Everybody should try a job in sales

Working in sales, even for just a year or two, may be the single most important investment you make in your career and in your life.

First, let’s talk about what sales is. When you hear that somebody works in sales, what do you think? Do you think of a slimy used car salesman, making promises and saying things like, “What’s it going to take to get you into this car by the end of the day”? Maybe you think about Willy Loman from “Death of a Salesman” – a man who believes that a person’s worth is tied to their financial success. Or, maybe you think about the scheming, unethical, backstabbing characters in Glen Gary Glenross, willing to do anything to get new leads and the chance for some new sales.

I once thought the same way. In my first job out of college I worked closely with a salesperson. We were a team – we’d visit customers, he’d handle the business questions (pricing, availability, bundling, etc.) and I’d handle the technical questions from the engineers (I did the REAL work, or so I thought). After I’d been in that role for a year or so we were having lunch and he told me that I should get into sales some day. I practically did a spit take. Me?? In sales? HELL NO. I told him there was no way I’d ever, ever give sales a try. He laughed and said he’d check back with me in a few years.

After 8 years in various technical positions my thinking had completely changed. I dove headfirst into sales 10 years ago and have never looked back.

What’s so great about spending some time in sales?

It improves your social skills

I was a shy kid. When I was with my friends I was talkative, outgoing, and confident, but I was very different around people I didn’t know. If I was in a one-on-one situation with stranger I could do ok, but if you put me in a room full of people I’d never met before I panicked. I didn’t like parties, I didn’t like meeting new people, and I just wanted to be with the people I already knew.

This persisted through high school, college, and into my early career. My shyness wasn’t actually much of a hinderance in my technical job, as I was mostly working with other engineers, who didn’t expect (or want) any small talk. But I couldn’t help feeling jealous of the salesman’s ease in talking to anybody and everybody. I wanted to be more like that. I thought about it and I realized that I hadn’t really developed my interpersonal skills because I didn’t NEED to. If I wanted to get better at talking to people and being at ease in a group then I needed to put myself into a position where I was forced to do those things over and over.

I made the switch to sales in part because I wanted to be forced to talk to new people in hopes of overcoming my shyness.  It worked! Every day I was forced to talk to people I didn’t know. I had to find ways to connect to people. I had to talk to happy customers, angry customers, people who were looking for a scapegoat, and everything in between. Each of these interactions made the next one a bit easier. Over time I became much more comfortable with new people.

This is a great skill to have in our personal lives as well. Every day we interact with people we don’t know. Some of these interactions are low risk interactions. We chat with somebody in line at the bank, or the person sitting next to you on the plane. The stakes are low. If you don’t hit it off, or the conversation peters out, no problem. You’ll never see that person again anyway. But sometimes the stakes are high. You see a woman at the bar you’d like to approach and ask out. You bump into an executive at a company party. You’re at a party and you don’t know anybody. These are times when being able to talk with anybody will help you.

Having lots of different interactions with lots of different people WILL improve your social skills, which will make you better in just about any situation.

Your compensation is tied to your results

Is there anybody out there who believes they are paid more than what they think they are worth? Everybody wants to make more money, and just about everybody thinks they should be paid more money. We make up all sorts of reasons for why we aren’t paid more – my boss doesn’t like me, the company doesn’t understand the contribution I’m making, my coworkers took credit for my idea, blah blah blah.

A job in sales cuts through all that bullshit. You get paid based on what you sell. You want to make more money? Sell more. You think you deserve a raise? Sell more.

When you’re in sales you’re measurable down to the dollar. You’re measurable every week, month, quarter, and year. Your performance can be compared to your colleagues’ performances. Yes, sometimes you do everything right and don’t get the deal, and sometimes you do nothing and a deal just falls into your lap, but those tend to average each other out. Ultimately you have a number attached to your name that quantifies the contribution you’re making to the company.

You want to sell more stuff? Work harder. You don’t want to put in longer hours? Then find ways to work smarter in the time you DO work. You want to sell a lot more stuff? Then find a way to work smarter and harder.

Sales is a strict meritocracy. If you sell a lot then you’ll make a lot. Your compensation is effectively unlimited. Sell twice as much stuff and you’ll make twice as much money. Sell nothing and you’ll make nothing and then get fired. There’s nowhere to hide.

In terms of compensation structure, sales is a lot like investing. You get paid more, on average, for taking the extra risk of investing in stocks versus investing in bonds. In sales you get paid more than in an engineering job because you’re assuming the risk that if you’re not successful you’ll make no money. In addition, a job in sales is notoriously short-lived. You miss your number for a few months in a row and you’re gone, even if you’ve been at the company for years.

In sales you get paid what you’re worth. Once you realize that your compensation is directly linked to your performance you start working harder. You get more discerning about where you focus your efforts so you don’t waste time on deal that just aren’t going to happen. Good salespeople easily make six figures, and the best ones can make mid-six figures to the low seven figures per year.

