Top Sellers Share Lessons They Learned the Hard Way — So You Don’t Have To

What’s better than learning from your failures? Learning from someone else’s. We asked 13 Salesblazers to share sales advice based on their own epic sales fails. We’re talking about the kinds of mistakes that are so big, the lessons live rent-free in these sellers’ heads. Mistakes like letting ego run amok, trading in work for sanity, and bringing doughnuts to an ambush. 

What we learned could fill a training manual. Below we share 13 dos and don’ts learned the hard way, so you can sell the easier way.

✔️ Do get to know your buyer thoroughly

Cherilynn Castleman, managing partner, CGI Executive Coaching➚

Even costly mistakes can be worth it in the end. Years ago, I was in charge of organising a medical conference for healthcare providers. I put together what I thought would be an awe-inspiring event: a sunny weekend at a summer jazz festival. I spent $100k securing gourmet food, room blocks, and entertainment. And we got … one registration. It was an epic “oops” moment. 

That’s when I realised the importance of understanding my audience before devising any grand plans. I hadn’t bothered to investigate the interests of my target audience. (Hint: Not jazz.) I spent the next few months diving into my buyer persona. The following year, I organised a conference on a golf course — a favourite haunt for my prospects. It was a smashing success. I’ve carried this lesson to my sales career: Before making moves, step into your customer’s world.

✔️ Do involve the economic buyer as soon as you can

Donald C. Kelly, founder, The Sales Evangelist

I thought everything was going great with my first big deal. I had built a great relationship with the champion and brought the whole thing right to the finish line, contract in hand. Then, the economic buyer — the person who controls the budget — blew it up. My instinct was to point my finger at them in anger. But when I reflected, I had no choice but to point that finger at myself.

I hadn’t been diligent enough in selling directly to the economic buyer. I’ve since learned to make that relationship a priority from the start. Sometimes this person is the CEO or the CFO. Other times it’s a manager with a big budget. No matter the title, this person has veto power over the deal, and they want a deep dive on value — getting a return on investment, mitigating risk, and thinking long-term. I’ll never overlook this stakeholder again.

✔️ Do put your well-being above everything else

Lindsey Boggs, global director of sales development, Quantum Metric

When my sister passed away abruptly in 2016, I had absolutely no idea how to process grief, so I turned to what I knew best: work. I wanted to avoid the feelings of grief. Instead, I burned out. I sought professional help.

Losing my sister made me realise that as much as we love sales, it’s just a job. No one’s life is at risk by selling software. The experience made me wish I’d been more present with my family when my sister passed. Today, I set boundaries at work. I shut down my computer at 5 p.m., I do digital detoxes often, and I make a point to spend time with my family. I’m not perfect, but that’s not the point. I’m on the right path.

✔️ Do follow the chain of influence, not the chain of command

Anita Nielson, sales expert and owner, LDK Advisory Services

I thought I was about to close the deal. I had a great relationship with the buyer. But there was something I didn’t know. A couple of times a day, she would go on a smoke break with someone from a different company in the same complex: an employee who worked for my competitor. Over hundreds of smoke breaks, this employee built a strong relationship with the buyer, eventually swaying her to buy from my competitor instead.

After the deal closed, the buyer said something that I can still hear in my head so many years later: “I’m sorry, but I couldn’t betray my friend. I wanted to buy from you, but I had to give her a chance.”

My sales advice is that you can’t trust an org chart to show you who really influences a buyer. Broaden your view to consider people who might be influencing your prospects outside of their organisation. Make it a point to find out who the smoke-break partner is, every time.

✔️ Do go off-script

Elyse Archer, founder and CEO, She Sells

Once, I had a sales call with someone who heard me speak at a conference and wanted to learn more. He was a hot lead, someone who should have been an easy sale. When it came time to close, my gut was telling me to deviate from our normal script and use a more direct, succinct approach. But I was afraid. I stuck to the script.

I lost the sale. Afterwards, he gave me difficult feedback: “I wish you’d just talked to me like a human.” The experience taught me that the most important thing in sales is authenticity. We have to speak to the customer like we’re speaking to a friend we care about, and tailor our message to meet them where they are.

✔️ Do join a company you believe in

Scott Leese, founder, Scott Leese Consulting

I once lasted less than eight months in a VP of sales role. Why? I did a terrible job vetting the company, founder, and product. The pay was great but the product wasn’t ready, and the team didn’t act with urgency — which is one of the things I value in a team. 

It was a painful lesson about what really matters in sales. Don’t chase titles, money, and equity. Instead, find companies that provide real value to their customers, with leaders who have the same mission and values as you.

✔️ Do connect with every decision-maker

Ian Koniak, CEO, Ian Koniak Sales Coaching

I once lost a $47 million deal. (That number is not a typo.) The CEO was on board, the terms were approved, and we were solving a major problem.

