Now answering calls 24/7 

3 Salespeople Who Missed The Mark (Real Life Examples)

You want to become a better salesperson.

Because if you do, then you can close more deals (without generating more leads), you can more quickly persuade motivated sellers to work with you, and ultimately, you can make the most of your marketing efforts.

(Boo-yah 😎)

Well, the good news is… sales is a skill — one that can be fine-tuned with hard work and practice. You can learn, in other words, to become a better salesperson.

And sometimes the best (*cough* most fun *cough*) way to learn how to do something the right way is to watch people do it the wrong way. So I scoured the internet for real-life examples of salespeople botching it. Here are 3 wonderfully terrible examples I found (with takeaways of what not to do).

Our expert, U.S.-based reps can answer the phone for you — interested?

Terrible Example #1: What does ass-u-me-ing do, Chad?

This first one comes from the big marketing company’s blog, HubSpot. To protect the perpetrator, the person reporting this story changed details (and replaced them with comical substitutes), but left as much of the bad as they could. Here it is.

Hi Peter,

I’ll be reaching out to you on the phone in the next couple of days/next week but I wanted to follow up with an email as well before the weekend.

We haven’t had the pleasure of meeting but I’m reaching out to introduce myself and see if we can schedule a 15-minute conversation sometime next week.

I work for a company called BoogerPickers — we help businesses better manage their digital booger picking technologies, and when I came across your website and assessed the tools you’re using, I realized this is a great opportunity for us to help you.

To be brief — we are a booger indexing solution that:

  • Eliminates the chaotic burden of hand picking boogers from your nose
  • Enables access to smaller, difficult to reach boogers in order to increase successful booger extraction
  • Optimizes the ROI from your existing booger pickers (reducing time and maximizing ROI)

Companies similar to yours in the industry rely on us to be the foundation for their entire booger picking stack and I think HubSpot Inc. could definitely see the value in BoogerPickers as well.

I’d love the opportunity to share this in a bit more detail and hear your feedback.

Are you available for 15 minutes sometime next week?

Can’t imagine a quick chat about increasing booger picking and optimizing your booger pile would be a waste.


Clueless Chad

Takeaway: Don’t make unfounded assumptions about your prospect

This email does a ton of things wrong. But in an effort to simplify those mistakes into a digestible piece of advice, I think that the worst thing this email does is consistently make unfounded assumptions about the prospect.

For instance…

  • “We haven’t had the pleasure of meeting” — How does Clueless Chad know that the prospect would want to meet, anyways?
  • “when I came across your website and assessed the tools you’re using, I realized this is a great opportunity for us to help you.” — How did Clueless Chad know that just by looking at the prospect’s website? Seems presumptuous…
  • “Can’t imagine a quick chat about increasing booger picking and optimizing your booger pile would be a waste.” — Clueless Chad doesn’t know the prospects schedule or priorities, but he’s pretending to… without any previous relationship to back him up.

Look — I get it. Salespeople often use these overly presumptuous tactics to seem confident to their prospect. But keep in mind, you don’t illustrate confidence by telling people how confident you are just like you don’t show people you’re a cool dude by telling them you’re a cool dude — doing so often illustrates the opposite of what you’re trying to communicate (i.e. that you’re not cool).

Instead, genuinely try to understand your prospect and their problems before making any assumptions — ask lots of questions, listen more than you talk. Only then can you actually provide (or pitch) a service that you know will be valuable to your prospect.

Terrible Example #2: Vague, template-y, and oh so kind…

This example comes from Jill Konrath and is so boring that it’s hard to read through (you’ve been warned).

[Your Name]

My name is Jennifer with XYZ Sales Training. We improve sales performance though our unique blend of sales technology and experience, resulting in 89% better quota achievement. Our industry-leading methodology has helped more than 650,000 sales professionals find and close more deals, and our proven sales process makes your forecast and pipelines accurate by putting science behind it.

It all gets delivered through our BigDeal® technology – the on-demand Sales Performance Automation application that operates standalone, or can be integrated with your existing CRM system to produced sustained, measurable results. And to ensure that your sales teams get the full benefit, our virtual learning system delivers on-the-job training worldwide – reinforced by expert coaching.

