Why the Best AI for Sales Still Leaves Room for the Human

Luke Wilson plays an average man who wakes up in the future to find that society has become so dumbed-down he’s now the smartest person alive.

Shortcuts are seductive—but sales still needs a brain, not just a bot. Most AI sales tools make bold claims. But if we’re not careful, we’re going to miss the point.

Let’s be clear: AI is not the enemy of sales. But mindless automation is.

The usual view of dystopian future has most of us becoming irrelevant replaced by robots looking and acting more and more “human.” The real danger pointed out by far fewer speculators is that humans start to behave more like robots (or AI). In fact, it’s the overly prescriptive, “just press send” kind of AI that is a sign of this. Tools that remove all friction, all thinking, and all responsibility from the seller’s process may feel like progress, but it’s the kind that gets us closer to the future portrayed in Idiocracy. A world where human thinking has gone the way of the dodo.

The Football Analogy: AI Gets You Up the Field, But You Still Have to Score

• Moving on from Hollywood (or maybe not) to pro football, here’s my favorite analogy - General-purpose AI tools? They’ll get you 50 yards. Purpose-built AI with domain knowledge? That’ll get you 80. But the last 20? That’s on you.

• Sales remains a field of nuance, judgment calls, reading defenses (aka buyers), and improvising under pressure. If your AI is trying to do all of that for you, you’re not selling—you’re outsourcing your brain. That’s why we believe in consciously designing gaps into AI tools—spaces where the human is meant to step in.

Why Humans Still Matter in AI-Driven Sales

• Take something like sales messaging. A lot of AI tools will auto-generate an email, add the recipient, and fire it off before the rep has even taken a breath. Efficiency? Sure. Effective? Probably not.

• The problem? It removes the moment of pause— where the seller says, “Does this actually make sense for this person, right now?” That pause is where better thinking happens. It’s where relevance and context reside. It’s where judgment kicks in. And if we automate that away, we don’t get better sellers. We become passengers.

That’s why AI in sales shouldn’t just be about speed. It should be about helping the seller think better, faster.

Beware the In-House Trap: Built by Technologists, Not Sellers

• Another trend we’re seeing is companies building their own in-house sales AI. On the surface, it sounds smart—more control, tailored to your data, customized workflows.

  
  

• But here’s the problem: most in-house AI projects are technology-driven, not sales-driven. They’re led by engineers, not sellers. They’re architected by people who think in  funnels and pipelines—but not politics, pressure, or the psychology of a skeptical buyer.

The result? Tools that are technically impressive but miss the subtle and messy realities of B2B sales—like knowing when to challenge a prospect versus when to listen, how to interpret buying signals, or how to detect a stalled deal.

Returning to the football analogy, AI without context and domain empathy is like running the same offensive plays paying no attention to how the defense lines up.

The Middle Path: Between General AI and Custom Rigid Systems

The sales AI landscape today looks like:

• general AI tools that offer useful, but generic shortcuts (a good place to start)

• Over simplified rigid tools with fixed, overly prescriptive outcomes

• Fully baked enterprise tools, that are expensive, complex, and confusing

We believe there’s a better path: It’s more about augmentation - assistance, not abdication.

That means building AI that knows what it’s doing—but also knows what it shouldn’t do.

The Bigger Picture: Human-in-the-Loop by Design

If you zoom out beyond sales, this is the larger philosophical challenge of AI in any domain: How do we keep humans meaningfully in the loop? You have to force them. Humans are hard-wired to extract as much utility for minimum inputs of energy and effort.

Because let’s face it: the danger of AI is not that it becomes super intelligent and takes over. The danger is that it becomes good enough that we stop trying, and then we wake up one day and we're living in an “Idiocracy.”

Final Thought: Progress Shouldn’t Be Passive

There’s nothing wrong with speed. Or shortcuts. Or efficiency. But when you outsource all the thinking, you also lose the learning. You lose the edge. AI should make sellers better. It should make mediocre ones more thoughtful. It should make great ones faster—but not passive.

Scoring that touchdown still takes a person, not just a playbook.

Unprepared Is Unprofessional: How B2B Sellers Break Trust Before They Even Speak

Trust isn't a warm, fuzzy ideal. It's the currency of every conversation. It’s the lubricant that keeps the commercial wheels turning. In B2B sales, one of the fastest ways to lose it is to show up to a prospect call, not just unprepared, but less prepared or ill-prepared.

