Why You Suck As a Salesperson
Lessons, Let's Get Personal
The Before-Face
In the beginning there was sales, and the Lord smiteth thee down, crying, you suck! Yet you persisted in your vain attempt to sell useless trinkets to people with no money and no use for trinkets. This is how sales have been for millenia. People convincing other people to buy useless crap they don't need with money they don't have. It's a quick way to make money. This then evolved into creating things and convincing everyone they need whatever it is. It reminds me of a book that I read to my kids on occasion, "The Lorax''. Whereby the Lorax confronts the character (the Once-ler) for chopping down the Truffula trees and the Once-ler retorts, "I'm being quite useful. This thing is a Thneed. A Thneed's a Fine-Something-That-All-People-Need! It's a shirt. It's a sock. It's a glove. It's a hat. But it has other uses. Yes, far beyond that."
It's entirely possible that there are legitimate arguments for the existence of salespeople, though I haven't personally observed this to be true. I cannot think back on something I've bought on recommendation from a salesperson where I didn't have some form of buyer's remorse. Whether from overpaying, to realising my life was not improved 1,000 fold as advertised. Unfortunately for salespeople, I see them all as those 'slick', greasy haired, slimy do-anything-for-a-sale turds, yes, women–that goes for you too.
I'm not what you would call an approachable person. It's most likely my body language. I don't think it matches my inner temperament. The whys and why fors don’t matter, the point is that it has given me the ultimate ‘sales-dar’. You see, it’s simple. No one approaches me unless they want something from me–usually money. So when you ladies walk out in front of me flashing what you think is a lovely smile, I just wave you away like a Jedi would to a fly–this is not the sale you are looking for, the money you want is not in these pockets, it’s in my bank where you won’t be touching it. I’m kidding, the money in my bank will shortly be taken out to pay bills. Jokes on you. Guys, don’t think you’re getting off the hook here either. Coming up on me all, hey bro, or, how you doin’, handsome–gimme a break, you’re not coaxing money out of my pockets any more than you are a date. These right here are perfect examples of ‘shotgun’ approaches and anyone with half a brain can see it a mile away.
It’s lazy.
It’s dated.
It’s pathetic.
It needs to stop.
And I’m here to stop it in its tracks.
If my insults haven’t offended you or dissuaded you from reading then let’s continue together, because now we’re best bros (or bro-ettes) and we’ll likely get along swimmingly. And if you’re a salesperson, you’re about to get some well-needed and valuable advice you should have received years ago.
This is the tale of two LinkedIn salespeople who pushed me to have some fun with them. In the process giving one some hearty laughs and the other some actionable advice that I genuinely hope gives them reason to ditch their template-shovel-leaning ways in lieu of human connection.
This is the story of how I became the Sales Whisperer.
The Shotgun Wedding Sale
Whether it’s through email or LinkedIn, the generic template message is the curse that keeps on cursing. It’s so bizarre to me that so many salespeople blindly follow this approach without ever considering there might be a more effective way of doing things.
Take the following for instance, there are two major issues I see:
I'm sending over 50 LinkedIn messages each day, so personalizing each one can be quite challenging.
Additionally, many users are not very active on LinkedIn, which makes it difficult to tailor my messaging effectively.
First off, as I will show later in this article, it’s not as challenging as it may seem. Secondly, this person freely admitted that users are not very active on LinkedIn. That’s like me going to the Sahara desert and complaining about the lack of fish. Sometimes we inadvertently say the things we need to hear yet we don’t listen to ourselves, or our instincts. They are essentially justifying their template-first approach to messaging because, well, no one will see it anyway so it doesn’t matter!
Lesson 1: Don’t waste your time screaming into the void. If fish don’t exist where you are, you’re gonna look a bit silly standing around in your fishing attire, rod and reel and stinky bait.
There are no real upsides to sending out impersonal, spammy mass messages. Unless of course you happen to send one to a person like me at the exact right moment, when all the right variables are in alignment.
If we take InMails through LinkedIn as an example, according to LinkedIn, those sent individually did 15% better than those sent in bulk. These stats are primarily for recruiting, and I imagine sales and other areas would follow a similar pattern.
And for the love of God, whatever you do—even if you decide to mass message people—don't, I repeat, don't ever put someone else's name as the recepient. That's like calling out another person's name in bed—a massive taboo. Just don't do it.
We Could All Do With a Little More Understanding
Not understanding your target audience is like farting into the wind—it feels good momentarily, but did it really have the effect you wanted?
