I recently got some great discussion on a LinkedIn post. It started as mostly a complaint, partially intended as general advice. At risk of being more the former than the latter, here’s a post with some practical thoughts on how you can be more effective in establishing meaningful contact with others.
To get there, we’re going to have to look at some bad examples first. Trust me, this exercise will be useful later.
The Bad Examples
I don’t appreciate most of the pitches I get in my LinkedIn direct messages. They’re frequently so impersonal and generic that they immediately sour my attitude toward the person making contact and whatever it is they’re pitching.
More than once, these pitches highlight a surprising lack of attention to detail. What frustrates me the most is the almost crass impersonality attached to a message portrayed as a personal contact.
Let’s look at some examples:

On the surface, this one isn’t terrible. It offers something of value, giving me a link to a free event right up front. I’m welcome to take the sender up on their offer, or not.
However, they missed one important point: military retirement is not a major player in my life right now. Yes, I may be able to retire this year or next. However, I won’t receive my reservist pension until roughly age 57. I made the transition from full-time military service to a full-time civilian job nearly a decade ago. I’m not sure what this webinar will cover, but I suspect the invite is hitting several years too early or too late.
I can understand the cold-caller’s error here. They’re probably using an algorithm to scrape all of LinkedIn for people nearing 20 years of military service. My profile clearly shows that I graduated from the USAF Academy in 2004, so it’s reasonable for a mindless computer algorithm to identify me as someone who could potentially be retiring next year. (Although, statistics show that 80% of military members don’t put in a full 20 years on active duty, and, especially in the military’s current staffing nightmare, it’s likely that a pilot who has stuck around for 20 years will have compelling opportunities for several additional years of service. You’ll see a common theme here: you need more information than a bot is likely able to provide.)
What this pitch really says to me is: “Jason, I pay for a 3rd party algorithm to identify people who fit a range of characteristics I want in a client, and your profile popped. I haven’t bothered to take even a passing glance at your LinkedIn profile, but I’d love to start a business relationship that will make me a lot of money by acting as steward of your family’s financial future.”
Sorry, but you need to do a lot better.
Let’s try another:

This one feels significantly less personal to me, despite the words “on a more personal note” appearing in the message.
For me, “Federal Employees” is one of the most generic categorizations possible. If you’ve read anything I’ve ever written, you’ve probably noticed my frequent underhanded barbs about the US government’s lack of efficiency. Lumping me into the broadest possible grouping of those inefficient workers is almost an insult in my opinion.
It wouldn’t have taken much effort to swap that phrase out with “military members,” “veterans,” or perhaps something as outlandish as “combat veterans,” especially if you had even glanced at my profile.
I suspect that some search algorithm matched us based on me being in the military and my frequent use of the phrase “financial independence” that also appeared in your message. However, you failed to note that much of my posting involves a book and associated website about how individuals can secure their own financial independence without having to pay someone like you.
If you’re cold-pitching your P.O.M. Method to people, I hope you believe it’s better than whatever it is I write about. However, if you’re going to pitch it to me in a personal message, at least do me the service of showing that you have some idea of where I’m coming from and include a single-line teaser evidencing that fact.
This next one was nearly frustrating enough to prompt this article’s creation without any other examples:

These four messages arrived anywhere from a few days to a few weeks apart, without any reply on my part.
Although specifying a preference for connecting with “Veterans” is better than “Federal Employees,” it’s still pretty generic. There’s a lot of pro-veteran rhetoric in America right now, though, so I let that one pass.
The next prompt screams generically impersonal though. What is it that you noticed in my profile when you looked at it? (Because you did actually look at it, right?)
Your “what’s next for you?” question was simply lazy.
If you had actually looked at my profile, you’d see that I’ve been a USAF Reservist for a while, and that I got a full-time civilian job when I transitioned from Active Duty. If you’d asked your lazy question a little over seven years ago, the answer would have been “I’m going to be an airline pilot.” At this point, it’s a pretty easy deduction to see that my current “what’s next” is “more of the same.”
This sender’s third message continues the impersonality and verges on desperate. I promise, if I was interested in what you’re pitching I would have responded by now. The fact that I haven’t should be a sign.
Then you mention “the training” for the first time ever. What is “the training”? If it’ll give me some sweet nunchuck skills, then you can shut up and take my money. If not, I’m going to need more information.
