Mastering the 'R' in CIRCLE - Part 2: Warm Outbound Calls (How to Win Prospects Without Feeling Pushy)

Wednesday, March 05, 2025

How I Went from Staring at a Phone to Having Prospects Chase Me

It was mid-2003. I had just surprised my wife—who wasn’t even my wife yet—that I was moving us across the country to take a new job as an account executive with an inside sales company called EquiFirst.

I’ll never forget this. I was sitting in my cubicle, staring at a long list of mortgage brokers in Minnesota that I was supposed to call. Now, me—this country-twang-sounding guy—trying to connect with Minnesotans? Not the easiest thing in the world.

I was holding this big stack of phone numbers in my hand, looking at the makeshift scripts they had given me, trying to piece together something that would actually work. And then, the guy who got me hired—Ryan Dunphey—walked up to my desk. Back then, this wasn’t an easy position to get. You had to work your way up as a loan officer first, and account executives were making obscene amounts of money before the mortgage crash.
Ryan looked at me, and I’ll never forget what he said next.

"What the f*** are you doing?"

I looked up at him from my little desk and said, "Man, I’m just kind of getting everything ready to make calls."

He shook his head and said something that would change my career forever.

"I didn’t get you hired here for you to sit there and stare at the phone. I want you making as many outbound calls as you can possibly make, every single day, from sunup to sundown."

That hit me hard. But I knew he knew what he was talking about. He was closing somewhere around ten million a month at EquiFirst, and he had been my only account executive who could close a loan in one day (yes you read that right). So, I got to work.

I started making outbound calls. And something crazy happened. In that huge office building in Charlotte, North Carolina, they tracked every single call we made. And for three months straight, I did nothing but outbound—cold calls, warm calls—it didn’t matter. Day in, day out, over and over again. At the end of the day, I’d get my call logs, and they’d show I had put in nine to ten hours of outbound dialing.

And then, something amazing happened.

Through all that repetition, I figured out what to say. By trial and error, I started to learn what worked. And after about three months, my outbound calls started turning into inbound calls. People wanted what I had. I’d walk in every morning, and before I even touched the phone, it would already be ringing. Next thing I knew, it was time to go home, and I had four or five loan packages in underwriting.

I’m telling you this because you don’t have to spend thousands of hours figuring this out the hard way like I did. Outbound is still the secret to large amounts of sales—even in 2025—it’s just changed a little bit.

Back then, it was more about consultative selling. Now, it’s about problem-solving.

And that starts with knowing how to connect.

Warm Outbound Call Script: The Connection Stage

If you’re making warm outbound calls, your prospects have likely engaged with your company in some way—maybe they downloaded a resource, attended a webinar, or requested information. The goal of the Connection Stage is to make them feel comfortable, lower resistance, and spark curiosity—so they lean in instead of pushing away.

1. What the Connection Stage Is (and Isn’t)

The Connection Stage isn’t about selling. It’s not about diving into their problems or presenting a solution. Your only goal at this stage is to lower resistance and engage them in a two-way conversation.

Think of it this way: If a stranger walked up to you on the street and immediately started pitching their product, you’d probably walk away. But if they made a casual, engaging remark that piqued your curiosity, you’d be more likely to stick around.

That’s exactly what we’re doing here—getting prospects to stick around.

2. Opening the Call (Connecting Questions)

The first few seconds of a call determine whether the prospect stays engaged or mentally checks out. Your goal here is to avoid sounding like a typical salesperson and, instead, trigger curiosity.

“Hey [Name], this is [Your Name] from [Company]. I saw that you recently [downloaded our guide/signed up for our webinar/requested info], and I just had a couple of quick questions to see if we can help. Is this an okay time?”

(If they say yes, proceed. If not, ask for a better time to call back.)

3. The Tonality and Pace That Make All the Difference

The words you say matter, but how you say them matters even more.

Use a neutral, calm tone—like you’re talking to a friend, not a salesperson trying to “close” them. Your pace should be slightly slower than normal, with small pauses that make the conversation feel organic rather than scripted.

For example, compare these two versions of the same line:

🔴 Salesy Version: (Fast, robotic, rushed) “Hey [Name], this is [Your Name] from [Company]. I saw you downloaded our guide, and I wanted to see if you’re interested in our services.”

🟢 Better Version: (Slower, conversational, neutral) “Hey [Name]… this is just [Your Name] over at [Company]… Looks like you had downloaded [resource] the other day, and I was just curious… what was it about that that caught your attention?” (Pause and let them answer.)

Notice the difference? One feels like a pitch, while the other feels like a genuine conversation.

4. Engaging the Prospect (Connecting Further)

Once the prospect responds, your job is to keep them engaged by asking open-ended questions. These questions make them feel in control while subtly guiding the conversation forward.

“What was it about [the resource they engaged with] that caught your attention?”

“Was there something specific you were hoping to get from it, or was it more out of curiosity?”

These questions accomplish two things:

1.) They remind the prospect why they engaged in the first place—often triggering an emotional connection to their problem.

2.) They shift the conversation from you to them—putting them in control and making them more comfortable.

5. Creating a Pattern Interrupt (Avoiding Resistance)

Most sales calls trigger immediate resistance because prospects assume they’re about to be pitched. A simple pattern interrupt can break this expectation.

“Hey [Name], I’m not quite sure we could help you yet… I’d have to know a little more about what you’re doing first.”

This flips the dynamic—it subtly implies that you might not be a fit for them, rather than assuming they’re a fit for you. This small shift makes the prospect more open to talking.

6. Ending the Connection Stage Without Jumping Ahead

The biggest mistake salespeople make is rushing through this stage and diving into problem-solving too early. The goal is not to diagnose or sell here—it’s simply to get them comfortable enough to have a real conversation.

Here’s a natural way to transition:

“Well, I appreciate you sharing that with me… Just to make sure I understand where you’re coming from, would it be okay if I ask you a couple of quick questions about how you’re handling [related issue] right now?”

At this point, the Connection Stage is complete, and you’re moving into Situation Questions, where you’ll start to uncover more about their current process. But remember—the smoother the connection, the easier the rest of the conversation will flow.

Why Mastering the Connection Stage Matters

Most salespeople lose the sale in the first 30 seconds—not because of a bad pitch, but because they failed to connect. If you rush into “sales mode” too quickly, you trigger resistance. If you focus on engagement and curiosity, you lower resistance and create a natural path for the conversation to continue.

When done correctly, the prospect should feel: ✅ Heard and understood

✅ Curious about the conversation

✅ Comfortable continuing to talk

When you build trust first, the rest of the sales process becomes effortless.

Next Up: How to Crush Cold Calls Without Feeling Like a Human Auto-Dialer

Cold calls don’t have to suck. In our next edition, I’ll break down exactly how to turn a total stranger into a potential client in 30 seconds or less.

Until next time,

Keith

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