Are salespeople “Hackers”?

There are many parallels to a salesperson and a hacker when looking at interactions with organizations and computers. First, let’s start with some terms to make sure conceptually we are on the same page.  A “Hacker” can be defined in several ways:


We are seeing the term used in more casual ways over time, so for this discussion let’s use the first definition with a dash of the third definition for easy comparison.

A salesperson acts in much the same way as a computer hacker. They exploit a weakness in a company or individual in order to gain opportunities and money. Now this may sound rather harsh, especially coming from me; however, the reality isn’t that far off and it isn’t always a bad thing.

Layers of security

Phone trees and receptionists are the Firewalls of companies and first line of defense. These are designed to let known traffic into the company and keep out everything else. Receptionist are highly effective at vetting inbound calls or visits. If you are not a known entity or do not have a specific name (pronounced correctly) they will either reject you outright or put you in a DMZ (perpetual voicemail). Methods to hack this initial security is to use social media networks to gain the right contact’s information (password), or engage with the receptionist directly. Get their name and understand their personality. If they will not direct you to your ultimate contact call back and address them by name as if they should know you. Spoofing familiarity will often drop their defenses and pass you on to the right person.

Once you do reach the right contact, the more subtle layers of security present themselves. These are often used in a machine-gun-fashion similar to antivirus software.

  • I don’t have a need right now.
  • I don’t have time right now.
  • I already have a vendor.
  • We aren’t that big.
  • No budget.
  • NO

Addressing each of these with Matrix-like agility becomes second nature but require patience and some more social hacking to get through. The first step is to convince the person you aren’t a threat. Empathize with them, get the alarm bells to stop blaring so you both have an opportunity to talk. If in fact this is a bad time, work with their schedule, find a time when other problems aren’t triggering their defenses. Understand what they are specifically reacting to and offer solutions, even no-cost solutions. This will help ensure they understand you are there for no malicious reasons. Once you have established that you are safe, you can move on to the last layer of security.

The final level of protection is often the most powerful and complex intrusion prevention solution (IPS). Even if you have breached the other defenses and proven you aren’t a threat, this last defense can often trip up the most prepared. This is the CFO. They are an isolated system with their own objectives. Oftentimes, above everything else, they eliminate all threats to their bottom line without regard to the wants of other departments. There is an alphabet soup of key terms they respond to, such as

  • ROI
  • TCO
  • OPEX

Understanding their motivations and long-term goals are often the only ways to communicate with this subsystem. It is essentially programmed in a different language to ensure the protection of the company. However, if you can communicate with the CFO in their own language, you can often demonstrate the most value to the company. This helps show long-term vision and an understanding of their long-term goals. Not only will your solutions solve immediate problems or needs, but will have an overall benefit to the company’s bottom line.

It shouldn’t be surprising that we built our organizations and systems with a similar model. Companies have been referred to a “Machine” for years, so being able to draw a parallel to a salesperson and a hacker isn’t much of a surprise. In complex organizations and systems, we use layered security to protect our assets and both hackers and sales people must exploit weaknesses in the system to gain entry. Whether it is for good or evil is subjective, but the net strategy remains the same.




It’s a Small World

We often talk about how small the world is getting; between the internet, social media, and organizations connections are getting easier to make and maintain. Most salesmen know to leverage these connections to find new opportunities and get into organizations we have had little success otherwise gaining attention. One thing most do not talk about, is leveraging connections to solidify relationships with current clients.

Previously, we discussed the mantra “People like doing business with people they like.”, and how that can help business but may not be enough to sustain it under diversity. One way to increase the value of the relationship is to introduce those clients to beneficial connections you know. In a high-pressure job like IT Manager or Director, changing jobs is pretty common, some reports indicate that the average job change is every 3 to 4 years. (Source) Maintaining your connections, or being the one to help facility a positive career change, can give you additional opportunities. As long as you maintain a relationship with the first company, as people move to other companies so does your network.

Additionally, if you find mutual connections with a client you can build additional areas in common. For instance, if you know the same people, or engage in the same groups you can build credibility and have something beside “work” to talk about. This allows more interaction without being all business. Being top-of-mind in a positive way always yields good results.

Finally, if there is a need for a solution and you are able to connect them with someone who may have the information you provide value beyond price. Often, IT Managers run into problems or situations that are outside of their comfort zone. These can usually be resolved with quick answers or pointed in the right direct and do not require a service contract. Being able to connect people to the right answer and allowing them to seem more competent than they were is invaluable.

It is always a good idea to leverage connections to build your network and get into new opportunities, but don’t stop there. Use your network to reinforce your relationships and increase that total value. As they say, it’s now what you know, but who you know…

The Myth of Relationship

Relationship-based sales… an ancient method that is the mantra of large sales organizations. “People buy from people they like.”, is a phrase often plastered on a ridiculous poster somewhere. Both of these things are highlighting merely one aspect of the whole. Relationship-based sales have been around longer than sales itself! You will obviously do business with someone you trust and know over the shady guy who rolls their wagon into town once a moon.

