The call went well. They nodded. They said "send me something."

You sent it the same evening. Then you waited.

One week. A polite nudge. Two weeks. A "just checking in." 🐬 Then silence.

You want deals that close on the second meeting, not the fifth. You want your evenings back from writing follow-ups nobody answers. Here's how you get both, without chasing anyone.

The advice that keeps deals stuck

Somewhere along the way you were told: don't be pushy.

So you soften the ask. You say "no pressure." You say "whenever you're ready." You let the buyer set the pace, because pushing feels like begging.

That advice tastes sweet. In sales it leaves a bitter bill. 🐯 That's how one deal becomes four meetings, a long proposal and a quiet inbox.

Jenny Wood, a former Google executive, wrote Wild Courage (Portfolio, 2025). It reclaims nine traits people are told to hide, like weird, selfish, nosy and bossy, as strengths. That idea sparked this series. This is part 1, and the trait is pushy.

Pushy and direct are not the same thing

Pushy is pressure on the buyer. It is your need, dressed up as urgency.

Direct is a clear question at the right moment. It is the buyer's own reality, said out loud. 🌴 Pushy chases. Direct leads.

And whoever leads holds control of the sales conversation. Not by talking more. By asking the right thing in the right order.

Buyers don't ghost you because you asked too much. They ghost you because you never asked the two questions that make the deal real.

The problem is the order

When a deal drags, the proposal usually went out too early.

The buyer liked the conversation. But they never said what doing nothing costs them. They never picked a date to start. So your proposal lands with no weight behind it.

It sits in a crowded inbox and goes stale. It loses. 🐬 Not because the offer was weak, but because the order was wrong.

And the cost lands on you. Every extra meeting is prep time you don't get back. Every quiet proposal is a deal that was already counted toward the target.

The method: be direct in this order

In the Sales Gym we practice the 8 Steps of the Repeatable Sale. Two of them carry the direct questions. They come before the proposal, every time.

1. Step 4, Cost of Inaction. Ask: "What happens if you do nothing about this?" Then stop talking. Feel the pause stretch, and let the silence work. The buyer names the cost, in their words, with their numbers.
2. Repeat their cost back, in their words. "So waiting another quarter means the new hire starts with no process." Say it calmly. You are not selling. You are holding up a mirror.
3. Step 7, Starting Date. Ask: "To which starting date are we committing?" Not "soon." Not "next month." A day on the calendar.
4. Then Step 8, Statement of Work. Only now does the proposal go out. It is written in their words, with their cost and their date inside it. 🐯 It reads like their plan, not your pitch.

That is direct. Two questions, asked in the right order, with a calm voice.

It's also the part you can hand over. A new salesperson can learn two questions in order. They can't copy your instinct.

What it looks like in numbers

Picture Daniel. Made-up name, very common founder.

Daniel runs a B2B consulting firm. A deal takes him four meetings. Each meeting costs about two hours of prep and follow-up. That is eight hours per deal, before the ghosting starts.

Now he asks the two questions in meeting two. The buyer says waiting costs them a missed quarter. They pick the first Monday of next month.

The proposal goes out after meeting two. 🌴 Same offer. Half the meetings. Four hours back per deal, to spend on the next buyer. And this buyer already said yes to a date.

Why direct feels safer for the buyer

Buyers want you to be direct.

A clear question sounds like someone who has done this before. It tells them someone is steering. You become the one in the room who sets the pace. When you soften every ask, the buyer has to do the steering, and that is work they did not sign up for.

So they postpone. 🐬 Postponing feels safe to them, and silent to you. Direct saves them meetings too.

Where this comes from

I coached 2,000+ teams, including Google, BMW and Airbus, before Strategy Sprints. Since then, 2,400+ B2B founders have gone through our programs.

The pattern I see again and again: the founders who close fastest are not the loudest. They are the ones who ask what doing nothing costs, and then ask for a date. 🐯 Calm, clear, in that order.

Your one move this week

Before your next sales call, write the two questions on a sticky note:

"What happens if you do nothing about this?"

"To which starting date are we committing?"

Ask both on every call this week, before you promise a proposal. Notice how the conversation changes. 🌴 You'll feel it in your shoulders first.

You don't have a personality problem. You have an order problem. And order is learnable.

Less chasing. More deals that close on a date you both picked. That's a Sprintlife.

Want to practice the 8 Steps next to founders doing the same work? Start your 7-day free trial in Sprint Club: https://www.strategysprints.com

Ready to accelerate now? Book a Discovery Call: https://calendly.com/strategysprint/discovery-call

Happy hunting.

Simon & The Sprinters 🐬⚡️🐆