Ron wants to know how to get CEOs to actually answer his cold calls (or at least respond). He runs a recruiting firm and finds that his cold calls to top executives often go unanswered, and it’s driving him nuts. He wants to know if there’s a better way to break through all the noise—or if he just needs to buckle down and make more calls.

On this Ask Jeb podcast episode I give Ron specific strategies for connecting with hard-to-reach prospects like CEOs.

Let’s face it: sales is tough, and it’s not getting any easier. With an explosion of AI-driven messages and automated outreach, our prospects—especially C-suite executives—are tuning out more than ever. We call this phenomenon the “great ignore.”

If you don’t stand out from the torrent of spam, you will get lost in the shuffle.

Ron’s question—“Do I just need to make more calls, or is there some next-best method?”—is a dilemma many of us face. The short answer?

It’s both. You do need volume, but you also have to differentiate. If you’re just another voice in the crowd, you’ll be ignored, no matter how many dials you make.

A key point I shared with Ron is the power of multi-threading. That means calling multiple people in the organization—not just the CEO. While the CEO might be the ultimate decision-maker, other stakeholders, like the COO or HR director, might be easier to reach. These people can also give you valuable intel on hiring needs, budget constraints, or timing.

This top-down, bottom-up approach helps you gather context, build rapport, and earn the right to talk to the CEO by proving you’re not just randomly dialing.

Ron admitted he’s not always sure whether to leave voicemails. Most of us have left hundreds of voicemails and gotten very few callbacks, so it’s tempting to skip them. But here’s the thing: in today’s world, voicemail transcripts often end up in a prospect’s email inbox or text messages.

Even if they don’t call back immediately, they’re hearing your name and your pitch. Over time, that repetition can pay off—especially if you combine voicemails with other forms of outreach.

The real magic is in creating a multichannel sequence over 30 to 60 days. It’s not just “call once and cross your fingers.” Instead, plan multiple touches that tie together:

Be creative. Use each step to reinforce the last, rather than just repeating the same “Hey, it’s me again!” message. Tell a story or highlight different benefits at each step. Show them you’re genuinely interested in their business—not just cold-calling from a script.

Sometimes the CEO won’t respond because there’s no immediate need for your product or service. For Ron, if they’re not hiring, they won’t care about a recruiter. That’s okay—it doesn’t mean you should vanish.

Remember, timing is everything. The moment they do need your service, you want to be top of mind.

When you discover a hot lead—someone is hiring, or they are launching a new division—compress your timeline:

With a clear business driver, you can (and should) dial up your frequency. If you’re genuinely offering a solution to a pressing problem, they want to hear from you.

-Don’t Rely on a Single Contact: Multi-threading is your friend.

-Always Leave a Voicemail: It’s a free shot to get your message in their ear or inbox.

-Build Thoughtful Sequences: Each touch should reference the last, giving your outreach momentum.

-Match Frequency to Need: Slow drip for “lukewarm,” heavy pursuit for “red hot.”

-Stay the Course: You won’t always see immediate ROI, but consistency wins over time.

If you’re wrestling with a tough sales or leadership challenge, I want to hear about it. Head to salesgravy.com/ask, fill out the form, and my producers will reach out to schedule you on an upcoming episode. It’s your chance to get real-world advice from someone who’s in the trenches every day.