Things I Wish Someone Had Told Me When First Starting Out in Sales

Andrew Carlton
7 min readJun 10, 2021
Photo by Joshua Earle on Unsplash
Photo by Joshua Earle on Unsplash

I wasn’t ready to dive into the real world. Especially sales. I majored in marketing. But there I was. My first job out of college. A sales position with one of the top insurance and investment companies in the world, Northwestern Mutual. I knew very little about the insurance business. My father kept telling me that it would be a valuable learning experience. I realized after many years that he was right.

My first day was packed with training. In fact, the first two weeks was all training. I learned the products, the people and the system. It was elaborate. The company had developed their own sales process, the most important aspect of their training. But they did not stop there. They paired each new hire with a mentor. Someone who had been selling for at least 20 years. I learned a ton by watching my mentor on sales calls. Again, a great experience. But there was a lot I didn’t know. Of course, I did not know what I did not know back then.

Here are some of the things I wish I had known early on:

1/. Sales Is A Long Game

Even back then, I was all about getting results today and if I didn’t, I would get discouraged. The role models I grew up observing sold the idea of using hard sales tactics to get what they wanted. It was all about the quick sale. Getting results now by manipulating customers. Were they successful? Sure, they were making money. But they dragged their customers across the finish line only to have those same customers regret it later. A better way for me was to change my perspective and learn patience. One of the most underrated skills. It’s a mind shift for most, but it can be learned. Once you master it, your focus will shift to helping your customer get what they want. When you do, you get what you want.

2/. It’s Not About The Money, No Really

Salespeople, especially younger salespeople, are motivated by money. I was. But I learned that a focus on money is not a sustainable long term motivator or even an indicator of making a lot of money. (In fact, higher motivators are opportunity and independence). Going back to my first job at the insurance company, the promise was all about making 6 and 7 figures. Simply build an ongoing book of business that paid out handsome residuals. Well, for many, that reality never happened. Here’s the lesson that I finally learned about making money in sales. Yes, it is true that sales is one of the highest paying professions on the planet. But if you make “bank” the sole focus of your occupational existence, you become a slave to it. You make poor decisions and you don’t always do what’s best for the company or the customer.

“A wise person should have money in their head, but not in their heart.” -Jonathan Swift

I learned that the focus can and should be helping the customer make the best buying decision possible while helping them actualize their goals and desires. AND by doing so, you build a great reputation as a salesperson. It pays huge dividends.

3/. Sales Can Kill You

The hard work, long hours and the daily grind of sales took a toll on me later in my career. Instead of finding other things in my life to care about like connecting with friends, hanging out with family or going on vacations, I decided instead, that the job was all about putting in the long hours and by doing so, became consumed by the work. I was all about it. There was even a time in my career when I came into the office on weekends to meet up with the CEO about scaling the company. We became an INC 5000 4x company. But the price I paid personally was incredibly high. I continued to work like a dog for many years and it led to a heart attack. Poor diet, poor sleep, and poor stress management, contributed greatly to my health scare. This is the hardest lesson I had to learn. In no uncertain terms, this event changed my life. Salespeople have to make a decision. Do you sacrifice other things in your life to get what you want (or say you want)? You may discover there is a more balanced approach to working in sales.

4/. There Is No Magic Pill For Lack Luster Sales

With the proliferation of technology, we have become enamored with the latest sales tools. Tools that promise to find leads, generate leads, and even sell for us. Don’t get me wrong. There are some great tools out there. I personally use BombBomb and LinkedIn Sales Navigator. New tools and innovations pull us in and promise to deliver grandiose outcomes. But the adoption of such tools has led to shallow connections with customers. We use the efficiency and novelty of the latest tools as an excuse to not truly personalize our communications. Bottom line, the salesperson is the differentiator. One who provides insights, not just information. Builds relationships not sells transactions. Shows humanity and avoids robotic and scripted acts.

5/. You Are Accountable For Everything — Freedom!

Well, not everything. The weather, macro economic events, apocalyptic zombie invasions are out of your control. But how you react to larger events that are seemingly out of your control will contribute greatly to your success. Do you use a bad economy as an excuse or do you find more creative ways to communicate your value? It’s easy to make excuses.

“The man who complains about the way the ball bounces is likely to be the one who dropped it.”Lou Holtz

As salespeople, we need to catch ourselves when we start using reasons for why we are not successful. Who does this help anyway? Not you. Not the customer. Not the company. An important lesson that I learned in selling is that you own how you react to the events around you. We can’t shift into auto-pilot and let our emotions run free. You can choose to react negatively or you can choose to let it bounce right off you and get back to work. In some cases, you can even use it to your advantage. Bad bosses, rude customers, socio-political events and self serving co-workers aren’t going to stop you. Achieve freedom by holding yourself to the standard of full accountability. You create the standards. You own your successes and failures. Don’t leave it to others to dictate what that looks like for you.

6/. Time Can Be Your Friend Or Worst Enemy

There is the same amount of time for everyone. How we value it and use it matters. In sales, we only have so much time to make an impact.

“Days are expensive. When you spend a day you have one less day to spend. So make sure you spend it wisely.” — Jim Rohn

Sales is about today. It’s about what you can do now to make an impact in your customer’s life. Do you value your time? I know there were moments when my use of time was less than stellar. Chatting it up with co-workers, procrastination born out of fear & perfectionism and getting that fancy overpriced coffee at Starbucks before work. Once we start to value time, we become more careful about how we use it. We protect it. There are no do overs (unless you’re Dr. Strange — Marvel). I learned that to be a high performer, mastering time was at the top of the list.

7/. Don’t Be Afraid To Play Big

Early in my career, I was ambitious and naive. Which worked great for me. I was selling insurance products to individuals at first. But then I realized I was playing in the minor leagues.

“Your playing small does not serve the world.” Marianne Williamson

Although satisfying and enjoyable, I was limiting myself to small individual products. I decided to target doctors/surgeons. Back then, there was no good way of reaching them? I literally had to hang out in corridors and hallways waiting for them to come out of surgery. Maybe not the smartest approach but with my enthusiasm, I was able to sell some very large policies. I didn’t stop there. How could I sell many doctors at one time? So, I started working with administrators in hospitals looking to insure doctor groups. This led to a very large group policy sale. The point is I decided to stop playing small ball. Don’t limit yourself. You are worthy and capable of your ambitions to do and achieve bigger things in sales.

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Andy Carlton helps salespeople and sales teams become top performers. He has the accolades to prove it: over $55M in contracts, part of one of the fastest growing companies in the country as cited by INC Magazine, for 4 consecutive years, launched a marketing SaaS platform that was awarded Cisco Innovation Award, and sold to some of the most prominent CEO’s for the first ecommerce marketplace in commercial internet history. Andy’s mission is clear: to remove the mistakes of the overworked and stressed-out sales culture and replace it with one based on intention, wellness and healthy motivation. This has led to top performers who love what they do and get the highest results without brutal sales training tactics nor 12-hour daily grinds.

Stay tuned for my latest sales workshops this summer. Follow me on LinkedIn.

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Andrew Carlton

I transform salespeople and sales teams into top performers producing higher levels of impact, fulfillment, happiness and results.