single day and you wonder, should I do this? Is this cutting edge? Where is this? And so the first question I want you to ask is, where is this in the ring? Is this something I wanna master? Is this something I wanna lead? Or is this something I just wanna watch? Remember, don't ever treat what you wanna watch like lead one. You don't wanna put all your energy into it. The second one is, what process is it touching? Is it touching a process that's already broken that I need to fix? Or is it a process that we've mastered and we just need to automate it or augment it? Where, where's the outcome? Is this gonna make us more money? Is this gonna drive ROI? Is this gonna reduce our operational cost? If it's not making you money, saving you money, or making you more money, why are you doing it? And the fourth one, which I think is so critical that I see that the best leaders ask, is they stop and say, where does this touch the human skill? How is this going to touch or impact the people on my team? Because it will. And if you say that it doesn't, you're not asking the right question. You wanna ask, what happens to humans when I do this? And if you can't answer that, ask AI. Just, I seriously, I, I always say, what happens to humans if I automate my assessments? How does this impact them? What happens to humans if they get their own report when they do their assessment versus waiting for me to send it? And, and, and is this good? Is this better for them or is this worse for them? And, and how does this impact them? The other question that I always ask is, how can I make this better? What am I missing? What, what am I missing by automating my assessments? And so always come back to how it impacts the human. So I wanna wrap up here by summarizing again the 3 assignments for that I'd like people to walk away from. The first one is automate 1 task this week. This month, run 1 agent, and this quarter, read 1 report and buy nothing. Just read 1 report. If you, um, again, you wanna master, lead, and watch and teach judgment because it's so important. For all 3. If you want a handout that summarizes this, connect with me on LinkedIn and DM me on LinkedIn and I will send it to you. Also, I publish a newsletter on LinkedIn every month and it's always, it's about AI and it's about being AI fluent, trust-led, and unignorable.

Incredible, Sherrilyn. We do have a question in the chat. And so Marie Diane Huden asked the question. She gave an example, but it's not the actual technology. So just as an example though, now that she's taken training on GTM AI, including Zapier, but not specifically related to Zapier, just as an example, how do I position this in an interview with a company that is not advanced in AI?

So I, so I, what I tell all my clients is you wanna lead, you wanna help companies figure out where their vision is. So when you come to the table and say, I'm looking at the 3 rings and here's, here's things that I've automated, here's things that I've augmented, here's how I build agents, um, and I, and here's things that I'm watching, I'd love to be part of your team and help you guys identify what those 3 rings are. So many companies, like I said, they're spending money on AI and they're not getting an ROI. They would love a salesperson who comes with some, some thought leadership. So position yourself as a subject matter expert in thought leadership.

Change management from there is interesting, isn't it? I have a friend who, uh, is just taking over at a very large brand and as an AI leader, and she's very excited, and she's been told she's going to have a lot, a lot of leeway. So I'm curious, she gets into the role, whether she actually has any leeway little, a lot. I don't know. It'll be, it'll be fascinating to see because that is change management at its finest.

It is.

One of the words that, uh, I— one of the words that I've added to change management, I tell people, is curiosity. Curiosity and judgment are the two critical skills for 2026. And as long as you come from approach of curiosity, that is where— that's where the change comes, is just say, I'm curious. I just tried this. I was failed. I was curious. I was successful. Like I said, I tried the assessment and it worked. It just blew me away. All I was was curious. Love that.

Okay, Gerhard, where are you going to go with this?

I think it's very challenging to elevate AI to a true partner. And you have shown us, Sherylynne, how to have AI speak in your voice by giving them prompts. That are intelligent where you explain what to say, what not to say, what words to use, what not to use, how long the sentences should be. I've been through the same thing and, you know, I have 6 AI agents and everyone does something a little bit different and they're almost like personalities that They keep forgetting things.

So once you create that document, I keep re-uploading it. Okay, it's in the memory. I know it's there, but every time I do it, I re-upload it. So it's right there, right on front. And I use the same document across all of my tools, all of my agents. And that's where I get that consistency.

AI can be incredibly dumb when you have like 6 or 7 conversations, then you have to remind them. You know, go back to conversation number 3. You have all the— oh, can you re-upload the document?

I just do it. I just, I automatically, I always start with my first thing I start with the prompt is I always use my document.

That's awesome.

Thank you.

Well, thank you for enlightening us, sharing your practical tips, and I encourage everybody to follow Sherylynne on LinkedIn, but also read her newsletters. Uh, you always are practical and ao ai focused. Thank you.

Thank you. Thank you for having me on. Tricia, it's great seeing you. Great seeing you again, Gerhard.