Building a better salesperson

My first tech job was with a regional VAR (value added reseller). I started in phone support, then moved up to bench tech, then to field engineer – a path that increased my exposure to customers and the rest of the business with each move.

I liked the technical work and helping people with their problems, but as I began to notice the sales engine that was at work around me, I started to dread coming to work.

Over time my reaction to the projects the owner and salespeople would bring to me went from “Yes, I’m on it!”, to “Huh, this is kinda weird.”, to “WTF is wrong with you people!?”

I found myself having conversations like:

Me: “Yes, we could upgrade every part in the customer’s PC, but wouldn’t it be better and cheaper for them to just buy a new computer?”

Salesperson: “Just put in the upgrades. It’s a big sale.”


Owner: “Go to their office, install this drive, and setup backups for them.”

Me: “Umm, we’re selling this? It’s 3 years old and the box is covered in dust.”

Owner: “It’s what we have in stock.”

Me: “But these things are worth like a 100th of the price on this invoice.”

Owner: “They don’t know that.”


Salesperson: “Can you look over this bid for these school lab computers?”

Me: “Why are you putting $1000 video conferencing codec cards in them?”

Salesperson: “Because we already have them and the grant allows it.”

By the end, I wanted to burn the building down with everyone locked inside. At the time I thought my experience was unique, that my employer was just particularly evil.

That was, of course, stupid. I was new to the workforce and naïve. Working for that VAR gave me the first insight into a cancer that is easily spread into any sales org.

Cracks in the system

Sales is an important job and I have met some amazing salespeople who are both good at their job and good at being decent humans. But sales is usually a pay for performance role which has inherent flaws, at least in the way it’s structured for most companies.

Quota-driven motivation tends to isolate the salespeople on a team and can lead to acts of desperation. Even some team-based quota models drive a culture of “every man for himself” that can never end well.

Traditional quotas recreate the cutthroat conditions of a medieval bazaar and living day-to-day in a system of “I must sell five more goats or my family will starve.” has an effect on the morality and judgement of an individual. How can it not?

I feel sympathy for people stuck in this situation. They have mortgages, kids to feed, whatever else and they feel like they don’t have the convenience of always fighting to do the right thing. It’s a crummy place to be – to have a moral compass and not be allowed to follow it.

In general, I find performance-based compensation off-putting.”You sell more, you make more.” makes sense and works pretty well on a small-scale, but crank it up to multi-million-dollar-mania levels and you’ve self-selected for a certain psychology.

The worst of humanity reveals itself when you put a bunch of people in a room who tie their level of effort to how much money they make. Extrinsic motivation is the stuff of pyramid scheme tycoons, politicians, and serial killers.

The status quo is ugly

On the customer side, I have multiple conversations a week that go a little like this:

Me: “In detail, here is the problem I am trying to solve. Could your widget help fix that problem?”

Salesperson: “Yes!”

Me: “So your product can cure cancer, solve world hunger, and keep our network free of viruses?”

Salesperson: “Yes!”

Me: “Do you understand anything that I’ve said?”

Salesperson: “No.”

Me: “And you still think your widget is the right solution for me?”

Salesperson: “Yes! It’s what I’m getting the highest comp on this quarter.”

I can’t express how frustrating this is and how much this sucks, especially when the person has swaggered in presenting themselves as a trusted advisor.

Customers need honest answers and guidance. They need help, even if it’s in the form of “Hey, I don’t think our product is a good fit for this problem.”

If you’re a salesperson who wants to build trust and a long-term pipeline that practically vomits money, be willing to walk away from a sale that doesn’t make sense. Spouting half-truths and outright lies may work in the short-term, but it’s a clichéd path that leads to gold chains, cocaine addictions, damaged relationships, and early heart attacks.

Personally, I respect the heck out of salespeople who tell me “no” and “I don’t know.” I will go out of my way to seek them out for future projects even if what they’re selling costs double the competition. I’ll come back to them when they change jobs and do my best to always take their calls.

A better path (maybe)

Being honest in sales requires a company culture that allows the person to be honest. The dude-bro, hyper-competitive environment that many companies create for their salespeople is not that. Quotas don’t support that, neither does performance pay. All those things box salespeople in and make them feel as if they have to lie, cheat, and steal to keep their job.

How about this:

  • Pay salespeople a good, fixed salary based on their skill and experience.
  • Get rid of sales quotas and replace them with other metrics like customer satisfaction and product usage. These are imperfect measures as well, but have a longer-term focus.
  • Manage salespeople like everyone else. If there’s a performance problem, coach and support them. If that doesn’t work, help them move on to something else.
  • Hire people who are motivated to do a good job because it’s the right thing to do, not because they want/need to chase carrots.

What about the salespeople who need the carrot? The ones who love the game, and are going to shuck and jive even when they don’t have to.

Honestly, eff those people. That’s not a personality trait that helps move humanity forward or builds a solid foundation for a business. If they can’t adapt to a healthier culture, they can go pound sand.