“He's a big bad wolf in your neighborhood
Not bad meaning bad, but bad meaning good”
—Run DMC, Peter Piper

Perhaps the most common mistake that I see a technical founder make when building her sales organization is she applies strategies that worked in building the engineering team to the sales hiring process. This may sound shocking, but sales people are different than engineers and treating them like engineers does not work well at all.

It starts with the hiring process. If you attempt to hire sales people using the same assumptions that worked with engineering, then here are some of the things that will go wrong:

The Interview
A good engineering interview will include some set of difficult problems to solve. It might even require that the candidate write a short program. In addition, it will test the candidate’s knowledge of the tools she uses in great depth. A small portion of the interview may address personality traits, but smart managers will tolerate a very wide variety of personalities to find the best engineers.

A good sales interview is the opposite. You can quiz them on hard sales problems all day long, but only a horrible sales rep won’t be able to bluff her way through the most intricate quiz on how to sell a complex account. On the other hand, great sales people tend to have very specific personality traits. Specifically, great sales people must be courageous, competitive and hungry. They also need enough intelligence to get the job done. That’s the magic formula. Hire engineers with that profile and you’ll fail. Hire sales people who are really smart problem solvers, but lack courage, hunger and competitiveness, and your company will go out of business.

Dick Harrison, CEO of Parametric Technologies, home of perhaps the greatest enterprise sales force ever built, interviewed Mark Cranney, the greatest sales manager I have ever met, as follows:

Dick: "I'll bet you got into a lot of fights when you were a youth didn't you?"
Mark: "Well yes, Dick, I did get into a few."
Dick: "Well, how'd you do?"
Mark: "Well, I was about 35-1."
Dick: "Tell me about the 1."
Mark tells him the story, which Dick enjoys immensely.
Dick: “Do you think you could kick my ass?”
Mark pauses and asks himself: “Is Dick questioning my courage or my intelligence?” Then replies: “Could or would?”

Dick hires Mark on the spot.
Ask an engineer that same set of questions and at best she’d be confused and at worst she’d be horrified. By asking Mark those questions, Dick quickly found out:
• If Mark had the courage to stay in the box and not get flustered
• That Mark came from a rough environment and was plenty hungry
• That Mark was super competitive, but smart enough to calculate his answer

Hiring sales people is different.

The Background
When screening engineers from other companies, it's smart to value engineers from great companies more than those from mediocre companies. All things being equal, always interview the Google engineer over the Quest Software engineer. Why? Because, as an engineer, you have to be way better to get a job at Google than at Quest. In addition, Google’s engineering environment and techniques are state-of-the-art, so engineers who come from there will be well trained in an environment with high standards.

In contrast, anybody with a pulse can sell a massively winning product like Google Ads or VMware hypervisors, but people who consistently sold Lanier copiers against Xerox were elite. In fact, it might be a good sign that a sales rep was successful at a bad company. To succeed at selling a losing product, you must develop seriously superior sales techniques. In addition, you have to be massively competitive and incredibly hungry to survive in that environment.

The Cost of Making a Mistake
Great engineering organizations strive never to make hiring mistakes as hiring mistakes can be very costly. Not only do you lose the productivity that you might have gained from the hire, but you might well incur severe technical debt. To make matters worse, even when an engineering manager recognizes she’s made a mistake, she’s often slow to correct it, leading to more debt and delay. In addition, building an engineering organization too quickly will cause all kinds of communication issues, which makes slow hiring in engineering a really smart thing to do.

On the other hand, you often can’t afford to build out your sales force too slowly, especially if you have significant competition. Sales people, when compared to engineers, work in relative isolation, so there’s productivity loss, but relatively little long-term debt or fast growth issues. Sales managers generally don’t have issues with firing poor performers, so sales people go fast. I have a friend who was fond of saying, “We have two kinds of sales people: rich and new.”

The Conclusion
Applying engineering hiring techniques to a sales organization is like eating poison ivy to get more green vegetables. You will get the opposite of what you want.