Sales improves your negotiation skills

Sales is negotiation. You’re constantly negotiating with your customers on prices, delivery dates, and features. You’re negotiating with others in your own company on prices, delivery dates, and features. Even if you’re selling an off-the-shelf product, your customer wants to buy the product at the lowest possible price and you want to sell it at the highest possible price.

I was finally open to making the transition from engineering to sales when I realized that good sales was nothing like the used car salesman image I had in my head. Good sales isn’t about tricking a customer. It’s not about selling ice to Eskimos. Good sales does not involve cramming something down a customer’s throat or ‘taking them to the cleaners’.

Good sales involves learning what the customer needs, helping them determine the value of that thing to them, and then seeing if you can profitably deliver that thing to them at a cost below the value to them. If you sell widgets and each widget allows a customer’s employees to work 10% faster, then your widget has value to your customer. If your customers’ average employee is paid $50,000, then the widget it worth 10% of that, or $5,000. If you can produce the widget for less than $5,000 you have an opportunity to do a deal that’s profitable for you and helps the customer. That’s good sales.

At the end of a successful sales engagement one of two things should have happened:

  • You make a deal. You provide them with a product or service at a price that allows you to make a profit and they are willing to pay.  You’re both better off than you were before the deal was done. It’s a win-win.
  • You realized there was no good deal to be had. You told the customer it wasn’t a good fit and didn’t waste any more of your time or their time. If the customer has unrealistic expectations, or no budget, or just plain wants something you can’t provide, you’re both MUCH better off if you walk away from the deal as early as possible. The customer will appreciate your honesty (and likely come back to you again in the future because they know you aren’t going to try to cram something down their throat). You can spend your time on opportunities with higher chances of success. It’s a win-win.

Eventually you realize that everything, both in business and your personal life, is a negotiable. And, since a good negotiation ends with both sides being better off than before, you just need to figure out what’s important to the other person. You start by asking questions to find out what’s important then figure out a way to deliver that in a way that makes both parties happy.

Your significant other wants to go to see a movie. You have no interest in that movie and you’d rather stay at home. You know if you say you don’t want to go to the movie a conflict will ensue. How do you resolve this?

Well, first you ask what the most important thing is to her – does she want to see that particular movie?  Does she want to spend time with you? Or is she just stressed and wants to do something relaxing for a little while? Once you know the real issue you can deliver what she wants in a way that works for both of you.

She really wants to see THAT movie? Suggest she go with a friend and you will cook dinner tonight and have it ready when she gets home. You have time at home,  she sees the movie, and you’ve sweetened the pot by handling dinner.

She wants to spend time with you? Great – find something around the house you can do together. Gardening, hanging pictures, etc. You get to stay at home, she gets to spend time together.

She just wants to relax? Maybe you can watch a movie at home together. Or maybe there’s a different movie playing that you’d both like to see. Both parties are happy.

The key is to ask questions, understand what’s important to the other person, then see if you can deliver it. The more times you’re forced to negotiate the better you’ll get at it, and eventually you’ll see negotiation NOT as a conflict but as a way to leave both parties better off.

You’ll improve your budgeting skills

Most sales jobs pay a base salary and a monthly commission. Your income can vary dramatically from paycheck to paycheck based on your sales. There are a number of ways to deal with this variable income. Most salespeople just average out their income over a year and organize their life to spend roughly 1/12th of their yearly income each month. In some months you’ll spend more than you made, in some months you’ll spend less, but the goal is to have it all average out in the end.

Smart salespeople approach their spending differently. They live on their base salary and invest the commissions when they receive them. They are forced to  develop self discipline and strong budgeting skills from dealing with a highly variable income.

Value long term relationships

There’s a term in sales for a certain type of salesperson – “James Bond”. A James Bond is a salesperson who gets the job done (i.e. makes the sale) but leaves a trail of destruction behind them. They don’t care about collateral damage. A James Bond salesperson will make promises that can’t be delivered, misrepresent the product, and lie about the price. In short, they’ll do anything to complete the mission, and once the sale is made they move on to the next prospect. These salespeople tend to be very successful for short periods of time, then they’ve burned their bridges and need to move on.

For many salespeople this isn’t a problem, as they don’t expect to be at their company for very long. A career in sales is a notoriously fickle proposition and there is a LOT of churn. If you don’t hit your number for a few months you’re gone, especially if you’re relatively new to the company.

Good sales is very different. The longer you’re in an industry or at a certain company the more likely you are to run into the same customers again and again. You eventually realize that the path to success is to think long-term. You only do deals that provide value to both sides. You become willing to take less money now, knowing that you’re setting yourself up for future success.

I’ve found the same things apply to my personal life. I’d certainly RATHER eat freshly baked chocolate chip cookies (my #1 food weakness) all day and split a bottle of wine with my wife every night, but I know that if I did I’d soon be in terrible health. Sometimes it’s hard to get up and workout, but I know that when I’m still in great shape at 50 and 60 and 70 I’ll be happy that I did.

