Can You Actually Make Cold Calling Fun?

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How to Make Cold Calling Fun (And Actually Look Forward to It)

Ask a room full of salespeople what they hate most about the job, and cold calling usually tops the list. The dial that goes nowhere. The brush-off in the first five seconds. The voice in your head telling you there are plenty of other things you could be doing instead.

What I’ve found is that the reps who are good on the phone are not built different. They have not found some secret script that makes strangers happy to hear from them.

What they have done is turn a grind into something with a little juice in it, so they pick up the phone more often and stay on it longer. That’s the truth. More calls beats better excuses, every time.

So, how do you make cold calling something you don’t dread? Think of it less as a chore and more as a challenge. Here are four ways to make that happen:

Block the Time and Get on a Roll

Cold calling feels awful partly because it hangs over your entire day as this fearful thing you are supposed to do. But like with anything we fear or hate, we procrastinate.

So, shrink your cold calling activity into an easy-to-handle box. Pick two windows, one in the morning and one in the afternoon, an hour each. At Sales Gravy, we call these blocks Power Hours.

During that time, your only job is to prospect. No email. No Slack. No “I’ve got a quick question.” Let your team know you’re unavailable, and block the time on your calendar so everyone, including you, treats it as a priority.

There’s another benefit to working in focused blocks. Every time you jump between calls, email, and other tasks, your brain has to reset. That constant switching drains your energy and makes it harder to build momentum. Stack your calls back to back instead, and something clicks around the tenth or fifteenth one.

• The words stop sounding like a script you are reading.
• The same three objections keep coming up, so they stop rattling you.
• You quit thinking about what you are going to say and start actually hearing the person on the other end.
• It is the difference between grinding out calls and getting on a roll, and getting on a roll feels great.

One small trick that makes the hour go faster: give the block a number instead of a clock. “Twenty-five dials,” not “call until three.” Keep a tally on a physical call tracking sheet. Trying to beat your own count turns a slow hour into a race, and races are much more fun than boring chores.

Do Not Call Alone

Almost everything is easier with someone next to you, and cold calling is no exception. Grab a teammate and run your block together, trading calls back and forth. Works just as well over a video call and a dialer if your team is remote.

A few things happen when you do this.

• With an audience, you sharpen up without even trying, because nobody wants to ramble in front of a peer.
• You get a real break between your own calls while your partner takes theirs, and you pick up plenty just from listening to how someone else handles a live prospect.
• When you keep hitting the same objection and cannot find the words, your partner can feed you a line on the spot, or you can hash it out the second you both hang up.

And honestly, it’s just more fun. When your buddy fumbles their opener, it is funny. Then it is your turn, so you had better bring it. That little bit of friendly pressure is exactly the kind that helps.

Make it a standing thing. Same partner, same two days a week, same time on the calendar. You will be surprised how fast the worst hour of your week turns into one you look forward to.

Build a Ritual that Flips the Switch

Watch any athlete before they compete. They don’t just show up and perform. They have a routine that gets them switched on, and you can steal the idea.

The goal is simple. You are trying to change your state in a hurry, from tired and reluctant to loose and ready. Whatever gets you there works.

• Play the same hype song before every block so your brain learns what is coming.
• Stand up for your first few calls, because your voice carries more energy on your feet than slumped in a chair.
• Say out loud, to yourself or the room, exactly what you are after today.

Teams can make this a group thing, and it is even better that way.

• A quick huddle before a power hour.
• Maybe a call and response you run together.
• Some short bit of noise that gets everyone off their heels.

It sounds corny right up until you have done it and felt a flat, half-asleep room turn loud and ready in under a minute. Then you get it.

Flying solo? Same idea, smaller. One song, one deep breath, one line you say to yourself, then dial. You are teaching your brain to tie the start of a call block to feeling good instead of feeling dread. Do it enough, and the phone stops being the thing you avoid.

Turn Cold Calling into a Game

The fastest way to make any boring task fun is to keep score, and cold calling was built for it.

