I was sending more emails, doing better research, and showing up more prepared for meetings. I was getting through my week faster. For most of the year, I was making the same amount of money.
That bothered me. I could point to plenty of things AI had made easier. I had a harder time pointing to a deal I’d won because of it. Once I started looking at where it changed an actual sales decision, I found three places I wanted it out of my way, three places I wanted more of it, and one place I wish I’d thought to use it sooner.
Selling with AI reminds me of what happened when I got LinkedIn. I’m old enough to remember selling without it. If you already knew how to build a network, LinkedIn gave you more ways to find people, understand how they were connected, and stay in touch. The license still left you with the job of giving somebody a reason to know you. AI gives you a similar opportunity, with a much bigger temptation to let the tool do the part you ought to be doing yourself.
When you ask AI to write a prospecting email, you can get a polished paragraph about almost anybody. Imagine getting one that opens with “congratulations on your company’s recent expansion!”, then pivots to the challenges of scaling, and ends by asking for fifteen minutes. Every sentence makes sense. The whole thing could have been sent to the person who runs the company across the street.
I want to know why I’m writing to this particular person right now. If a prospect has announced a second distribution center, I can use AI to help find the announcement and get my bearings. Then I read what the company actually said. Maybe the new site is taking over a product line from the old one. That gives me a specific reason to write, assuming I have something relevant to say about that kind of move. The thinking that happens between finding the announcement and writing the first sentence is a large part of the work.
Selling with AI often looks like sending ten thousand versions of a weak email gives ten thousand people a chance to decide you had very little reason to write. I’d like email to remain a place where a good salesperson can get somebody’s attention. That begins with taking responsibility for the words that arrive under your name.
An AI coach can check whether you answered a question. Suppose a buyer asked about implementation and you spent two minutes talking about support. There’s some value in having that pointed out. I’m more interested in what happened just before the question, and what you understood the buyer to be asking.
Maybe they’d already told you that the last rollout cost their team three weekends. When they ask, “How long does implementation take?” they may be trying to work out whose weekends are about to disappear. A tidy answer about the number of weeks could score well and leave the buyer with the same worry. A coach who catches that moment can help you practice a better response. Start by finding out which part of the rollout fell on their team last time.
I’d want to know who designed the coaching, what they taught the system to look for, and whether its feedback made a salesperson better in the next conversation. I’ve seen enough feedback that sounds reasonable on paper. Reasonable on paper is a fairly low bar for someone you’re trusting to change how you sell.
Give AI a transcript and a qualification checklist and it can find the places where the two appear to line up. The buyer mentioned Bob. Bob controls the budget. There’s your economic buyer in MEDDPICC. Put a check in the box.
Now tell me what Bob has DONE. Has he joined a meeting? Asked to see the numbers? Told your contact to bring another vendor into the evaluation? Those are three different deals with the same name in the same box. Even “Bob approved it” needs a little attention. He may have approved the project in principle while somebody else still has to release the money.
I could buy a cookbook, make my own pasta, and follow every instruction for lasagna. I’d have lasagna at the end. (I’d also have a kitchen I’d rather you didn’t see.) A good chef knows how the sauce ought to taste before it goes in the oven and what to do if it tastes wrong. That judgment comes from knowing what’s happening as you work. In a deal review, I want to hear what the buyer did, what we learned from it, and where we’re still guessing. That’s how I decide what to do next.
This is where selling with AI has made me better prepared in a way I can feel in a live conversation. I can get oriented on a competitor’s offering, positioning, customers, and approach to onboarding. I can also find companies I hadn’t realized a buyer might consider. Then I can go back to the material the companies actually published and see what they say for themselves.
Say a buyer brings up a competitor that emphasizes getting a team up and running quickly. If I know how that offer is described, I can ask what the buyer expects to have running in the first month. One buyer might mean a pilot for six people. Another might mean a complete rollout across four locations. That’s a far better conversation than trying to convince them we’re faster before either of us has said what “fast” means.
