This Outbound Psychology Trick Helped Close $10M+

by Jen Allen-Knuth

May 16, 2025
Prospecting

You've probably seen this headline: "The frenzy to create Ghibli-style AI art using ChatGPT's image-generation tool led to an additional 1M users in one hour on Monday".

Here's what's interesting to me about it.

Much of my LinkedIn feed lately has been people posting ChatGPT images of themselves. In Ghibli style. In the action figure style. In Simpsons style.  

Isn't it interesting that when given a new technology, our first instinct is often to see what it makes us look like?

(BTW - I'm not judging. My first experiment with it was creating the above image of me eating a Taco Bell Crunchwrap Supreme, surrounded by dogs, with a newspaper headline of "Kyle Asay Imprisoned For Slander".)

What’s interesting is how much this reiterates our very human desire to see ourselves through a different lens. To compare what our output looks like vs. others. In a way, it's a form of benchmarking.

We see what someone else has done. Now, we want to see what it looks like for us.

It’s why so many of us LOVE to share our Spotify Unwrapped lists.

When I think about great outbound messaging that creates a magnetic pull, it's because it gives the reader/viewer the ability to benchmark themselves.

So, how do we create these A-HA moments for our B2B outbound prospects?

Example A-HA Moment From Lavender

Here’s an example from when I worked at Lavender.

We all write cold emails. We don't have an objective way of knowing if they're "good".

When I saw Lavender's scoring mechanism as an AE, I couldn't wait to see if my “good” emails scored an A.

Most of the ones I submitted scored a C.

That created dissonance. It, on my own terms and without anyone else's involvement, showed me a gap. It taught me I had a need.

So, when I joined Lavender, my first thought was, “How can I get sellers at target outbound accounts to have that same “a-ha” moment I did?”

Here are 3 tactics I used, using 3 different channels:

1. Events

We sponsored small to mid-sized dinner events.

Before the event, I emailed registered prospects with an offer for them to submit a “good” target account email so they could see their score + feedback. I brought their results with me to the event. It made it easy for me to start a convo + created an insightful discussion about their current state.

If I wasn’t able to attend the event, I sent them their results + feedback before the event, and mentioned the name of my peer who would be attending the event (to make it easier for them to strike up a conversation).

2. LinkedIn

I wrote posts offering to grade + share feedback with the first 50 people who commented with a cold email.

I wrote posts talking about long-standing beliefs and assumptions I held about cold email, before seeing the Lavender data.

I wrote posts with lessons learned from graded emails that were submitted by the community.

I didn’t have to explicitly ask people to try Lavender. The content was simply meant to spark curiosity in seeing what their grade would be. It wasn’t a push. It was a pull.

3. Email

I wrote outbound emails to spark curiosity that didn’t reference the product/company name at all.

Instead, I used my Problem Prompter framework.

"Heard Kelly speak about the goal to drive $50M in aftermarket services revenue by 2025.
Looks like much of that revenue is expected to come from AM/CSM convos with existing customers.
Not sure if those AMs and CSMs have much experience writing outbound emails to upsell customers.
ACME’s customer teams were writing emails that scored a “C”.
Open to sending me one of your AM/CSM’s upsell emails and I’ll reply with how it scores?”

Instead of leading with the product, I’m leading with the customer’s objective + a problem hypothesis + giving them a way to gauge if there’s a problem worth solving.

I’m not telling them they HAVE a problem. I’m giving them a way to decide for themselves.

Wrap Up

As much as things are changing, human behavior is so very predictable.

It's why I'm a big believer that becoming great at Sales isn't about mastering the newest, flashiest tactic.

It's about understanding basic human psychology.

Ask yourself: “How can I use a diagnostic, a calculator, a set of questions, or benchmarking data that holds up a mirror to underappreciated risks/costs of their current state?”

Want to hear how companies like G2, IBM, Square, Autodesk, and Juniper Networks are training their teams to create A-HA moments with outbound prospects? Visit www.demandjen.com. Or, follow along with the free, tactical advice I share on my LinkedIn.

How to create your own A-HA moments with outbound prospects

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Jen Allen-Knuth
Jen Allen-Knuth is the Founder of DemandJen and spent the last 18 years selling and advising CEOs, Chief Sales Officers, and Chief Marketing Officers, for Challenger Inc, Corporate Executive Board (CEB) and Gartner.
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Want more tactics like this? Keep reading:

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