Your original message implied that you just like connecting with vets. Your next one asked some impersonal and poorly researched questions. Then, you (or your algorithm) forgot to even send me the automated message pitching your training to me.
The final message here is shocking. It arrived more than a month after their initial contact attempt. After failing to gain my attention with their other approaches, this sender finally presents something remotely concrete – a post-military career path other than something in corporate America.
For the right target, this might finally provide some useful information. However, it shows a complete absence of interest in me as an individual. My basic profile information makes it painfully obvious that I already left full-time military service. Although I don’t work in a cubicle (thank God!) I am enjoying a day job in corporate America. My career progression should make it completely obvious that I’m very happy with this job.
I also happen to post links to a lot of my writing on my LinkedIn profile. If you’ve read any of them, you’d see that I love my corporate America job in part because it already gives me the free time to pursue entrepreneurial projects. That’s right, I both work in corporate America, and have found some satisfying niches outside it as well. If you actually want to entice me, your pitch would need to include something to the effect of:
“It seems like you enjoy side hustles that bring rewards beyond those offered in corporate America. My training can help you enjoy opportunities like those, while making more money from them. “
I’m probably still not interested, but this would improve your chances with most prospects.
I’d back-burnered my draft of this article for several months, thinking it was too cynical to publish. However, I’ve continued receiving unwanted pitches from personal financial advisors on LinkedIn. It’s frustrating. This recent addition prompted me to dust this article off and publish it:

Once again, tell me you hired a bot without telling me you hired a bot….
Optimize my pension? As I’ve mentioned, I won’t get a pension until at least age 57. I wouldn’t expect every financial advisor to know this. However, the particular individual sending this pitch advertises on his profile that he was a USAF pilot who served for a full 23 years! Even a passing glance at my profile should make my pension situation relatively clear for a long-time USAF pilot.
Next, if he’s read anything I’ve ever written, especially some recent stuff, he should realize that I’m against paying people to pick stocks for me. I’m not sure what he’s going to do with my TSP to optimize it. I know of several services that charge clients a bunch of money for picking funds within the TSP, a strategy that is all but guaranteed to fail a majority of the time.
I am genuinely curious about how he thinks he could improve the tax advantages of the TSP. However, the rest of the message, in the context of the rest of this post, is off-putting enough that I’m content to go with what’s been working.
Finally, he tries to entice me by branding his financial strategies as a version of the MDMP…the Military Decision Making Process. (If you don’t know what this is, here are 100+ pages of eye-gouging US Army handbook on this bureaucratic nightmare.)
If this person had any idea of who I am, they couldn’t help but perceive my seething disdain for bloated military bureaucracy. I avoided military staff work like the plague. I understand its necessity and value. I appreciate those patriots who serve in those billets. However, I value clear, efficient, and effective action. Branding your product based on the MDMP is the worst possible way to pitch me on anything.
Thanks for enduring these so far. One more and we’ll get to some take-aways.
I feel bad picking apart all these examples, but we need to consider the one that pushed me over the edge on finally writing this full post:

Simply put: this feels manipulative. If your content is so good that you think I’ll love it, then give it to me up front and let it speak for itself. I promise that if you impress me, I’ll give you that feedback and seek out more of your content. Entrepreneurship podcasts are a dime a dozen, and I can get most of them without having to send your bot a thumbs-up emoji.
This message says to me: “I put minimal effort into some content that serves as part of my client funnel. It’s not good enough to hook you on its own, so I’m using this cheap manipulation to get you engaged without knowing whether I’m presenting anything of interest or not.”
I feel like this message was generated by a 3rd party application and that the sender would have no idea if I, specifically, responded. It seems likely they’d only see my response as part of a dataset on an analytics dashboard.
If this sender had the good sense to just include their podcast episode in the first place, this message wouldn’t have needed my action to be effective. All they would have had to do is mention some specific, personal reason they think I might be interested in entrepreneurship and feel like I need some help with it.
And that, finally, leads us to some better ideas.
Fundamental Principles for Better Contacts
I see people on social media who seem to treat contacts, friends, or followers like seashells in a collection. They might be nice individually, but mostly they’re something they count and then put back on a shelf or into a box.
