I learned something about that as a buyer. I was looking for a service that could take some IT administrative work off my plate, so I emailed a prospective company with a few questions. A sales rep, whom I’ll call Darren, responded by calling me. I missed the call. He left a voicemail answering my questions and asking a few of his own. It was a reasonable response to a real inquiry, delivered through a different channel than the one I had used.
I emailed him back with my answers and some additional questions. He responded with another voicemail. I sent another email. He left another message. This continued until he called while I was at my desk. By then, I had seen his number on my caller ID enough times to recognize it. I stopped what I was doing, picked up the phone, and shortly afterward became a customer.
Darren had earned enough of my attention that when the opportunity for a conversation finally arrived, I took it. This is a useful lesson for any salesperson trying to get a buyer to respond. Before you can move an opportunity forward, you need a place among the things that person is willing to act on.
At the time, even on a busy day, I rarely received more than a few voicemails. My Inbox, however, could easily receive a few hundred emails. Those were my circumstances, and they mattered. Darren’s messages were arriving in a much smaller collection of things to review. He had found a way to get my attention while other messages waited alongside everything else competing for it.
Email’s convenience creates a challenge for the sender. It is easy to write, easy to send, and easy to send again. Naturally, plenty of people use it. Your carefully considered message can arrive next to a customer request, an internal update, a calendar notification, and several other salespeople’s carefully considered messages. The buyer has to decide what deserves attention now and what can wait. Being relevant helps, but relevance does not automatically put you first.
Darren’s voicemail also carried information I had asked for. That detail is important. He was answering my questions and giving me a reason to continue the exchange. If he had repeatedly left messages announcing that he was “following up,” there would have been much less for me to engage with. His choice of channel helped the message get noticed. The substance of the message helped keep the conversation alive.
I cannot know exactly what would have happened if he had responded only by email. I might have purchased from his company eventually. I might have chosen someone else. What I remember is that the voicemail exchange kept bringing him back to my attention, and the eventual live conversation moved us forward. His approach fit the situation well enough that I remained engaged even while responding through my preferred channel.
On an initial prospecting call, salespeople can ask the interaction to accomplish far too much. They want to introduce themselves, explain the company, establish credibility, describe the product, uncover a need, and secure a meeting. Then they try to compress ALL of that into a voicemail. he resulting message can require more attention than the recipient was prepared to give before they even know why you called.
I think about earning a place near the top of the buyer’s to-do list. That means giving them a credible reason to pay attention and a manageable next step. The first exchange should make continuing the conversation feel worthwhile. When you are already responding to an inquiry, as Darren was, the buyer has supplied a starting point. Their questions tell you something about what interests them. You can begin there without delivering your entire company presentation.
A voicemail should have a purpose the recipient can understand. In an ongoing exchange, that might be answering a question and identifying the one detail you need to clarify. It might be explaining that you have information relevant to a decision they are making. The next conversation should follow naturally from the message. “Call me back so I can tell you why I called” asks the buyer to do rather a lot of the work.
This also gives you a useful preparation exercise. B efore dialing, know what you will say if the buyer answers and what you will leave if they do not. Those are different situations. A live conversation allows you to listen and adapt. A voicemail requires you to make your point without that feedback. P reparing for both helps you avoid the rambling message that begins when the recording tone catches you by surprise.
There are plenty of situations where email is the sensible choice. A buyer may need a document, a written answer to a detailed question, or information they can share with colleagues. Making them transcribe technical details from a voicemail creates unnecessary work. If they need to compare several requirements or review something carefully, give them a format that supports that task. Being willing to call should make you easier to work with.
Accessibility matters. A salesperson who insists on handling every exchange by phone can become difficult to reach in a useful way. The buyer may have a short opening between meetings to send a question, with no opportunity for a conversation. Responding appropriately keeps the process moving. Your selling style needs enough flexibility to accommodate how the buyer works and what the moment requires.
My experience with Darren illustrates that flexibility in an interesting way. I continued replying by email while he continued leaving voicemails. We were using different channels within the same conversation. I had initiated the inquiry, and I kept participating. Those details should shape how you interpret the story. It would be a mistake to turn it into a rule that every unanswered email deserves another call, regardless of the relationship or the buyer’s wishes.
If someone explicitly asks you to use email, that preference belongs in your decision. So do the urgency of the issue, the complexity of the information, and your existing relationship. Good communication requires judgment. A rigid rule about always calling or always emailing can become an excuse to stop paying attention to the person you are trying to reach. The buyer should experience a useful conversation, even when that conversation moves between channels.
Email can feel comfortable for reasons that have very little to do with the buyer. You can edit it. You can reread it. You can send it without having to respond immediately to another person’s reaction. You can even ask Claude to write it for you entirely. Afterward, there is a visible record that you did something. Your sent folder looks productive. (Your sent folder is rarely the one approving the purchase.) That comfort can make email the default even when a conversation would be more useful.
A phone call introduces uncertainty. Someone might answer before you feel ready. They might ask a question you did not anticipate. They might tell you the project has changed or that they are no longer interested. Those possibilities can make another email feel attractive. Yet the information you are reluctant to hear may be exactly what you need to decide where to spend your time.
This is where I ask myself a question: “Which one takes more courage?” I leave some room to consider the answer. Sometimes the call is the action I have been avoiding. Sometimes I need to put something clearly in writing instead of hoping a friendly conversation will resolve it. The question helps me examine whether I am choosing a channel because it serves the situation or because it makes me feel more comfortable.
Choosing the more uncomfortable action is a way to challenge your own habits. It still requires preparation, relevance, and respect for the buyer. Calling without a reason will not become effective simply because you were nervous about it. A meaningful question, a useful answer, or a genuine need to clarify the next step gives the action its purpose. Courage helps you carry out that action when hesitation would otherwise keep you stuck.
There is also a difference between being willing to hear an answer and trying to force one. A buyer can be unavailable, distracted, or uninterested. Your job is to make a reasonable effort to communicate and pay attention to what happens next. Darren had evidence that our exchange was active: I kept answering his questions and asking more. My participation gave him a reason to continue. That is a much stronger foundation than persistence based entirely on your own enthusiasm.
The practical lesson is to stay engaged with the actual exchange. Read what the buyer asks. Notice whether they are contributing information. Consider whether your last message made the next step clear. Then choose a channel that can help you make progress. If the only explanation for another email is that you would rather avoid dialing, you have discovered something worth working on.
Darren’s approach worked because several things came together. I had a real need. He responded to my questions. His voicemails reached me through a channel that had room for his message. The repeated, useful exchanges made him familiar enough that I answered when he finally reached me at my desk. The story gives us something more practical than a universal rule about phones and inboxes: pay attention to the buyer’s circumstances and make the next interaction count.
A salesperson needs the confidence to call and the judgment to write. Both skills improve when you practice them deliberately. A crowded inbox can make a thoughtful voicemail valuable. A complicated question can make a clear email valuable. An uncertain opportunity can make a live conversation especially valuable. The decision deserves more thought than simply repeating whichever action feels easiest.
I want my communication to give the buyer a reason to respond. That starts with curiosity about their situation and enough confidence to use the channel that fits. When I catch myself hesitating, I return to that question about courage. It reminds me that being heard sometimes requires doing the thing I was hoping to avoid. The next useful conversation may be waiting on the other side of that hesitation.
Happy Selling!®, Jeff
