The Top Mistakes Salespeople Make With Outbound Sales

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  • Sales is more of an art than a science. There’s no one method, answer, or magic bullet. But we can learn from others’ mistakes, avoid common pitfalls, and sharpen our skills.
  • Legendary Leadgen founder Dana Lindahl says automated tools for LinkedIn and other platforms have made selling easier, but it hasn’t been a net positive for the industry because they lead to “poor behavior” like spammy messages and lack of research.
  • Dana shares the seven biggest mistakes in outbound sales as well as strategies to counter them.

To err is human. We all make mistakes, and most of the time, they’re just proof we’re trying. 

We can classify most of them, to quote Bob Ross, as “happy accidents.”

However, some mistakes are decidedly un-happy –– not just because they’re easy to avoid, but because making them can affect your bottom line in a major way.

Dana Lindahl, the founder of Legendary Leadgen, which helps companies set sales appointments with best-fit prospects and the author of “LinkedIn Sales Success: B2B Lead Generation and Sales,” says “social selling and automated tools for LinkedIn have made things a lot easier for people to put their messages out there and to reach more people at an affordable price. But that hasn’t actually made the industry better –– it’s made it a lot worse.”

Lately, he sees “a lot of poor campaigns and generally poor behavior” on LinkedIn (as well as email), like spammy and convoluted messages, that have a detrimental effect on sales success.

On an episode of INSIDE Inside Sales, Dana talks about the seven deadly sins of outbound sales –– common mistakes that can waste your time and energy, turn off prospects and even damage your reputation –– as well as strategies to counter them.

‘Spray and pray’

Dana thinks the biggest mistake salespeople make is not targeting their messages to prospects. 

“There are so many databases these days,” he says. “Sales Navigator makes it easy to spin up a list with filters and blast people  …, And so many tools are just focused on getting this automated to a point where it’s completely hands-off. I think that that’s wrong. People need to actually be focused on who they’re targeting.”

His “golden rule” is: “You can say the wrong things to the right people and still make sales some of the time, but you can never say the right thing or the wrong thing to the wrong people and still expect that to work.”

At the very least, targeting the wrong people starts your campaign off on the wrong foot. You’ll end up annoying people for sure. But there could be even more dire consequences: You might get your email account blocked, or your LinkedIn account suspended –– “and damage your reputation in the process,” Dana says.

‘Me’ messaging

All too often, salespeople make their messaging all about themselves, says Dana. 

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“It’s really hard not to. It’s especially difficult for business owners, but it happens with salespeople as well.

They’re so in the product; they’re so in the day-to-day of it all that they only speak from their own perspective.”

So Dana recommends centering your messaging on the prospect. You can do this through research –– looking for information you can mention in your outreach messages. If you can’t customize them for every prospect, focus on their industry.

“If you have more I’s and we’s than you’s, you’re doing something wrong. People don’t really resonate with messages about someone they’ve never met, but people always like to hear things about themselves.”

Connecting without a cause

This one is more specific to LinkedIn than email but absolutely crucial. 

People often reach out with a vague rationale –– like we’re in the same industry, I’d love to connect

“This just screams I’m gonna get a pitch in my inbox,” says Dana. “Being in the same industry is not a compelling reason to connect.”

Others might say, I see we have a mutual connection –– a so-so approach. Dana prefers something more along the lines of We have 82 connections in common. How do we not know each other? 

Even better, say something about their business: I noticed what you’re doing in your company; I think there’s a lot of room for us to do a joint venture

“It needs to be compelling,” Dana explains, noting that many LinkedIn users got “a bit desperate” during the pandemic and “just blasted everyone in their networks trying to get business.”

So now we see prospects who are increasingly choosy about who they connect with because they don’t want to have to process an inbox full of spam.

When you go the extra mile to personalize your message, you exponentially increase the likelihood of your message breaking through.

Play the blame game

It’s hard to believe, but sometimes sales reps send out messages that literally blame the recipient for not responding: I sent you a message the other day, and you didn’t respond back.

“I don’t understand why people do this –– I think it’s misunderstanding how their messages come across,” Dana says. “But it’s just so arrogant. No one owes you a response for anything. Yet I see people doing it all the time, and it just puts the other person on the defensive.”

Not only that, the prospect might refuse to hear anything else you have to say.

When you follow up, you can simply write: I thought I would follow up again. Or I sent you some material but realized I forgot something. Here’s some more information.

“My philosophy on outbound marketing is, if you have a good product or service that helps your target market, you owe it to [prospects] to let them know you have something that can save them, or make them, money,” says Dana.

Off-base content and premature asks

It seems like we’ve seen a lot of this one lately: a Calendly link directly in an initial outreach message. Even if the recipient doesn’t find it rude, they might find it a bit presumptuous to send it along before there’s been any establishment of interest whatsoever. 

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“Most people ask for too much before they’ve given anything upfront,” says Dana.

He likes to send prospects useful content first, which can help confirm they have a real interest in what his company does. Make sure it’s actionable content that can truly help them solve a problem –– perhaps a blog post or a video called 10 ways we solve X problem in your industry –– with a note that says, I thought you’d find value in this. Let me know what you think.

Or you might ask: As an expert in your field, do you have any feedback for me on this content? 

“People love to feel respected and seen as authorities,” Dana notes. 

“Usually, they’re more than willing to share. And if it’s a problem they’re actually struggling with, and you’re the solution for it, you’ve just started a very organic conversation with someone with no pretense. It almost becomes the prospect’s idea to hire you.” 

Lack of research

Here’s where Dana sees salespeople drop the ball just as they’re drumming up interest: not doing research into their prospects when they’re following up. 

Of course, he recommends researching them before reaching out at all. But he advises doing a deeper level of research after you get a response. 

That’s because you won’t receive responses from everyone, so there’s no need to go deep before you even know they’re interested. But you should definitely be armed with basic knowledge about every prospect and company you connect with. 

Sometimes, Dana audits campaigns and sees what can go wrong when that doesn’t happen.

One cringe-worthy example: A salesperson had a company’s founder on the line and asked her whether there were salespeople in her organization.

“Why would you ask that?” Dana says. “There are so many ways to find this information on your own. You look like a fool when you’re asking questions about things that are publicly available.”

Once you establish that initial interest, “this now becomes a real prospect for you,” he adds. “Resist the urge to just fire off a response. Do a little bit more work. People will appreciate your extra effort.”

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