The Good, the Bad, and the Ugly – Real Sales Stories and Insights from Steve Bookbinder

The Good, the Bad, and the Ugly - Real Sales Stories and Insights from Steve Bookbinder

By: Steve Bookbinder

Sales is a complex profession with a lot of nuances.

More than a job, successful selling is a result of skill and practice. The most successful salespeople work incessantly toward improvement, practice regularly, and grow incrementally with each experience. But acquiring exceptional sales skills requires time and dedication.

I know because, over the past decade, I have had the privilege of training thousands of top business-to-business salespeople who sell for some of the world’s leading companies.

This has given me the opportunity to observe, analyze, and reflect upon both common and uncommon sales situations and circumstances.

While I can’t share all of my observations today, I’ve summarized a few common scenarios and will break down the good, the bad, and the ugly aspects of selling in those conditions.

In this post, we will share common sales stories, insights, and tips for improving your own sales performance.

Looking for a few quick sales tips?

Story #1: The Disappearing Prospect

A salesperson once told me they were working on a hot prospect and the first meeting went great. They did their research, established a strong connection with the prospect, who said they have a need, budget, and timeline. The seller set up a scheduled next step with the prospect plus their boss. Things are looking good. Now, the prospect invited the seller to present their solution. During the presentation, heads are nodding and everyone is engaged. At the end of the presentation, the prospect told the seller they will be making a decision by the end of the week. Sounds like a done deal. Think again…

I’ve seen this happen time and time again. Great meetings followed by silence.

The responses I’ve seen from salespeople break down into three categories:

The Good

The best response to this situation that I’ve come across boils down to not giving up, and being deliberate and thoughtful about how and what you’re communicating with the prospect.

Instead of calling or sending an email that’s focused on “checking in” you need to consider something that will make your message stand out and add value. For instance:

“I’m reaching out because I’ve been thinking about you and what you’re trying to accomplish. I met with [insert name or company] to get more insight into the challenges you’re facing and I uncovered a few new ideas. Give me a call or shoot me an email back and I would love to share what I’ve found.”

You’ll need to find your own words and phrasing, but the point here is to find something of value and incentivize the prospect to get back in touch with you.

The Bad

A not so good, AKA bad, response to this is giving up too soon. Based on what I’ve heard from a variety of salespeople, there’s a common theme of not enough follow through.

In fact, a study by Marketing Donut stated that 80% of sales take 5 follow-up phone calls after the initial meeting to close. However, the study cites that almost half of salespeople give up after just one follow-up.

It’s a frustrating feeling when a seemingly interested prospect goes dark, but if you have a consistent follow-up plan in place, it will keep you ahead of the game.

The Ugly

Over the years, I’ve worked with salespeople who refuse to believe a deal is dead. They just kept chasing the deal. Week after week. Month after month. Even year after year.

It’s one thing to be persistent and follow-up, it’s another thing shamelessly hound the prospect into responding to you. Even that won’t necessarily work!

The longer an opportunity goes beyond your normal sales cycle, the less likely it is to close. Remember that the next time you’re tempted to spend too much time on any one prospect.

The Lesson

There are so many reasons a prospect could go dark on you. And believe me, I’ve heard them all. But the lesson here doesn’t let this type of reaction derail your sales momentum.

Story #2: Death by Sales Pitch

I was sitting in on a first sales meeting recently and the salesperson started the meeting by giving a presentation of who they are and what their company does. Doesn’t sound too bad, right?

Well, fast forward 20 minutes — and the seller was still talking. When the rep finally took a breather, everyone in the room was tuned out and visibly distracted. The rep didn’t stop once to ask a question or make sure everyone was still following.

I’ve seen salespeople, both beginners and experts alike, make this mistake. In some cases, I’ve been pleasantly surprised with how the rep rebounded. In other cases, it felt a lot like watching a sinking ship.

We all make mistakes, but how you recognize the mistake and handle yourself after the fact is what separates the good, the bad, and the ugly:

The Good

You’re probably thinking, how could this situation have a good ending? And you’re right, but in this case, the salesperson was able to turnaround the conversation. After the rep realized the audience was lost, they pivoted by saying:

“Well, now that I’ve given you a general overview of our company, I’d like to learn more about why you took this meeting and how you envision using a solution like ours within your organization.”

While this seller didn’t start the meeting in a way that encouraged an open conversation, they got the meeting back on track by redirecting the discussion back to the prospect’s goals, challenges, and priorities.

The Bad

In another example, the rep recognized they had lost the audience, but instead of re-engaging them by asking a question or opening the floor to someone else, they just kept talking. They continued by telling a success story about a recent customer.

On the surface, this sounds like a good idea, but not all success stories are created equally.

The rep launched into a story about the many great features and benefits of the solution and how it has helped other similar companies achieve success, but this doesn’t really help the prospect make a more informed decision.

Instead, tell a story that puts you in your customer’s’ shoes. What do they want? If your product or service helps them get there, talk to them about what it’s like to get there and be there. Are you confident that using your product or service will help your customer be great? Show it by helping them visualize it.

The Ugly

The worst response to this I’ve seen was a rep who was oblivious to the “temperature” of the room. After they finished their 20-minute pitch, they asked the prospect if there were any questions. They had no questions. Simply asked, “how much?” So the rep said, “why don’t I just send you a proposal?”

This is a great example of what NOT to do. Whether this response was from a lack of confidence or sheer laziness, selling is a process that requires give and take. You must do the preparation in order to feel confident in your knowledge and ability to ask the right questions in order to lead an effective meeting.

The Lesson

Think of your pitch as a conversation, rather than a presentation.

Asking the prospect questions will help you tailor your talking points to better suit their needs. It will also help clients become engaged and more interested in what you do have to say.

Salespeople tend to default to simply regurgitating product knowledge, rather than mapping recommended solutions for the customer’s business problems.

Commit to Good Sales Habits

Successful selling requires having good habits. It means being able to learn from your own experiences as well as others.

Overall, what I’ve learned is no matter your level of experience, there’s always more to learn and improve upon.

These situations are just two common examples from a much longer list of sales stories from the front lines.


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