When you’re buying something, do you walk into the store with a blindfold on? Do you then proceed to to grasp at the shelves randomly? Tossing whatever you get your hands on into a shopping cart and head on down to the checkout? Oh and pay the store every month for the privilege? Unless you are made of money or have a few screws loose upstairs this doesn’t make a whole lot of sense.
So then why would you as a salesperson decide to randomly slide into people’s DMs with a vague sense of a product match in mind? There would be a number of reasons. Pressure to reach certain KPIs would be one of the biggest. Though how far can that be used as an excuse? If you’re sending out dozens of messages a week and not getting any sales, either the KPIs are useless or your approach is fundamentally flawed. It’s not just about meeting quotas—it’s about understanding your audience and tailoring your outreach to provide genuine value. If your strategy doesn’t evolve with feedback, you’re essentially shouting into the void, hoping someone will listen.
Lesson 2: Don’t walk into the shops with a blindfold on. Go in there armed with a purpose and your eyes open. Become the tailor you would want to have fit your own clothes—the salesperson with understanding who can see past the superficial.
“But [insert as many excuses here as you’d like],” I hear you say. Once you have all of the excuses out of the way we can continue. How long did it take you to create that “masterpiece” of a LinkedIn or email template? The one you’ve been littering everyone with for the past few months. The one that’s been getting little-to-no or negative engagement. In the back of your mind you might be thinking that the time you saved by sending all those generic messages at one time is worth getting a low response rate. And that in the end it’ll work out because you have faith in your shotgun approach and the holy list of KPIs you abide by. Unfortunately this isn’t the case. No matter how many times you repeat,
“By the power of KPIs, I have the spam!”
“One template to rule them all, and in the inbox bind them!”
“Every rejection is just a step closer to … another rejection!”
“If at first, you don’t succeed, send the same message again!”
“In templates we trust, ignore all this dust!”
“Why tailor when you can template?”
“Consistency in failure is still consistency!”
“KPIs are my commandments, and templates are my gospel!”
“Because nothing says, ‘I care’ like copy-paste!”
“Blessed be the shotgun, for it shall spread my word far and wide!”
I Wanna Get Personal, Let’s Get Into Personal
How do you break free from the template circle of hell? We gotta get personal. But not too personal. Think OSINT1, not Creepy-SINT. Picture this, you're watching some speed dating event and there's two guys going around, one is using some corny pick-up line with everyone, and the other is noticing some small detail about each person and using it as a conversation starter, "oh those are cool earrings, did you make them yourself?", or something more humorous / lighthearted, "I love that you brought tiny pieces of art along with you to the event, do you like to [insert relatable thing] as well?".
The above image is a great example of how, even after a small pep talk, salespeople can reignite their inner-human once again. It’s fantastic to see! My advice that led to this message was as follows:
TLDR; I get tonnes of these messages and they just become spam for the most part. I don't even look into the product because I don't feel understood at all, go beyond surface level and I'm sure you'll see more success—less shotgun, more sniper rifle (less phishing, more spear phishing / whaling 😉)
Yeah I hear ya! You probably have quotas, KPIs and what not or at the very least pressure to get sales. For me personally I get a lot of these messages so it's easy to see from a mile off, and they never seem to be tailored at all.
If you're approaching people cold, especially in security (we're a bit more weary as you can imagine), even just one piece of personalisation I feel would go a long way. Whether it's something they've posted or some little nugget of information that you stumbled across—you could do some OSINT, though remember there's a fine line between "wow I forgot about that" and, "what are you, a stalker" 😂
Imagine you're watching some speed dating event and there's two guys going around, one is using some corny pick-up line with everyone, and the other is noticing some small detail about each person and using it as a conversation starter, "oh those are cool earrings, did you make them yourself?", or something more humorous / lighthearted, "I love that you brought tiny pieces of art along with you to the event, do you like to [insert relatable thing] as well?".
And it's not only personalisation, I would also consider the company of the person you're approaching, what are their needs? Are you sure what you're offering will provide value for them? I don't remember one product I've been pitched where I legitimately thought, wow we could really use that—primarily because we know what we need and we do research ourselves. There is a LOT of diversity when it comes to how companies handle security so in my experience it's very rare that you'll find a product that has all the features, all the right connections, etc. And that's a good thing IMO because a company that tries to do everything is doomed to fail or not reach its full potential, stick to what you know for something more sustainable.
You're a people person, you're asking the question because you love learning new things—so less Netflix and more Louis Grenier (https://www.everyonehatesmarketers.com/) and Seth Godin.
