The key question every sales leader should ask

Every sales leader — and every seller — wants to know one thing: “When will this deal close?”

You’ve heard it before: “It’s coming in this quarter, boss. Trust me.” Then six weeks later… no signature, no progress, just a new “commit” date.

Yes, the rep owns the number. But management owns the forecast. And there’s one simple coaching habit that changes everything:

👉 “What is the precise path from here to closure?”

Ask it. Every time. No exceptions.

It’s not about catching your rep out. It’s about forcing clarity — for them, and for you.

A good answer sounds like this:

⚽ The evaluation wraps by end of July. 3 of 4 success criteria met, final one hinges on Feature X.

⚽ Procurement onboarding started. Takes 4 weeks, we’re on track for mid-August.

⚽ Budget is ~25% short, but Champion is pushing for more. We also have scope flexibility.

⚽ EB is ready for a meeting on August 2 — contingent on successful evaluation.

⚽ Competitor Y has a strong internal sponsor and leverage on Feature Z. That’s our biggest risk.

⚽ Legal usually takes 3 weeks, but we’re planning for 6 given summer slowdowns.

⚽ Go-live plan agreed and reviewed weekly with the customer.

This seller knows where their towel is.

For smaller, faster deals? You might only need 2–3 bullets. But always:

🚀 Get customer agreement on steps and timing

🚀 Expose and validate any known risks

🚀 Involve multiple stakeholders (unless it’s truly tiny)

It’s a simple question. But it reveals everything.

So next time a rep says, “We’ve got this” — just ask: “What’s the precise path from here to closure?”

Let me know how it goes. Or better: forward this to a manager who needs it.