I used to think I was pretty good at talking about my competition. I’m much less likely now to get caught flat-footed by a name or an offering I should recognize. The payoff is that I can stay curious when the competitor comes up. I have enough context to ask a decent question without scrambling to defend my own company.
I also use AI as a mirror. I’ll approach my own company as if I’m a buyer coming into the category cold. I want to see what I might learn about our offer, which companies I might put alongside us, and where I might come away with the wrong idea. I know how I talk about my company. It takes a little more effort to see what somebody else can piece together before we’ve ever spoken.
Imagine the public material a buyer finds gives them the impression that we only work with large enterprise teams. If I see where that impression came from, I can understand why a smaller team might show up expecting an offer built for somebody else. I can ask how their team is organized and what kind of help they’re looking for. I can also check whether our materials leave a fair impression of who we serve.
The answer I get from AI is one view of what somebody could find. I still have to ask the person in front of me what they’ve seen and how they’re thinking about the decision. The exercise gives me a better shot at understanding the question behind the question when they finally ask it.
Before a customer meeting, I use AI to get deeper into their industry and their competitors. I want to know what’s changing around them, where competitors are putting their attention, and which developments might touch the project we’re discussing. Then I can walk in with questions that begin in their world.
Suppose you sell to a distributor whose competitors are advertising later order cutoffs. The customer wants to talk about reducing errors in the warehouse. Those two facts may be connected. You could ask what happens to the last wave of orders when the warehouse gets busy. Maybe the buyer tells you they’re looking at later cutoffs themselves and are worried about squeezing another hour of orders through the same operation. You can now talk about what the error rate means to the business, with the buyer supplying the part you could never have learned from the outside.
Research earns its place when it makes you more curious. There’s little pleasure in listening to a salesperson recite a summary of your own industry. A salesperson who notices a change and asks how it’s playing out for your team can be worth talking to. Leave enough room for the customer to tell you where your research sent you in the wrong direction.
The biggest change for me has been using AI to track deal velocity. In deals that are moving toward a close, I often see the space between buyer actions shrink. A buyer takes a meeting. A few days later they bring in a colleague. Then the questions about the contract start coming in closer together. In a deal that’s losing steam, the second meeting gets pushed, the next email takes longer to arrive, and eventually you’re looking at a calendar invite that used to have a date.
When I’m working two deals, I can usually feel that change. When I’m working a lot of opportunities, my attention goes to whatever happened most recently. A deal can be slowing down for weeks while I’m still carrying around the impression from a terrific first meeting.
I tag my customer meetings and emails by account and log relevant calls. Then I have AI look across those records each week and show me a heat map based on the time between customer actions. An email they send counts. A call they make counts. A meeting they agree to counts. The follow-up emails I sent while waiting for them to respond are my activity. If I count those, I can make a stalled deal look wonderfully busy all by myself.
Imagine a buyer who used to engage every week and has now gone two weeks between meaningful interactions, then three. The change is worth looking into. They may have told you their finance lead is away, in which case the gap makes sense. Or you may realize you’ve been waiting for an introduction that nobody actually agreed to make. A red mark on a heat map gets my attention. The details of the deal tell me whether to press for a decision, reset the next step, or move on.
The green marks deserve the same attention. If a buyer has brought in a new stakeholder and sent contract questions in the same week, I want to understand what’s driving the pace. Maybe there’s a deadline I can help them meet. I can get the right people on my side involved while the buyer is already doing work on theirs.
That weekly view has helped me close some deals sooner and get out of others sooner. Both give me room to work more opportunities. That’s the first place where I could look at what AI was doing, point to a decision I made because of it, and see how that decision affected what I sold. I still appreciate getting through my inbox faster. I’m a lot more interested in noticing that a buyer has started calling me twice a week.
Happy Selling!®, Jeff