I am not sure if you would be the appropriate contact, but I am trying to find the person at your organization who evaluates our type of program offering. Would it be possible for us to speak for 5 minutes or can you point me to the correct person to contact? Find out how organizations like Microsoft, Xerox, Honeywell, Siemens, United Healthcare and Adobe have found success with our offering and how [not provided] can find similar achievement.

Thank you in advance for any assistance you can provide. I kindly await your response!

Takeaway: Don’t use vague data to back up powerful claims

Again, terrible. You and I both could probably point to 10 spots that made us cringe or gave us the anxiety-sweats. BUT, as your humble simplifier of mistakes and takeaways, I’m going to focus on the first paragraph, where the salesperson tries to back up his powerful claim (“We improve sales performance” and “industry-leading methodology”) with vague and meaningless data (“resulting in 89% better quota achievement” and “helped more than 650,000 sales professionals find and close more deals”).

As a salesperson, you’re going to make a lot of powerful claims (“I can buy your house fast for cash” or “I can close in 7 days”, for example). And that’s good — you need to do that. But after you’ve told the prospect what you’re capable of doing for them, do not back up your powerful promise with “Yeah! We’ve helped 100 people just this year!” While that claim might be honest, it’s too vague to be meaningful. Instead, try telling the prospect a personal story about an individual you helped who was in a similar situation to the prospect. That will feel more authentic, build more trust, and prove to the prospect that you’re capable of helping them out of their difficult situation.

Terrible Example #3: How well can you bluff, David? Oh — not very well…

This example comes from Sales Shift. Drum roll please… I saved the best for last. 😀

David: Good morning Jill, this is David at ABC Company. I’m sure you’re always looking for ways to grow your business faster.”

Jill: “Uh Yes.” (I’m curious to see where this goes)

David: “Well I work for ABC Company and we can help you grow your business faster by providing you a constant stream of pre-qualified hot leads. Does that sound of interest to you?”

Jill: “Damn right it does David. So how do you do that?”

David: “We sit with you to identify your target audience and create messages that our team then uses to contact potential prospects. We’ll qualify them and then provide you with the best leads.”

Jill: “Interesting. And so what makes you think you can do a better job of this than me or my team David?” (Now remember who David is speaking to).

David: “Well we have the expertise. We do this every day.”

Jill: “So David. What do you know about my company?”


Jill: “David do you know what I do?”


Jill: “David did you even look at my website before this call? Do you not realize how ludicrous it sounds that you are offering to make multiple prospecting calls on my behalf and yet you’ve failed to make one credible call to me? Right now what do you think the odds are that I’ll say yes to you today?”

David: “I planned to take a look at your site, just ran out of time. But I do plan to take a look when I get off this call.”

Jill: “Not good enough David. But I’m going to cut you some slack. You’re talking to someone who works with sales teams for a living so I’m going to give you a second chance at this. Go away and do your homework and then call back and let me know how, and why, you think you can provide specific value to me.” (I can be a sweetie when I choose to be!)

David: “Ok, I’ll do that. Thanks Jill.”

One month later…

David: “Good morning Jill this is David at ABC Company. I’m sure you’re always looking for ways to grow your business faster.” (It’s as if the previous conversation never happened.)

Jill: “David, you’re back. Good for you. So what did you learn about me?”


Jill: “David?”

Click. And David was gone forever.

Takeaway: Don’t fake it. People can tell when you fake it.

Boy, that was spicy.

The ultimate takeaway here is simple: don’t fake it. The best salespeople in the world are people who prospects love to hang around — they’re people who make you feel like you’re buying from a friend rather than a business. They’re there to support you, answer questions, make jokes, and generally be a pleasant person. They rarely give you a hard-pitch, and when they do, it’s because (let’s be honest) you were asking for it.

So… be yourself. Learn to ask your prospects more questions (people love talking about themselves), listen to what they have to say, and authentically care about their answers. Don’t make assumptions. Don’t fake it. And definitely don’t pretend to be someone that you’re not.


To become the salesperson of your (and your prospect’s) dreams, you’ll need to practice. Don’t be afraid to role-play with friends, test out new approaches, and even use breathing exercises to calm your nerves. With that, you’ll be a much more successful salesperson — you’ll close more deals, build longer relationships, and get more referrals.

And you can use the above three examples as reminders of what happens when salespeople don’t practice their craft and instead, approach the discipline carelessly: madness — terrible, sales-less madness.

Our expert, U.S.-based reps can answer the phone for you — interested?