That might sound harsh—but if we’re honest, we’ve all seen it. Sellers turn up asking questions they could’ve answered with ten minutes of desk research. They ask the prospect to walk them through the company background. The industry. Even the job title. The problems, the “what keeps up at night” routine.

And just like that, trust erodes. Quietly, but decisively.

It’s More than Sloppy. It’s Selfish.

When a seller shows up without doing the work, it signals one of two things:

1. They couldn’t be bothered. They’ve prioritized their own time over the prospect’s. Instead of investing in understanding the buyer’s world, they’re hoping the buyer will bring them up to speed. This is an imposition on the prospect.

2. They didn’t know how to meaningfully prepare. Maybe they don’t know where to look, what to look for, or how to connect the dots. The single biggest determining factor between great sellers and the rest is the ability to connect the dots from the prospect’s challenges or opportunities to your solution. But from the buyer’s perspective, it’s still a big miss.

Either way, the message is the same:

“You weren’t worth the effort.”

And that’s the moment the prospect tunes out.

The Modern Buyer Doesn’t Have Time for Your Discovery

Let’s face it—buyers are flooded. Their calendars are brutal. Their patience is short. If you’ve been lucky enough to get on their schedule, they’re hoping—expecting—that you’ll come with something meaningful to offer. An informed hypothesis. An observation they hadn’t considered. A point of view that shows you’ve been paying attention. They’re supposedly already 70% of the way through their buyer journey so when we say we have to “meet them in the moment” the least you can do is show up in the same moment!

That’s how trust is built now. Not by being likeable. By being useful.

And usefulness starts with preparation.

Preparation Is the First Demonstration of Respect

It says:

• I value your time enough to do my homework.

• I understand your world (and am brave enough) enough to offer a perspective.

• I’ve earned the right to ask for yours in return.

That’s not just good manners. That’s trust-building behavior.

But Let’s Be Real—Prep Takes Time

The kind of insight-led preparation that earns trust? It’s not light lifting. And most sellers are drowning in admin, CRM updates, internal meetings, and quota pressure. So they cut corners. They go in cold. And they hope for magic.

That’s why we built Shadow—an AI sales readiness tool for the real world.

Shadow helps B2B sellers prepare faster and better. It surfaces relevant insights and synergies, builds context around your prospect’s world, and helps you shape a smart, tailored point of view—so you can show up not just informed, but trustworthy.

Because in today’s B2B landscape, the first ask isn’t for a meeting. It’s for trust. And you only get one shot to earn it.

Putting the "u" in Trust

Trust is the lubricant that eases the frictions of life and business…but now we’re just grinding our gears!

Trust is one of those words everyone throws around—especially in B2B circles—but ask a dozen people what it really means, and you’ll get a dozen different answers (and half of them will contradict each other). The sad truth is that we all agree “trust matters,” yet we routinely break it, often without even realizing it. That irony becomes painfully clear when you dig into the little things—because, these days, everything really is a game of inches. But for all the nods to nuance, most revenue teams treat trust like a checkbox rather than something that demands constant care.

Why “Trust” Feels So Elusive

• Everyone Talks, Few Understand

  
  

  We’ve all seen corporate mission statements blather on about “building trusted partnerships.” We spout it in sales pitches: “Our clients trust us.” Internally, we trot out trust as a KPI. Yet when push comes to shove, so many of us treat trust like an afterthought. The result? Clients feel betrayed, teams become cynical, and everyone ends up worse off.

• Details Matter—Until They Don’t

  
  

  You’ll hear leaders preach, “It’s all about the details,” or “Success is a game of inches.” But when quotas and dashboards take center stage, details vanish. Promises are made (and broken), prospects are misled (even if unintentionally), and the “trust” we brag about evaporates, and we don’t seem to notice!

  
  

Listen to the Pod:

A Cautionary Tale from Maddie Bell Maddie Bell (CEO over at Scheduler AI) recently called this out on LinkedIn, spotlighting the dangers of poorly qualified (or downright bogus – my words) sales meetings. Revenue teams are so measured by and rewarded according to hit rates—number of meetings booked, demos delivered, SQLs created. Not surprisingly they’ll take a meeting with anyone who can fog a mirror.

That’s our first betrayal of trust. By agreeing to talk to someone who clearly doesn’t belong, or want to be, in our funnel, we’re telling prospects: “We care more about hitting our numbers than helping you solve a real problem.” We’ll come back to this.

