September 20, 2025 | Read online​

Quotas, Headaches, and Why Your Team is Struggling

by Kevin 'KD' Dorsey

I’ve been hearing the same thing over and over again from VPs and CROs lately:

Sound familiar?

Here’s the harsh truth: most sales orgs are suffering not because the economy is tight (it is), but because they’re trying to fix the wrong problems. They’re obsessing over results when results are already in the past.

You can’t change results. You can only change what causes them.

That’s where real sales leadership starts.

Today, I’m going to show you:

1. Why quotas must have a mathematical path (and how to stress test them).
2. Why issue diagnosis is the missing skill for most managers.
3. How to build a culture of responsibility, not micromanagement.

Let’s break it down.

1. Quotas Without Math Are Just Vibes

I’ll say it plain: if you can’t map out a path to quota on a napkin, it’s vaporware.

I see this all the time: a rep’s quota is $200K. Average deal size? $10K. That means 20 deals. If the team’s close rate is 20%, they’ll need 100 opportunities.

Question: do they even have that much pipeline?

If the math doesn’t work, the quota doesn’t work.

Leaders love to inflate quotas in down markets. Budgets get tighter, buyers get stingier—and somehow quotas go up. That’s not strategy. That’s setting your team up for failure, churn, and turnover.

Instead, start with pipeline over everything (POE).

• If your annual revenue goal is $20M, how much pipeline do you need to generate?
• Then ask: given rep capacity, is that realistic?

The quota conversation has to be grounded in pipeline capacity, not wishful thinking.

👉 Takeaway: Before you sign off on next quarter’s number, run the stress test. Deals × ACV × close rate. If the pipeline math doesn’t check out, your strategy doesn’t either.

2. Sales Is a Diagnosis Game

There’s an old cliché: “Sales isn’t a numbers game.”

I call BS.

Sales is a numbers game—but every number has a behavior, a process, or a skill behind it.

• A low close rate? That’s not the problem. That’s the headache. The problem might be poor discovery, not getting to decision makers, or weak follow-up.
• A bloated pipeline? The problem might be bad qualification, or reps sandbagging.
• Low activity? Maybe it’s a time-blocking issue, not motivation.

Your job as a leader is to move past the symptom and find the cause.

Here’s the framework:

1. Identify the metric that’s lagging.
2. Diagnose what’s driving it—behavior, process, or skill.
3. Prescribe the fix with clarity and buy-in.

Think like a surgeon, not a cheerleader. The Checklist Manifesto (Gawande – 2009) showed how simple checklists reduced errors and deaths in hospitals. Apply the same rigor to sales: metric by metric, diagnosis by diagnosis.

👉 Takeaway: Don’t just tell reps to “raise their close rate.” Pull the call recordings. Spot where deals are slipping. Prescribe the fix.

3. From Accountability to Responsibility

Here’s an uncomfortable truth: most accountability problems are leadership problems.

If a rep isn’t following through, ask yourself:

• Did I diagnose the issue properly?
• Did I connect it back to their personal goals?
• Did I show them the “why” (rational + emotional)?
• Did we agree on the “how” together?

If the answer is no, then it’s not an accountability issue—it’s a leadership miss.

Real accountability comes from responsibility.

• Reps should fill out their own one-on-ones.
• They should understand and track their metrics.
• They should run their own diagnosis checklists.

When ownership shifts from manager → rep, accountability stops being something you enforce. It becomes something they live.

And here’s the kicker: the best orgs build peer accountability. Reps call each other out for living (or breaking) the culture. That’s when you know you’ve built something special.

👉 Takeaway: Stop micromanaging. Start being micro-aware. Your job isn’t to bark orders. It’s to notice where reps need help, provide tools, and create a culture where responsibility is the norm.

How to Apply This Week

Here’s your tactical playbook:

✅ Run a quota stress test

• Quota ÷ ACV = deals needed.
• Deals ÷ close rate = opps needed.
• Opps ÷ weeks in quarter = opps per week.
• Compare that to current pipeline and capacity.

✅ Pick 1 metric per rep​
Don’t overwhelm. Identify the one lever that would have the biggest impact on performance.

✅ Do a diagnosis drill​
Ask: “What’s the result behind the result?” If revenue is down, is it deal size? If deal size is down, is it lack of multi-threading? Keep peeling the onion.

✅ Build micro-awareness rituals​
Instead of asking “Why aren’t you at quota?” ask:

• “What’s one thing you’d change about your prospecting block?”
• “Where are deals getting stuck in your pipeline?”
• “What support would make next week easier?”

Final Word

We’re in a tough sales climate. Budgets are shrinking. Buyers are cautious. Quotas are still climbing.

But here’s the good news:

You don’t need more dashboards. You don’t need more “motivation speeches.”

You need math. You need diagnosis. You need responsibility.

Because sales leadership isn’t about managing results—it’s about managing what creates results.

The leaders who figure that out? They build resilient, record-breaking teams—even in downturns.

So this week, stress test your quotas. Run a diagnosis drill. And remember:

Results are history. Causes are your job.

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