I’m headed to the IMTS show this week in Chicago. If you’re going to be there, let’s see if we can’t connect.

A few weeks ago, I read a great piece by David Brock. His opening line: “AI is better than your SDRs. That's true. And it's beside the point.”

You should read it. I love the points he makes about the work we should absolutely offload to AI, and the bigger one about how sales roles were broken before AI even got involved. We segmented knowledge work into interchangeable parts and measured what was easy to count instead of what actually mattered.

Afterward, Dave and I sat down and talked about it. He encouraged me to add my own thoughts to the piece, and to “feel free to plagiarize his work with his full blessing.”

The last part made me smile. How could I not accept such a generous offer?

I’m not here to plagiarize, but with a nod to the thoughtful conversation he started, I’d like to take it a step further. Dave argues, and I agree, that selling requires an apprenticeship, and we’ve been measuring the wrong things. I believe we need to think a lot more about how outsourcing to AI hurts a seller’s development, and how that hurts our customers.

I started my career selling medical devices. My most complex sales involved total joint replacements with the aid of a laser-guided navigation system (sound cool? It was).

There was a ton of inertia to overcome, close relationships to work around, and multiple stakeholders with different buying motives and political pressures. Oh, and everybody’s implants were essentially identical… They were made of the same materials, and some were almost indistinguishable on X-ray. Sound familiar?

I’d start conversations by asking questions, but most of them fell pretty flat. What do you think about this new technology? Could you leverage it to market and build your practice? What do you love most about your current implant?

They were usually intrigued by the system, but not willing to switch because of the learning curve and not willing to invest in the practice's growth. The favorite part about their current system was almost always the rep and the company behind them.

Surface-level questions led to surface-level answers. I was technically “doing it right,” but it wasn’t getting me anywhere. I really made headway when I started talking about surgery, and what we were learning in the OR with this new system that had been forgotten by most surgeons.

“Doc, ever wonder why you externally rotate your femoral component by 3 degrees?”“Yeah, it’s to help the patella track through knee flexion.”
_“Most people say that. It’s actually to balance your flexion gaps. Ever wonder why sometimes that’s too much or not enough? It varies by patient. Dr. Insall wrote about it in the 70s.” _

I earned a lot of credibility with this gambit, and there was no way I was getting there if I hadn’t done the earlier work. I earned the right to ask those kinds of questions by putting in the time and effort before I asked them.

More significantly, I had to fall flat with my earlier efforts to understand that I needed to get a little edgier. If I wanted to be someone worth talking to, I had to have something worth talking about. The questions that worked weren’t soft conversation-openers. They made the impression that I was someone who would make them think differently.

That nuance didn’t arrive on its own. It took time in the field, and hundreds of hours with my manager and mentor.

This is the part of the sales apprenticeship that is under-appreciated… the conversations over a beer at the end of the day, the workshopping, the practice, the text messages long after the workday has ended… that’s where the work of reflection is done. You’re removed from the heat of the moment, and you process what happened. When AI just books the meetings for you, you don’t get that firsthand experience of what worked, what didn’t, and why.

Ok, but is that a bad thing?

Yeah… I think it is. I think we underestimate the value of learning what it takes to complete a puzzle from the start rather than just getting to place the last few pieces. It’s not just about the puzzle in front of us. It’s about every puzzle that comes after this one. It’s appreciating the nuance of when a piece looks like it should fit, but you can just feel when it isn’t right.

You accumulate valuable experience by being wrong, often publicly. Those early attempts and failures build judgment later. We have to ask ourselves if we want to skip past them.

By now you’ve heard that a majority of them prefer a rep-free buying experience. Bullshit. With due respect to the research firms publishing that data, I’m firmly in the camp that they feel that way because their current reps just aren’t very good. With due respect to those reps, it’s largely because they’re trying (while fighting the urge) to become the interchangeable parts Dave mentioned in his article.

When AI does all of that work, the initial connection is no longer between a seller and a customer. It's between a robot and a customer. That means the relationship with the real seller starts at a midpoint instead of the beginning, and the buyer often needs to retrace some of their steps. It might be fine, but it’s usually unpleasant. Either way, it’s clear that the selling team benefits from this, not the buyer.

When was the last time you asked a good customer why they bought from you? What did they say? There might be a feature that tipped the scales, but it was more likely the buying experience you created that made the difference.

The customer is not always right, at least out of the box. They probably make a purchase like this once or twice in a career. Reps sell it every day, and they’ve seen good efforts go sideways. They point out blind spots that a customer might only find the hard way, like I used to with my three degrees question.

How does a rep earn that kind of judgment? You know exactly where I’m going with this.