P.S. Make sure you double check who you're sending to as well.
Good luck, [Sales Padawan] and have a great weekend!
Not only did I include what would have made the experience more enticing from my perspective, I also included an anecdote to help seal the theory. And for this section, I even went out of my way to do a quick bit of OSINT to be more relatable:
You're a people person, you're asking the question because you love learning new things—so less Netflix
This:
love learning new things
And this:
so less Netflix
Were pulled from information I found on their profile.
It really doesn't take much to greatly improve your chances of getting a sale. I spent a few minutes thoughtfully giving feedback and as you can tell, the reception was great. Now, you're not going to be able to pump out 50 high quality messages / conversations every day, far from it. That's not the point, the point is I want you to break free from this way of thinking. We've evolved way past being able to hamfist our way through to people, potential clients, using impersonal templated messages.
Use some small, personal detail from their profile—follow a link from their profile and take a minute to read through things they’ve written. In the grand scheme of things, adding small personal touches to your initial messages will greatly boost your rapport with the person and it won’t take that much extra time—the more you do it, the more proficient you’ll get and the less time it will take each time you do it. Try not to fall into the same trap as before with the templates. Use your imagination and think of novel ways you can engage with people—templates work great for computers but not so much for people.
Lesson 3: learn to OSINT, ensuring you don't venture into Creepy-SINT. Allow people to feel seen, not just someone you want to “wow” with your template making skills.
Dude, Where’s My Value?
I understand that when you’re sending out your templated messages, you might truly believe what you’re trying to sell is the greatest thing since sliced cheese sandwiches. However, that’s not how the people on the receiving end see it. You see things from your point of view, they see things from theirs. You see the value you think you can bring, though if it’s not communicated in a way that is palatable for the other person there’s going to be a big disconnect. You both should be speaking the same language. Both in the literal sense and metaphorically, if you’re not speaking the same literal language, online translating services are likely to mess up your game, sorry. Though there are better ways of translating these days, they’re still not perfect.
Success in the modern sales landscape takes more than trying to shove a one-size-fits all product down everyone’s throat and expecting them to swallow it with a smile on their face. Especially if they would be paying for an entire product and only using 10% of it. That wouldn’t make much sense from a financial perspective, would it? Instead of claiming your tool can do everything, do some research beforehand—if you can find their tech stack or a little bit about how they operate this can give you clues as to where and how to focus your time and the information you think would be most valuable to them. Remember it’s not about it’s not so much about, I have this fantastic product and you should also appreciate how great it is, so much as it is, I’ve identified a possible issue I think you might have and we have just the product for you to solve it—which will save you x amount of time and y amount of money. There are many ways the last point can be reworded, the main point is to put the customer’s needs first, not your product. As I wrote above in the LinkedIn message, I find myself inundated with templated messages from people and they put no effort into understanding, so why should I put any effort into replying? I may as well set up a bot to respond to these and we can waste LinkedIn’s storage and mess up their analytics stats together.
Gimme Some Insight, Not Inflight Entertainment
As the value of your sale goes up, so should the effort you put into researching and understanding. People these days seem to be stuck in the mentality of that one big break, or relying on “luck”—not realising that luck is made, it’s not really a real thing—well it is real but rarely occurs naturally. If you position yourself in the right place at the right time and put the work in, you’ll discover that your luck will magically increase by a large margin—if you consciously did this and saw your luck increase, would you still believe everything is just because of luck of the draw?
It’s All About Industry
Not all industries are created equal and all will have different requirements and needs. I’ll stick to security examples because that’s what I’ve involved most in. When you’re approaching someone in a particular industry, it’s a good idea to understand more than the single word that describes the industry.
Finance
Healthcare
Utilities
Do knowing the above words make you an expert, or even knowledgeable? If you approached someone and said, wow, you work in healthcare! I have this awesome tool that automates logic gates in electricity grids! You need it right now!, how do you think that would go? Let me help you out a bit:
Finance
In the world of finance, they’re pretty big on compliance, regulatory requirements, data protection. The specifics will depend on the region and so on, the rest you can research—this is a good starting point.
Healthcare
The healthcare industry are strong proponents of patient data security, HIPAA (in the US) compliance and sensitive information handling. Their hardware is a lot more locked down than in other industries for obvious reasons—or not, if you don’t understand why you can research it!
Utilities
Critical infrastructure protection, more physical security controls, SCADA system security as well as regulatory compliance. Don’t know what SCADA is? Great opportunity to learn!
