Outbound Sales: 6 Crazy Stories from the Field

(And what you can learn from them)

When you’ve spent a decade, or in my case two decades, in a sales role, you have quite the arsenal of stories and memories. There were some pretty incredible sales victories over the years. And plenty of failures dot my timeline, too. More importantly, sales has allowed me to cross paths with some fantastic people, many of whom taught me lessons in life. Since we’re preparing for the holidays and now’s the time you’re likely reflecting on your sales metrics for 2022, I thought it might make sense to share some memorable stories from the field. These are just some of the most career-impacting lessons I’ve learned in the field, cold-calling and presenting products and services. Maybe you can be inspired to reflect on some of your own sales lessons and take those lessons-learned into your sales strategy for 2023.

1. Be Kind to CompetitorsFree Image by Stefan Schweihofer from Pixabay

Lesson Learned: Don’t just call on your clients; be kind to your competitors. As much as you’d love to “beat them” in landing new business, you’re all in the same industry together. And building great relationships with them can be incredibly rewarding.

Years ago, sales meant getting in your car, driving to client locations, and trying to ask for the meeting in person. And it was best to plan your day geographically, to hit all your businesses in proximity to each other. It was also a best practice to not show up empty-handed. So, depending on where we were going or which top prospects we planned to visit, we’d go all-out and bring delightfully decorated cupcakes, boxes of donuts, or even full pizzas.

One day, with extra donuts in hand, a co-worker visited a competitor. It was a small business that had been in the market for years before our company arrived and had a majority of the clients signed on with her. Friendly conversations ensued with the delivery of the extra box of donuts, and it soon became a regular pitstop. No matter who went to that territory with goodies, our biggest competitor always got some.

One day, and out of the blue, one of our top client prospects called and asked to schedule a meeting with our reps. Then another hot prospect called, and another. Finally, we discovered that our biggest competitor had decided to retire. And because of all those friendly visits with donuts and candy, she called every one of her customers and told them to contact our company to take over their services.

2. Planting Relationship Seeds Early

Lesson Learned: Planting relationship seeds early and often pays off in a big way. And even when you’re not asking for the business, building rapport with your prospects will ensure you’re top of mind when they do decide they’re ready to chat.

There are always some prospects on your list that never buy. They’re never interested in meeting with you, nor do they have time to chat. But there they are, on your sales funnel, and you have to make your calls anyway. One such “never-going-to-buy-from-you” prospect was on my list as a brand-new salesperson for this television station. My job was to sell local advertising. And this client was a sizable organization with branded national television spots already in place.

So, as a newbie, I visited this business first. I went in, introduced myself as the new girl, and met the decision-maker. Nice enough guy, but as I had been forewarned, he wasn’t interested in buying anything from me. I continued to visit occasionally, just popping in and saying, “Just making sure you’re still not interested” in my jovial way. And politely, he would always laugh and say, “still not interested.”

Until, one day, he was interested. He had a new product line to sell that didn’t get a mention in any of his nationally-produced ads. And of all the major television networks in town, he chose to call me and schedule the meeting. I had built the relationship with him over time, never selling him, just making myself available. And when he was ready, those early relationship-building efforts paid off in a big way.

3. Mistakes Make You Human; Embrace Them

Lesson Learned: So, this isn’t my story, but it’s a gem. In sales, we’re trained to be polished, have all the answers, and to never make mistakes. But my co-worker Nella proved to me that mistakes are human nature. And being human is far more effective than being a salesperson.

There was a prospect all of us salespeople knew well. It was a family-owned furniture business with a notorious reputation for not only refusing television ad reps but also for being nasty to them. We’ll call her Donna, and let me tell you; she was a pitstop none of us wanted to ever make – that is, until Nella came along. A longtime veteran of television sales who had taken a career reprieve was back in the sales saddle. She was lively, hilarious, and really great in this role. And she was going to make a visit to see Donna on her first day back in the field. We all silently prayed for her.

When Nella got back to the office, she shared the story. And, yes, notorious Donna had agreed to meet with her. Whether her technique was intentional or not, it worked. Nella brought the human element to her approach in a brilliant way – she did something stupid.

Nella shared that she has a habit of taking her heels off when she’s driving. Arriving at this furniture store, she pulled into her parking spot, right in front of the giant glass doors and windows of the showroom floor, slipped her heels back on, and walked in to meet her fate. Donna was there and promptly told her to leave, grumbling at her in disbelief that anyone from our station would even bother stopping in to meet. Nella thanked her and headed back out to her car. She sat in the driver’s seat, slipped off her heels, and unexpectedly got a call. As she fielded the call, she pulled out of the parking lot, and it wasn’t until she was a few blocks away that she realized the worst had happened. She’d left her heels in the parking lot of the furniture store.

