Almost Timely News: 🗞️ How Sales is Changing in a Chaotic, AI World (2025-09-14)

Almost Timely News: 🗞️ How Sales is Changing in a Chaotic, AI World (2025-09-14) :: View in Browser

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What's On My Mind: How Sales is Changing in a Chaotic, AI World

I’ve been giving a lot of thought as to how sales is changing, not just from AI, but from how people are changing too. And after a whole bunch of research, the conclusion I’ve reached is that most sales methodologies are pretty badly broken. Not because the sales methodologies themselves are bad, but because well, when they were created, they were fine. They worked in the era they were made in. But times change, people change, behaviors change.

So this week, I’ll share my thoughts on the topic and some things we can do to potentially adapt. None of this should be brand new - humans don’t change that fast. Some of it will have practical AI tips, but sales is not yet an AI-led process, so there are limits as to what we can and can’t do with AI.

Most important, these are thoughts that I have about sales. Please don't take them as some sort of mandate or a definitive statement. This is just thinking and me sharing my thinking with you.

Part 1: The Big Picture

How many of us look forward to the sales process as a customer?

Yeah. About as many of us look forward to being on the receiving end of sales as we do dental work. It’s necessary, but it’s not necessarily enjoyable. When you start the sales process as a customer, you know what you’re in for.

Endless emails. Calls. Reminders. Cutesy “are you the right person” and “I don’t want to pester (and yet I will)”. Even more endless meetings, and depending on the purchase size, buyer committees, RFPs, presentation after presentation until every vendor blurs together and you pick the one that brought the best snacks or the cheapest one or the one the senior most stakeholder liked because the vendor took him out golfing or they were roommates in college or fraternity brothers or whatever.

There’s no shortage of ways the sales process sucks as a customer.

If we had our druthers and we were honest, we’d delegate the entire thing if we could until the very end where we quickly look at a high level summary of who meets our criteria, we pick one, and we get on with our lives. We would not want to invest the hours or days or weeks or months in dealing with the sales process as customers.

Increasingly, people are using generative AI, tools like Copilot, ChatGPT, Gemini, et. Al. To do exactly that. More on that in a little bit.

The other macro thing we have to acknowledge is that the big picture really kind of sucks right now. Deep uncertainty in the economy, job losses left and right, a planet that is on fire (in some cases literally) - I don’t need to rehash the massive psychological toll that reality is taking on us. Go over to Google Trends and look at “bar near me open now” and you’ll see some pretty interesting trends, especially in the 5 year timeframe.

What that does to us, what that has done to us over the past 5 years, ever since March 2020, is place enormous psychological and emotional stress on us. We’re given more to do than ever before in the name of productivity, more challenges, and fewer resources. That in turn means that we have less bandwidth to devote to any particular process - and especially the sales process.

This is where my commentary about sales frameworks comes into play - many sales frameworks are predicated on a key assumption: that people are willing and able to devote significant time to be rational, reflective, thoughtful, and thorough in the sales process.

We’re not, unless it’s something we deeply care about. We will overthink the hell out of stuff we care about.

That pile of sales RFP responses? That’s probably not even on the list of things we care about.

In turn, that means even if we have the outward appearance of being thoughtful, reviewing RFPs, etc. There’s a good chance we don’t actually care or we’ve delegated it off to someone or something else. (RFP response processing is a prime AI task).

So where does that leave the selling process? Mostly in shambles. Talk to any business owner now, especially if the business is a complex sale (i.e. not a simple transaction like buying a pack of gum or blindly clicking buy on Amazon at 3 AM). Sales cycles have slowed down. Decisions take longer. More sales end in “no decision”. No decision is our number one competitor. And I hear this a lot from other agency owners and from other folks who have complex sales. We're not losing to some big named competitor. We're losing to nothing at all. No decision. Prospects ghost you more than an Ivan Reitman film.

As someone with something to sell, I feel this in both directions. I get tons of pitches every day and I ignore virtually all of them. And as someone selling, I make tons of pitches a day and get very few responses.

So what do we do? Well, let’s think about sales itself.

Part 2: Moving to Buyer Enablement

Consultants love to come up with new, expensive-sounding words (mainly to justify ongoing high fees), from solution selling to sales enablement to RevOps. But all of sales is predicated mainly on the central idea that it’s the salesperson’s job to sell and behave as though they are the gatekeeper of knowledge about the customer.

Every framework, from the old-fashioned “grab ‘em by the tie and choke them till they buy” to Challenger Sales Methodology to SNAP Selling all assume the customer wants to take the time to learn, to be educated on the options, to make a rational choice, to be thoughtful and reflective. Agencies like Trust Insights especially are told in sales frameworks like Challenger that we need to reframe the customer’s problem, educate them on surprising ways the customer isn’t thinking about the problem, explain how they’re drowning, and show how we’re the novel solution to that problem.

The question is: is that how people actually buy these days?

During the conference and events I speak at, at the bar, in the halls, waiting in lines, I hear the same refrain more and more these days when I ask people about sales From their perspective as a customer. “Oh, I just ask ChatGPT about it.” And we know how reliable generative AI is at getting its facts straight, especially very specific facts.

But that’s how people WANT to buy. They want to delegate work they don’t enjoy to AI - and that’s what we’ve all been advocating as the best use case for AI. DOn’t give AI the work you love to do, the creative, the expressive, the things that fulfill you. Give AI the crap you don’t want to do, that you don’t have time for, that’s so repetitive and boring and painful that you wish it would go away. We call that the TRIPS framework - what to give AI versus what you want to keep - time, repetitiveness, importance, pain, and sufficient data. Katie Robbert walks you through this in our new course, the AI-Ready Strategist.

Guess where dealing with the sales process fits? Yeah. It’s time intensive. It’s repetitive. It’s important but not mission critical most of the time. It’s PAINFUL. And we certainly have enough data, what with RFPs and things, to evaluate whether a vendor meets our needs.

What if we approached sales from the perspective of the buyer?
I know a lot of sales methodologies have given lip service to this concept, but they don't actually do it.

Sales enablement is predicated on the idea of giving sales folks materials that enable selling, case studies and scripts and downloads. What if you flipped that on its head to buyer enablement? What if we just gav