The key to longevity in sales

Published: Wed, 07/30/25

Updated: Mon, 08/04/25

July 30, 2025

TOGETHER WITH

Welcome back to another issue of The Quota. This is our last newsletter in July, so you know what that means (we actually don’t know, but you do). In this week’s issue, we interview an equipment leasing broker/owner who’s been in the business for 40 years. Then, we’ll share a Sales Fail about asking for a call back, and give some advice to a rep whose customer just retired and left the business to his son. Let’s do this.

NUMBER OF THE WEEK

50 & 84

50% of salespeople say they avoid being pushy, but 84% of buyers have had negative experiences due to pushy salespeople.

Source: HubSpot

SALES ROUNDUP

Here’s what’s happening in the sales world this week:

A saleswoman won a maternity discrimination case after her new female boss 'laughed' at her when she said she wanted her job back. Sarah Lindup had an agreement that she would return to her lucrative job after she came back to work following the birth of her daughter, a UK tribunal heard. But while on maternity leave, Ms.Lindup had her role taken away. New sales director Jayde Stott called Ms.Lindup and informed her she would not be returning to the sales team. Ms.Lindup said that Ms Stott 'laughed' at the idea of her returning to the same post as if it was a 'ludicrous idea'. You can read more about it here.
The US housing market just logged its slowest spring season in more than a dozen years, according to a recent article in Bloomberg. By April, mortgage rates dipped, price growth flattened, and the years-long inventory drought looked like it had finally broken. But fewer sales contracts were signed in the US from April through June than in any year since 2012, according to data from Redfin. That was back when the housing market was still finding its footing after the collapse that fueled the financial crisis. You can read more about it here.

FEATURE

Amanda Rollins in Switzerland

An interview with Deb Sands, an equipment leasing broker/owner with over 40 years in sales

Deb Sands reached out to us about one of the memes in The Quota newsletter. After a few emails back and forth, we knew we had to share her story. With over 40 years in sales, and the last 30 as a business owner, Deb offers a unique perspective on how the industry has changed over the decades and what it takes to stay consistent through it all.

1. You’ve been selling your entire career, for over 40 years. How did you get your start in sales?

I grew up in Calgary, Canada and studied broadcasting at college. I really wanted to be Barbara Walters or Oprah Winfrey but didn’t have the nerve to leave my hometown. A job came along in writing radio commercials, so I grabbed it. I wrote radio copy for 5 years before going into radio sales (after seeing how much money I could make). In the spring of 1988, I couldn’t stand radio sales any longer so I quit. I took the summer off and a headhunter found me in the fall. She got me into equipment leasing at Pitney Bowes, I was there for 4 years before I decided to make the jump and hang my own shingle, becoming an equipment leasing broker.

2. What was the sales culture like in the ‘80s or ‘90s? How was it different from sales today? Can you paint a picture of what a typical day in sales looked like for you? Was it more difficult being a woman in sales back then?

Our tools for reaching clients were either making phone calls on an analog phone or just showing up in person. My office at the radio station was part of a cubicle system with 8 other reps in an open area. It was so noisy and disruptive that I arranged with a friend to use her phone in her apartment. I would go there in the afternoons to make cold calls.

A typical day in sales in the 80s at the radio station was making appointments over the phone, and then going to those appointments the same day. If the meeting went well, I would do a proposal based on a needs analysis. In contrast, a day in equipment leasing would be spent personally visiting equipment suppliers.

I’ve had to deal with the “women in sales” issue. In my sales career, I have been solicited, groped, kissed, and leered at. All of which could land someone in jail today. Back then, it was: “Suck it up sister, this is life in sales.” In cases when the above happened, I left and never called on those accounts again. No explanation, no confrontation. No reporting. I just never went back. There was no amount of commission that would make that harassment tolerable.

3. You’ve run your own equipment leasing business now for 30 years. What made you take the leap to start your own business and what has been the key to longevity?

Radio sales were tough but necessary. I learned so much by trial and error. However, selling leasing equipment is more fun and much easier. I was with Pitney Bowes Leasing just shy of 4 years. When they closed, I had a good base of equipment sellers and a growing list of customers. It made sense to hang out my shingle and keep going.

