To Err Is Human, to Spam Is Unforgivable: 5 Prospecting Mistakes to Avoid

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  • Prospecting is hard. But if you know how to avoid the pitfalls, you can approach potential clients with confidence. It’s time for effective prospecting.
  • Sales legend Anthony Iannarino has identified five common prospecting mistakes as well as what you should do instead: his formula for outreach, ways to offer content way before you pitch, and ways to be persistent without being annoying. 
  • His advice is classic, bold, and above all, human. Some might seem counterintuitive, like the first rule of social selling: Don’t sell.

Ah, life in 2020. Even in the midst of a pandemic, we can order almost anything on demand: a ride, a movie, dinner ––  plus, a bottle of wine (or several), and even the glasses to drink them from. We can meet a special someone to enjoy all those things with, too. Swipe right and toast to progress! 

But the ubiquity of our smartphone-centric lives, dominated by DMs, texts, and social media, has given rise to a set of myopic assumptions about selling in the 21st century. 

Among them: cold calling is dead; if you interrupt someone, they’ll never buy from you.

That’s just not true, says Anthony Iannarino, co-founder of the OutBound Conference and blogging machine on an episode of INSIDE Inside Sales.

Expanding on a blog post he wrote titled “The Five Enormous Mistakes in Your Prospecting Sequence,” Anthony came to tell us what not to do when approaching potential clients.

Mistake 1: Automate everything

It’s a big mistake to rely on automation for everything. (Though, of course, VanillaSoft and other lead management systems are brilliant at automating the more menial tasks of prospecting.)

Anthony recently received a series of three sales emails –– with each previous message pasted below the new one. He ignored them until he got the fourth –– and replied with a note that said: Listen, this isn’t working for you.

About a week later, he got a reply from the salesperson whose name was on those emails. Turns out the rep didn’t actually send them –– they all came from that company’s chief marketing officer.

That represents a huge disconnect. And it sent a clear message to Anthony: You don’t care about me. 

So it’s important to make sure your messages have a human touch. (And communicate with your marketing team, because you won’t have a guru like Anthony to call their fouls.)

“You can’t automate this,” he says. “People still buy from human beings.”

Mistake 2: Flood their inbox

sales prospecting techniques

If you’re angling for a meeting and every ask you make is over email… take a page from Dr. Phil and ask: how’s that working for you?

Chances are, it’s not. That’s because, as Anthony explains, your prospect doesn’t know you yet. They don’t know your theory on why they need your product or service.

If your sequence is just emails (and/or LinkedIn messages), you’re not creating any real value.

“You’re just a spammer at that point,” he says.

The worst thing you can do is send a straight pitch: here’s who we are, here’s what we do, here’s why we’re so great at it.

Prospects will think: Okay… why do I care? 

You shouldn’t ask prospects to define your value proposition or connect the dots to understand how your product solves their pain. They don’t have time to do that. It’s your job!

Plus, you’re using a medium that gives them the easiest way to say no. All they need to do is hit the delete key. (Or ignore your message entirely).

Many people see it as a numbers game: Send crap-tons of email out, get enough responses to stay afloat.

But “pissing off 98.9% of the people in your database might not be the best idea,” Anthony points out. 

Instead, he advises, “mixing it up.” Approach your prospects in a variety of places and ways, with personalized, human-to-human messages.

Mistake 3: Call it quits –– much too soon

This might seem controversial to some, but Anthony holds firm: Too few phone calls are a yuuge mistake. 

His typical sequence includes at least four calls, always with voicemails. “But I never ask you to call me back,” he says. He follows his initial call up with an email. In later calls, his voice messages clearly articulate the value proposition. 

For example: “Darryl, I want to give you a 20-minute executive briefing on the four trends we think will have the biggest impact on personal branding over the next 18 to 24 months,” Anthony says. 

You can’t do that easily using anything other than the phone. 

Then if –– scratch that, when –– you score a meeting, you can pitch how your product or service brings value to their day-to-day work.

Anyone who advises against leaving voicemails is wrong, Anthony adds. 

“Do you knock on someone’s door and run?” 

Of course not. At least not since you were 12, after you TP’d your grumpy neighbor’s tree. 

If you’re calling a prospect, you’re asking them for their attention. So leave a message like a grown adult, and you’ll increase the likelihood of getting an answer one way or the other.

Not everybody’s going to be happy or impressed with your persistence. But many will be and say: I know you’ve been trying to reach me. Sorry –– we’ve been super busy. What is it you want to share?

And voilà: a real conversation begins.

Mistake 4: Honey, badger them 

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“If every time you reach out and touch somebody, it’s ask, ask, ask … stop, and give them something,” Anthony says. 

Share a fresh insight. Then keep on doing it. Think of insights as gifts –– content that’s useful to your prospect, whether they hire you or somebody else. Karma, dude.

Soon enough, you’ll be shaping the way your prospect thinks, and you won’t have to ask every time.

Mistake 5: Slide into their DMs

Even social selling advocates say: The first rule of social selling is don’t sell

It seems like a paradox, but they’re right. There’s a way and a place to do it.

“Twitter is not that place,” Anthony says.

Social media platforms are mediums like any other. They can help you build a reputation and develop relationships –– to add value. They’re just not the right environment to make an ask, whether it’s for a meeting or anything else. 

A LinkedIn InMail with a Calendly link (with every appointment time as yet unclaimed, natch) is definitely not of value. Messages like that can register as spammy AF to your prospects. Bonus mystery-meat points for phrases like: The best part is, if you don’t get new clients, we don’t get paid.

“No, the best part is the delete key,” Anthony quips.

Or: I’ve helped over 2,793 clients.

That’s when the prospect thinks: Let’s make it 2,794. (Read: You’ve helped me see through your bullshit.)

Even after all this time, “people try to sell me sales training,” Anthony adds.

Take it from him: don’t be that guy. 

Kick Sales Up a Notch with Effective Prospecting

Now, it’s time to take your prospecting to the next level. Avoid making these mistakes and start connecting with your prospects. It’s time to ask yourself the Dr. Phil question, “How’s that working for you?” and ditch the old way of doing things and begin connecting with your customers.

What other mistakes do you see sales reps making? Share them in the comments.

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