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6 Signs You’re Sending Creepy Emails

As sales reps, our tendency is to flatter prospects by pointing out their accomplishments. We say things like, "I see you went to Duke," "I understand you were at EMC," and "I saw you were named Marketing VP of the Year!" In addition to buttering up our prospects, these statements make us feel we've done our homework.

The problem is people don’t trust flattery from strangers. Think about a time someone you didn’t know told you what a good [blank] you were. It's uncomfortable -- and it immediately makes you wonder what this person wants.

Avoid the missteps outlined below, and ensure prospects never glance over their shoulder expecting to see you standing in their window wearing a clown suit.

6 Creepy Email Habits to Drop

1) You’re assuming social media engagement = qualified prospect

Viewing your LinkedIn profile or “liking” an article you’ve shared is often enough for someone to be considered a prospect. But how qualified are they? Before sending them an email, consider that this person could have come across your profile by sheer luck or mistake. They might even have viewed your profile incognito -- unaware you have tools that can still decipher who they are.

In these scenarios, sending an email saying “I saw you stumbled across my profile. Can I answer any questions about XYZ Company?” risks creeping out potential prospects or wasting valuable time on someone who was never interested in your product/service to begin with.

Best Practice: When sending outreach emails, don’t indicate a person’s interest on social media. Leave those anonymous actions … anonymous.

The exception to this rule is when someone conspicuously engages with your profile or activity. If they like a post you shared, retweet you, or comment on your status update -- reply in kind. That doesn’t mean you should immediately send them an email saying, “Thanks for sharing my article. Want to schedule a demo?” Instead, leave your thanks in the comment section to mirror their engagement.

2) You’re using email tracking tools with abandon

Calling someone 30 seconds after they’ve opened your email is creepy. Opening an email is not an indicator of qualified interest. And if someone’s on the fence about you or your company, an instant phone call could alienate them.

Want to take the creepiness up five notches? Call someone directly after they’ve opened your email and pretend you have no idea they’re reading it. This is insulting to their intelligence and oozes sleaze.

Avoid this issue by waiting until an email has gained traction with employees at a specific company. Then find out who their executives are and write a message saying, “I sent an email and see there have been several opens amongst your team. Is there a way I can be of help to your company?

It’s in the executive’s best interest to learn what you do and why their employees are experiencing these pain points, so they’ll be more apt to listen. Plus, you’ve avoiding creeping out the innocent administrator who read your email while clearing out her inbox.

Editor’s note: HubSpot sales director Dan Tyre recommends the opposite approach -- calling prospects while they’re on your website. Click here for his take.

3) You’re a conference stalker

If you’re following up with conference attendees who scanned their badges at your booth a week ago, your success rate is probably low.

The week after a prospect returns from a conference or trade show is always busy. They’re answering emails, returning calls, and getting back into their day-to-day workflow.

If you send a generic email saying, “Hi Anna, I know you stopped by our booth at Corporate Conference 2017 last week. I’m sorry I didn’t get a chance to talk to you, but I’d love to follow up this week,” it’s going to be ignored or shelved until the opportunity is cold.

Best Practice: Instead of following up after an event, reach out while it’s still going on. Chances are, your prospect had to justify being at this conference. That means they’re looking for ways to prove they’re working, making valuable connections, and bringing tangible lessons back to the company.

During the event, send your prospect an email or give them a call and say, “Hi Anna, I see you stopped by our booth a few hours ago. I’m not at the event, but I’ve got a question for you. Can you call me back?” You’ll increase the likelihood of a returned call, and if they’re looking for ways to prove the value of their attendance, a demo becomes an easier ask.

4) You know too much about them

Today’s tools and technology make it easy to learn a lot about a person you’ve never met. It’s tempting to call someone armed with the name of their college dorm, birth date, and recent promotion details -- but don’t.

Best Practice: Embrace what you don’t know, and try seeming a little lost. Salespeople are often overconfident. Stop trying to be credible and start trying to be curious. From corporate challenges to their weekend plans, the more questions you can ask, the more natural the conversation will flow and build.

Remember, people naturally want to help others. If you say, “Hi Anna, I understand you’re migrating to a new platform and I’d like to tell you about how I can make that process easier,” there’s nothing for Anna to help you with -- and she might be spending more time wondering how you know that her company’s migrating systems.

Instead, say “Hi Anna. This is my first call to your company and I’m not sure where to start. Can you help me?” This allows Anna to listen to who you are and what you do. It also gives Anna the chance to help you and put you in touch with someone who’s more of a decision maker.

5) You’re focusing on what the prospect’s done, instead of what they’ve said

I see that you went to UNC! Go Tar Heels!” Forget about the school and work history, summary, awards, and references sections on LinkedIn. When I review a prospect’s profile, I go straight to the associations, groups, and network sections.

Best Practice: Once I know what they’re interested in, I research my prospect’s online engagement with those groups. Has this person been interviewed for their organization's magazine or newsletter? Have they shared commentary in a blog or even on their own Twitter account?

That way, when I send them an email, I can say, “I’m not a member of X group, but I saw what you said about Y topic and I had a question for you.” This builds rapport and is a more authentic way of building a relationship than recalling generic information that can easily be found on the web.

6) You’re not citing sources

Cite your sources. Don’t say, "I understand you recently moved jobs," "I'm aware you are looking for new software," or "I heard you also know Bob.” These statements make the prospect question how you know and whether you really understand -- two things they shouldn’t be asking themselves.

Best Practice: Always err on the side of over-citing. Everyone already knows you just plugged his or her name into Google and poked around on LinkedIn. Just say so.

In the example above I said, "I'm actually not a member of that group, but ..." It may sound trivial, but that’s an important phrase to include because it saves you from being a know-it-all and keeps the prospect feeling like the expert.

At some point, you'll need to switch roles and become the one leading the way, but begin the conversation by placing the power in the prospect's hands. You'll find they're far more eager to open up to you when this is the case.

Stop making these creepy email mistakes and say hello to stronger prospect relationships and more deals closed.

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