Defining Trust: A Confident Relationship with the Unknown At its core, trust is about embracing uncertainty. It’s establishing a more confident relationship with the future. If I’m going to rely on you, I must believe you’ll do right by me when the unexpected happens.

The Two Pillars of Trust: Ability and Character It helps to break trust down into two main components: Ability and Character.

1. Ability (Competence + Reliability)

   • Competence: Do you actually know how to cut the grass, or in our world, deliver on a complex software integration?

   • Reliability: Can I count on you to show up every Wednesday (or hit your project milestones) without fail?

 → Both are conditional. I might trust you to cut my grass every Wednesday, but I probably wouldn’t trust you to cut my hair!  

2. Character (Benevolence + Integrity)

   • Benevolence: Will you put my interests on par with—or preferably ahead of—your own? In other words, do you genuinely care about my success, not just your commission/results/revenue/goal?

   • Integrity: Are you basically honest? If you say you’ll do something, will you?

 → Character is far more decisive than Ability. A technically brilliant partner who treats you like a number is far less trustworthy than a “good enough” partner who genuinely has your back.

Why Character Always Trumps (and Then Fuels) Ability Think of Character as the engine that powers Ability. If someone has the skills (competence) and shows up (reliability) but doesn’t care about your success (benevolence) or fudges the truth when it suits them (lack of integrity), trust implodes. In contrast, a vendor who might not be the absolute top expert—but who consistently tells you the truth, not just what they think you want to hear, —wins every time.

Back to BDRs Booking Bad Meetings: A Trust Meltdown BDR teams, measured and rewarded on “meetings set,” will chase any lead, no matter how irrelevant. Why? Because we’ve turned business development into an engineering problem: pour X contacts/leads into the top of the funnel, churn them through a process, and out pops Y “Sales Qualified Leads.” Numbers make neat PowerPoint slides, but they do zero for trust.

• Prospect’s Trust Is Lost: When you schedule a call that’s obviously irrelevant, the prospect feels like you wasted their time. They walk away thinking, “These folks don’t care about my business. They only want my calendar.”

• Sales Team’s Trust in BDRs Shatters: AEs get a set of meetings that look good on paper but are cluttered with unqualified leads. Suddenly, AEs start rolling their eyes at every “SQL” that comes their way. They don’t bother preparing, because they assume it’ll be another waste of time. Now the entire revenue machine grinds to a miserable halt.

This is a textbook case of promoting your interests (hitting meeting quota) above everyone else’s (prospect relevance and AE productivity). It’s a betrayal of benevolence: you’re not putting the prospect’s interests first, you’re putting yours.

The Ripple Effect of Betrayed Trust

1. Prospect Disengagement: They ghost you or, worse, bad-mouth your company.

2. Sales Team Cynicism: AEs become “meeting skeptics,” assuming every BDR lead is junk, so they don’t prepare which means they’re more likely to fumble the real ones as well.

Welcome to the culture of distrust. Trust is the lubricant that eases the frictions of life and business allowing them to run more smoothly…but now we’re just grinding our gears!

So, What Now? Building (and Keeping) Trust

• Measure the Right Things: Instead of “meetings set,” track “meetings with a clear business outcome.” Reward BDRs who qualify ruthlessly, even if their numbers look lower.

• Train for Character, Not Just Competence: Role-play scenarios where a “no” is the right answer. Celebrate BDRs who walk away from weak leads.

• Foster Cross-Functional Respect: Get AEs and BDRs to collaborate on ideal customer profiles (ICPs), so qualifiers don’t feel like gatekeepers, and AEs see the value up front.

• Embrace Transparent Communication: Encourage everyone to flag when a metric is pushing them to cut corners. If a BDR says, “I feel shaky about this appointment,” dig in rather than shrug it off.

A Final Warning: Greed and the VC/PE Factor There’s a more fundamental problem underpinning the whole mess: greed. Founders think they can launch a startup, raise VC or PE dollars, and cash out for millions in a few years. So they take investment capital from firms that only know one language: numbers.

Venture capital and private equity firms structure everything around hitting quarterly targets, scaling revenue at all costs, and pumping up “valuation multiples.” If your cap table is full of investors demanding 3× returns by next year, guess what happens? You’re incentivized to push numbers—any numbers—knowing full well that spreadsheets don’t care about trust, nuance, or genuine customer success. Until founders and their investors shift from a purely financial mindset to one that values trusting relationships as much as short-term metrics, this cycle of trust betrayal will never change.