You Have a New Sales Rep. Here's How to Win at Cold Calling Training

Let’s be honest up front. Cold calling is nobody’s favorite part of sales. In fact, LinkedIn data reports that a healthy majority of sellers (63%) say it’s the worst part of the job — and it’s not hard to see why. The same research indicates just 2% of cold calls result in a booked meeting, and other literature suggests that dismal figure might actually be on the optimistic side.

Sitting down to cold call means spending hours on the phone, with few connections, fewer conversations, and almost no conversions. And yet, despite cold calling’s diminishing reputation as a viable sales strategy — or perhaps because of it — it continues to produce results. HubSpot research indicates that more than a third of sales reps (37%) produce the most leads from cold calls, and data from the RAIN Group finds that most C-level buyers (57%) prefer to be contacted by phone.

Whether or not you’re using cold calling as a standalone strategy will depend in large part on your industry and deal size. No matter what you’re selling, the phone is a vital touchpoint in any proactive outreach campaign, which means it’s critical to include some cold calling training whenever you’re onboarding new sales reps.

“Smile and dial” won’t cut it, so here’s my best advice for teaching your reps to embrace the phone and reap the benefits.

7 Top Tips for Cold Calling Training

Tip #1: Focus on Mindset

No matter where you source your statistics on cold calling success rates, reps are looking at a mountain of rejection whenever they step up to the phones. Anyone can dial, but the difference between sustainable, long-term success and burnout is largely about mindset — which is why getting demoralized is one of the biggest cold calling mistakes reps make.

Emphasize success stories, showing reps what they can achieve when they put in the work and hone their craft. I also like to point out that rejections are part of the process and explain that getting a “yes” is only possible by first getting a lot of “nos.”

When reps can embrace the numbers game and see rejection as an essential step to reaching their next win, they’ll be much more resilient. Marc Wayshak, founder of cold calling training firm Sales Insights Lab, agrees: “Building resilience to handle discomfort is vital when mastering cold calling. While many salespeople initially find making cold calls extremely intimidating, the more you expose yourself to cold calling, the easier it becomes.”

Tip #2: Demonstrate Rapid Research

Personalization and research will undeniably improve cold calling conversion rates for your reps, but there are diminishing returns that your cold calling sales training should take into account. Most prospects will never answer the phone, so if a rep spends nearly 30 minutes researching and can only make two cold calls per hour, it will take weeks or months to book a meeting.

I recommend teaching reps how to conduct quick, effective research that gives them an edge without sacrificing efficiency. My main source of information has always been LinkedIn Sales Navigator — within 2-3 minutes, you can look at a prospect’s position and work history and spot any mutual connections that might be contextually relevant to your conversation, setting you up for a warmer cold call with minimal time invested. This step also lets you confirm your data is still accurate, and it’s saved me from embarrassment countless times.

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Tip #3: Incorporate Role Play

There’s no getting around the fact that role-playing is awkward. Know what else is awkward? Calling strangers to sell them something. Reps who can embrace the discomfort of enthusiastic, improvisational role play are going to be more successful cold callers who can riff with prospects, redirect conversations, and even handle rejection gracefully to preserve the possibility of future wins.

Remember that role play isn’t only for the participants, and spectators can also benefit from watching an interaction play out. However, because role play can be uncomfortable at first, I like to incorporate it into cold calling sales training by having reps perform it in pairs before getting the team together and putting participants on the spot.

Tip #4: Soften the Script

Scripts should never be set in stone, and building flexibility into your scripts could be a groundbreaking move.

According to Dan Tyre, former HubSpot sales executive and now founder and CEO at Tyre Angel, “Scripts are out, and playbooks — a series of effective questions to control the situation — are the new and more effective approach. Every connected call is different, and the SDR needs to be nimble and responsive to the situation while still following an outline to get important information.”

As Tyre mentions, questions are the key: “If you start talking about your product or service, you’re cooked.” Not sure what questions to ask? Here are a variety of proven call scripts for your cold calling training. Take pieces of each of these and incorporate them into your playbook.

As you’re conducting your cold calling training, you might notice that some basic aspects of cold calling are still somewhat unintuitive. In addition to asking questions instead of raving about your product, reps should learn to give the prospect time to think and respond instead of trying to fill up every moment of uncomfortable silence, and callers should use language that demonstrates empathy and shows you understand what real issues the prospect is dealing with.

Cold calling requires a lot of soft skills, and while they’re more difficult to measure, improving them can make a huge difference. Research from Sales Insights Lab, for example, found that top performers ask 39% more questions in discovery conversations and spend just half the time discussing product features.

Remember, it’s about them and not you.

Tip #5: Teach the Tech Stack

Dialing numbers sounds simple, but tools like your CRM and autodialer will add a lot of complexity in addition to the functionality they bring to your cold calling campaigns. Teach your reps to use these technologies effectively, identifying shortcuts and best practices that can save time and increase efficiency. Even saving a few seconds here and there will reap dividends when your team is dialing thousands and thousands of times.

Besides the know-how to execute calls and record notes, reps should be able to pull basic reports at any time and track their progress. Focus on appointments booked rather than call volume. As Tyre explains, “If the conversations aren’t effective, why would anyone want you to do more of them?”

When reps are focused on quality over quantity, they’ll do better qualification up front and only reach out to prospects whose pain points make them a good fit for your product.

Tip #6: Optimize Your Outreach

Training your sales team to cold call will require a significant investment of time and money, but what if there was a way you could improve outcomes for your reps without spending a dime? It sounds too good to be true, but calling at the right time can make a big difference in the success of your campaigns.

Check out this HubSpot blog post for the full rundown on the best time to make a sales call. According to research from CallHippo analyzing 15,000 calls, connections are three times more likely on Wednesday (33.9%) than Friday (10.4%). Monday is also somewhat unproductive, with just 15.7% of calls connecting. The same study also found impacts in time of day, with 10-11 AM and 4-5 PM resulting in more connected calls.

In my experience, what’s more important than perfect timing is paying attention to your prospect’s time zone. Calling someone in California at 9 AM EST is probably going to land you on their bad side.

Tip #7: Remember Time Management

The hardest part of cold calling is starting, so your cold calling training should teach your reps to successfully kick off the initiative. My two main focuses here are time blocks and lead scoring. Time blocks should be 60-90 minutes max, with breaks to avoid burnout, and they should incorporate the timing research above to make them as effective as possible. By making calls at the same time each day or week, initially hesitant reps will begin to pick up the phone out of habit.

Because the first few dials of the day can also be a little shaky, I often encourage reps to start with a few lower-value leads before diving into those with the highest lead score in the CRM. This technique won’t necessarily apply to everyone — if a rep feels they do their best cold calling right off the bat, don’t force them to “warm up” on lower-quality leads with a dubious ROI.

Ready to Roll Up Your Sleeves?

The above tips aside, if your job is to train a sales team, you’d better be ready to roll up your sleeves and make some dials. Even if you’re a little rusty on the phone — and we all are for the first few dials each day — your call recordings will serve as good teaching material and your willingness to step into the trenches will build your credibility with the team.

30 Free Sales Call Templates

Have better conversations with your sales prospects using these free templates.

• Discovery call template
• Follow-up call template
• Standard outreach template
• And more!

Download for free Learn more Download for free

Download Free

All fields are required.

You're all set!

Click this link to access this resource at any time.

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