Run a call blitz. Pick an hour, get the whole team dialing at the same time, and track one simple thing where everyone can see it, a whiteboard or a shared doc. Most dials. Most live conversations. First appointment of the day. The energy of everyone going at once is half the fun by itself.

Two rules keep it from backfiring.

• First, score the behavior, not just the result. You cannot control who says yes, so do not stake the game on it, or one slow morning tanks the whole room’s mood. Reward the things you actually control: dials made, decision makers reached, clean openers.
• Second, keep the stakes small and a little silly. Loser buys the coffee. Winner picks Friday’s playlist. A cheap plastic trophy that moves from desk to desk all week. The prize was never the point. The scoreboard is.

No team to compete with? Compete with yourself. Write down your best day and try to beat it. Watching your own number climb is its own reward, and it keeps you honest on the days you would rather coast.

Five Cold Calling Games to Try With Your Team

Here are five cold-calling games you can run with your sales team that are fun without turning the call itself into a gimmick. They reinforce the behaviors you actually want: dialing, conversations, asking, resilience, and appointments.

Cold Call Bingo: Give each rep a bingo card with squares based on things that happen during a prospecting block: “Got a hard no,” “Reached a decision maker,” “Asked for the appointment,” “Prospect said ‘send me an email,’” “Got transferred,” “Made someone laugh,” “Handled an objection,” “Booked an appointment,” “Made 10 dials without stopping,” etc. First to Bingo wins. The beauty is that even rejection helps fill the card.

Beat the Clock: Set a 20- or 30-minute timer, and everybody dials together. The objective is simply to generate as many quality conversations as possible before the buzzer. Award points: 1 for a live conversation, 2 for reaching the right person, 3 for completing the pitch/ask, and 5 for setting an appointment. Run three rounds and crown the winner. This creates short bursts of intensity instead of an intimidating two-hour call block.

The Objection Jackpot: Before the call block, put the most common objections on cards: “Not interested,” “We already have a vendor,” “Send me something,” “Too busy,” “Call me next quarter,” “No budget,” etc. Reps draw an objection. If they actually encounter their objection during a call, they get a point. If they handle it effectively and keep the conversation going, they get another two points. If it leads to an appointment, five points. Suddenly reps are hoping to hear objections instead of fearing them.

NO! Poker: Every legitimate rejection earns a playing card. Five rejections = a five-card poker hand. Then reps can earn opportunities to exchange cards by reaching decision makers or setting appointments. At the end of the prospecting block, the best poker hand wins. This is especially good for newer reps because it completely changes the emotional relationship with rejection: you can’t win unless you collect some NOs.

Appointment Horse Race: Put everyone’s name on a whiteboard and draw a 10-space racetrack. A meaningful conversation moves you one space. A qualified opportunity moves you two. A booked appointment moves you three. The first person across the finish line wins; or, if nobody finishes, whoever is furthest down the track when the prospecting block ends wins. The visual competition makes this one especially effective when the whole team is prospecting together.

One twist I particularly like: make the prizes small and immediate. $10 gift cards, lunch, first choice of leads, ridiculous trophies, candy, or simply bragging rights. The game itself should create the energy. You don’t need a $500 prize to get people competing.

And I would deliberately rotate the games. Bingo on Monday, Beat the Clock Tuesday, Objection Jackpot Wednesday, NO! Poker Thursday, Horse Race Friday. That keeps prospecting blocks from becoming stale while still reinforcing the fundamentals.

One Honest Caveat Before You Go

Let me be straight with you so you are not disappointed later. Fun is a multiplier, not a magic trick. It will not rescue a weak pitch or a garbage list. You still have to prepare, run your call framework, know your messaging, and role-play your objections with your team until the responses come out automatically.

If your team is not role-playing, you are skipping the single cheapest way to get better. Fun is what gets you calling, and calling is what makes you good.

Stick with this long enough, and the thing you have been dreading starts to feel different. The knot in your stomach turns into a little bit of a rush. And once the phone stops feeling like a punishment, you make more calls, which was the whole point from the beginning.

As Jeb Blount always says: “The pipe is life.” You might as well enjoy filling it.

Common Questions Salespeople Ask About Making Cold Calling Fun

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