How to Start Using AI in Sales (Ask Jeb)

You know AI is transforming sales, everyone's talking about it, but you're still staring at ChatGPT like it's some mysterious black box, wondering what magical question you should type in first. That's the reality for most salespeople even now. They know they need to embrace AI, they've heard the success stories, but they're paralyzed by the complexity and overwhelmed by the options. If you're nodding your head right now, you're not alone. The biggest barrier to AI adoption isn't technical—it's mental. Salespeople are asking the wrong question entirely. The Wrong Question That's Keeping You Stuck Most people approach AI like it's some mystical oracle they need to appease with the perfect question. They think there's some secret prompt that will unlock AI's full potential, like finding the right combination to a safe. They're wrong. There is no perfect first question for AI. The real problem isn't what to ask—it's how you're thinking about the problem. Instead of asking "What should I ask AI?" you need to flip the script entirely. The Mental Shift That Changes Everything Twenty minutes before recording our latest Ask Jeb episode, I was working on a new training program for Sales Gravy University. I had a slide deck and workbook that needed proofreading, and my first instinct was to think, "Who can I get to proofread this thing?" That's how most of us think: "How can someone else do this?" or "How can I get this done?" But I caught myself and asked a different question: "How can AI do this?" I uploaded the slide deck to AI and asked it to proofread for me. Fifteen seconds later, I had a response—not perfect, but a starting point. I refined my prompt, asking for typos organized slide by slide, and boom—seven minutes later, the entire deck was cleaned up. What would have taken me 45 minutes and still resulted in missed errors was done in minutes, with better accuracy than I could achieve manually. Why You're Already Qualified to Use AI Will Frattini from ZoomInfo pointed out that "You already know how to use AI. You've been doing it for years." If you've ever asked Siri for directions, told Alexa to turn up the music, or typed a question into Google—congratulations, you've been using AI. The only difference now is the sophistication and power of what's available. The barrier isn't technical competency. It's the mental block of overthinking it. You don't need to understand large language models or machine learning algorithms. You just need to ask a question and hit enter. That's it. That's the profound simplicity everyone's missing. Think Like a Conductor, Not a Solo Act Stop thinking of yourself as someone who needs to learn AI. Start thinking of yourself as a conductor standing in front of a symphony orchestra. You've got Claude for certain tasks, ChatGPT for others, ZoomInfo Copilot for prospecting intelligence, Gemini for research—each AI is like a different instrument in your orchestra. Your job isn't to play every instrument; it's to conduct them all to create something beautiful. The apex predators in sales aren't going to be the people who master one AI tool. They're going to be the conductors who know when to use which AI for maximum impact, iterating and refining until they get exactly what they need. This means developing your prospecting methodology becomes even more critical. You need to know what outcome you're trying to achieve before you can direct your AI orchestra to help you get there. Your Practical Starting Point Stop overthinking this. Here's your action plan: Step 1: Pick one AI tool you have access to right now. Your company probably already provides something. If not, start with ChatGPT, Claude, or any of the major platforms. Step 2: Identify one recurring task that eats up your time. Email templates, research, call preparation—anything that's necessary but not your highest value activity. Step 3: Ask the AI how it can help with that specific task.