Work with and around voicemail

We now have e-mail, text chat, Twitter, mail and more. So why does anyone still bother to sell over the phone?

The secret of those marketers who use telemarketing in their contact mix is simple: It’s all about conversion.

A successful telemarketing program can convert prospects at 10 times the rate of a mail program, 100 times the success rate of an e-mail program. Despite our best efforts in technology and creative, no marketing tool can replace the dynamic of a live person-to-person conversation.

With these results, why don’t more companies leverage the phone? One piece of technology has become a barrier to these conversations — voicemail. We have all run up against voicemail, with its cheery personal message of absence or cold, automated outright rejection, which prevents us from reaching our intended audience.

If your job is to find new prospects or to rekindle a relationship with a past customer, voicemail can be difficult to overcome. But there are various solutions to this challenge.


Sometimes the best way to get through voicemail is to go around voicemail. When calling a prospect, never start by leaving a message the first time you hear a voicemail prompt. There are a few options to test that can lead directly to a live conversation.

First, listen to the message — oftentimes you will hear another extension or name of an assistant to speak with. Better to speak with an alternate live person than a machine.

Most people are happy to help with a simple inquiry of “I was trying to reach xxx, is he/she in today?” The answer to that may suggest when to try again — the next day or a later time in the day.

You may also be able to confirm a key detail or gain some insight into the current state of activity at the location by asking a simple “Is he/she always this hard to reach?” or “Are you folks extra crazy today?” Any information you glean can help you tailor your approach to the first contact and, if need be, leave a more effective message later on.

If the voicemail greeting does not offer another live option, try hitting “0” for the operator and ask for assistance finding your target. When you reach an operator or receptionist, the same concepts apply as with a referral or assistant — ask for help and information.

You may also inquire if there is another contact in that department who is more easily available. A simple, confident request of “Does xxx have a colleague or assistant I can speak with?” is much more effective than “Can you connect me with the person responsible for purchasing XYZ?”

The second inquiry establishes you as the human equivalent of junk mail. And then, no matter how relevant your call may be, you will be unceremoniously dumped into voicemail.

At this stage, you may find your go-between acting as a human voicemail system, looking to screen your call on behalf of your contact. If so, be sure to highlight a relationship with the contact.

For instance, try “John suggested I speak with xxx” or “I was told to speak with xxx, is there a time when he/she will be free?”, as opposed to trying to have the actual conversation through an intermediary. Don’t say “Tell him I’m calling to see if he needs any ABC widgets …” — disaster!


Having a hard time getting connected or reaching an automated system with no live operator? You still have options to try before resorting to a message.

Timing is often the secret to reaching people at their desk. Establish a cycle to follow if you don’t reach your prospect on the first call.

Try early in the morning, before normal business hours, or late in the day after business hours. Usually these are times you can reach people at their desks as they are getting started or wrapping up.

This helps when you are trying to reach a high-level executive with both human and technological screens operating throughout the day. You may also try just after lunch — people are more relaxed (assuming they’ve had lunch) and this can lead to a longer conversation opportunity than an early call.

It’s usually easier to reach someone in the last 15 minutes of the hour. Most meetings are scheduled on the hour, and therefore people tend to have more free time planned before a meeting starts.

Track the time and day of your prior attempts when trying to reach an elusive contact. Some techniques work best with large companies, some with small, all both have value and tend to hold true over time for a specific contact.


So you’ve tried all the techniques to avoid voicemail and reach your prospect directly, but to no avail. What now? What message should you leave?

First, remember that the goal of a good prospecting voicemail is to generate a callback. Not close a sale. Not build a relationship. Just to generate a callback.

The golden rule of voicemail success is: Keep it short. A simple message that asks for a callback works twice as well as a message that overexplains why you are hoping for a call. Save your questions for the callback, don’t waste them on a message.

We all receive poorly crafted messages that give us enough information to ensure we will never call back. You know the messages I mean: “Hi, Mr. xxx. I’m calling on behalf of ABC company to offer you a special 10% discount on your bundle of widgets if you order by next Tuesday. If you want to order, you can call back at 800-321-4321 and speak to a representative.”

This kind of message works only when your prospect is already planning to order. In this case, you have done nothing more than offer a free discount.

Oftentimes, the shortest message of all works best: “Hi, xxxx. It’s Terry Flynn, Market Chord. I have a quick question for you. Call me back at 603-321-4321. That’s 603-321-4321.”

Next Page: Three elements you want to include in each message


Brief is best, but there are three elements you want to include in each message:

  1. Create curiosity Curiosity comes from what you don’t say more often than from what you do say. Think of voicemail as a teaser for the conversation to follow. Messages should imply knowledge or benefit: “I have a quick update for you” or “I have an opportunity I wanted to go over with you.”

    Even telling your contacts that you have a question for them — without giving the question — creates curiosity. If you can pique a prospect’s interest, you will receive the callback. Just make sure you deliver on your promise with a tidbit of information to share.

  2. Limit risk Your next key is to limit the prospect’s sense of risk in returning your call. Many prospects will fear a callback will either waste time (the deadly lengthy phone survey) or that you will just pitch them mercilessly to buy your latest widget.

    Say why your call will be relevant to your prospect. Highlighting a referral source can establish credibility and the sense that you will be considerate of their expectations. Including mentions such as, “John asked me to call you” or “Susan suggested I speak with you” implies that you have in a sense been prescreened for suitability.

  3. Ask for the callback If you don’t ask for a callback, you won’t get it. Even a great voicemail message can be sabotaged with language like “if you want, you can call me at …” or “just call me if you want to …” Remove the “if” and see your callbacks increase.

    You can take this even further by suggesting a time and date for the call. “Call me tomorrow. I’ll be available in the morning before 10 a.m. EST.”

    This is better than “I’ll try you again later this week,” because it keeps the expectation on the listener to pick up the phone. When you set an expectation that you will make the effort, you remove the need for your prospect to call you back.

These techniques may take a little time, but they can give you a dramatic increase in the effectiveness of your phone calls — whether you manage to bypass voicemail or use voicemail to generate a callback.

It is a wonderful moment when you leave a voicemail message for someone you have spent energy and time trying to reach, and he or she actually picks up the phone and makes the effort to contact you. What happens next is up to you.

Terry Flynn ( is president of consulting firm Market Chord Direct Group in Amherst, NH.


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