Nella said she turned around and went back. There were her stylish, slingback pumps, sitting in the parking lot, right in front of all those windows and front doors of the store. She realized she had an audience watching her, too, and Nella took that opportunity to go back into the business. “I’m sorry, but I had to share what happened,” Nella told the staff members laughing at herself, and Donna emerged from a back office. Playing off her own blunder, the group laughed and sympathized. And even Donna lightened her tone, engaged in conversation, and ended by telling Nella she could come back the next Tuesday for a meeting.

4. Every Door, Store, Floor, Cranny, and Nook

Lesson Learned: When you’re pounding pavement, and making cold calls, remember it’s always a numbers game. The more doors you walk through, the better your odds of finding a “yes” client. Don’t skip any pit stops along your way. Hit every door, floor, store, nook, and cranny. You might otherwise be missing out on a goldmine.

Don’t judge me, but at one point in my career, I sold toys and widgets out of the trunk of my car. You know the guys, the young men and women who approach you in a parking lot offering executive laser pens or remote-control cars for $10 or $20. Yes, I was one of those guys, and the sales technique involved canvassing areas, door by door, and popping in to sell our cheap wares on impulse. I was a peddler.

I did learn a lot about sales in this role, especially the value of a “no.” I knew I’d have to talk to 100 people in a day to effectively sell everything in my trunk. So, no one was off limits. I’d find them all. We’d sell in pairs, often splitting up to tackle opposite sides of the street and meeting back up to move on to the next street or industrial park. This particular day, my partner had been taking a lot of rejection, so I offered to help. I asked if he had hit every open door on his side of the street, including a pole barn-looking metal building between two businesses. He said he hadn’t gone in there because he didn’t think it was a legitimate business since it looked more like a private garage.

I made my sales buddy follow me, and together, we knocked and entered. To our surprise, there was a group of about 20 hunting men, all in their coveralls, drinking beer in this man cave of a garage. I explained what we were doing and what we had to sell, and this group welcomed us with open arms. We sold everything we had in the trunk that day, and those guys told us anytime we were in town to stop by and show them what we had for sale. My sales partner learned the value of hitting every door, every time.

5. Sell the Solution, Not Your Product

Lesson Learned: Don’t focus on selling your product or service. Instead, be focused on selling the solution. Clients won’t be sold but they will consider more efficient, lucrative, or cost-effective solutions.

Before I broke into television, I worked for a startup phone company. I had a sales support role, often accompanying salespeople on their sales calls to help sell the support side of changing company phone service providers. And we had new technology to offer, too, including internet, which was relatively new back then. And one day, I tagged along on a sales call to the CBS affiliate television station, with plans to sell them on switching their phone and internet service.

This business had 30+ phone lines, and during the sales conversation, the general manager and my rep were going back and forth about price points per phone line, upgrade fees, and logistics. I then jumped in and switched gears. Instead of changing your 30+ phone lines over to our service as-is, what about having us install a T1 trunk line (a more innovative solution for phone service engineering at the time) to digitize your service, provide you with the ability to have up to 40 phone lines, for less than maintaining your current 30-line setup?

The silence turned to a resounding “yes!” I had stepped out of the sales pitch and offered a more innovative solution. We not only got the business from this television station, but that general manager called me privately later and offered me my first job in television because he had been impressed with my strategy.

6. The Power of a Thank You

Lesson Learned: In today’s age of digital correspondence, you can stand apart from other sales reps by sending the hand-written thank you card. Here’s one instance that the snail-mailed thank you card helped me land a $3 million contract.

I had a National Sales Supervisory role with a staffing agency. I would try to participate in RFP bids for giant, multi-location manufacturing and distribution companies that would routinely use temporary staff throughout their busy seasons and year-round. One massive prospect agreed to have a phone call with me to discuss our services before allowing us to participate in their company bidding process. Company HQ was three states away, so I would have to make an impression on the phone, which would be difficult to do. The call went well, and he said he would circle back and let me know about his final decision within a few weeks.

I decided to hand-write a thank you card, sharing my appreciation for his time to talk with me about being a new staffing provider. I included my card, on which I had also written “thank you,” and a few company-branded swag items. About two weeks later, I received the email that read, “thank you for your card and for sharing your company offerings.” That email included a contract for services that included my company as the staffing provider for the next three years. Billable revenue for the duration of that contract translated to $3 million. My little thank you card had made a big impression where others had relied on digital correspondence.

With the year wrapping up, now is the perfect time for reflection. As a company leader, you can look back, too, on all of your sales experience in the field to identify great lessons learned. Hopefully, you enjoyed these few of mine from memory lane, and you get inspired to share your experiences with your teams.

Today’s sales and marketing efforts are vastly different from years ago. But always be looking for those lessons learned because even yesterday’s lessons can still be applicable strategies today. And don’t forget; when you need content, including sales collateral, newsletters, and web messaging, let Ghost Blog Writers help!

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