Almost Timely News: ๐️ How to Improve Sales Skills with Generative AI (2025-11-02)
Almost Timely News: 🗞️ How to Improve Sales Skills with Generative AI (2025-11-02)the leads aren't weak
Almost Timely News: 🗞️ How to Improve Sales Skills with Generative AI (2025-11-02) :: View in Browser
The Big Plug👉 Watch my MAICON 2025 session, From Text to Video in Seconds, a session on AI video generation! Content Authenticity Statement100% of this week’s newsletter was generated by me, the human. You will see bountiful AI outputs in the video, especially in the implementation. Learn why this kind of disclosure is a good idea and might be required for anyone doing business in any capacity with the EU in the near future. Watch This Newsletter On YouTube 📺 Click here for the video 📺 version of this newsletter on YouTube » Click here for an MP3 audio 🎧 only version » What’s On My Mind: How to Improve Sales Skills with Generative AIThis week, let’s talk about how to dramatically improve your selling skills with generative AI. Large language models like the ones that power ChatGPT are masters of language, with encyclopedic knowledge of nearly every way language can be used. In some cases, they’re dangerously persuasive, convincing or reinforcing beliefs even in the absence of any evidence. We can put those capabilities to productive use by helping us become better at the profession of selling. Like I say all the time, AI takes the good and makes it better, takes the bad and makes it worse, so before we dig into selling skills, we should briefly touch on AI sales ethics. As with any use of AI, ethics revolves around how we use the technology. It is largely amoral - neither good nor evil. How we apply it, how we use it, is what determines an ethical or unethical outcome. If you’re selling a product or service that genuinely helps and benefits people, AI can help you sell it faster and better. If you’re selling a product or service that’s an outright scam, AI can help you sell that better and faster, too. The key message here is that you have to have your ethics sorted out before you use AI to become better at selling what you already sell. Because if what you’re selling or the way your company does business is unethical, AI won’t fix that. Part 1 : Understanding Who You Sell ToThink through all the ways you’ve been taught to sell. For a lot of sales professionals, you’re often taught all these different frameworks and selling methods. You’ve heard everything from “grab them by the tie and choke them till they buy” to a sea of acronyms for different sales methods. But what almost every sales training does wrong is ignore the customer or pay modest lip service to the customer. Katie Robbert pointed this out recently in a conversation about sales frameworks, which we cover in an upcoming episode of the Trust Insights podcast, In-Ear Insights.. Who are we selling to? What do they want? Generally speaking, they never want to just give us money. They never want to just spend money for no reason. They want a solution to a problem they have, and they want us to make their pain go away. But if we don’t understand them, we can’t understand their point of view. This is where customer profiling comes in. Who are your customers today, especially your best customers? Who do you want to have as a customer? Do you know? Perhaps you already have something like an ideal customer profile. Is it backed by data, or just by the opinion of folks at your company? Is it realistic? Sure, Trust Insights would enjoy having Apple as a client, or Walmart. Is that realistic and the best use of time for our sales efforts? Probably not. Here’s a simple hack to get started validating your existing customer profiles. On the social media platform that is the best fit for your audience, find and download the 5 social media profiles of either your ideal customer decision makers (if you’re B2B) or your ideal buyer (if you’re B2C). you’re on LinkedIn, chances are you’re doing B2B. If you’re spending a lot of your time on Instagram, chances are B2C. Get your data from the place where most of your customers hang out. Use a prompt like this with the smartest AI model you have access to:
Take the results of the analysis, discuss, perhaps do another iteration with more data, and then update your ideal customer profiles accordingly. Most important, make sure you have it stored in some machine-readable format (like plain text) that you can use with AI models going forward. You’re going to need it. Shameless plug: if you don’t have an ideal customer profile to start with, Trust Insights builds those for clients. Learn more here. Part 2 : Understanding What You SellNow that you know who you’re selling to, it’s time to audit what you sell. Here’s where the rubber meets the road - what you think you sell and what you actually sell are probably different. More important, what you think you sell and what your customer thinks you sell are probably different, and that difference can be what wins or loses the buyer. So here’s what you’ll do. Using the Deep Research tool of your choice (Gemini, ChatGPT, Copilot Research Agent, Claude, etc.), you’ll commission a Deep Research project on your own company. Here’s a starting prompt to use:
You’ll notice that we’re not working with the ideal customer profile yet. That’s by design. You will also notice that in that prompt I kept saying over and over again what the company says because we want to try on what your company is saying, not what the AI model thinks, but literally what does the company say about your products and services. Next, take the results of your Deep Research tool and… this part’s going to hurt, probably. Using the smartest AI model you have, have it compare the two documents.
