🎙️ Podcast – We’re Not on Easy Mode Anymore EP 04

Forecasting Without Fairy Dust

Sales leaders love to brag about nailing the forecast. Then you watch what it takes to get there and you realize the accuracy is real, but the method is unhinged.

That was the core tension in my recent podcast conversation with Scott. We started with the usual weather chat and commuter misery, because nothing says modern revenue leadership like being trapped on a train while your pipeline lies to you. Then we got to the actual point, a lot of forecasts are “right” in the same way a magician is “right” about what card you picked. It works, but the trick requires effort, pressure, and a suspicious amount of vibe-reading.

I called it forecasting without fairy dust because I’m tired of watching teams sprinkle optimism on deals that are structurally late. I’m even more tired of watching CROs spend their best hours playing detective instead of field general. If your forecast is accurate because you personally interrogated every rep, decoded every “should be fine,” and then shaved the number down like a nervous barber, you do not have a forecasting system. You have a coping mechanism.

“It’s basically their full time job is to actually figure out what the reality on the ground is.”

That line is the whole problem. Forecasting has become a second job, stapled onto the actual job of winning.

The Job Isn't the Spreadsheet

What Scott and I kept circling is something most teams do not want to admit out loud. Forecasting is not a math problem, it is an information integrity problem.

The forecast isn’t broken because sales leaders cannot do arithmetic. It’s broken because the org does not reliably know what is true about deals. Leaders end up badgering reps, not because they love micromanagement, but because the business needs truth and the CRM mostly contains narrative.

There’s a reason so many leaders claim they “nail it.” They do nail it, at the cost of their time, their energy, and their relationships. They nail it by applying judgment at the last minute, which is like being proud you caught the falling knife after you knocked it off the counter.

The modern sales leader job should be closer to commanding the field than interrogating the troops. The team should spend its time moving deals forward, unblocking procurement, coaching discovery, building pipeline. Instead, too many leaders spend Monday to Thursday doing archaeology on opportunities that should have been understood weeks earlier.

Asking the Question Everyone Dodges

One of the simplest ideas in the episode is also the one that makes people squirm. Ask the buyer when they will sign. Ask early. Ask directly. Ask like a professional, not like a hostage negotiator.

Scott nailed the dynamic I have seen a thousand times. Reps hint. Buyers hint back. Everyone performs the dance of plausible deniability. Then December 28 arrives, legal is out, procurement is out, your champion is skiing, and the deal “surprisingly” slips.

This is not bad luck. This is a refusal to ask a basic question because it feels confrontational.

I’m not saying you should ask it like a cartoon villain. I’m saying you should respect the buyer enough to be explicit about timelines. Buyers are not fragile, they are busy. They expect sales to lead, not to politely hover.

The kicker is that asking late turns you into the desperate sales guy, the one offering 25 percent off like you’re shaking a tin cup outside finance. Asking early turns you into a planner, and planning is the closest thing sales has to dignity.

Hope Is Not a Forecast, It Is a Personality Trait

We talked about “hope forecasting,” the idea that you call a number because you want it to be true. It sounds childish until you realize how common it is.

A hope forecast is built on the rep’s feeling. It is reinforced by executive pressure. It is justified by “they said all the right things.” Then it collapses exactly when the business needs it most.

The damage is not only missing a quarter. The damage is trust erosion. If leadership cannot trust the forecast, they cannot run the company. The CEO cannot decide when to hire. The CFO cannot decide when to cut. The board starts asking questions that feel like accusations, because in a way they are.

Forecast accuracy is not about ego. It is about resource allocation. If you call five million and deliver four, fine, explain the delta and learn. If you call five and deliver one, you just taught the company that sales reality is fiction.

Early Stage Forecasting Is Life or Death

One part of the conversation I keep replaying is the difference between big company forecasting and early stage forecasting.

A massive company can treat revenue like a probabilistic system. Enough volume creates predictability. Missing by a million barely registers.

Early stage does not get that luxury. A few deals swing the entire month. A single slip changes hiring. A single churn changes runway. You are not forecasting for investor theater, you are forecasting for survival.

That’s why I said it feels like life or death. It’s not melodrama. It is the operating reality of small revenue bases.

The forecast is also where leadership can actually help. If a deal is at risk, I want to know while there’s still time to change the outcome. Finding out at the 11th hour is not information, it’s an autopsy.

Why Med Pick Both Matters and Does Not

We had a healthy little disagreement about Med Pick. I think frameworks are useful until they become religion. Scott pushed, correctly, that decision process and paperwork process are vital for forecast accuracy.

Both things can be true.

Med Pick can be a powerful scaffold, especially for reps who are still learning how to think. It can also become a box checking ritual that produces false confidence. I have seen deals with every letter satisfied that still die. I have also seen deals close fast because the buyer already decided and the rep had the sense not to force a qualifying interrogation.