Working out, developing strong social and business networks, staying educated on what’s new in your field, and investing are all things that don’t always have a great payoff now, but the benefits build over time.

Tomorrow comes faster than you think.

Get used to rejection

This might be the single most valuable lesson I’ve learned from sales. When you’re in sales you’re told “no” all the time. At first it was painful – I internalized everything. Was the customer not buying because I did something wrong? Could I have done something differently? Was I just not cut out for sales? How did all these other salespeople handle the constant rejection?

I eventually realized that rejection is never personal, even when it’s personal. Companies, and people, make decisions that they believe are right for them based on the information they have. This often has very little to do with you and what you did or didn’t do. Maybe your product just wasn’t a good fit. Maybe the project got cancelled and that’s why the company isn’t returning your calls. Maybe the girl who isn’t interested in a second date likes men with beards and you’re clean shaven. These things don’t necessarily have anything to do with you and a rejection isn’t personal.

And frankly, sometimes you just screwed something up. You said the wrong thing, or did the wrong thing, or offended somebody, and THAT is why you’re getting rejected.

When you get told “no” enough times you realize that it’s not that big a deal. When a company, or person, rejects you the world doesn’t stop spinning. The best thing you can do is accept the rejection, understand why it happened, and try to learn from it. I’ve found that most people are pretty open to giving you feedback if you approach it the right way.

If you say something like, “What did I do wrong?” or “why aren’t you buying our product” the other person will likely assume that you’re trying to change their mind, so they’ll give you answers like, “it wasn’t a good fit” or “it was nothing specific” or “it’s us, not you” so you don’t have anything specific to argue against. They won’t be completely honest with you.

If you say something like, “I’m disappointed with your decision, but I respect it and I appreciate you letting me know. Could you do me a favor? I’d love some feedback on what factored into your decision so I can I get better in the future” you’ll find that people are more open to sharing. By acknowledging the decision you alleviate their fears that you’re trying to change their mind. By framing it as a favor they are more likely to want to help you, especially if they’ve just rejected you in some way. Then listen to what they have to say, don’t argue with them, and genuinely thank them at the end. Then, most importantly, try to use the feedback to get better in the future.


If you’d told me 15 years ago that my future self would have a very happy and successful career in sales I would have laughed in your face. However, I can honestly say that spending time in sales has been of the formative experiences in my life. It’s improved my social and negotiation skills, it’s helped me think long-term in both life and work, it’s helped me accept and learn from rejection, and it’s dramatically improved my financial position.

I believe the skills learned from even a brief stint in sales will dramatically improve anybody’s life.

How about you? Have you spent time in a sales position? If yes, what did you learn from it? If not, why not?



8 thoughts on “Everybody should try a job in sales

    1. Yes, there’s definitely a LOT of that! One thing I’ve learned is that the better qualified the opportunity, the higher the chance of success. I now devote a huge percentage of my selling time trying to disqualify a prospect. This has resulted in much higher success rates and more sales.

  1. Excellent article. I am 30 yrs old. I really liked the transition of yours from engineering to sales. I always gets compliments from my friends when I introduce a product that I use daily or explain the value that the product brings into their lives. They say I should give a shot at sales because I am really good at it naturally.

    I am on the same boat as you were. I am still hesitant to kind of switch from a nice cushy s/w job which pays me good 125-150k figure salary. Money is important for me but I really like selling people value of a product/service which I will definitely enjoy more than writing s/w.

    Loved the line “Look at Negotiation NOT as a conflict but as a way to leave both parties better off, “Tomorrow comes faster than you think.”

    1. Thanks for the kind words. I really do think that spending some time in a sales job can help just about anybody. Not only will it sharpen your interpersonal skills, but it will sharpen the link between work and compensation.

      It sounds like you might be a good candidate to make the leap. The hardest part is walking away from something comfortable and cushy to try something new and risky.

  2. Great topic. I spent 6 years in engineering and then transitioned to program management, and never regretted my decision. Engineering, whether it’s SW, HW, mechanical, aeronautical, etc is important to society, but most engineers, with the rare exception who are truly technically brilliant, have a relatively short shelf life.

    People should learn as much as possible in their 20s not only their professions and different opportunities, but for many engineering professionals, it’s equally important to learn the social skills and self awareness skills that can be just as valuable long term. My personal observation has been that because many of us grew up being among the smartest in the class academic wise, usually on the shy/introverted side, socially awkward etc, we feel that technical acumen somehow will always be better than these other intangible skills you described here.

    1. That describes me perfectly! It wasn’t until later in my 20’s that I realized that happiness doesn’t come from being the smartest guy in the room, but from having the most quality social connections. A handful of great friends and lots of quality acquaintances will result in more long term happiness than all the technical mastery in the world.

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