Diagnose Before You Demand: The Leadership Move That Saves Teams

Sixty days without a closed deal.

 

I was sitting across from a sales rep I’d been hired to coach, and I’d already written the ending in my head. He was the problem. The pit in my stomach, that urge to walk out and tell the CEO to cut him loose, it felt justified. Sixty days is a long time. Long enough that everyone around this rep had built a story. The CEO had one. The team had one. The rep definitely had one. And I walked in leaning toward my own.

Then he said something that changed everything.

“I’m worried about fulfillment.”

Not “I can’t sell.” Not “the leads are bad.” He said, “I don’t think we can handle one more client.”

The second he said it, my body reacted. But not because I was mad at him. Because I was scared. If this was real, it was much bigger than a sales problem. And immediately, my first story showed up: the rep and the company aren’t aligned. Maybe he’s the problem. Maybe this is one of those situations where the answer is just replacement.

Then the urge hit. That hot, confident, totally unhelpful urge. I wanted to tell him he was single-handedly tanking the business. I wanted to walk straight to the CEO and say “fire him.” That would feel clean. It would feel decisive.

It would also be me reacting to an impression and pretending it was a fact.

So here’s where I had a decision to make. I could demand or I could diagnose. I could give him a speech about responsibility, urgency, standards, and effort. Or I could get curious about what was actually true.

I chose the harder move. I slowed down and asked him three questions.

I want you to hear how plain they are, because that’s really the whole point:

“What’s your split right now between ops and sales?”

“What have your conversations with the CEO looked like around this?”

“What breaks in ops if you close one more client?”

Two things happened. One, he relaxed a little. I wasn’t attacking him. I wasn’t doing what he expected, which was pressure and judgment. And two, we got to the truth faster.

The rep wasn’t just selling. He was also carrying real weight on the ops and fulfillment side. He wasn’t helping out. He was in the delivery weeds. He was running the team. He was backed up.

And in his mind, closing another client wasn’t a win. It was a threat. Because he didn’t think he could survive one more.

So he wasn’t tanking deals. He just wasn’t pushing them forward either. Not because he hated the job. Not because he didn’t care. Not because he didn’t get along with the CEO. They actually had a great relationship. It was because his internal math was: if I close this, we break. And if we break, I’m the one who suffers.

That’s a real constraint. So we stopped pretending it was a motivation issue and treated it like what it actually was: a role design problem and a capacity problem.

I worked with the owner to get this rep prioritized toward sales. We clarified responsibilities. We reduced the load on ops. We created breathing room. And within a couple of weeks, deals started closing again.

I was afraid after I heard the rep’s side. I wasn’t sure I could help. Because if fulfillment really was the constraint, you can’t sales-coach your way out of that.

But once we saw clearly, the path got obvious. The revenue from closing would provide the cash flow to invest more into ops. And the tension resolved.

Here’s what I want to land, because it’s really the whole point: I wanted to tell the CEO to fire this guy. But the move was to understand his reasoning, fix the real blocker, and train him up to close more deals.

That’s diagnosis before you demand.

When most leaders see sixty days with no closes, they go straight to volume. More dials. More outreach. More pipeline. More pressure. They start threatening targets. They send team-wide messages that basically say “step it up.”

In fact, that was already happening before I got there.

And maybe that works for a day. But most of the time it doesn’t fix the constraint. It just makes the room louder and increases tension.

The reason leaders do it is simple: pressure feels like action and diagnosis feels like delay. But pressure without diagnosis is how you punish symptoms. And symptoms don’t care how loud you are. They care what’s actually causing them.

Epictetus wrote something that hits this perfectly. In the Discourses, he says: “Show them where they’ve gone wrong and you’ll see them desist from their mistakes. If they don’t see what you’re getting at, they remain bogged down in their mistaken beliefs.”

That’s what happened here. This rep wasn’t waking up trying to hurt the company. He was acting from a belief that made sense to him: if I close more, fulfillment breaks. This belief isn’t evil. It might be wrong or incomplete or out of date, but it’s coherent.

So as a leader, your job isn’t to win the argument. It’s to surface that belief and test it. And if it’s mistaken, you correct it. Not with humiliation. Not with dominance. With clarity.

