My blog posts are mostly inspired by real world sales interactions that I’ve experienced first hand.  That includes both the good and bad sales experiences. Being a perpetual student of the sales game, I collect the extreme examples of both in my own little Sales Hall of Fame and Hall of Shame. Admission is free to all sales professionals!

Last week, a new entrant was submitted for consideration and immediately granted unanimous entry into the aforementioned Sales Hall of Shame. Unfortunately, as much as I’d like to tell you that this was a one off situation, I’m seeing this become the norm and not the exception in dealing with many sales people.

But first a little context…what I’ve observed in 25 years of enterprise selling is that every 3-5 years a new sales strategy or methodology will emerge backed by thoughtful research that creates a buzz. There usually isn’t anything revolutionary about these new hot sales strategies, rather they tend to look at things through a slightly different lens and present their perspective in a compelling way that resonates.  They build new sales frameworks to use with customers.

And then everyone jumps on the bandwagon and tries to start using this new sales methodology in their selling efforts. And with mixed results. Why? Because translating the strategy/theory into actionable sales tactics is harder than most people think. Sometimes the research and theory don’t translate into real world effectiveness. And worst of all, the lazy companies that read a blog post or article and decide that is what they are going to do without understanding the rigor and discipline that is required to do so effectively.

The Challenger Sale by Corporate Executive Board (CEB) is a perfect example of this ( Now I’ve read the book and agree with many of the key assertions expressed in it and generally find it to be a great resource. However, I’d suggest there are a lot of enterprise sales people like myself who have been selling in a Challenger mode for many years without needing the validation from CEB’s research that it was the most effective way to sell.

Now back to my Sales Hall of Shame experience last week. I received a sales email that was attempting to use the Challenger sales model. Needless to say it failed miserably. In fact, not only did it not engage me, it offended me to the point where I forwarded it to several other fellow VPs of Sales in my network to get their opinion. There was a unanimous opinion that this was rampant in the industry as people try to apply the Challenger sales model and fail miserably.

Here’s the sales email with the names redacted to protect the innocent:


I’m getting worried. One of a few things is happening here, either: 

  1. You are interested in XXX just been super swamped and haven’t been able to reach out. If that’s the case whats the best number to reach you and I’ll give you the quick 2 min synopsis to see if this is even worth scheduling a demo.
  2. You are not interested in XXX but love getting my emails so don’t want to respond to get me to stop. If that’s the case let me know anyway and I can give you some better ones.
  3. You’ve been eaten by an alligator and it’s really difficult to respond to emails from it’s belly. If that’s the case I understand. Rough break. 

Fun Fact: Ashton Kutcher really likes XXX!

-Crappy Sales Rep

Crappy Sales Rep’s Phone #: 415-XXX-XXXX

As mentioned previously, I forwarded this to several VPs of Sales that I know and respect along with this note:


Hall of Shame sales email candidate below, thought you’d appreciate it!   They email me every three days and act like they are owed a response.  BTW, the reference to Ashton Kutcher is hilarious, perhaps they should know that I would care if Warren Buffet was an investor, not the guy who was married to Demi Moore.  Now if you’re talking about Bruce Willis, he made much better movies than Ashton and that’s not saying much… 

It really strikes me that these companies of twenty something year olds (backed by the likes of none other than Ashton Kutcher:-) heard about the Challenger Sale and think they are being edgy, disruptive and clever when they’re actually coming across as cliché, unprofessional and rude. 



Here are two of the replies that I received but quite representative of all the replies:

“Agree with you on the email below.  It’s a disturbing trend and I don’t think it works. I don’t think they’ve even read it.  They read XXX XXXX’s blog and then they all tell each about their pithy emails and then copy each other.” 

-Smart, Experienced and Highly Successful VP of Sales

“Good god… that just makes me sad that people think this approach works…

Maybe it’s a generational thing…”

-Another Smart, Experienced and Highly Successful VP of Sales 

So I looked up the antonyms for the words “Challenger” and “Disruptive” online and the results that I found were hilarious and ironic at the same time. The opposite of “Challenger” is simply “Non-Competitive” (source: And the opposite of “Disruptive” is “Quiet” (source:

So the moral of this real world sales story is that you need to know that when you try and fail at being a challenger or disruptive at sales, know that you are coming across as non-competitive and quiet to the customer. Just what all Sales VPs want to hear about their sales reps:-) Just as a funny footnote, spellcheck flags Ashton Kutcher’s last name and suggests “Butcher” instead.