However, relationship sales also breeds the false sense of comfort that the relationship is stronger than most other influences; such as, price, availability, competition, etc. As Salespeople, we perceive the relationship as been equally important to both parties; when in fact, the relationship almost always means more to US than it does to THEM.

Let’s put this into perspective. As a salesperson, you have a limited number of clients and thus a limited number of “relationships”. These are valuable to you as they are your livelihood. Conversely, your clients have a near-infinite amount of options to obtain said goods/services. Now they are less likely to arbitrarily change who they obtain the goods and services through if they like the relationship; but if there is a major change in the status quo, it is very easy for them to adapt. The relationship is stronger for the salesman.

With this in mind, as a good salesperson, it is your job to stack layers of value in any single engagement. Relationship is certainly a strong first step; however, you also need to add layers of tangible value that reinforce your foundation. This value is through service, availability, knowledge, and yes, price. With these added layers, relationships can be a key ingredient to a lasting business relationship, but not the only one.

Concise Speech Speaks Volumes

There is a difference between marketing and reality. I understand that marketing is trying to paint a picture, evoke an emotion, or captivate an audience that has no attention span and little more interest. Sales is not marketing. If we evoke an emotion, it should be through our own excitement about a product’s features and benefits, or even the ability to solve a problem. All too often I hear sales people use phrases like:

“It’s like ____ but on steroids!!”

(So it uses illegal substances to cheat? It has a serious condition and is taking medication?) What is this supposed to evoke in me? Is it a sense of awe at the amazingness of it all? What does it tell you about “____”? Absolutely nothing. This is a huge missed opportunity; a way to encapsulate how you are like “___” but better. Want to build excitement in me? Say something like:

“It’s like _____ but with better features at a lower cost!” Or “It’s like ____ but with easier manageability and faster ROI!”

These are things at mean something in the real world. You can’t compare an Apple to an Apple on Steroids, that doesn’t make sense. You can compare a product to one that has an obvious benefit, solves a problem, or makes life easier.

I see presentations daily eerily similar to the “Jabberwocky”  episode of “Better off Ted” (Amazon Prime Link). An entire presentation of buzz words that evoke “emotion” without talking about he product or service. There are days I honestly think they didn’t have a product but had a presentation already scheduled!

Buzz words serve a purpose; Cloud, XaaS, Software Defined X, Virtualization, and more give us an initial impression of what the product is out to do. The next step is to tell me, or the client, how this specific product/solution stands out or is the best fit for this situation. “On Steroids”, is never a valid answer.

The Vendor Mentality – Not All Flavors Are Vanilla

It is always interesting when someone refers to me as a vendor. As defined below:


1. A person or company offering something for sale, esp. a trader in the street: “and Italian ice cream vendor”.

2. A person or company whose principal product lines are office supplies and equipment.


What is the obvious connotation to that title? The explicit trade of money for products. Nowhere in that definition is there room for service, support, personal interest, or compassion. Now, I do not mean to insult Italian ice cream vendors, I am sure there is a lot of pride in that profession, but the transaction is simplistic. Person goes up to the stand and says I want ‘x’ flavor in ‘y’ size. Thank you, bye.

In IT sales especially, but in most sales realistically, the path is rarely that easy. Often times I receive an e-mail or call that says “I need ‘x’.” My immediate questions are, “Why?”, “What are your objectives?”. With an original goal of ‘B’, we often wind up at in a different direction or get there through different means because what they were selecting wasn’t the best option; either they were overshooting, diagnosing the symptom and not the problem, or weren’t aware of other solutions out there that were a better fit. Taking the time to ask the question, take an interest, and engage as a partner leads to a batter answer.

Overcoming this “I get products from you and give you money and that is all there is to the relationship” idea is a difficult one. A great way to start is showing the value of your advice. In this instance, I literally mean how much money you saved them, or how much better the solution was, or  how I validated their original solution. There is a very real dollar amount associated with the right solution.

To over-simplify the point, let’s look at the ultimate vendor, the vending machine. We deposit money, make our selection, and expect our desire to drop out of the bottom. End of relationship. What happens when you hit the wrong item? Does the machine care? Can you take it back? No, you suffer with that choice or pay more money for a replacement. How much value is there if the machine said “You have never purchased that before, are you sure you want B1 and not B10?” (This actually happens at work often, who make a 10 button anyway!?) There is an immediate savings if you had not intended to get B1, and a validation of the right choice if you did. Both are win-win.

The underlying goal of this salesman (which is a synonym), is to be a partner. To borrow from a friend and client, “a partner willing to make partner decisions.” These decisions may not be the most profitable all the time, but they are the right ones. Convincing them that this solution, regardless of whether it is a lower-cost, or un-spiffed, is the right solution will show that you have their interests in mind. That is invaluable in the long term.


