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Direct Messaging Mistakes You Won't Want to Make on LinkedIn (example included).

Updated: Sep 14, 2019

It’s happened to us all. You accept an invitation to connect with someone on LinkedIn whom you don’t know but think may be reaching out to inquire about your own product or service.

Instead, you get SLAMMED with an auto-generated sales pitch.

LinkedIn Sponsored InMail
LinkedIn is an oven, not a microwave. It takes time for trust to be built before you can start selling.

This recently happened to me (again) and I know it happens every minute on social media, which means there’s a big opportunity for anyone who does business online to improve their sales methods. And maybe I’m fortunate because as a copywriter, I’m on the inside of the online marketing world. I know the rules, what works, and what turns off a prospect or connection faster than a blink.

Now, keep in mind that with the example I’m about to share with you, I did what everyone should do, which is check out the person’s profile prior to accepting the connection. In this case, this profile was of interest to me because it was severely flawed. Meaning:

  1. Her headline and summary didn’t tell me anything relevant about her

  2. Her about section was generic and didn’t provide any value

  3. Her profile picture was a selfie that looked like it belonged on her personal Facebook page

  4. She didn’t have a banner image

And since I specialize in SUPERCHARGING LinkedIn profiles for my clients, I thought she could really use some help and that I could be of value to her.

But that wasn’t the case. When I read the message that came through, I cringed, knowing how this tactic - if you can even call it one - makes a terrible first impression. I often roll my eyes when these come to my inbox because they are 100% unauthentic junk mail and offer nothing in the way of a personal connection. And they almost NEVER lead with value. So even if I was interested in the product or service, I wouldn’t have acted because the approach was so off-putting.

Think of it this way - we all know that nobody in their right mind is going to accept a marriage proposal from someone they don’t know. Now, if you get nothing else out of this post, I want you to at least walk away with this:

LinkedIn is an oven, not a microwave. It takes time for trust to be built and relationships to form before you can start selling.

There’s a right way and a wrong way to use LinkedIn for social selling. And the example I’m about to show you is without a doubt the WRONG way. In my experience, it’s also lazy, makes a negative first impression, and slaughters your credibility.

Keep in mind this is an actual conversation that I copied and pasted to show you what happened the instant I accepted the connection. I added my comments to point out what went wrong and what should have happened instead. I also replaced the person’s name with ANONYMOUS to protect her identity.

Here's the feed:

JUN 7 ANONYMOUS sent the following message at 9:02 AM


Hi, my name is ANONYMOUS, and I represent COMPANY, a Public Relations agency. I found your profile searching for your company and I would like to connect with you. Thank you.

WHAT WENT WRONG: The area of opportunity in this message would have been to add something personal she learned about me from my profile. Overall, it wouldn’t have been the worst start if it wasn’t scripted, which of course it was. Otherwise I may have thought she was a LinkedIn rookie, brand new to the platform, and with the right guidance could have gotten better with her approach.

WHAT TO DO INSTEAD: Lose the script, especially on the initial request to connect. Take the time to be genuine and make it personal.

JUN 7 Janine Hogan - Copywriter sent the following message at 9:13 AM

Thanks for reaching out, Angela! I am happy to hear from you and would be glad to connect. Why did you want to connect with me? I’d love to learn more about what you do.

WHAT WORKED: It’s always a good idea to directly address the contact you are connecting with. As you can see here, I used her name. It isn’t rocket science, but it is a minor detail that often gets left out. I also engaged with a specific question and showed interest in her to get the ball rolling.

JUN 8 ANONYMOUS sent the following messages at 10:22 AM


Janine, thanks for accepting my connection request. We would be interested in featuring your company on top editorials such as Forbes, HuffingtonPost, Entrepreneur, INC, etc. Also, if our outreach efforts don’t result in publishing an article for you, you won’t pay us! Please let me know if this is something that might interest you so that I can send you on here additional information.

WHAT WENT WRONG: This is the first pitch - and this could have been of interest to me until I read “you won’t pay us!” This is a clear indicator that I’m being sold to before we've even had a chance to have a conversation. Beyond that, my question was not addressed, which solidified that it was a scripted, impersonal response.

WHAT TO DO INSTEAD: Auto-pilot response scripts don’t answer questions, but YOU do! If you want to qualify a lead, then read their response and reply accordingly! That’s not to say that an auto-message can’t work. They can, if done right (which I'll address later in this post). But in this case, the messages go right for the sale before even qualifying me as a good lead. Which also leads to suspicion that her targeting is flawed.

JUN 15 ANONYMOUS sent the following messages at 9:55 PM


Janine, thanks for accepting my connection request. We would be interested in featuring your company on top editorials such as Forbes, HuffingtonPost, Entrepreneur, INC, etc. Also, if our outreach efforts don’t result in publishing an article for you, you won’t pay us! Please let me know if this is something that might interest you so that I can send you on here additional information.

