This deal dwarfed anything we’d ever done before. Our software performed well supporting a dozen users but we’d never landed a client who would have over 500 simultaneous users on the system. The application was designed to handle large volumes of users but to this point, none of our clients ever proved the design. We desperately needed the revenue but more importantly, validating that our software could move upmarket to support much larger companies was the real goal. The contract terms limited payment for the software until the implementation was completed and signed off by the client.

Why Are We Going to Get Our Ass Kicked?

“Why are we going to speak with the CFO?” I asked my boss. 

“To get the contract signed,” he said like it was so obvious. 

My boss must be delusional. He just called me that morning to get a meeting with the CFO and fetch him from the airport. This guy we were meeting was the sponsor for the project. Most project sponsors are actually excited about the change they’ve decided on but not this fellow.  It was clear to me, he was an angry and unhappy man. 

This guy wasn’t the glass half empty type. His glass never had anything in it, not even dust. Several of my teammates and I spent the past nine months working at this large oil and gas client implementing the application. The implementation was a nightmare — If something could go wrong, it did. Our efforts to help this organization only seemed to turn into fuel for the CFO’s vulgar and insulting comments toward my team and I. 

It’s About to Get Ugly

You know things are gonna get ugly when the company’s management treats their staff like dirt. It was no shock to us that they treated their vendors, or “partners,”as they commonly referred to us, like the doormat where they cleaned their shoes. 

Earlier that day, I’d attended a meeting with some of the CFO’s staff where f- bombs were used as nouns, adjectives, and verbs to describe the state of the project. Now my boss wants to waltz into the CFO’s office and ask for the order?!

I told my boss it seemed like poor timing, I was not comfortable attending and preferred not to go. 

“I didn’t ask if you wanted to go, you’re going,” he spat the words at me in disgust. ”Grow a spine, why don’t you?” I think he probably referred to me as a cat, if you know what I mean.

An Odd Palatial Suite

The elevator ride took forever while I shifted from one foot to the next. I was trying to think of something to say to cut the tension but nothing came out. My boss was the calmest and most cool-headed person on the planet, clearly any tension was mine.

Stepping out of the elevator, my gaze was drawn to offices bounded by clear glass. It was like a square fishbowl where you could see everyone’s office. Every direction you looked, the sparkle of lights shimmered off the surrounding glass skyscrapers. We exited on the top floor of this massive new building and found our way to the executive row lobby area. Executive row was where all the C-level guys offices were located. 

Nervousness and Discomfort

The only person left on the entire floor was our host who looked up behind his desk to see us stroll into the lobby. His expression was the definition of disdain. My nervousness during the elevator ride didn’t dissipate while I repeatedly rose from my chair, paced the room and returned  like an expectant father. 

While marching around the lobby  I couldn’t help but catch the penetrating stare of the CFO. It must have happened a dozen times, each one was more awkward than the previous one. My boss gave me explicit instructions on the drive from the airport for this meeting. 

“Don’t say a word, I mean nothing,” he demanded. “If he asks you a question, I’ll do the talking.” 

“Fine by me,” I thought. 

I’d just spent the past nine months working at one of the bottom ten most abrasive and rude employers in Houston, if such a list existed. My boss knew I’d grown defensive. He also knew I had every dumb decision the client made documented and approved by them. I was waiting for the opportunity to point the finger back at them.

Let the Fireworks Begin

The CFO finally finished his call (well over an hour after we’d arrived). He opened the door and stormed right past us to the men’s room. 

“There better be a good reason to be meeting this late in the evening,” he yelled back as he zoomed away.

We found a seat in his office. Thirty minutes flew by while I sat listening in on the single most uncomfortable conversation ever. Per my instructions, I sat there quietly and tried not to look angry. I’ve never heard business dialog like I heard that night. The explicative filled rant was all one-sided as my boss listened intently and appeared to enjoy the venomous slang in the strangest of ways. 

I didn’t like it one bit. 

Getting a finger pointed at me multiple times, being yelled at, and hearing myself called a motherf*cker over and over was about all I could stand. I wanted to jump over the CFO’s desk and break his wagging finger. 

Every time my boss spoke, he delivered an unemotional question for the CFO. Eventually, some semblance of order took over in the meeting. Then, my boss ran out of questions. My eyes darted around from the discomfort of silence that enveloped the room. 

But my boss didn’t blink. He reached down into his bag, revealing a manila folder with the client’s name scribbled on the label. 

“Holy shit, holy shit, holy shit” was running through my brain on repeat. I figured this would be the last straw for the angry CFO, I could just see him jump to his feet and start an actual fistfight with my boss.

Ask for the Order, Always Ask for the Order

He opened the folder, picked out the contract which was conveniently turned to the signature page. The contract stared the CFO down, in the way I wish I could have. 

He looked as surprised as I did to see the contract laying right in front of him. I can’t recall exactly what was said for the next five minutes. Most of it had to do with our mothers, our heritage and the other 7 words you can’t say on TV. 

My mouth was glued shut and now my boss’ was, too. Finally, the CFO stopped his rant and shot icy daggers at my boss with his eyes. It felt like minutes passed and with each breath, a lot less oxygen was left in the room to fill our lungs. 

To my complete and utter surprise, that hot-headed, belligerent CFO grabbed a pen, scratched his signature on the contract and flipped it back across the desk. His final instructions were to get the fuck out of his office and fix the rest of the problems.

We stepped into the elevator.  I was in awe. 

”Holy shit, I can’t believe you got the order,” was all I could say to my boss. 

He looked at me like the inexperienced salesman that I was and asked why he wouldn’t have. It was clear from my expression I didn’t know the answer. Maybe it was a rhetorical question. Either way, I still didn’t know the answer.

He explained that we’d completed the acceptance terms of the contract even though the client argued otherwise. 

“Ask for the order,” he said, putting a point on the statement. “There’s never a perfect situation, just get it done.” Had the client said no, my boss went on to explain, we could have figured out what it was going to take to get us to a signature.

What’s the Worst That Can Happen?

I’ve had a lot of fun retelling this story to many of my colleagues over the years. Since then, I’ve not come even remotely close to any conversation or relationship with a client where gutter language was used in just about every interaction. 

The sales experience that evening was invaluable. Whether the ask is for the order or any other number of tough questions, not asking them is the worst thing we can do as salespeople. The worst thing the customer can say is no.