Then, at the last minute, someone on the board who happened to be friends with Bill Gates asked for a competing bid from Microsoft. Uh-oh. The deal got delayed, then killed. According to “The Challenger Customer,” the average enterprise sale must be approved by  five or six decision-makers. I’ve since learned to identify them all, and do everything in my power to connect with them.

❌ Don’t skip the discovery stage

 Larry Long, Jr., sales trainer and CEO, LLJR Enterprises

Early in my career, an inbound prospect reached out and said they were excited to talk. I was so psyched that I set up a meeting right away and gave them a sales pitch based off a generic script. I figured their enthusiasm was enough to keep the conversation going. Instead, there was only silence. After the call, I waited, followed up, and waited some more. Nothing. I got ghosted, toasted, and roasted. Every seller knows the feeling.

What did I do wrong? I didn’t dig deep enough. If you want to know my sales advice, it’s that the most important stage in the sales process is discovery: understanding what the prospect needs and why. Until you know someone’s pains, goals, and dreams, you’re flying blind.

❌ Prepare for meetings so you don’t bring doughnuts to an ambush

Alexine Mudawar, CEO, Women in Sales

I once was asked to upsell one of our company’s largest accounts. I was used to net-new deals, so a customer expansion sounded easy. I scheduled an in-person meeting in our fanciest conference room and walked in carrying two dozen doughnuts, ready for a layup deal. Instead, I found a table full of angry executives who told me my company had dropped the ball.

I kept my laptop in my bag, leaving my presentation for another day, and I brought out a notebook and pen instead. I owned the miss and went around the table to hear everyone out, taking notes as they spoke. I held onto the account, and I held onto the lesson, too: Do your research before you walk into the room — so you know whether to offer gifts or apologies.

❌ Don’t let your ego tank a deal

Marcus Chan, founder and president, Venli Consulting Group

I thought I had a $520k opportunity in the bag. I gave the demo of my life and made a clear business case. I was so confident in the close that I neglected some key decision-makers and didn’t sell competitively against the status quo.

Sure enough, I got the phone call: They decided to stay with their current vendor. I was crushed, mostly because their rejection didn’t gel with the image I had in my head of me being a sales rep at the top of my game.

Looking back, I’m glad it happened. I needed to be humbled. It was a great reminder that the only time we really lose in sales is when we lose the lessons that come from our mistakes. I applied these lessons to the next quarter and closed $1.1 million in new business, never losing sight of the ball.

❌ Don’t fall in love with your own voice

Niraj Kapur, LinkedIn trainer and author, “Everybody Works In Sales“

When I first got into sales, I gave a presentation to one of my prospects and remember thinking that I nailed it. Surely, I was going to get the deal. Instead, the prospect went elsewhere. Eager to learn, I reached out and asked them what I did wrong. They said I spent too much time talking about my achievements and too little time asking questions.

This mistake was a turning point for me. If you’ve made a similar mistake, here’s my sales advice: Talking is silver; listening is gold. As Dale Carnegie’s Sunita Gill said, with relationship selling: “We have to listen intently to understand the customer’s real needs, and build a relationship that earns us the right to keep talking.”

❌ Don’t force your working style on your team

Dini Mehta, former chief revenue officer, Lattice

When I first got promoted to manager, I made the mistake of telling my sales team exactly what to do. I gave detailed notes on what to say in emails, when responding to objections, while negotiating key terms … the list goes on. 

Instead of coaching them to improve, I was doing the selling for them. I’ve since learned that my job isn’t to teach, but to pave the way for sellers to find their own unique path to winning. My advice for new leaders is this: Run your own race, and help your team run theirs.

❌ Don’t take too long to lose a deal

John Barrows, CEO, JBarrows Training

I’d just met with a key decision-maker for a $200k deal. We mapped out the plan, set the timeline, and as far as I knew, the product-customer fit was there. Then came the dreaded phrase: “We need more time.” For weeks, I followed up. I did more research, lined up more meetings, and created more pitches. Eventually, I lost the deal.

I wish I’d listened to my spidey sense and realised sooner that I was going to lose the deal. Then I would have let go sooner. Sellers are often told to push through “no” to get to “yes.” But I believe that “no” is often an actual “no.” To discover the truth behind a “no,” we have to ask the right questions and determine whether the prospect even has the ability to buy. 

Share your own sales advice and build your network

Sales stars: They’re just like us. The next time you make a mistake on the job, remember that you’re not alone, and take it as an opportunity to learn and improve.

Have you learned some lessons the hard way? Tell us what happened and what you learned. The conversation is happening in the Salesblazer community, the largest and most successful community of sales professionals anywhere.