Now, I know this can be abused. Sometimes fulfillment is a real constraint. And sometimes it’s a story we hide behind. The leader’s job is to tell the difference fast.

And how do you do that? Not by vibe. By questions.

What’s your split between ops and sales? What have your conversations with the CEO looked like? What breaks if you close one more client?

That’s how you turn a vague excuse into a concrete constraint. Or expose that it’s neither.

This is where a lot of leaders get it wrong. They label something as a bad attitude or a bad fit, and sometimes they’re right. But a lot of the time, it’s bad role design. Mismatched incentives. Unclear ownership. Capacity issues.

And if you don’t diagnose, you’ll keep replacing people and keep recreating the same bottleneck.

Just to be clear: diagnosis is not softness. It’s precision. It’s surgical. Because once you know what’s real, you can set expectations that actually make sense.

There’s another passage from the Discourses that lands here. Epictetus writes about being on a ship, peering into the depths, looking at the sea all around with no land in sight. He becomes unsettled and imagines swallowing all that water if the ship goes down. Then he catches himself: “It doesn’t occur to me that three pints is all it takes. What is it that’s disturbing me? The sea? No, my judgment.”

That was me in this scene. My first judgment was huge. The rep is the problem. This is catastrophic. The business is sinking.

That’s the “sea.” Diagnosis shrinks it. Not by pretending it’s fine, but by narrowing it to what’s true. What’s the split between ops and sales? What conversations have already happened with the CEO? What breaks if one more client closes?

Once we asked those questions, the catastrophe turned into a solvable constraint. A capacity issue. A role clarity issue. A prioritization issue.

This ties directly into controlling what you can. When numbers slip, you can’t control the scoreboard in the moment. But you can control your judgment. You can control the quality of your inquiry. You can control whether you turn anxiety into pressure or into questions.

One of those builds clarity. The other just spreads stress.

If you’ve led a team, you know the feeling. You see a dashboard and your brain starts writing fan fiction. Worst-case scenarios. Who’s failing. What it means about you. What it means about the business.

The stoic move isn’t to shut it down with positivity. It’s to catch it. To say, “That’s an impression. Let me test it.”

Because the first story in your head is usually not leadership. It’s your nervous system trying to protect you.

So here’s the move: understand the full reasoning before you instruct or react. That’s it. Understand the full reasoning before you demand more effort.

Here’s what that looks like in practice:

Before you give instructions, ask for the full reasoning behind the rep’s behavior. Not the excuse. The reasoning.

Then separate what sits in their control from what sits in yours. They control outreach, preparation, follow-up, deal strategy. You control role design, capacity, process, tools, and clarity.

Then make it safe for them to surface constraints so you can fix the system instead of punishing symptoms or micromanaging.

Because here’s what would have happened if I’d gone with my first story. I would have pushed harder, demanded more, and might have even gotten the rep fired. And the real blocker, fulfillment capacity, would still be sitting there. The business would still be stuck, just with a different person wearing the problem.

One question I want you to sit with: what’s the full reasoning behind my rep’s lack of performance from their point of view?

That’s the anchor. Here’s a repeatable move you can run in sixty seconds.

Before any high-pressure conversation about missed numbers, ask yourself:

What do I know factually, not what do I suspect?

What’s the constraint here? Is it pipeline? Skill? Or is it something in the system like capacity, process, or role design?

What’s in their control this week? What’s in mine?

What’s the smallest thing we could test in the next seven days?

And here’s the rule: no instructions until you’ve answered those. Not because you’re being cautious. Because you’re being accurate. Surgical.

Here’s a mantra worth adopting: on this team, we diagnose with evidence before we demand more effort.

Because demands without evidence are how you lead from stress. Diagnosis with evidence is how you lead from reason.

If you want to do this well, you need visibility. Not vibes. Not “I think.” Not “it feels like.” You need clean insight into what’s actually happening. Where deals stall. Where follow-ups drop. What’s consistent and what’s not.

Next time you feel that pressure spike, before you send the message, before you drop the demand, before you announce the new rule, run the checklist. Ask the questions.

Diagnose before you demand.