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Make Someone Say YES using 4 Powerful Questions! 

 May 6, 2025

By  Tom Jackobs

Make Someone Say YES using 4 Powerful Questions!

Ahhh, that sweet, sweet sound of success—a client saying, “Yes, I’m in!” Never gets old, does it? Discover these powerful questions and make someone say YES that you need!

To Make Someone Say YES is the best feeling, right?

But let’s be real for a sec… not every sales call ends with that glorious high-five moment. If you’ve ever hung up thinking, “But they needed this! Why didn’t they say yes?” — it’s frustrating, right? And before you start questioning your skills or feel tempted to slip into pushy salesperson mode (ew, no thanks), let me share a little truth bomb:

👉 It’s not about selling harder.
👉 It’s not about talking louder.
👉 It’s definitely not about pressure.

It’s about asking the right questions in the right order—questions that flip the switch in your prospect’s brain and get them to see (and say out loud) what you already know:

They have a problem.
Your program solves it.
And the time to fix it? Is now.

So buckle up, because I’m about to hand you the 4 most powerful questions to make someone say YES I use in every sales call—and they’ve helped my clients close without being pushy or salesy. 

🧭 Step 1: “What is your goal?”

Picture this: You’re on a call with a client who clearly needs your help—but they’re hesitating. Ugh. Been there?

Start here. Ask: “What is your goal?”

Why? Because saying their goal out loud does two things:

  1. It gets them emotionally engaged.
  2. It paints a clear destination—and people don’t invest in vague dreams.

When they articulate what they want, they hear themselves say it… and that’s when the wheels start turning. Suddenly, their desire has shape, meaning, and urgency. Boom. You make someone say YES!

❤️ Step 2: “Why is that goal important to you?”

Now we’re diving in.

This is where you shift from surface-level to soul-level. Ask: “Why is that goal important to you?”

Let them dig deep. Maybe it’s about feeling confident again. Maybe it’s about showing their kids what’s possible. Maybe it’s about proving something to themselves.

Whatever the reason, this question taps into the emotional fuel that powers real decisions. Without it? You’re just selling a solution to a problem they’re not truly connected to. And that, my friend, is where sales go to die.

🔁 Step 3: “What have you tried before to solve this?”

Oof. This one stings—in a good way.

Ask: “What have you already tried to fix this?” and watch the floodgates open. They’ll list it all: the courses, the coaches, the YouTube rabbit holes, the money wasted, the dreams deferred.

It’s like a highlight reel of everything that didn’t work.

But here’s the genius part: when you ask this with genuine curiosity (not judgment), they start to see the pattern for themselves. The frustration builds… and suddenly, they’re craving a better solution. That’s where you come in.

⏳ Step 4: “Why is NOW the right time?”

My favorite. This question is the espresso shot of urgency.

Ask: “Why is now the right time for you to make this change?” Then—brace yourself—follow it with:
👉 “Why not in six months?”
👉 “Why not next year?”

That’s when the magic happens. They’ll begin justifying their own urgency. Their own readiness. And poof—your job isn’t to convince them anymore. They’ve convinced themselves.

Now that’s a sales conversation with soul to make someone say yes!

Ready to Use These Like a Pro?

If you’re thinking, “Okay this is GOLD, but how do I use it naturally on a call?”—I’ve got you covered.

💥 I put together a free training that walks you through this exact process:
The What, Why, What, Why Method—because let’s be honest, asking questions like this takes finesse.

Grab it here: WHAT-WHY-WHAT-WHY Framework.

Sales isn’t about pressure. It’s about connection.

With the right questions, your prospects don’t feel pushed—they feel seen, heard, and ready to invest in themselves (through you, of course).

So go ahead—ditch the script, keep your heart in the convo, and ask better questions to make someone say yes!

Because every “yes” starts with you asking the right question.

Scaling a business isn’t just about selling more — it’s about leading better. Learn Why Small Businesses Are Hiring Fractional Sales Managers (Instead of Full-Time VPs) 

Tom Jackobs


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