Beware Of Sales Enablement Experts Prospecting


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Every day, each of us gets dozens of horrendously bad prospecting emails.  My friend, Hank Barnes, of Gartner has made a regular #FridayFails series featuring his worst of the week.

Fortunately, spam filters take care of most of them, but some filter through anyway.  I’ve limited my writing about these–there’s just too much bad material that it gets repetitive.  But I can’t refrain from writing about a certain category of prospecting letters.  It’s those written by self proclaimed experts in sales, marketing, sales enablement, prospecting, content.

I write about these for several reasons.  First, even people who know better do stupid things.  Second, if they are using the methods and techniques they espouse as “best practice,” then their prospecting is actually a representation of their work–and what they can do for you.  Read Buyer Beware!  Finally, I do get some sort of perverse joy at calling these horrendous effort to people’s attention.

Before I go further, I’ve done terribly bad prospecting before, I’ll probably fall victim to some bad efforts in the future.  We all make mistakes, hopefully, learn and improve.  But the examples I highlight from these self proclaimed guru’s represent systemic approaches they use.  It’s not just one ill conceived approach, but it’s them consciously executing the very worst of prospecting, inflicting it over and over in a mindless way.

About a week ago, a good friend and client, let’s call him John, forwarded me an email stream, saying, “This is just horrible prospecting!  It’s from someone who does similar stuff to you…..”  John  is EVP of Sales and Marketing for a $B plus organization.  He’s done some tremendous things in building the capability of the organization, and we’ve been proud to help in those efforts.  So it was funny to see his reaction to this person’s prospecting efforts.

This morning, he forwarded me the email stream, yes the madness continued.  His note simply said, “This takes the cake for all time worst email prospecting!”

I’ve reproduced the email flow below, as you would expect, all names and links have been changed.

Email 1:


I notice on LinkedIn that we have several connections in common. As the Executive Vice President of Global Sales and Marketing at XYZ, I would think that we also have similar challenges driving growth and results.

We’ve been successful at helping other Sales & Marketing VPs at companies like Company A, Company B, and Company C to hit their numbers through our Sales Enablement technology.

Here is a quick 1-minute video on our website that better explains it [Link to self promotional video]

Do you have a few minutes to talk next week?

Regards, Bob, CEO, [Sales Enablement Company]

Email 2, 5 days later, this was a forward of the original email with the new note leading:


Just following up on my previous email.

Best Regards, Bob, CEO, [Sales Enablement Company]

Email 3, 5 days later, another build on the prior emails:


Sorry to keep bothering you.   I just think that we can really help you drive revenue at XYZ through sales effectiveness.

Regards, Bob, CEO, [Sales Enablement Company]

Email 4, 5 days later, same pattern:

John, just following up.

Bob. CEO, [Sales Enablement company]

Email 5, 1 day later, you guessed it same pattern:


I should stop bugging you soon. I don’t want you to think that I’m as annoying as this other “Canadian”, Justin Bieber.

[Link to Justin Bieber song]

Regards, Bob, CEO, [Sales Enablement Company]


What in the world is “Bob” trying to accomplish, and is this a demonstration of his organization’s competence and expertise in selling?

He’s not creating any value in his messaging.  He might have in the first, but while he chose references in the same industry as John’s, the references were B2B2C examples, and John runs a B2B business.  So there wasn’t much he could learn from those references—beside the links took him to “here’s our fantastic products.”

Bob could have demonstrated his knowledge by providing some insight into the challenges the industry is facing (tremendous industry consolidation, regulatory, restructuring issues impacting all players).  He could have provided some examples of how his organization helped similar companies address those challenges.  But he didn’t.

Then in his subsequent emails, he didn’t build on anything.  He didn’t expand his message, he didn’t address other issues, he didn’t demonstrate any knowledge of the issues John may have been facing.  He didn’t provide any insight into industry activity (It so happened John’s company made a major disruptive acquisition, but of course Chris didn’t take the time to acknowledge that or even talk about the integration challenges of that acquisition.).

Bob was simply too lazy to build a message that demonstrated knowledge, delivered insight, or provoked interest.  But I suppose, his company thinks that volume and touches count, not content.

Bob goes further in insulting John.  He acknowledges, two times, that his messages are nothing more than harassment.  That he isn’t engaging, that he isn’t trying to create value.  All he wants to do is “bug” and waste John’s time.

What Bob has done has been not just squander a potential to build a relationship and help my friend.  He’s created a “prospect” actively telling his friends, “If this is an example of their work, stay away from them!”

John asked me what to do.  I gave a few snide suggestions, but in the end told him not to react, just “SPAM” it.  I added, you can expect he will give you 9-11 additional emails because that’s what the data says–it takes 14-16 touches to get someone to respond.  It’s already programmed into his drip campaign, we know the mailing pattern, so we can predict the days you are likely to get an email.

John sighed, he just created a rule to move all messages from Bob’s company into his SPAM filter.

The profession of selling deserves better than this!  Our customers deserve better than this!

As you evaluate vendors, including companies like mine, make sure we practice what we preach.  The way we prospect and develop relationships with you, the way we engage and create value for you and your team is likely to be what we will drive in working with your team.  If you think “Bob’s” approach is right, if it builds the relationships and engages customers in the way that you think represents your company well–then clearly he has a solution for you.  If not, then don’t waste your time.

Republished with author's permission from original post.

Dave Brock
Dave has spent his career developing high performance organizations. He worked in sales, marketing, and executive management capacities with IBM, Tektronix and Keithley Instruments. His consulting clients include companies in the semiconductor, aerospace, electronics, consumer products, computer, telecommunications, retailing, internet, software, professional and financial services industries.


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