Tag: connect and pitch strategy

  • Why “Connect and Pitch” is a Bad Strategy on LinkedIn: A Cautionary Tale Featuring “John”

    Why “Connect and Pitch” is a Bad Strategy on LinkedIn: A Cautionary Tale Featuring “John”

    Let’s be real for a second. LinkedIn is supposed to be the professional equivalent of a dinner party—polite introductions, meaningful conversations, and maybe a connection or two. So, when someone treats it like a cold-calling free-for-all, it’s like they showed up, skipped the niceties, and started selling Tupperware.

    Cue “John.” John is the embodiment of everything wrong with the “connect and pitch” strategy. Here’s our delightful interaction, broken down for your amusement and education: (The names and some information have been changed or X’d out to protect the—ahem—innocent).

    John:

    Hey Jill,

    Great to connect.

    Reason for the message is I already work with quite a few [XXXX]. I’m a [XXXX] who specifically works with [XXXX] to burn up to 30 lbs of body fat, [XXXX], and increase [XXXX] in 90 days without fad diets or living in the gym.

    I would love to see if I can hook you up with some free trainings on how they’re burning up to 30lbs of body fat, increasing their [XXXX], and [XXXX] levels.

    Lemme know below if you’re open to it (totally cool either way).

    Have an awesome day,

    John

    Me:

    Radio silence. Because, you know, I’m a busy, career-driven individual. Scratch that. I’m a frazzled autism momma doing it solo, desperately trying to switch career paths in my late 50’s, who doesn’t have time for unsolicited pitches.

    John (a few days later):

    Just bumping this up to the top of your inbox in case you forgot to reply?

    Me:

    I didn’t forget to reply, John. I didn’t want to reply. I dislike it when you can’t even be bothered to establish a relationship or find out what I’m all about before hitting me up for my business. No warm-up there at all and certainly no reciprocity.

    (I know, I know, I was harsh…but I’m just so tired of these kinds of interactions…and I should point out, it’s 90% men who do this. Coincidink? Me thinks not…but I digress).

    John:

    Hey Jill, never asked for business, was simply offering free resources. And I do build a relationship with those I do who appreciate the help, as I obviously can’t help anyone unless I get to know them and their situation better, which you were closed off to doing, which is no problem at all. All the best!

    Me (fully done with John’s nonsense):

    John, where do I even begin?

    First, if I’ve learned anything in life, it’s that nothing is free.

    Second, why would you reach out with the assumption I needed to lose weight?

    Third, we both know that your approach is the epitome of the connect and pitch, which is just tacky and spammy. I’ve included a link to an article explaining why this strategy is a bad idea: Connect and Pitch Is As Low As You Can Go On LinkedIn

    Fourth, trying to gaslight me into thinking that wasn’t your intention is not a good look… and yes, that was gaslighting.

    Fifth, I’m a level 4/5 master coach with 30 years of experience training elite athletes. I’ve got an honours degree in kinesiology and have spent three decades learning about energy systems, sports injuries, on and off-ice training, nutrition, etc.

    Perhaps if you had gotten to know me before pitching me, you might have known that.

    You sound like a smart, driven, accomplished person. Please take this as feedback on how to approach new prospects in a way that will serve you better and not appear so spammy.

    Seriously, it turns people off—especially women like me. And if I’m your target market, I’ve just given you some valuable insight. 

    Take it or leave it.

    Why the “Connect and Pitch” Strategy is a Lose-Lose (Starring John’s Final Reply)

    Ah, John. He couldn’t resist one last parting shot to truly drive home why the “connect and pitch” strategy is a universal turnoff. Let’s add his grand finale to our cautionary tale:

    John:

    Thanks for your response, Jill! To be honest, you’re the first person it’s turned off, so I’ll continue to take my business advice from my trusted business mentors. And again, yes, I’m offering free resources and trainings.

    Let’s pause for a second. This response is the chef’s kiss of dismissive backpedalling. But before we dissect the flaws, let’s address this whole “free resources” argument.

    Why “Free” Isn’t Actually Free

    John’s insistence that he’s offering something “free” might sound altruistic, but let’s not kid ourselves—it’s Marketing 101. Free resources are a lead generation tactic designed to build trust, showcase expertise, and eventually convert prospects into paying customers. It’s not inherently bad—when done right, it can provide real value.

    But here’s the catch: If you push these resources before building any trust or understanding, it reeks of insincerity. John’s foot-in-the-door approach might work on some, but for others—like me—it comes across as disingenuous and manipulative.

    Addressing John’s Final Defense

    1. “You’re the first person it’s turned off…”

    Sure, John. I’m the lone outlier in a sea of delighted recipients. Or maybe I’m just the first person to tell you directly that this tactic is irritating. Most people would ghost or block you instead of bothering to give constructive feedback.

    2. “I’ll continue to take my business advice from my trusted mentors…”

    Translation: “I’m dismissing your valid critique because it doesn’t align with my current strategy.” Cool, John. Just remember that even trusted mentors can be wrong sometimes, especially if they’re peddling outdated or spammy approaches.

    3. “Yes, I’m offering free resources and trainings…”

    And yes, we all know what that really means: “I’m offering free resources to hook you into my sales funnel.” Again, nothing wrong with this strategy if it’s done with authenticity and respect for the other person’s time and needs.

    Why This Approach Fails (Again)

    John’s refusal to acknowledge my feedback illustrates exactly why “connect and pitch” falls flat:

    • It’s One-Sided: He’s not open to hearing constructive criticism. If you’re unwilling to adapt, you’re limiting your potential to improve.
    • It Undermines Credibility: Doubling down on a questionable strategy doesn’t inspire confidence.
    • It’s Short-Sighted: Burning bridges with one potential connection to defend a flawed tactic is a loss in the long run.

    The Final Lesson

    “Free” is never really free, and everyone knows it. Offering resources isn’t the issue—plenty of people genuinely appreciate helpful content. The problem lies in the delivery. If you shove your resources at someone without first building trust or understanding their needs, it feels like a bait-and-switch.

    To all the Johns out there: If your strategy depends on flooding people’s inboxes with generic pitches, maybe take a step back. Listen to feedback. Adapt. Because let’s be real: For every person who tolerates your approach, there are probably ten others rolling their eyes and clicking “unfollow.”

    As for me, I’ll keep building connections the old-fashioned way—with sincerity, respect, and maybe even a little humour. And John? I sincerely hope he takes this as the tough love it’s meant to be.

    Let me know your thoughts—especially if you’ve had your own “John” encounter. Together, we can make LinkedIn a little less cringe-worthy and a lot more authentic.

    — Jill