How I Use Horrible Cold Calls to Teach New Sales Reps to Leave Perfect Voicemails

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Dan Tyre
Dan Tyre



I could be the only person in the United States who still listens to cold calls.

Well, that’s not entirely true. Lots of managers and directors who are in charge of hiring salespeople listen to cold calls to try and identify good talent -- at least the first 15 seconds of the cold call.

But I might be the only buyer in America who still picks up cold calls.

Download Now: 25 Sales Voicemail Script Prompts I’m like a chef who visits great restaurants to see if there are any innovations he’s missing. Whether it’s morbid curiosity or sheer entertainment, I feel compelled to listen to my voicemails and occasionally (maybe four times a year), I pick up my phone randomly and connect.

From what I’ve seen over the last few years, there’s a huge variation in sales voicemail quality. The typical cold caller is a fast-talking script reader in a noisy environment. They’re dialing quickly in the hopes of finding anyone with a pulse so they can jam in a free offer or quick question to get my attention.

I can tell that these cold callers are in a hurry because they don’t really care who they’re talking to. They sometimes mispronounce my name, rarely ask how I’m doing, and it doesn’t really sound like they breathe -- they just try to cram in as many words as possible.

I usually say “Hello?”, then listen for something (anything) of value before saying thank you and hanging up. Sometimes I have to interrupt their stream of consciousness just to say that.

But once in a very long while (maybe once a year), I’ll get a good warm call. Despite being interruption calls, these warm calls are bolstered by the fact that the rep clearly did their homework. They sound relaxed, conversational, and are respectful of my time. They know who I am, reference something I’ve published recently, or an event I’ve spoken at.

These people get a full 90 seconds to make their case. Usually it’s because I’m telling them to interview at HubSpot, because just a little bit of effort is a significant enough departure from the norm that I want to let the caller know that I can tell the difference.

Warm calling is what I practice and preach. It’s about being human, doing your research, adding value in the first 15 seconds, and having fun -- I think of it as delivering a playful puppy to my prospects’ ears.

At HubSpot, we teach warm calling best practices to new reps or SDRs. We teach them how to make prospects smile, how to get over the fear of calling someone they’ve never met, how to keep prospects engaged, and how to keep the conversation flowing. We do a lot of role playing and we rate them on every aspect of the call until they score an average of eight out of 10 or higher.

All these things help. After all, understanding the theory behind how to do something and then putting it into practice is essential to learning.

But it’s just as important to understand what not to do. I literally keep a USB drive with recordings of the worst cold calls I’ve gotten that range from the bad to the skin-crawlingly obnoxious.

Listening to one terrible cold call can often be more instructive than ten good warm calls. Once you hear them, you know exactly what you never want to sound like. Here’s how I use cold calls as a coaching opportunity.

How to Use Bad Cold Calls For Sales Coaching

The first thing to set up is a prospecting call rubric. That way you can break down a prospecting call into each of its components and do a thorough assessment of its strengths and weaknesses. Here’s what I assess (each category is scored out of 10)

  1. Prep: How much does the rep know about me? How specific is their research -- do they just say, “I saw your website,” or do they say, “I read your blog post on corporate governance that you published last week”?
  2. Opening: Is it human? Does it get me to smile, laugh, or engage?
  3. Content: Is the rep adding immediate value? Are they giving specific tips that help me or just providing generic advice that’s not really helpful?
  4. Pace: Is the rep able to provide value without rushing so I can understand what they are saying?
  5. Length: Voicemails shouldn’t exceed 30 seconds -- any longer, and prospects will get bored, confused or just hang up.
  6. Phone number: You’d be surprised how many reps blather through their phone number unintelligibly. Can you understand what the person is saying?
  7. Follow-up: Did the rep send a follow-up email to the effect of “As per my voicemail … “? This lets me know a rep is interested in getting a response, helps me easily respond, and differentiates her from other people vying for my attention.

We tee up five to 10 calls to go through in an hour, ask everyone to score the call using the above rubric and then we discuss weaknesses, strong points, and whether we’d call back. After listening to a few traditional (usually horrible) cold calls and getting familiar with the scorecard, I have reps score each other’s voicemails.

Reps that are newer to sales may not be good at warm prospecting yet. You’ll see in your reps’ body language which ones recognize mistakes they make themselves, and by putting up examples of good and bad prospecting calls you’ll help them distinguish between what they should do and what they shouldn’t.

The main thing new reps gather from this exercise is confidence. They’ll have a scorecard with points they know they have to hit in their next voicemail or prospecting call, and walking them through actual recordings gives them real points of comparison. In this way, you can turn awful cold calls into a productive learning tool.

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