Our popular Winning the Challenger Sale Series is now entering its third season. This monthly live webinar invites sales professionals and commercial leaders to join us Thursdays at 11 AM ET as we open up the Challenger™ playbook.

More than just a webinar series, sellers, managers, coaches, and sales leaders get practical advice and actionable insight for the day-to-day execution of the sales skills and behaviors proven to win in complex selling and buying environments. Our third episode aired live April 14 and covered “Email Pitfalls To Avoid.”

To kick things off in their latest webinar, our hosts, Mike Randazzo and Jen Allen took a poll, asking whether email is dead. 94% of the audience said, “No,” and Jen agreed, saying, “Email isn’t dead, but bad emails are.”

This begs the question: How many of our hearts stop momentarily when we hit SEND on an initial sales email and suddenly think, “Oops, should I have done that?” Because, as they say (and “they” is everybody by the way), “You only get one chance to make a first impression.”

Appropriately, “Email Pitfalls To Avoid” is what Mike and Jen are best at, and what a great (and universal) topic it is, because the truth is that most of our emails get stuck in the “mental spam filter” of our intended customer.

What does that mean, you ask?

Well, as Lavender—a digital marketing agency focused on connection-driven sales strategies—says, “Because potential buyers have adapted to an endless stream of inbound requests, the average read time for them to categorize the email (reply, forward, delete) is 13.4 seconds.”

So, fine, people have short attention spans, but what’s the impact to a seller? It means that you have a limited amount of time to engage your potential buyer, so make it count!

The problem is, as Mike and Jen put it, we either spend too much or too little time crafting our emails, and for various reasons. But rather than over or underthinking, your emails need to be:

  • Relevant
  • Thought-provoking
  • Built to teach

The webinar goes on to discuss Challenger Emails, where Mike and Jen analyze sample emails and their core components:

  • Subject line
  • Credibility
  • Reframe/Curiosity
  • Powerful Request

And the three big pitfalls to avoid:

  1. Mistaking “Personalization” with “Relevance.”
  2. Telling them they have a problem vs. asking them thought-provoking questions.
  3. Overlooking the importance of your CTA/request.

Number 3 in this list is interesting because Mike and Jen point out something that can be more important than CTAs, and that’s the CTL (“Call to Learn”), because without the CTL, the CTA can be foggy at best.

The two hosts finish up the webinar by explaining the difference between “Getting the call scheduled” and “Getting the prospect in the right frame of mind prior to the call.” They also discuss the Do’s and Don’ts of “Challenger Email Pitfalls to Avoid,” General Rules, and, as always, Key Takeaways.

So next time you hit SEND on an initial sales email, you can now breathe a sigh of relief (which is actually doctor-recommended).


By the way, you can also review Challenger Emails 101 by checking out our archived Season 1, Episode 2 episode called: “Capture Attention by Leading With Insight.”

Our next webinar, which is on the second Thursday of every month, is “Opportunity Prioritization,” airing live on May 12, 2022. Register for this episode and the full series here. If you missed this webinar on “Email Pitfalls to Avoid,” you can watch it here.

Want more ideas on how to win? Catch the latest Winning the Challenger Sale podcast here.

Challenger, Inc.

Challenger is the global leader in training, technology, and consulting to win today’s complex sale. Our sales transformation and training programs are supported by ongoing research and backed by our best-selling books, The Challenger Sale, The Challenger Customer, and The Effortless Experience.