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To Leave a Voicemail or Not: Navigating the Decision in Cold Calling Sessions

The estimated reading time for this post is 6 minutes

In the dynamic world of sales, every phone call holds the potential to be a game-changer. As a seasoned cold calling expert, you’re well aware that each decision you make during a calling session can impact your success. 

One of the perennial questions that arises is whether to leave a voicemail or not. This seemingly simple decision is nuanced and can significantly influence your outcomes. Let’s delve into the situations that can guide your choice and help you master the art of voicemail strategy.

The Element of Mystery

In the art of cold calling, piquing curiosity is an invaluable tactic. Leaving a well-crafted voicemail that offers a tantalizing hint about a valuable solution or benefit can prompt prospects to return your call out of sheer intrigue. The element of mystery can be a powerful tool, especially if you’re confident that your product or service addresses a specific pain point for the prospect.

Respecting the Decision-Maker’s Time

In the fast-paced business world, decision-makers are often inundated with tasks and responsibilities. A lengthy voicemail might deter them from listening to your message altogether. Keeping your voicemails concise, clear, and focused on a specific value proposition showcases your respect for their time.

By delivering a succinct yet impactful message, you’re more likely to capture their attention and encourage a call back.  We recommend that voicemails be no more than 35 seconds in duration.

Voicemail as a Follow-Up Strategy

Cold calling isn’t a one-and-done endeavor. It often involves multiple touchpoints to cultivate a connection. Voicemails can serve as strategic follow-ups to initial calls or previous interactions. A well-structured voicemail that references your previous conversation and reaffirms your commitment to addressing their needs can leave a positive impression.

This approach reinforces your dedication and keeps your offering top-of-mind, increasing the likelihood of continued engagement.  We like to think of voicemails as a mini-advertisement that builds familiarity with the prospecting using a human voice (yours!).

The Absence of a Voicemail

Just as a well-timed voicemail can enhance your efforts, there are situations where the absence of a voicemail can be equally impactful. For instance, if you’ve recently sent an introductory email and your prospect is expecting your call, skipping the voicemail can prompt them to recognize your number and answer your call. 

This technique capitalizes on the element of surprise and increases the chances of an immediate connection.  We rarely leave voicemails on our first outreach attempt because the purpose of the initial call is to confirm the phone number’s validity or connect with the prospect.

Timing is Everything

When is the best time to start making cold outreach phone calls?  How about right now.  

Imagine this scenario: you’re in the middle of a productive calling session, and suddenly, you hit a series of voicemails. It’s frustrating, right? Your prospects feel the same way. Strategically timing your voicemails can mitigate this frustration and increase your chances of engagement. 

Conciseness is critical when leaving sales voicemail messages – strive to keep them within a 30-second window. Equally, it’s not advisable to mention unsuccessful prior voicemail attempts as this can be counterproductive. 

Furthermore, empirical data suggests that the most effective times for leaving voicemail messages are between 6:45 AM and 8:00 AM, as well as between 4:30 PM and 6:30 PM in your prospect’s local time. This may mirror unconventional work hours, yet you must remember that these are the operational hours of your potential clients!

See this post referencing Jill Konrath’s work on call timing. You can see the original Inside Sales/MIT study here led by Professor James Oldroyd of MIT

The Power of Personalization

When you find yourself on a calling session, the pressure to connect with as many prospects as possible can be intense. However, bombarding voicemail boxes with generic messages might yield minimal results. 

The key lies in personalization. If you have detailed insights about a prospect or their pain points, leveraging this knowledge in a brief, impactful voicemail can make you stand out from the crowd. 

A personalized voicemail signals your commitment and genuine interest, enticing the prospect to return your call.

Here’s an example of something you might want to use.

Hi PROSPECT NAME, it’s AGENT NAME from COMPANY NAME.  I can be reached at XXX.XXX.XXXX (phone number).

We’ve never spoken before so I thought I’d leave this short message as to why I’m calling.

We help people like you …… SOLVE YOUR BIGGEST PROBLEM (from your Power Statement Work).

If this sounds like you, then feel welcome to call me back for a 3-minute conversation.


How do we use voicemail?

We’re big proponents of cold phone outreach.  Because we know that phone outreach is the quickest and easiest way to reach people to determine if they have interest, intent and information about our client’s services and products.  Voicemail is a bridge channel that uses the most personalized content available – the voice of another person!

Here’s what we do:

  1. We don’t leave always leave a voicemail

On our initial calling sets we rarely leave a voicemail because we’ve never spoken to our prospect before and want to have a real conversation with them before they’ve heard our voice.

  1. When we leave personal voicemails

Once we’ve spoken to a prospect or we’re still working through our secondary or tertiary calling sets we’ll leave personal voicemails wherein we re-introduce ourselves, make a value statement and leave contact details.

If we’re following up from a previous conversation or reschedule of a meeting that’s been missed, we’ll leave a voicemail referencing the conversation or meeting and request a call back.

  1. When we “drop” a voicemail

Various dialer technologies allow you to pre-record a standardized voice recording and then “drop” it into the prospects voicemail.  We use dropped voicemails when we’re trying to build brand recognition and equity for our clients as part of our outreach efforts.  

We think of it as a 30-second radio commercial with a material value proposition that relates to the persona.  While we leave our call back number, we don’t specifically ask for a meeting, because when was the last time you heard a radio message that asked you to schedule a meeting?.

So when should you leave a voicemail?

There are multiple times and reasons for why you should leave a voicemail.  We’ve mentioned a few above, but the one thing that’s clear is that you should know the purpose or WHY you’re leaving the message by voicemail before you even speak into your prospect’s voicemail box.

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