“…and You’re Ugly, Too”: The Perils of Challenger Selling

Would you buy what he’s selling?

I generally agree with the premise of challenger selling, that you should be willing to provide sometimes uncomfortable insights to your customers. Sometimes customers don’t know what they don’t know, and you provide value by educating them in ways that they can be better off.

But doing so requires a certain amount of tact, a quality totally lacking from the email I received last night. Here’s the first part: Team,

I thought you might like to know some reasons why you are not getting enough Social Media and Organic search engine traffic for

1. Your website is not ranking top in Google organic searches for many competitive keyword phrases.

2. Your company is not doing well in most of the Social Media Websites.

3. Your site is not user friendly on mobile devices.


There are many additional improvements that could be made to your website…

What’s wrong with this message? For all I know, it’s probably true, and I would probably benefit from some of the services this company can offer, BUT…

I’m human, and my immediate reaction to being told I’m doing something wrong is to either defend what I’m doing or to take offense at the messenger. In this case, my gut reaction was a combination of both of those. (Then I was thankful for having a blog topic idea dumped in my lap, but that’s not the main point.)

If you’re going to give someone an uncomfortable truth, you have to prepare them to receive our message, and earn the right to deliver it.

How could he have improved his message so that I would be willing to engage further?

First, make the salutation personal. Some companies make it difficult to figure out who the decision maker is, but it’s obvious from the name of the site to the home page that my web site is about one person, so why not address the email to that one person? The fact that he did not indicates to me that he really didn’t study my site, as he claims later in the email.

Second, begin with a compliment or two. Quite frankly, flattery works. At the very least, it will get me in the right frame of mind to read the rest of the message. He could have said he was impressed by my web site, tossed in one or two specific things he liked about it, and then given me the message about how he could make it even better.

Third, earn my trust. Here’s another part of the email:

Sound interesting? Feel free to email us or alternatively you can provide me with your phone number and the best time to call you. I am also available to meet you in person and present you this website audit report.

PS I: I am not spamming. I have studied your website and believe I can help with your business promotion. If you still want us to not contact you, you can ignore this email or ask to remove and I will not contact again.

There are two things wrong with this. First, if he really had studied my website, he would have known my phone number. He also says if I ignore the email he will not contact me again, but in fact this is at least the second message I’ve received.

There is tremendous value in being able to bring challenging insights to potential clients, but truth is not enough. Truths that are ignored don’t do anyone any good. When doctors have a good bedside manner, their patients are more likely to trust them and follow instructions, as well as less likely to sue them for malpractice. Wise doctors know that it’s not only what you say, but how you say it.

The bottom line for this guy is that he probably just made a sale—for someone else. I’m intrigued enough to consider hiring someone to improve my web site, but it will probably someone else. That’s probably irrational, I know, but then isn’t that how most decisions are made?

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  • Jack,

    I get these same emails about my site, but it’s awesome how you analyzed it to reveal the reasons it created such a negative response in you. I’m no sales genius, but isn’t marketing supposed to create a positive response, create interest, and cause you to resonate with, embrace and integrate the new idea into your existing schema?

    Some other things I see, now that I’m looking at it:

    – It never links any of these negative vibes to a business consequence.
    – It never explains what the lost opportunity is; why you should care.
    – It never asks a question of you until they are all done sales puking (going on and on about their assertions,) and then it’s not even a strong question.

    And I love the part about “I am not spamming.” Classic! Oh! You’re not spamming me? Just sending me unsolicited email twice a week… Cool. 😀

    Don F Perkins

  • Jack: there’s so much wrong with email marketing that it’s hard to know where to start. You’ve provided a stellar example of what happens when people ‘shortcut’ the selling process, and think they have license to say whatever they want because they are the purported expert. And that is a nuance that The Challenger Sale doesn’t explain.

    I trust that this message might have been more acceptable if it had come from someone who you know well, who you respect, and who you’ve worked with in the past. All three would be ideal.

    Except in the rarest of circumstances, shaming people into taking action is a poor selling approach.

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