One of the reasons I like LinkedIn is that it generally rises above the petty drama and outrageous life-crafting of other social media platforms. It feels like people go there to actually accomplish something of value.
I don’t see anything terribly wrong in sending a connection request to a stranger that I find interesting on LinkedIn. I’ve “connected” with several celebrities (aviation writers and accomplished pilots like Elliot Seguin) without any expectation of actual personal interaction. However, I’d jump at an opportunity to interact, and I hope that sharing a connection might help facilitate a conversation if I manage to leave a valuable comment on something they post someday.
This is Fundamental Principle #1. If you have no existing relationship with a person, then connecting on social media does not count as a meaningful relationship. At best, this is you subscribing to updates on content they produce.
Next, let’s discuss hiring a bot to scrape LinkedIn for you.
In principle, there’s nothing wrong with this. Although we don’t like to admit it, social media is a brilliant scheme to get users to provide a whole bunch of personal data for businesses like mine. (If you’re not okay with that, then run, screaming, from such platforms!)
It would be a waste if people didn’t create bots to comb through these large populations to find target customers based on your specific criteria. I hope you support the best of these providers.
If you’re selling something ubiquitous like diapers, coffee, or shoes, then it’s okay for your bot to pitch people automatically. This is called advertising. Google, Facebook, and all the others make billions of dollars by selling ads narrowly targeted to people who most closely meet specific criteria. (Twitter seems to be losing ground here. Remember: speech is and should be free, but the consequences of your speech are not.)
If you’re selling something generic, then buy ads. There are entire companies who will help you choose the right criteria and design your ad to maximize performance.
However, and here is Fundamental Principle #2: if you are attempting to generate business that relies on an ongoing personal relationship, then generic is your enemy.
Any schmuck with an internet connection can go to Vanguard or Fidelity right now, and have a brokerage account set up within a few short minutes. They can buy the lowest-fee index funds known to humanity. Statistically, those funds are more likely to approach the performance of their index than any actively-managed fund.
When speaking with friends, acquaintances, FOs, and others, I strongly recommend they not pay people like you to pick stocks for them. And so, you must offer something else, something better.
Yes, your pitch offers that…via a webinar, or podcast episode, or an introductory call. However, you should realize right now that you are in a saturated market. Simply stating that you have something to offer is not good enough.
Do you want to know Fundamental Principle #3? The most important thing a financial advisor can offer is diligent, individual attention to each and every client.
Like it or not, your industry is not great at this. Your model only works if you sign up as many clients as possible. The problem is that the more people you sign up, the less attention any one client gets. So, you systematize things and hire a team. We hate that though. We don’t hire an individual pro to get shunted off to a far-less-qualified sub-specialist (unless your firm’s performance is seamless and amazing).
Do I sound cynical? It’s because of past experience.
If you want to cold-pitch me on LinkedIn, your most important objective should be a display of your attention to individual clients so impressive that it rises to the level of “shock and awe.”
Given the abysmal examples I’ve included here (and several that didn’t even make that cut) the bar is pretty low right now.
I’d be extremely impressed by a cold-caller who included 1-2 lines in their pitch subtly revealing that they’d actually read through at least some portion of my LinkedIn profile. The fact that almost nobody seems to have figured this out leaves me hanging my head in frustration.
Even better would be a pitcher who demonstrated some idea of my personal circumstances, and had some specific advice tailored to me and my family.
Such a pitch would never imply a connection based on a buzzword like “federal employee,” “veteran,” or even just “pilot.”
This leads to Fundamental Principle #4: automated tools are just that, tools. They are not final solutions!
You cannot, you must not send out automated pitches based on automated search results without any human intervention. Sorry, but if you want any hope of enticing me to form a long-term business relationship with you, you must show me that you put in the effort to look at each one of your search results and made the effort to start providing individual attention before you even reached out to me.
That sounds like a lot to invest without any guarantee of success. Let me ask you though: how successful is your generic, automated LinkedIn client generation right now?
I recently had a great conversation with a financial advisor that we’ll discuss more shortly. However, one of his comments was that he once tried using LinkedIn for automated client generation and gave up because it performed so poorly. I suspect that if you compared the value of putting your time into better, personalized pitches, you’d get more client generation value than simply by paying for another month of search results that you don’t even bother looking at before the system sends out painfully ignorant or even manipulative cold-pitches on your behalf.
