How to Drop the Dread and Cold Call with Confidence (Money Monday)

0:04This is Jeb Blount and it's Money Monday on the Sales Gravy Podcast.

0:19Hello, my name is Sarah Greer. I'm filling in for Jeb Blount and this is Money Monday. I want to talk to you today about cold calling. I know, I know, the thought alone sent a shudder right through you. Whenever I ask a room full of salespeople what they like least about their job, the top answer is almost always cold calling. But here's what I found. To consistently succeed on the phone, you don't have to be fearless and there's no magic script. You just have to find ways to make your calls more engaging for your prospects and yourself. Think of it as just a conversation you're having with another person.

0:53The more often you make the calls and the longer you stay on the phone, the naturally better your results will start to get. More engaging, more frequent conversations with your prospects really will change the whole game. So how do you make cold calling something you don't dread? Let me walk you through a few ways you can make that happen for yourself. To start, block off a specific time to make your calls. Cold calling feels overwhelming because it hangs over your entire day. The more you avoid it, the bigger it gets in your head. So instead, put your prospecting into a manageable box. scheduling two call windows, one in the morning, one in the afternoon, and about an hour each.

1:29At Sales Gravy, we call these power hours or HIPS, which stands for high-intensity prospecting sprints. During that time, your only job is to prospect. No email, no teens chats, no one stopping by with another quick question for you. Let your team know you're unavailable, block it on your calendar, and treat it like the priority it actually is. There's a reason this works. Every time you jump between calls and emails and other tasks, your brain has to reset. That constant switching drains your energy and makes it harder to build any momentum. But when you stay in prospecting mode, something starts to shift.

2:02After 10 or 15 calls, your opener gets more natural. The objections stop catching you off guard. Instead of thinking about what you're going to say next, you actually start listening to the person on the other end of the phone. That's when prospecting gets a lot easier and it starts to feel less like a grind and more like a rhythm. One trick that helps here is to give yourself a number instead of a time limit. Instead of saying, I'll make calls for the next hour, commit to 25 dials. Keep a tally and try to beat your previous best. It turns prospecting into a personal challenge instead of just another task on your list.

2:36Some of the best prospectors I know track this stuff like an athlete tracks stats. They know their numbers and they're always trying to set a new personal best. If you're still having trouble dialing in and getting your calls done on your own, call with others. Almost everything is easier when you're doing it alongside someone and cold calling is no different. Grab a teammate and schedule a prospecting block together. If you're remote, hop on a video call and prospect side by side. Knowing someone's listening naturally sharpens your focus. While your partner's on a call, you get a short mental break and if one of you hits a tough objection, you can compare notes right there and coach each other through it before the next call.

3:14You're basically getting free coaching in real time from someone who's in the trenches with you. It's also just more fun. When your partner stumbles through an opener, you'll probably laugh and it's your turn and you naturally want to raise the game. That little bit of friendly competition goes a long way. Make it part of your routine. Same partner, same days, same time each week. And before long, the hardest hour of your week becomes one you actually look forward to. It also helps to build a ritual. Watch any athlete before they compete. They don't just show up and perform. They've got a routine that gets them focused.

3:47Prospecting works the same way. The goal is to move from reluctant to ready before you make that first call. Maybe it's the same song before every power hour. Maybe you stand up for your first few calls because your voice carries more energy that way. Maybe it's just saying your goal out loud before you get started. If you're working with a team, make it something everyone does together. A quick huddle, a win from the day before, even a chant. 60 seconds of energy can completely change the mood before everyone starts dialing. If you're on your own, keep it simple. One song, one deep breath, one reminder of what you're going to accomplish.

4:23Over time, your brain starts associating the start of a prospecting block with confidence instead of dread. That shift can change how you feel about your entire day. And here's a bonus tip. Turn prospecting into a game. One of the fastest ways to make any repetitive task more engaging is to keep score and prospecting gives you plenty of things to track and score. Run a call blitz with your team. Pick an hour. Everyone prospects together and track one metric on a whiteboard or shared doc. Total dials, live conversations, appointments booked, whatever you choose. Use your scores to reward yourselves, not just when the deals are made, but when you get a prospect who agrees to a meeting or you get through a batch of calls consistently and confidently.

5:04Let the winner pick where you get lunch on Friday or who controls the hype song. And if you're prospecting solo, compete against yourself. Track your best power hour and see if you can beat it next week. Grab a coffee from your favorite shop the next day or give yourself an extra chapter in the book you're reading. The real prize is the accountability and confidence you and your team built through the process. Now, one important reminder, making prospecting more enjoyable helps you stay consistent, but it doesn't replace the fundamentals of cold calling. You still need strong messaging, a quality list, a solid call framework, and real practice in handling objections.

5:38If your team isn't role-playing regularly, you're missing one of the fastest ways to improve. Confidence doesn't come from reading a script. It comes from repetition, from coaching, from hearing yourself work through real conversations before you're ever talking to a prospect. Stick with these habits long enough and something starts to change. The phone doesn't feel as intimidating. Your confidence grows. The conversations get more natural. Before long, prospecting becomes just another part of your routine instead of something you dread. Jed Blunt likes to say the pipe is life. The more consistently you fill your pipeline, the more opportunities you create for yourself and for your customers.

6:16Go pick up the phone and keep your pipe full. This is Sarah Greer, and you've been listening to Money Monday on the Sales Gravy Podcast.

6:29again. I need some C notes, some cheddar and a stack of ends. I need a bowl of dough. I don't need no Facebook friends. I need a pack of them snaps, a handful of Fetty wops and rubber band on my green backs. Look, doll, don't be playing with my paper. I need every red cent. That's why I brought my little scraper.