You’ll now have a roadmap that explains how well you meet the buyer’s needs. “But product marketing isn’t a sales job” you’ll hear from the various stakeholders in your organization. It doesn’t matter whose job it is. If the sales team is trying to sell something that the buyer doesn’t want, you’re wasting everyone’s time. Fix your product market fit first before worrying about the sales process. Part 3 : Understanding How You SellAt long last, we’re finally ready to get to the topic of this newsletter. As convoluted as the road has been to get here, it’s vitally important. If we don’t know who we’re selling to, and we don’t know why anyone would buy from us, no amount of sales training or methodology is going to make a lick of difference in improving our sales beyond minor incremental improvements. I’ll give you an example. Once upon a time I worked for a software company. We had a product that was twice the price and half the quality of our top competitor. Literally no one wanted our product because in a head to head with our competition, we lost every time. Instead of fixing the product, pricing, or better understanding our customer, our CEO just demanded more leads to give to sales, and sales kept closing leads at a 1% closing rate. Who was at fault? Ultimately, the CEO, but definitely the product team because what we had for sale simply wasn’t competitive. The only deals the sales team won were those customers who hadn’t had the presence of mind to Google for our competitors. So you need to absolutely nail parts 1 and 2 first. Once you have those locked in, then you can talk about sales process. There are tons and tons of sales frameworks, more than you can shake a stick at. Different sales frameworks have different purposes and work in different situations. Your first step, then, is to ask the AI of your choice to research and evaluate sales frameworks. In the Deep Research tool of your choice, use the following starter prompt in addition to your complete ICP and your product market fit documents generated from parts 1 and 2.
What you’ll end up with is a prescriptive guide of each framework and how it applies to you. Read through it. Once you understand and evaluate whether a given framework is the best fit for your company and your customer, take that portion of the report and save it as a knowledge block, a piece of reusable text. Now we get to the golden moment. We take that knowledge block, we take transcripts, emails, phone calls, any form of communication we have as sales professionals with actual customers, and we put those plus our knowledge block into the smartest AI we have, and we prompt in a new chat:
With this report, you should have a roadmap of what you need to do, why you need to do it, and how to get it done. Part 4: Wrapping UpThis guide is to help you sell better, as an organization, as a department, and as an individual. If you’re selling to the wrong people, or you’re selling the wrong thing, sales will continue to be below expectations. If you have a solid foundation, and you have the data, you can use generative AI to find the best fitting sales techniques for your specific situation, evaluate how well you perform them, and give you concrete performance tools to become a best-selling professional. Give these tools a try, and see how they improve your sales performance. How Was This Issue?Rate this week’s newsletter issue with a single click/tap. Your feedback over time helps me figure out what content to create for you. Here’s The UnsubscribeIt took me a while to find a convenient way to link it up, but here’s how to get to the unsubscribe. If you don’t see anything, here’s the text link to copy and paste: https://almosttimely.substack.com/action/disable_email Share With a Friend or ColleagueIf you enjoy this newsletter and want to share it with a friend/colleague, please do. Send this URL to your friend/colleague: https://www.christopherspenn.com/newsletter For enrolled subscribers on Substack, there are referral rewards if you refer 100, 200, or 300 other readers. Visit the Leaderboard here. Advertisement: The Unofficial LinkedIn Algorithm GuideIf you’re wondering whether the LinkedIn ‘algorithm’ has changed, the entire system has changed. I refreshed the Trust Insights Unofficial LinkedIn Algorithm Guide with the latest technical papers, blog posts, and data from LinkedIn Engineering. The big news is that not only has the system changed since our last version of the paper (back in May), it’s changed MASSIVELY. It behaves very differently now because there’s all new technology under the hood that’s very clever but focuses much more heavily on relevance than recency, courtesy of a custom-tuned LLM under the hood. In the updated guide, you’ll learn what the system is, how it works, and most important, what you should do with your profile, content, and engagement to align with the technical aspects of the system, derived from LinkedIn’s own engineering content. 👉 Here’s where to get it, free of financial cost (but with a form fill) ICYMI: In Case You Missed ItHere’s content from the last week in case things fell through the cracks:
On The TubesHere’s what debuted on my YouTube channel this week: Skill Up With ClassesThese are just a few of the classes I have available over at the Trust Insights website that you can take. PremiumFree
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There are also private events that aren’t open to the public. If you’re an event organizer, let me help your event shine. Visit my speaking page for more details. Can’t be at an event? Stop by my private Slack group instead, Analytics for Marketers. Required DisclosuresEvents with links have purchased sponsorships in this newsletter and as a result, I receive direct financial compensation for promoting them. Advertisements in this newsletter have paid to be promoted, and as a result, I receive direct financial compensation for promoting them. My company, Trust Insights, maintains business partnerships with companies including, but not limited to, IBM, Cisco Systems, Amazon, Talkwalker, MarketingProfs, MarketMuse, Agorapulse, Hubspot, Informa, Demandbase, The Marketing AI Institute, and others. While links shared from partners are not explicit endorsements, nor do they directly financially benefit Trust Insights, a commercial relationship exists for which Trust Insights may receive indirect financial benefit, and thus I may receive indirect financial benefit from them as well. Thank YouThanks for subscribing and reading this far. I appreciate it. As always, thank you for your support, your attention, and your kindness. See you next week, Christopher S. Penn Invite your friends and earn rewardsIf you enjoy Almost Timely Newsletter, share it with your friends and earn rewards when they subscribe.
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