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7 Ways to Add Personality to the Sales Process

As comedian John Mulaney so aptly put it, “We spend half of our day convincing robots that we are not, in fact, robots.” Unfortunately, a lot of us in sales are doing a darn good job of imitating droids with our robotic “I think you’d really enjoy this new tool blah blah” emails.

This isn’t to say you shouldn’t distribute your company content through your sales emails, because you should absolutely be doing that. But part of talking to real humans (and earning the right to sell to them) is proving that you yourself are human -- by communicating in authentic ways and sending the kinds of emails even you might actually want to read. Tap into some basic human empathy, and borrow these tactics that I use every day to prove I’m really not a sales robot:

1) Maximize meaningful moments.

I once sent a woman I sat next to at a conference in the sweltering desert heat an email with the subject line “Nice sweating next to you @ Inc. 5000.”

I wanted to help her recall a moment we shared together and make myself stand out. Now, you can’t bait and switch here. If you use a personal, relevant subject line, deliver the goods in your actual email, too.

Your full message should mention some of those meaningful moments you’ve shared and prove the recipient isn’t just another sale to you. You’re trying to build a long-term relationship with this person, so reference the little things, follow through on your commitments, and make them feel special.

2) Focus on them first.

You may be working toward a sale for your company to meet your goals, but you can only do that when you focus your attention on the other person. One of the best ways to do that is challenging yourself to use “I” no more than once or twice in an email.

The first few sentences -- at least -- of every message you send should focus on the person you’re emailing: “Your company is doing a great job at X. Do you have a plan for incorporating Y in the future?” Or for warmer inbound leads: “You recently filled out a contact form to learn more about X.”

3) Humanize yourself.

You’re asking a lot of people by corresponding about sales and the future of their business operations. The least you can do is tell them a little bit about who they’re talking to.

Let your hair down. Show some personality. Share some fun-yet-appropriate pieces of information about your life. Note: I hope stories from your life don’t involve you ending up in a campsite next to a bunch of rambunctious tweens, but you get where I’m going with this example:

I hope you all had a wonderful and relaxing weekend. I spent mine camping and hiking in Arkansas and somehow secured the one campsite next to 35 middle schoolers on a youth retreat. It was a sea of hormones and fidget spinners.

For our call Wednesday, please take a look at this initial draft of the proposal, and jot down any questions or edits. After we’ve walked through this draft, I’ll make sure it’s polished and get it back to you ASAP.

4) Do your homework (but don’t be a creep).

You want to demonstrate that you took time to look into your prospect before reaching out, but you definitely don’t want to overdo it. There’s a fine line between Internet Researcher Extraordinaire and Creep You Want to Avoid.

(What I’m saying is that I don’t recommend doing what I did on my first date with my boyfriend -- i.e., referencing his niece by name after seeing a pic of them together on Instagram.)

Instead, find out something cool about your prospect or congratulate her on a recent success, as I did with this contact from a maritime insurance company:

5) Remember, you’re not a regular salesperson -- you’re a cool salesperson.

There are no rules in this house that say you’ve got to be all business, all the time. Include something in your correspondence just for fun. Did your prospect mention a podcast she’s really into right now? A new book or an author she loves? If you can use these little details to connect with your point of contact, then reference the heck out of ’em.

For example, a buyer in Dallas mentioned in passing that she’d be brunching and going to the farmers market over the weekend, so I wrote her the following note. It was completely unrelated to our sales conversation, but it did strengthen our relationship:

6) Capitalize on that sweet OOO-message real estate.

Sales reps travel a lot, and when you’re away from your email, you’re probably setting up out-of-office messages. This doesn’t have to be your standard throwaway “Thanks for your email. I’m OOO until XX/XX and will respond to your message when I return.” (I think I fell asleep writing that, it was so lame.)

Mix it up by including links to popular thought leadership content authored by people in your company, and take it a step further with some personality. One of my go-to OOO messages reads:

7) Forget email.

It’s 2017! We have delivery people coming straight up into our homes -- who even needs email? Ditch your traditional methods, and test something new. I like to send prospects who’ve ghosted me a pair of Influence & Co. socks with a note that says, “Hope you’re not getting cold feet. Looking forward to working together.”

If socks aren’t your thing, then slide (respectfully) into their Twitter DMs with a personal message. Send a $5 Starbucks gift card (or earn bonus points by finding a favorite local shop instead), and invite them to virtual coffee. Or go offline entirely, and send a handwritten note. They still exist. Heck, you can even fly a drone to their office with a cookie cake that says, “Just following up.”

In a world of automation, there’s still a desire for human connection. It takes time and a bit of creative flair, but it’s worth it for you and your prospects. Write the email you would want to read, and then let the deals close as they may.

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