The News Isn’t Just For Creating Negative Emotions
If you focus on a particular industry, you should keep up with any relevant news. Keep an eye out for news affecting potential client companies—figure out their pain points and challenges they might be having. There are always clues to be found.
Make use of social media for more than sharing cat pictures—we know cats exist, there are billions of images of them online, you posting 3 more isn’t groundbreaking and the 10 likes you get—is it really that important? Use social media to follow companies and industry. Keep up, things change rapidly within technology.
What’s Public Between Friends?
Is it simply enough for you to know the name of the company and their industry? If you answered yes, it might be best to mosey on back to the start of this article and start again. There is a wealth of information out there, we have the Internet now, so it’s easier than ever. It’s not like back in the day when you had to go down to the library and search for things manually—back when you had to already know stuff. Now you can literally ask a search engine the most mundane questions and get answers in less than a second, questions like, “How many chickens would it take to restart an elephant?”. The possibilities are endless.
If you’re approaching someone who is representing a company, or works for one—the first thing you should do is go to the company’s website and have a look around. Check their public-facing security documentation (or whatever theme you’re sales is in) for clues. Take into account the company’s size and its structure. The company’s approach to security spending and methodologies will differ depending on this and many other variables.
What are the leaders’ priorities? Is it clear from their LinkedIn profile, posts, company blog? Dig, Lazarus, dig! Don’t be afraid to look at information—it’s in the public, so you’re literally supposed to be able to see it and read it.
Show Me The Value!
Be Specific
If you have a solution that you believe will save time and other resources, discuss them—making sure they are relevant. With finance and healthcare these are particularly important.
Example Me Surprised
Provide case studies, examples of how other companies (in similar industries) have successfully implemented your solution to solve specific problems. It shouldn’t need to be said, though you should obviously use caution when it comes to specifically what information you share. If you’re unsure, it’s best to speak internally within your own company.
Be (Industry) Specific
For finance, how is your solution going to help adhering to regulatory requirements and protect sensitive financial and other data?
Within healthcare, how is your solution going to assist in ensuring patient data security, HIPAA (or other) compliance as well as handling sensitive information?
In the utilities sector, you should demonstrate how your solution enhances the protection of critical infrastructure as well as how it would improve SCADA security.
Now It’s Your Turn—Craft Me Something Beautiful
Remember To Personalise
To begin having rapport with the person you’re messaging, mention something unique about them, their company—this could be recent projects they’ve posted about, events they’ve attended (that are publicly available), challenges, anything. You should stand out—if you put the time in, your efforts will stand out. You won’t always get the reaction you want—though if you're getting mostly silence with your templated messages (and because you work in sales) you should be quite used to it, don't sweat it. I'll create a thread and you can share your successes and attempts. It'll be linked here.
Value-Added Messages
The other person (your potential client) should feel as though there is legitimate value in whatever your offering—but beyond that, understand this is not a sprint. You can't expect to gain the rapport and trust you need on top of providing enough value (remember, if they respond they're taking time out of their busy day) to make it worthwhile continuing the conversation beyond one message, let alone enough to the point where they're willing to hand over money and / or sign a contract. The market has changed. How much free information and tools are available on the Internet? Tonnes. Simply saying, *my product is awesome* is not enough. People are wiser, and depending on the economy, a lot more thrifty.
This means give them something upfront. Provide free resources, without any expectation of getting something in return. The idea is to plant a seed, not throw a pot plant in their face. There will be times when it's better to play the long game—conversely it will be almost impossible to get a sale within one or two messages. The effort you should put in will be semi-proportional to the value they bring in at the end. Remember, we don't get anything for free in this world—just because the cost isn't obvious doesn't mean there isn't one.
One last thing here—**ask insightful questions!** Don't spend the whole time talking, OSINT isn't the only way to gather information, you have a source right at your fingertips. Asking questions doesn't mean *interrogate*—be genuine and inquisitive.
Lesson 4: ask, don't tell. Provide value.
Conclusion, Sort Of
So that's it. I hope you got some value, or at least as much entertainment as I had writing it. Do you really want me to summarise all that I wrote above? I'm tired and I think that's enough writing for one week. If you wanted a summary, you should have been taking notes. Silly Billy. Now get out there and get better at selling, or being a person, whatever your goal is—use the above information to get it done! Give me engagement, I really appreciate it—write comments about how I use em dashes too much, or commas too little, or how my articles always seem to be so long. Want more of this stuff? Let me know, dang it!
That's it for now, as always, good luck, stay safe and be well.
OSINT stands for Open Source Intelligence, a technique for gathering information that is publicly available.