The key to longevity for me has been SERVICE. Getting the job done quickly, efficiently and with the least amount of hassle has been the key to my success and longevity. I always visit suppliers and customers in person when I can. I look them in the eye, shake their hand, and deliver on my promises.

4. What advice would you give to someone who is just a few years into working in sales but plans to make it their career?

Grow a thick skin. There will be days when your mother’s advice to become a piano player in a brothel will seem to have been the better choice.
Keep a document of your wins and positive comments from happy clients. Read them over on bad days. I keep all my Google reviews in a scrapbook.
People really do buy from people they “know, like and trust.” Make eye contact, smile, be personable, and authentic. It goes a long way.
Always be nice to the receptionist or assistant. They can make or break your meeting with the decision maker.
Let the bad day go as soon as you can. Give yourself time to mourn the loss. But get back on the horse as soon as possible. Read over your wins. There’s always another deal to be found.
Believe in your product WITHOUT A DOUBT. You can’t sell what you don’t believe in.

6. After 40 years in sales, what do you still love about it that makes you keep going every day?

It’s so gratifying when you truly help someone solve a problem. You feel like a hero. Sometimes, this feels better than the money.

7. What is your favorite sales movie?

Erin Brokovich. It’s not always about the money.

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MEME OF THE WEEK

Source: Instagram -- Sales Humor

QUIZ

What was the second prize offered by Alec Baldwin’s character in Glengarry Glen Ross?

A. A set of Michelin tires
B. A set of steak knives
C. A set of wine glasses
D. A set of golf clubs

SALES FAILS

Each week, we bring you the most cringe-worthy sales moments from across the web. To submit your sales fail story for consideration, click here. (Don't worry, you'll remain completely anonymous).

I managed to sign a deal on several buildings with the Head of Asset Management for one of Europe's biggest owners on the private investment side. He put me in touch with his colleague, “John Doe,” Head of Asset Management on the institutional investment side. We had a smooth on-site initial meeting with his team. Then, John suddenly cancelled our next meeting.

I wrote an email to propose a time to reschedule the meeting, and one guy from his team told me that John was on holiday and invited me to call him another day. I sent him a text message asking if he'd like to call me back. He called me back.... and said he was attending his mother's funeral :/

Obviously, he wasn't happy. Fortunately, the internal champions took over and I was able to make his teams an offer for 2 buildings.

Anonymous France

GRAPH OF THE WEEK

Source: LinkedIn Poll -- July 2025

WORTH A PEEK

How do you deal with a sales manager who’s simply incompetent? We’ve all been there, right? This was a question posted to Reddit, with a handful of interesting responses. Check out the conversation here.

ASK THE QUOTA

Want to submit a question and be featured in our advice column? Click here. (Don't worry, you'll remain completely anonymous).

Dear Quota Team,

I've been selling commercial cleaning supplies to a family-owned restaurant chain for over 10 years, building a strong relationship with the original owner who always trusted my recommendations and paid invoices promptly. Last month, he retired and handed the business over to his 35-year-old son, who seems determined to prove he's not his father. The son questions every invoice, demands detailed justifications for products his dad bought without hesitation, and has started getting quotes from competitors for the first time in a decade. He's told me directly that he thinks his father was "too trusting" and that he plans to "run things more professionally." I understand wanting to make his own mark, but he's treating our established partnership like it means nothing and acting like I've been overcharging them for years. How do I rebuild trust with someone who seems to view our long history as a liability rather than an asset?

Starting Over in Location withheld

Dear Starting Over,

This is a classic generational transition challenge where the son feels pressure to differentiate himself from his father's approach, and unfortunately, you represent the "old way" of doing business. Rather than defending your past relationship, embrace his desire for professionalism by providing the detailed documentation and competitive analysis he's requesting. This actually gives you an opportunity to demonstrate your value more thoroughly than you ever did with his father. Schedule a formal business review meeting where you present your service history, cost savings delivered, and industry expertise, treating him like a new prospect rather than assuming inherited loyalty. Most importantly, ask him directly about his goals for the business and how your partnership can support his vision. Show respect for his leadership while positioning yourself as a valuable resource for his success rather than a relic from his father's era. Good luck!

Quiz Answer: B. The second prize offered by Alec Baldwin’s character in Glengarry Glen Ross was a set of steak knives.

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Today's email was written by Ken Kupchik, Erica Furgiuele, Steve Rado, and Emily Hill.

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