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Why Big Enterprise Sent You a Dear John Letter

Rejection letters come in many forms—the antiquated handwritten letter, the dismissive email or text, and even the dreaded “unfollow” on social media. When the message arrives, it reveals a profound misalignment between the receiver’s exuberant view of the future and the sender’s opinion that a relationship isn’t possible at this time.

It’s time for a little dating advice for the thought leaders pursuing a relationship with a large organization. Let’s all agree that global brands are sexy; everyone wants in on those enterprise sales. These massive organizations routinely face unique challenges in people, process, and culture on a scale of complexity that no one else can touch.

I’ve seen thought leaders swoon when they think about working with a specific brand. During the first steps of the dance, it’s easy to get giddy. It starts with a keynote to top leaders from a global brand at some spectacular (even exotic) offsite location. At the reception, you make small talk, looking for a chance to score that second date—another speech, a workshop, maybe even a consulting engagement. The signs are encouraging, suggesting you talk more after the event. Then, after the first event, you go home, dutifully sending warm follow-ups and thank yous.  That night, your dreams are filled with the big company’s logo.

“These ideas will change their entire company.”         “This could be an HBR case study!”

Things go well at first. The executive connects you with the head of HR. After a few calls maybe you’re asked to submit a proposal, you might even land a workshop or a small pilot. It’s that gleeful, butterflies in your gut, backflips and kittens, first kiss emotional high. All the praise and momentum is settling in, and you convince yourself that this could finally be the real thing.

And then, suddenly, the tone of the communication shifts, and after a few weeks of unreturned calls, there’s the Dear John letter in your inbox: “We love your content, but it’s not the right time to bring you in for an engagement.”

Rejection letters are tough to receive; they replace the optimistic view of the future with a bleak dead-end. It’s a tough crash that leaves many thought leaders asking, “What went wrong?”

The answer is a misalignment between the thought leader and the prospect.

For a thought leader, there are a two issues that exist outside of your control—the prospect’s timing and their budget. Many large organizations often think in multi-year cycles and plan major initiatives accordingly. Even large organizations have limited resources. They can only successfully execute a limited number of initiatives per year. So, if a large organization says that its dance card is full for the next two years, then that may be entirely truthful.

But, there are many controllable factors when trying to lock down enterprise sales. While actively courting that prospect, they’re vetting you from many different angles. Let’s look at three criteria that trigger the “Dear John” rejection letter from an organization.


The enterprise ready thought leader has to avoid being pigeonholed as a smart solo practitioner. Websites and collateral with weak visual branding will erode your chance for success as quickly as going to a first date with messy hair and rumpled clothes. A company named “Me & Associates” works just fine for a small local law firm, but it doesn’t inspire confidence among global organizations.

Content Maturity

Enterprise buyers demand crisp and well-articulated intellectual property. They won’t fall for vague hand-waving and ambiguous tricks. If your core model is a seven level pyramid, it can’t be renamed and re-sequenced each month. Organizational buyers expect you to come to the table with stable, validated, models—whether through previous engagements or statistical analysis. Admittedly, one client will have to be that first case study but even the visionary endeavor needs hard data to assure the content’s been thought through.


Thought leaders need to signal that this isn’t their first time at the big dance. Knowing what to expect inspires confidence in the buyer—learn the business jargon, get caught up with the business reality, and brush up on standard sales and procurement cycles. Otherwise skepticism will quickly appear, and the buyer will cut and run.

However, the good news is that every time you interact with the market, you’re getting feedback on your enterprise readiness and can use that information to adapt and change your content accordingly.

When the corporate buyer receives the right signals, it reduces the odds they’ll send that dreaded “Dear John” letter, and increases the chance of giving that big project proposal a, “Yes!”

Bill Sherman works with thought leaders to launch big ideas within well-known brands. He is the COO of Thought Leadership Leverage. Visit Bill on Twitter

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