Selling is not a skill to be taught. It is a craft to be pursued, and perfection will never be reached. It's as much an art form as a science. My mentor used to say there's no cookbook for it.

In a controlled environment, you can train a bot to know how to act. In the real world, you need judgment and wisdom. So many things can be done, but usually what gets executed are the options that feel best to the consensus of the buyer(s) and the seller. There’s no repeatable algorithm for this, and there never will be. Sellers need to develop the judgment that the algorithm is attempting to replace.

Developing your craft means taking the raw materials from your sales calls and running them through the filter of someone who’s made thousands of calls before and knows what to do with them because they’ve made the same mistakes. You figure some of this out on your own through trial and error, but things accelerate quickly when you have someone to guide you.

And what happens when there is no guide? This isn’t a “someday maybe” problem. There are too many software sales managers right now who can’t guide their own teams on how to create opportunities because their sales careers consisted of 10-15 years in a market where money was cheap and the objective was growth at any cost. Reps are bringing the raw material, but there’s nobody with a real-world filter to help accelerate their growth. They get trial and error and nothing else. People are leaving the profession because year three still feels like year one.

Companies are leveraging AI to increase volume, but is mediocrity at scale going to move the needle the way you want?

Top performers aren't doing more of what everybody else does. After time in the field, they're actually doing fewer activities with higher rates of success. They call it “instincts,” but it’s built over 30,000 sales calls replayed in their heads. They know exactly who to call, when, and why that person should pick up. It's a sharp increase in effectiveness, not a volume play. They’ve earned that by making the mistakes robots are currently replacing.

If you want to distill selling to a numbers game, I don't know how to do it more effectively than with a machine that never calls in sick, rarely makes an error, and never shuts off. But if you think that's what sales effectiveness looks like, you've probably never sold anything to someone more than twice.

The human element of all of this is exactly what makes your buyer’s experience so fulfilling. There is never a perfectly clear solution to the problem they’re trying to solve. If there were, you wouldn’t have any competitors (or a job).

They bring you into the process for more than just a solution. You’re entering the arena together to solve this. You both have skin in the game. You’re taking the risk that your ideas and solutions will do the job. They’re taking a risk that it might not work (and it might cost a lot more than the solution).

That is why every surgeon’s favorite part of their current implant was the rep who helped them in the operating room. Those reps guided them through the decision-making process when they needed more than tech specs. They needed to rely on experience from hundreds of other operating rooms.

Buying the perfect solution would be boring anyway. The real thrill of a relationship like this is in going to battle together to solve a problem. When you just do what an algorithm spits out, nobody has skin in the game. The buyer has plausible deniability, and the bot has no skin.

I’ve since talked to surgeons who were my customers back then. What we did was about more than an implant and a computer in an OR. It was about sticking your neck out and exploring what becomes possible. Almost every one of them told me that our system and the way we thought about surgery made them better surgeons.

There’s plenty of discussion about the material rewards that come along with being a good seller (and they’re a lot of fun to talk about). I don’t think we talk enough about the intangibles like this. In a great buyer-seller relationship, both parties come out of the arena better for having entered it.

The search for efficiency, and thus, reliable profitability, is valid. But the way we’re going about it is undermining what makes our profession magical. In that, it’s eliminating the very reasons our best customers chose (and continue to choose) us in the first place.

The cost of knowledge has gone through the floor, while the value of expertise is going through the roof.

I, like Dave, am all for using AI. In fact, I relied on it heavily to edit this piece as I wrote it and to make sure I didn’t drift from my initial thesis. I’ve always felt like a pretty good writer, but I’ve never had so many arguments about antecedents, compound subjects, and trailing qualifiers. While it points out some things I don’t know (come on, man… I’m just a salesman), I also have enough experience to know where it misses. I’ve made plenty of bad sales calls and written articles that are no longer suitable for the internet.

We can’t afford to outsource our expertise. I’ll bet if you asked your best customers, they’d say the same thing.

Tom Alaimo is someone I've watched make hard calls and make them well.

I snapped a photo of him last summer when I borrowed an office at his coworking space in Chicago. He was building TA Sales, and everything about it looked intentional and promising. Then in January, he tore it down and did something different.

That takes guts. Recognizing that something fulfilling still isn't getting you where you need to go, and acting on it, is one of the harder things a person can do.

Now he's doing GTM work at 1mind, and I'm certain he's making the same kind of impact there. That focused energy is intoxicating to be around.

Thanks for showing up, setting a high bar, and creating distance on more than just Fridays.

This week’s piece was a bit longer than usual, and I appreciate you sticking around to the end. Do you like the longer stuff like this, or would you prefer I keep it short?

Lemme know. Either way, I’ll see you next week.

Cheers,
JB