WHAT WENT WRONG: The same exact script was sent again - if I didn’t respond the first time, odds are the same post won’t get my interest just because you resent it.

WHAT TO DO INSTEAD: The moral of the story: don’t use scripts to communicate with new connections. And if you do use scripts, don’t be repetitive. It shows you don’t respect your prospect’s time and kills trust instantly, making them feel like a pawn in your numbers game. It’s not a numbers game; it’s a people game. Meaning, if you connect with the right prospect, you will see results. Just trying to reach as many people as you can is like throwing sh*t against the wall to see what sticks. Instead, have a clear focus and put the time and work in to target the right people and build relationships with them first. Earn their trust before you try to sell them.

JUL 13 ANONYMOUS sent the following messages at 3:23 AM


Hi Janine, we are promotionally offering for the price of $199 and a week delivery time: - One brand mention on; - One interview featuring you or your CEO published on Google News and DigitalJournal; - Interview distribution to over 200 top sites (including CBS, CW, Fox & NBC affiliated station websites); - Syndication on Medium and LinkedIn. This includes article writing, these will be sent to you first for approval before getting published. Else, you can check the full list of outlets we have available with prices: (

WHAT WENT WRONG: By this time, trust is nonexistent and I'm tired of getting spammed. The probability is high that I would never do business with this person. Without a move from me, she showed her hand and laid all her cards on the table. The entire thread felt like a bribe by flashing the names of big online publishers without actually offering any value. For instance: the only time she mentioned any glimpse of value was when she briefly mentioned their “outreach efforts” in her second (and third) script. But even that was unconvincingly vague.

WHAT TO DO INSTEAD: If she had focused mainly on value and results to make the pitch more credible, there may have been an enticing reason to inquire further. Instead, she focused on a promotional price point, which felt like a hard sell.

Keep this in mind: offering VALUE makes the offer VALUABLE. Lead with PRICE, and you lead with selling, which is exactly what you need to avoid.

Overall, I felt like I was on a bad date. This person’s approach to take me straight to bed as soon as I opened the door was a huge turn off. I purposely chose to not respond for several reasons:

  1. She didn’t answer my own question or make a relevant response to my message. This was clearly an auto-generated message, which means this person did not make any effort at all to learn a thing about me or my business before presenting me with an offer.

  2. A week later, the same exact message was sent telling me I was just a number in her prospect database. Now, if you’re going to send an auto-generated follow-up message, at least change it up to try and get my attention. But that didn’t happen here.

  3. The third message was an actual request for the sale without us ever having an actual, GENUINE conversation about my needs.

  4. There was NO VALUE in her proposition.

  5. And the BIGGEST reason is that she didn’t form a connection. She used the platform to try and hard sell me, which does not work on LinkedIn.


If you want to bake a cake, you must first heat up the oven. You don’t put the batter in the microwave, and certainly wouldn't put it in a cold oven and expect it to rise. You must give the oven time to heat up and once it reaches the desired temperature, it will stay hot as long as you don’t turn it off. Once the oven is hot, you can bake your cake.

Unfortunately, this type of bad sales technique happens all the time on LinkedIn. It’s one of the best ways to turn off a potential client. If she had done it right by making the message personal, I may have be interested in learning more. But in this case, she made the classic mistake of spamming her connection.

And spamming your connections is the fastest way to slaughter your credibility and lose your audience.

However, LinkedIn’s Sponsored InMail can certainly work for you if it’s done right.

Apply the following elements to give your direct messages a better chance for success:

  1. Know your audience well. The content should be helpful, informative, and entertaining, as well as tailored to your target audience’s interests.

  2. The content in the message should clearly explain how it would help the prospect achieve professional success.

  3. Hook by leading with value. What problem are you solving?

  4. Keep subject lines short, but impactful.

  5. Address your target with a sincere, personal greeting.

  6. Use an image (when applicable) to enhance your message and brand voice.

  7. CTA’s (call-to-action) should be clear.

  8. The sender should be credible and relevant to your audience.

And remember, the purpose of LinkedIn messenger is to start driving more leads, not to be pushy and ask for a sale. If you work on making messages more relevant to your target and provide them with value, you'll attract more qualified leads.

For more LinkedIn marketing tips, visit my website:

About the Author

Janine Hogan

Would you like help in making LinkedIn one of your most powerful business marketing and professional networking tools? I'm on a mission to help entrepreneurs and business professionals better leverage their LinkedIn profiles and make the most of their connections. I start by transforming underperforming, uninspiring, unattractive LinkedIn profiles into SUPERCHARGED, scroll-stopping marketing tools that make you and your product or service stand out from the crowd.

You can start by emailing me at or connecting with me on LinkedIn.

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