Your Forecast Call Is a Deposition

And Other Signs You're Managing Like a Prosecutor

I watched a CRO spend fifteen minutes in a forecast meeting interrogating a rep about a $200K deal.

“Walk me through your last conversation.”

“What’s your confidence level?”

“Why didn’t you engage the economic buyer sooner?”

“Can you defend a 70% commit on this?”

The rep—one of the best on the team—answered every question. Documented every interaction. Justified every decision.

At the end, the VP said, “Okay, I’ll accept your forecast. But you need to get legal on the call before the end of the week.”

The rep nodded. We moved to the next person.

The deal closed three weeks later. Exactly as the rep said it would.

Here’s what nobody talked about: we just spent fifteen minutes proving the rep followed process instead of asking what would help them close faster.

That’s when I understood the problem.

We’ve turned sales leadership into a legal practice when it should be an engineering discipline.

We’ve Replaced Building with Arguing

I recently listened to an episode of the Freakonomics podcast featuring author Dan Wang called “China Is Run by Engineers, America Is Run by Lawyers.” His argument: modern America has become a society that argues instead of builds. We’ve replaced construction with compliance. Progress now requires approval from seventeen committees, none of whom are accountable for the outcome.

That’s not just infrastructure.

That’s your sales team.

Look at the pattern:

• Your forecast call is a courtroom. Reps justify pipeline coverage while managers cross-examine confidence levels. Nobody asks, “What do you need from us to move this forward?” They ask, “Can you prove you’ll hit your number?”

• Your deal desk operates like a legal review. A customer wants to adjust payment terms? That’s three approvals, two contract reviews, and a written explanation of why this discount won’t set a dangerous precedent for the entire Western Hemisphere.

• Your CRM is a compliance engine. Reps spend more time documenting that they followed the process than actually improving their pipeline. The system exists to protect the company from the rep, not to help the rep close deals.

• Your leadership is terrified of mistakes. Every decision gets filtered through “What if this goes wrong?” instead of “What do we learn if we try?” Risk is something to be mitigated, not managed.

The result? Sales teams that are airtight on documentation but wheezing for momentum.

Lawyers are great at protecting what you have. They’re terrible at building what’s next.

How Engineers Think About Failure

When an engineer encounters a problem, they:

1. Define it precisely

2. Design a system to test it

3. Measure what happens

4. Iterate until it works

Notice what’s missing?

Blame. Justification. A seventeen-page memo explaining why the first attempt failed.

An engineer treats failure as data. A lawyer treats failure as liability.

Now imagine your sales team operated that way.

Instead of a weekly pipeline tribunal where reps defend their forecasts, you’d run design reviews. Instead of “Why isn’t this deal closing?” you’d ask “What part of our system broke, and how do we fix it by Friday?”

That’s the difference between managing by interrogation and leading by iteration.

This Isn’t About Personality

Years ago, Dahlia Lithwick wrote a piece in Slate about chaos muppets and order muppets.

The framework is simple: every Muppet—and every person—falls into one of two categories. Order muppets (like Bert) need structure, predictability, and control. Chaos muppets (like Ernie) thrive on spontaneity, experimentation, and creative disorder.

For years, I thought I was a chaos muppet. I love to experiment. I hate compliance-driven processes. I get energized by building new systems and testing new approaches.

But I’ve realized: I’m not a chaos muppet.

I’m an order muppet who thinks like an engineer.

I love structure and systems. I just want those systems designed to enable learning, not prevent mistakes.

That’s the critical insight: the lawyer/engineer distinction isn’t about temperament. It’s about methodology.

You can map these as quadrants:

• Chaos Muppet + Lawyer: Spontaneous but defensive. Tries new things but immediately writes policies to prevent anyone else from doing them differently. (“That worked, but now let’s lock it down so nothing changes.”)

• Order Muppet + Lawyer: Structured and protective. Loves process, documentation, and compliance. Designs systems to prevent failure. (This is most sales organizations.)

• Chaos Muppet + Engineer: Experimental and iterative. Tries everything, measures nothing, builds no systems to capture what works. High energy, low compounding. (This is a lot of early-stage startup sales teams.)

• Order Muppet + Engineer: Structured and iterative. Loves process, but designs systems that make it easy to test, learn, and improve. Builds infrastructure for experimentation. (This is where you want to be.)

Here’s what this means: you don’t have to become spontaneous and unstructured to lead like an engineer. You can be detail-oriented, process-driven, and systematic—and still build a culture of iteration.

The question isn’t whether you like structure.

It’s whether your structure is designed to protect what you have or build what’s next.

What This Actually Looks Like

I was coaching a rep whose deals kept stalling at the same stage: right after the demo, prospects would go dark for three weeks.

