Avoid the 7 Deadly Sins of Messaging for Killer Prospecting

September 3, 2019

Shawn Parrotte

Building a good rapport with prospects is crucial to winning their business. Yet so many sales pros will say or do exactly the wrong thing when reaching out to potential buyers. They apply what they believe are best practices for making a connection — but in reality, are big turnoffs.

In the latest session of our webinar series, “Flip the Script,” Becc Holland, Head of Sales Development for Chorus.ai, breaks down seven of the “deadly sins” of messaging for outbound sales with help from a very special guest: our CEO and Co-Founder, Roy Raanani.

Here’s a quick look at the 7 Deadly Sins of Messaging to avoid when you're talking to prospects!

Deadly Sin #1: Being too casual or silly when meeting prospects for the first time. #

Many reps think the quick path to developing a good rapport with a potential buyer is to treat them like an old friend — even though they’re just meeting them for the first time.

That’s an easy way to hit the wrong note with a prospect who is expecting more respect out of the gate. As Roy explains, “There is very little downside to starting things out professionally.”

Don't Do This: “Hey there, [Prospect Name]!” as your overly familiar cold call greeting

Deadly Sin #2: Writing messages to prospects that include ‘wasted text.’ #

How many times have you sent a message to a prospect with a first sentence that begins with something like, “Just following up on this …”?

It's a natural build up for your ask, but ultimately you’ve just wasted valuable text — as well as the prospect’s time.

According to Roy, the first sentence of an email to a prospect is just as important as the subject line.

If you're using filler text, your prospect will likely read the first couple of words of your message on their phone before archiving it. So, choose your words carefully. get straight to the point and show you’ve down your homework.

As Roy puts it: “The best way to build rapport is by telling me something I don’t know about my business."

Don't Do This: “I know you’re busy, but …”

Deadly Sin #3: Sounding like you wield authority over a prospect. #

Roy says when he receives a message from a sales rep that begins with “Roy,” instead of a salutation like “Hi, Roy,” he finds it off-putting. Such a greeting seems overly formal, even cold and unapproachable.

While you may be trying to emphasize to the prospect that you respect their schedule, you instead risk coming across like someone who is telling them what to do.

Don't Do This: "Let me know what time works for you."

Deadly Sin #4: Questioning a prospect’s authority. #

You want to connect with the right decision-makers when you’re selling, of course. But boldly asking a prospect, “Are you the decision-maker?” can backfire.

If you are speaking to a decision-maker, that person may be hesitant to confirm their position. If you’re talking to someone more junior, they might say they are a decision-maker, just so they sound more important. At the very least, they will get the impression that they aren’t worth your time.

A better approach, says Roy, is to ask a question like this: “When your company bought X in the past, who was involved in that process?” That way, you are respectfully inviting the prospect to share their status and offer their help in connecting you to the right people.

Don't Do This: "Are you the decision maker?"

Deadly Sin #5: Insulting the prospect by suggesting they’re responsible for bad decisions. #

Trying to convince a buyer that your product or service is superior to whatever they are using now should not result in that person feeling bad about their past investments.

When you are mud-slinging at the competition, for example, you are, essentially, trashing the prospect’s purchase decision. And, according to Becc, insulting a buyer’s decision-making can be “even more powerful than insulting them directly.”

Another insult: Sending a “breakup” message to an unresponsive prospect. If the buyer hasn’t responded to you, it is likely because your outreach hasn’t been compelling—not because they did something wrong, say Roy and Becc.

Don't Do This: "I’ve tried several times to reach you and I haven’t heard anything from you, so …”

Deadly Sin #6: Insulting the prospect by making them feel stupid. #

When you put a prospect on the spot in a cold call by asking, “Do you know who we are?” or hit them with, “Does that all make sense to you?” following a demo, you risk making that person feel uninformed or incompetent.

To avoid that situation, Becc and Roy recommend that reps use questions like, “Am I making sense?” with prospects. That way, they are taking responsibility for making themselves clear. Plus, they are making it “psychologically easy” for the prospect to engage with them and feel positive about the interaction.

Don't Do This: “Does that make sense?”

Deadly Sin #7: Glorifying yourself. #

Yes, you want to impress a prospect. But using your talk time with a potential buyer to gush about how great your product, company, and clients are can leave the prospect feeling like you don’t care much about them and their needs.

It may even motivate the buyer to go out of their way to find something wrong with your product, company, clients—and you.

Becc suggests that reps avoid starring in “The Me Show” and instead focus the conversation on the client. A question to consider asking a prospect: “Let me know more about your world, so I can tell you how we might fit in and add value.”

Don't Do This: Say how great or experienced your are. Don't say it, show it.

Hitting the right note in your outreach is essential to any outbound sales strategy. Find other hard hitting insights from Becc's Flip the Script sessions on the Chorus YouTube Channel.

For more cold calling insights check out: Flip the Script Session 2: Cold Calling. Becc dives deep into how to make your cold calls effective by showing your prospect that you've done your research and you understand how to make a genuine connection.

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