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🎙️ Podcast – We’re Not on Easy Mode Anymore EP 05

In the latest episode of We're Not On Easy Mode Anymore we get into why sales stages simplify reporting but distort reality. Deals move through effort, time, and risk (not...

🎙️ Podcast – We’re Not on Easy Mode Anymore EP 05

Sales stages are not how deals move

I have never watched a real deal move the way a CRM says it does. Not once. Deals lurch, stall, loop back, pick up unexpected speed, then freeze for reasons nobody wants to document. The fiction is not that we know this. The fiction is that we keep pretending stages describe motion rather than summarize a guess.

Sales stages exist because reporting needs nouns. Deals exist because people make decisions under constraints. Those two realities overlap just enough to be dangerous.

What this episode is really arguing is simple and uncomfortable. Stages are mostly a reporting hack. Useful for dashboards. Necessary for workflows. Weak as a description of reality.

Process survives. Stages get questioned

A sales process still matters. Discovery has to happen. Value has to be understood. Risk has to be addressed. Security reviews, procurement, legal, internal alignment. None of that disappears.

What breaks is the idea that this work can be compressed into a single label at a single moment. When someone says a deal is in Stage 3, they are not describing the work remaining. They are classifying it into a bucket that makes a report render.

One of the cleanest lines in the episode is this:

“I think sales process and sales stages are two different things.”

That distinction is operational. Process is a checklist of work that must be completed to get money. Stages are a convenience layer built on top of that checklist. We treat them like truth because they are visible and sortable.

Procurement is not a stage. It is a range of outcomes

Nothing exposes the weakness of stages faster than procurement. The word looks precise and it's not.

One buyer’s procurement is a single signature and a vendor form. Another buyer’s procurement involves legal review, data protection, internal AI policy, regional compliance, and a monthly committee meeting that slips when someone is on vacation. Two deals can sit in the same stage and have nothing in common in terms of remaining effort or time.

“Putting them both in this bucket of procurement… doesn’t actually tell you the reality of what’s happening.”

That is not a philosophical critique. It is a real forecasting problem. When leaders ask why the forecast missed, the answer is often hidden in these false equivalences. Same stage. Wildly different paths.

Stages add cognitive load for reps

There is a quiet tax we rarely acknowledge. The more granular the stages, the harder it is for a rep to classify correctly. Stage definitions multiply. Edge cases grow. Deals stop fitting cleanly. Reps make a choice between accuracy and speed. Speed wins. The CRM gets an answer that looks compliant but drifts further from reality.

“The more stages that you have, the harder it is… for the sales rep to get it right.”

This is a system design problem. Humans are bad at repeated forced classification when the categories do not match how the work actually unfolds. The result is shallow updates and deep uncertainty.

Reporting wants labels. Management wants foresight

Stages are attractive because they compress complexity. That compression is exactly why they fail when used as predictors.

A stage tells you where a deal is supposed to be. It does not tell you how healthy it is, how fast it is moving, or how much work remains. Leaders then layer probability percentages on top and act surprised when the math lies.

“Stages are purely a reporting mechanism.”

Once you accept that, a lot of downstream frustration makes sense. Dashboards feel authoritative. Forecast calls feel fuzzy. The gap is not execution. The gap is the model.

Time is the real variable we avoid naming

“What is the least amount of work that I could be doing to get money from you?”

That question is uncomfortable because it reframes progress. Not in terms of steps completed, but in terms of effort remaining. Effort has a time component. Time is where deals quietly die.

“Time kills all deals.”

Stages are bad at time. A deal can sit in the same stage for two days or two quarters. The label does not change. The risk does. When we talk about surprise losses, time was usually the surprise.

What AI can do that stages cannot

The argument is not that AI magically closes deals. It is that AI can model signals that stages ignore.

Instead of asking a rep to choose a bucket, the system can observe behavior. Engagement patterns. Stakeholder expansion. Response latency. Document exchange. Calendar density. These are imperfect signals, but they map closer to reality than a dropdown.

Two outputs matter more than stage.

  1. Deal health, a directional sense of momentum.
  2. Time to close, an estimate of remaining effort given this buyer, this company, this context.

Neither needs to be perfectly accurate. They need to be comparably wrong across deals. That is enough to rank attention and surface risk.

Disagreement is where management actually happens

One of the strongest points in the episode is also the least threatening.

“Disagreeing with the reps is probably the most important thing that we can do.”

This is not about calling someone wrong. It is about creating a focal point for conversation. When the system thinks a deal is slowing and the rep thinks it is fine, that gap is useful. It narrows the discussion to missing context.

The alternative is the classic forecast call. Thirty minutes of narrative reconstruction. Little signal. High fatigue.

When disagreement is expected, it stops being punitive. It becomes diagnostic.

Tooling inertia is real and it will win for a while

“I don’t think we’ll ever… get rid of sales stages… too many things tied to that.”

This is the practical concession. CRMs like Salesforce and HubSpot are built around stages. Automations depend on them. Dashboards assume them. Removing stages would break too much plumbing.

So stages will remain. Not because they are good. Because they are embedded.

The mistake is letting that legacy shape how the business is run. Systems constraints are not strategy.

A better metaphor than stages

“At some point it becomes more like a progress bar… this deal’s 80% done.”

The metaphor matters because it shapes behavior. A progress bar implies movement that can stall or reverse. A chess evaluation implies advantage that shifts with each move. Neither pretends the path is linear.

Tracking deal momentum over time, watching health move up and down, noting why it shifted. That history is more valuable than the current label. It shows where friction actually lives.

The operating takeaway for sales leaders

If you keep stages, treat them as infrastructure. Necessary. Boring. Not strategic.

Run the business on signals that reflect reality. Health. Remaining work. Time. Use disagreement between humans and systems as a prompt to inspect, not a scorecard to punish.

Sales will always involve judgment. The goal is not to remove judgment. The goal is to stop pretending that a dropdown captured it.

That is the argument. Not that stages are evil. That they are insufficient. And that we already know it, even if our dashboards do not.

About the Author

Robert Moseley

Robert Moseley IV is the Founder and CEO of GTM Engine, a pipeline execution platform that’s changing the way modern revenue teams work. With a background in sales leadership, product strategy, and data architecture, he’s spent more than 10 years helping fast-growing companies move away from manual processes and adopt smarter, scalable systems. At GTM Engine, Robert is building what he calls the go-to-market nervous system. It tracks every interaction, uses AI to enrich CRM data, and gives teams the real-time visibility they need to stay on track. His true north is simple. To take the guesswork out of sales and help revenue teams make decisions based on facts, not gut feel.

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