10 Things I Learned From Working For An Asshole

One day at one of my previous jobs, my boss called me into his office. One of our biggest competitors had fired one of their top producers, whom we’ll call Fred. My boss had decided to hire Fred, but he first wanted make sure that he could count on me to work as this Fred’s analyst. As a young up-and-comer, and completely oblivious to this guy’s reputation, I was excited to be given the opportunity to work with such a heavy hitter.

After agreeing to take on the assignment, I was tipped off to the potential hazards when my boss told me to keep him informed of “anything out of the ordinary.”

That shouldn’t have been my first clue. The biggest clue that something was awry should have been this: how does a top producer get fired from a company? Answer: by screwing up royally.

We all have our own faults, some of which can manifest themselves into legitimate problems in the business world. While I never was given the “official” reason for Fred’s forced departure from his previous job, what I gathered from multiple sources was that he was fired for simply being an asshole.

What made this guy an asshole? He treated analysts, investors, and many clients like shit. He would call people constantly for no reason. He wouldn’t do any work on his own – literally calling clients and asking them to dictate a document to him. He wanted things done his way 100% of the time, regardless whether his method was correct, acceptable, or honest.

Despite all of his faults, this guy still closed deals. A lot of them. So he must have been doing something right.

After working for this guy myself and then observing other people working for him, I came to understand what made him successful and what was holding him back.

1.) Never Accept No

This guy would absolutely never let up. He would present the same deal to the same investor time and time again despite being told no. Some investors would eventually fold and invest in a deal, others would tell him to go to hell and never call again (but he would anyways). The investors he ultimately won over were largely pursuaded because he employed the next two tactics.

2.) Ask questions

If he was told no, Fred would ask tons of questions “Why don’t you like this deal,” “what deals are you investing in these days?” “What could we change to make this deal interesting to you?” After a seamingly endless barrage of questions, he would have a great understanding of how to alter the deal to make it paletable to that investor.

3.) Make it personal

Whenever selling a deal, Fred would make his sales tactics as personal as possible. To set up, or “frame,” a deal, he would use anything and everything that he could to make a personal connection between the investor and the deal. Sometimes they would be linking the investor to a the client through previous employers, golf clubs, alma maters, or previous transactions. Other times, the connections would be very loose. I overheard conversations like this all of the time:

Fred: “Your office is on the corner of 5th and Main, right?”

Investor: “Yes.”

Fred: “Well our client’s biggest competitor, XYZ Corp, is headquartered two blocks north of you. Let me tell you, my client is knocking the pants off of XYZ!”

These extremely superficial connections would actually be the catalyst to get some individuals interested in investing in a deal!

4.) Subjective Exagerations

The most dumbfounding tactic that Fred employed was subjective exaggeration. As noted in the conversation in point #3, Fred said “my client is knocking the pants off of XYZ!” There was no substantiation of this claim, just something simple enough to get the investor interested in the deal. Furthermore, most of these claims were completely unverifable.

At times, he would get more bold and proclaim “this company is extremely profitable, in my opinion.” In his oppinion??? That could mean they made $100 million last year or it could mean that they only lost $100 million.

Regardless of how absolutely rediculous his claims sounded, he wouldn’t get much pushback from investors.

5.) Get the client engaged

While the first four points wouldn’t get a client to invest in a deal, they were enough to get a client to give it a hard look. Getting an investor, client, or customer to give your product or service real consideration is the only way to close a sale. Fred would stop at nothing until the investor had the deal on his desk and had actually reviewed it.

6.) Get everyone else engaged

Fred never sent an email to just one person. He would cc everyone who had even the smallest interest in a deal. While this is extremely annoying to those who have little or no interest in a deal it does have a positive effect when trying to close a sale.

Let’s pretend Fred has a client named Joe. You know Joe and he occasionally hires you as a consultant for his company. Fred knows that you consult Joe and has copied you on emails that he sent to Joe. Next time you speak with Joe, without even thinking about it, you will discuss the subject of Fred’s emails with Joe.

If you multiply this effect two, three, or even ten times, this subtle urging by associates of Joe will have a major impact on Joe’s decision making. Because of the expectations of his associates it may even become a matter of pride for Joe to close the deal or make the purchase.

7.) Stay in front of clients 24/7

Fred would spend every minute of every day in the office calling clients. The calls would often consist of little more than small talk and the question “are you working on any deals?” This is how Fred would get clients to give him a deal. He would be the first financier to call a client and they would tell him about the deal.

In most sales, timing is everything. You can greatly increase your odds of having good timing if you are constantly in front of your clients, whether online, in person, or over the phone.

8.) Get what you can and BS the rest

As the proud holder of a Master of Science in Finance I want cold, hard, quantitative facts to constuct a model. The problem was that when I worked for Fred, he would often not have all of the facts needed to construct a model. This was sometimes because the client didn’t provide him with all of the information (clients were often annoyed by his constant calls) other times the deal was too new to the client and the client didn’t have all of the information. There were times when he was told explicitly to not work on a deal, so we would have extremely limited resources.

Fred would give me a partial budget, incomplete historical financials, or a broker prepared pro forma (these are worse than useless) and command me to prepare a pitchbook based upon these incomplete facts. My MS in Finance screamed out that this could not be done. However, Fred instructed me to use what I knew and “fill in the rest.” We’d use best-case industry standards to complete pro formas (and sometimes historical statements which is a big no-no). While I would refuse to put my name on these statements and models, Fred would.

Creating these models allowed Fred to begin contacting investors long before a deal even existed! This ensured that he would have first crack at the deal if it did materialize.

I don’t reccomend overstepping your bounds and constructing information from thin air. However, if you are resourceful you can make a little bit of information go a long way to give you a head start on a sale.

9.) Make the sale as easy as possible

By staying in front of your clients and working on the sale with whatever information you can get your hands on, you make the sale very easy for the client to complete. Why would a client go to another company if you’ve already got a huge head start? People like instant gratification, and if you get to work on a deal before the competition, you’ll be able to provide more immediate gratification to your clients than anyone else.

10.) Treat everyone as a customer

Fred would treat his most of his clients like kings, but he would berate and harass investors. This alienated many investors and caused some to refuse to even take his calls. From my observations, Fred could have gotten many more deals done if he recognized that he was really in the middle of a supply chain. When you’ve got suppliers and customers, you should treat both with the same level of respect.

In hindsight, the experience of working for Fred was invaluable, but I hated every minute of it. There’s no way to truly portray his personality through words, but being forced to work with him on a daily basis was nothing short of traumatizing. Other than what I’ve outlined above, there is an added benefit when you work for someone who is universally considered to have an impossible personality. The fact that I survived working for Fred served as a sort of badge of courage to people in the industry. I had people who would seek me out at networking events to congratulate me for sticking it out and not quitting. Managers at several other companies invited me out to lunch simply so they could meet me, because they knew that it took a huge amount of skill and patience to work with Fred, and I stayed on longer than most.

I wouldn’t wish the trauma of working for a person such as Fred upon anyone, but if you find yourself in such a situation look for positive aspects of the experience and learn as much as possible.

Tagged as: boss, business, Marketing, sales