A little bit of sugar, and a whole lot of self control

The temptation is always there; the need to reinforce the fact that you are so much better than the competition. But in doing so with a new prospect, you must be careful to avoid a couple common pitfalls.

The first common pitfall is insulting their current decision. Whether intentionally or not, you have to support their current choice by complimenting a couple low-hanging positives while carefully talking about how you can compliment that solution in an area they may not be as strong in. You will almost never get into an opportunity by completely kicking out the incumbent unless they make an error (which we will talk to shortly). The easiest way into a new client is by offering something their current provide can’t do or doesn’t do well.

Another common pitfall is when the competition does falter and you have the opportunity to save the day, offer your sympathy but don’t bash. Taking the higher road will help you maintain a professional attitude; and let’s be honest, these things can happen to any of us and are sometimes out of our control. Rising to the occasion will speak for itself when it comes to service and reliability. You do not need to point it out.

Finally, keep the dialog going. Offer the customer additional services you can provide to help them understand your full capabilities and offerings. This can be a subtle way of demonstrating that you are a better fit for this environment.

It is important to constantly add a bit of sugar to your recipe. Showing how you are an attractive complimentary solution, can provide a wide expanse of services, and be there when you are needed, and can provide a wide expanse of service. But like any recipe, a dose of self control can help prevent ruining the final dish.

I want you to want me…

As Cheap Trick put it:

“I want you to want me.
I need you to need me.
I’d love you to love me.
I’m beggin’ you to beg me.”

Although this sentiment was for a more romantic relationship, the underlying meaning still holds true in sales. We all have companies we idolize or are passionate about; whether it is a brand of electronics, or a company that makes a difference in the world. There is a driving need to work with a company you are fanatical about and a desperation to get them to accept you. This has little to do with dropping names, but more like a sports fan getting an opportunity to work with their favorite team.

Unfortunately, this means there are certain companies that are bound to get more cold calls than others, and those companies usually have the highest walls built around their company. Often, this is the start of the resentment of sales individuals. Trust me, we get it. We know you have had 100 calls just today!

“But I am different! I promise! Just give me the chance to show you.” (Every salesperson alive)

Consequently, it is that desire to show you that this person is different, that we understand, that perpetuates the cycle.

So how do we fix this? We don’t. (period) To some of us “Salesmen” you are a famous actor or athlete. We want you to acknowledge us, work with us, and tell us that we are better than the last guy you worked with. But try to understand, it is not always to make a sale, sometimes we just want to be associated with the brand. Sometimes, we just “want you to want me…”

The Awkward Invitation

I was having trouble composing an e-mail to a prospect; this was a person that I have had minimal interaction with that was not able to attend an event they had originally RSVP’ed for. I was trying to send a quick e-mail acknowledging the fact as well as trying to suggest another day for us to meet up, possibly over lunch of coffee. I was struggling to phrase the proposal with an objective without coming off like I was hitting on him. I suddenly felt like a teenager again asking out the attractive girl from class…

“… how about next week we can meet for lunch to get to know each other better?”

No, that’s not right.

“I have some free time on Wednesday of next week, how about we grab some coffee and discuss how I can… ‘add value to the relationship?’ ‘become a partner?’ ‘discuss your pain points?'”

I am tired of the cliche’s; two of those are still illegal in some states and the last one, sounds like I am interviewing for an S&M engagement. Half-way though writing my e-mail I felt like I should just write “Do you like me? Yes/No (Circle One)”.

Ultimately, I decided to look at it from his perspective. He was originally going in order to learn something that was presumably relevant to him and get free food. Since I have an opportunity to get some one-on-one time with him (oh, stop), I might as well try to maximize both of those objectives.

“What information were you looking to get out of the even and how does that relate to your business? I can put together a tailor-made presentation of just what is relevant to you. Since lunch was originally going to be served, I feel I still owe you that, pick a local place and we can discuss this casually. Tuesday and Wednesday have the best availability for me, what works with your schedule?”

The Self-Aware Salesman (Explained)

Often times, I post snippets on Facebook about my job, experiences, and observations. Recently I posted a short personal insight and was met with the following comment:

“This is why you’re a good salesman, Jason. Most sales guys aren’t so self-aware.” – Anthony

I was reflecting on this comment and thought that within his post was not just an observation I had not considered about me personally, but commentary on the “sales” profession. Most people are on one of the two sides; the seller or the victim, right? Well, I have the unique opportunity to be in between those contrasting views often. I am actively selling to my existing clients as well as trying to obtain new ones (*shivers* cold calling!). Yet, on the other hand, I deal with other sales people almost as often. These are in the form of manufacturer partners pushing their latest-and-greatest, or trying to find the status of that PO. (Sound familiar?) I work with some very talented people, who have accidentally said some ridiculous things; and some utterly ridiculous people who have stumbled on some remarkable insight.

With this blog, I want to shed some light on each side, maybe vent a little, or perhaps bring a chuckle occasionally. But ultimately, I hope that by writing down my thoughts and observations and engaging in dialog, I can become a better person and salesman.