The deeper point is that forecasting depends on what you do not know. The framework matters only if it reveals blind spots. If it becomes a compliance exercise, it makes you feel safe while the deal quietly drifts into next quarter.

QBRs Are Either a Weapon or a Multiplier

Quarterly business reviews have a reputation problem for a reason. Too many of them are theater, punishment, or both.

When QBRs are run with fear, reps tell rosier stories. They sandbag, they hide risk, they avoid surfacing messy truths. The meeting becomes a performance designed to survive, not a workshop designed to win.

When QBRs are run with trust, they become a multiplier. I described my approach pretty plainly. No laptops, no phones, full engagement, real peer input, deep dives on the biggest deals, and a strong bias toward making the rep more effective after they leave the room.

“We’re not here to beat you up, we’re here to help you figure out what are your blind spots.”

That is the line that changes everything. A QBR should end with a list of actions, not a feeling of shame.

• The best QBRs do a few things at once.
• They force honesty about last quarter and why.
• They focus on the handful of deals that actually matter.
• They pull in the wisdom of the room, not just the opinion of the leader.
• They surface process stupidity and fix it.
• They make the rep feel supported and accountable at the same time.

The worst QBRs do something else. They turn into a public trial where the goal is to catch someone slipping. Those orgs think they are building rigor. They are building lying.

The Jesse’s Girl Problem, When a Deal Becomes a Myth

Every sales org has its legend. In the episode I told the story of the rep with the never-ending Lockheed deal and the champion named Jesse. The team turned it into a joke, complete with walkup music.

It is funny, and it’s also revealing.

When a deal lasts multiple quarters with no visible progression, it stops being an opportunity and becomes a myth the rep tells to stay relevant. The rep confuses friendliness with traction. Leadership confuses activity with probability. Everyone wastes time.

The red flag is not that deals can be long. Some deals are long. The red flag is when nothing changes and the rep keeps narrating the same chapter.

My personal tell is when someone describes the buyer as “a nice guy.” That often means you made a friend, not a champion with urgency.

The Secret Sauce Is Annoyingly Human

People want forecasting to be a system. It is, but it is also trust.

I said I weigh the seller. That can sound subjective, but it’s reality. Some reps are reliable narrators. Some are improvisers. You learn who is who.

I also weigh involvement and executive parity. Not because leaders are magical closers, but because presence usually means seriousness. Deals with no internal visibility tend to be the ones that surprise you, in the bad way.

This creates a weird truth. The more you act like a field general, the more accurate your forecast becomes, because you are close enough to reality to see it. The downside is scale. You cannot be close to everything when you have 40 sellers.

So you focus on the marquee deals and build a leadership model that can responsibly roll up the rest. If that middle layer is weak, the forecast becomes folklore.

Culture Is a Forecasting Tool

We landed on something I believe deeply. Culture is not vibes. Culture is an operating system.

If your sales team believes you want them to get rich, they will tell you the truth because truth helps them win. If they believe you want them to look stupid, they will hide, because hiding helps them survive.

I said I love writing big commission checks. I mean it. Nothing builds loyalty like a leader who is genuinely excited when a rep has a monster quarter. You cannot fake that.

A culture that celebrates rep success also makes cross-functional work possible. I talked about inviting the whole company to QBRs, product, CS, marketing, whoever wants to learn. Most people will not show. The ones who do often contribute something that speeds up a deal.

That is not a nice-to-have. That is revenue acceleration.

Process Should Serve the Deal, Not Trap It

We also hit a nerve that I think every buyer has felt. When a rep wants to send a contract and the company’s process forces 40 qualification questions, the process is not supporting sales. It is strangling it.

Rigid gating inside Salesforce makes leaders feel in control. It makes buyers feel trapped.

The right move is not chaos. The right move is adaptability. Train reps to ask smart questions in most cases, then give them a clear override path for the edge cases, the buyer who says they used you before and they want to buy now.

If your process cannot handle the easiest kind of deal, it is not a process, it is a bureaucracy cosplay.

I Think Sales Stages Are Dying

Near the end, I threw out a provocation I still believe. Sales stages, as most teams use them, are arbitrary. They are folk maps. They were invented to create forecasting percentages, which are often guessed, rarely recalibrated, and almost never tied to actual buyer behavior.

Stages can still be useful for coaching and for identifying stuck deals through aging triggers. I use that. When a deal sits in a stage for double the normal duration, it’s a flare. It tells you to investigate.

But the big idea is that buyers do not buy in your stages. They buy in their process. If you want forecasting without fairy dust, you need a model that reflects the buyer’s route, not your internal spreadsheet convenience.

In the episode we used a GPS analogy. Old directions said turn at the yellow building. Modern GPS says there’s traffic on 101, here’s your updated arrival time. That is where forecasting needs to go, away from stage rituals, toward predictive understanding of what actually remains in the buyer’s path.