Good Examples
I hope my rambling here got the point across. Those Fundamental Principles should sound somewhat repetitive, because they’re really just different ways of expressing the same idea. Please consider applying them to do better.
In hopes of ending on a positive note, I want to tell you about two financial advisors who haven’t cold-pitched me, per se, and whom I actually respect.
The first is Tim Pope. He’s a Certified Financial Planner and I am not his client. We got in contact because he read an article I wrote and followed up by actually reading my LinkedIn profile. He contacted my editor at the time, sending a very personalized message focused on Networking, rather than a sales pitch.
We chatted and connected on LinkedIn, and now seem to end up in the same discussions on LinkedIn posts on a fairly frequent basis. I like his balanced perspective and professionalism. I like that we agree a lot of the time, and that he respectfully challenges others’ ideas (especially mine!) when his perspective differs.
He’s occasionally offered me his services as a CFP, but it’s never been a hard sales pitch. Since we have some measure of existing relationship, and since I know he’s actually considered who I am as a human being, I know that when he offers me a service it’s because he already has a concrete idea for how he could help me.
Tim is starting a new project soon, and I may play a very small part in some of it. One of the entering arguments for our discussion of that project was his acknowledgement that we don’t agree philosophically on everything…and that’s okay.
I still don’t feel like I personally need to hire Tim to help with my family’s finances, but if I did I’d be much more likely to reach out based on his individual attention and him taking the time to form a meaningful networking relationship. When I encounter pilots who do need a CFP, I always recommend they include Tim in the list of people they interview for the job!
My next (and final) positive example is Matthew Vann. He read a recent post where I came down hard on whole life insurance policies, and disagreed with my position.
He also took the time to look at my LinkedIn profile and found that we share several similarities. (I’m jealous that he flies the Airbus while I’m stuck on the guppy). He also noted that we have a mutual contact at his financial advice firm. He contacted his friend first to get some background (bonus points there!), then reached out to me.
He didn’t reach out to try and sell me a whole life policy. He didn’t even necessarily try to justify selling a product that I’d spoken so strongly against. He approached me to have a discussion about these products in general to make sure he’s not missing some gotcha that makes them a bad deal for his clients.
We had a phone call that was mostly him showing me information, but I was happy to spend that hour with him. Our conversation is still ongoing, and he has been very open to my input and even criticism (sorry Matt, I owe you a response but I’m busy writing this).
Would he like to sell me a whole life policy? I’m sure he would! However, if he does it’ll be because he took the time to understand who I am and tailor a discussion to me as an individual. It will not happen because some generic algorithm sent me a cold-pitch message on LinkedIn.
If you’re interviewing financial advisors, I feel like Matt would also give you some meaningful, individual attention. Maybe ask him to hold off on insurance until he and I get further into our discussion, but there are plenty of other valuable services he might be able to offer you as well.
Wrap-Up
Life expectancies for Americans are in the 70s and (hopefully) climbing. If you land someone like me as a client, we’re looking at a 30+ year relationship. If you manage to snag a much younger professional pilot, that relationship will probably have a minimum timeframe exceeding 50 years.
Would you start a serious romantic relationship by hiring a bot to swipe through Match, or Tinder, or Bumble for you and throw out automated date invitations on your behalf? You’re pursuing a business relationship that could potentially last longer than a lot of marriages. How dare you even consider pitching potential clients with a similarly impersonal approach!
Bots are fine if you use them correctly. (My current favorite bot is the one masterfully written by author Martha Wells.) Let your bots generate a list of potential clients for you. However, at that point the bot is done! (Send them off to recharge and watch Sanctuary Moon.) From there, it’s up to you to diligently learn what you can about a given prospect before crafting a tight, specific pitch that shows how much individual attention you’re interested in putting into a relationship with them.
If you do this, I can only assume you’ll see more success than you are now. If you’re not willing to do this, then please find a new occupation because we, your clients, deserve better.
If I responded to your cold-pitch with nothing more than a hyperlink to this post, I appreciate you reading all the way to the end. I’ll be honest, it would take a pretty compelling offer for me to hire you. Don’t be offended by that…there are plenty of more fish in the sea. However, if you want to try again with me, at least now you know how to get started.
This post’s featured image is by Brett Jordan on Unsplash.