In our 1:1s, I’d ask the usual questions: “Why didn’t you set a clear next step? Did you ask for the business? What’s your follow-up cadence?”

She had answers. Reps always have answers.

But her deals kept stalling in the exact same spot.

Finally, I stopped interrogating and started observing. I sat in on three of her demos in one week.

The pattern was obvious: sixty slides, one-hour meeting, every feature we had. By the end, prospects looked exhausted. They’d say “This looks great, let me discuss with the team”—which is buyer language for “I need time to process what you just dumped on me.”

That’s when I realized: this wasn’t a rep problem. This was a systems problem. And I was the one who’d trained her on that demo deck.

We redesigned it together: twenty slides, focused on three specific use cases tied to what came up in her discovery calls. We stopped trying to show everything and started showing what mattered.

Her deals started moving again.

That’s engineering thinking. When the same failure repeats, you don’t fix the person—you redesign the system.

The Real Cost

The lawyerization of sales isn’t just annoying. It’s expensive.

Every minute your rep spends justifying a deal instead of advancing it is a minute you paid for nothing. Every approval layer adds a day. Every policy written in fear adds friction.

But here’s what actually kills you: it destroys trust.

I once watched a rep in a forecast call inflate a deal’s probability from 50% to 90%. Not because they believed it. Because saying 50% meant getting interrogated about why they weren’t doing more.

So they told their manager what the manager wanted to hear, hoped for the best, and planned to update the forecast when the deal inevitably slipped.

When you manage like a prosecutor, your reps act like defendants. They filter information. They hide risk. They tell you what you want to hear instead of what you need to know.

You wanted accountability. What you got was a team that’s terrified to tell you the truth.

Real accountability doesn’t come from interrogation. It comes from ownership. It comes from reps who believe their job is to make the system better, not just survive it.

Three Moves

You don’t need to blow everything up. You need to change how you respond when things break.

1. Diagnose Systems, Not People

When a deal falls apart, your reflex is to ask: “What did the rep do wrong?”

Try this instead: “What did our system fail to provide?”

Maybe your discovery framework doesn’t uncover the real buyer. Maybe your pricing model creates too much friction. Maybe your demo shows too much and proves too little.

You can’t see those problems when you’re busy assigning blame.

Replace this: “Why didn’t you follow the process?”
With this: “What about the process didn’t work for this situation?”

The second question opens up learning. The first one shuts it down.

2. Run Real Post-Mortems

In engineering cultures, failure produces insight. In lawyerly cultures, failure produces excuses.

Most sales teams don’t do post-mortems on lost deals. And when they do, it’s usually a checkbox exercise: “Competitor had better pricing. Moving on.”

Here’s what a real post-mortem looks like:

• What surprised us? Not “what went wrong”—what didn’t match our assumptions?

• Where did our process break? What did we miss in discovery that would’ve changed our approach?

• What would we do differently next time? Not in theory—specifically, with this buyer profile, in this situation.

• What does this teach us about our system? Is this a one-off, or have we seen this pattern before?

When you treat every deal—won or lost—as an experiment, your team gets smarter every quarter. When you treat losses as failures to be hidden, you keep making the same mistakes.

3. Ship Now. Improve Tomorrow

Lawyers wait for certainty. Engineers ship and iterate.

How many enablement projects are stuck in committee right now because someone said, “Let’s get more input”? By the time you’ve gathered it, the quarter is over.

Version 1.0 beats Version None.

I’ve watched sales teams debate a new objection-handling framework for six weeks, trying to make it “perfect” before rolling it out. Meanwhile, reps are in the field making up their own answers, with no consistency and no shared learning.

Better approach: “Here’s a framework that covers the most common objections we’re hearing. Use it this week. Friday, we’ll debrief what worked and what didn’t. We’ll improve it and re-release Version 2.0 next Monday.”

That’s how you build momentum. That’s how you learn what actually works instead of what theoretically should work.

The Turn

Here’s what changes when you lead sales like an engineer instead of a lawyer:

You stop asking “Who screwed up?” You start asking “What broke?”

You stop demanding certainty. You start creating learning loops.

You stop protecting the process. You start improving it.

In lawyerly cultures, people defend decisions. In engineering cultures, people test hypotheses.

In lawyerly cultures, failure is hidden. In engineering cultures, failure is data.

In lawyerly cultures, innovation dies in committee. In engineering cultures, it ships on Monday.

You need both mindsets in sales. You need legal rigor when it comes to contracts, compliance, and customer commitments.

But when it comes to how you lead, you need to think like an engineer.

Because sales isn’t a courtroom.

It’s a construction site.

And the only question that matters is: what are we building next?

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