Walk On #2
WMMM #105- This week, I’m setting my sights on 2026.
Jeff Keplar Newsletter January 3, 2026 3 min read
But Wait!
Upon my return, I queried Gemini about the challenges facing enterprise salespeople.
I was looking to check the pulse on the here and now.
What was Gemini’s response?
“The ‘Standard Seller' role has largely been automated…AI agents now handle prospecting, lead qualification, and basic Q&A.”
Hmmm.
Illusion of Explanatory Depth?
The last edition of Win More, Make More was in September.
After 104 editions, I took a break.
I asked myself some questions.
Am I contributing value?
Does my content matter?
Do I still enjoy telling our stories and writing this newsletter?
To answer the first two, I turned to content I published in September of 2023.
Had I fallen victim to the illusion of explanatory depth?
You may remember the concept.
We all think we know how a zipper or a flush toilet works, but when asked to explain it step by step, we realize we don't.
I needed to distinguish my first-hand experience from the actual patterns in my writing.
Was I conveying what I intended?
It is easy to mistake community knowledge for our own.
My Use of AI
I routinely use AI to augment my consulting work.
I use it mainly as a high-level research assistant.
On this occasion, I selected Google’s Notebook LM.
I loaded over 100 pieces of content that I have created into the learning model.
(If you are worried about the “hallucinations” that users have reported about GenAI tools like ChatGPT and Grok, eliminate that concern by using Notebook LM. It builds a learning model from the data you provide. Predicting the next best part of a sequence is less relevant.)
I fed my entire archive into Notebook LM to have it explain my strategies back to me.
I used AI to interrogate my own content.
Did it find the hubris that often plagues “experts,” especially those offering their services for a fee?
Did it find hidden patterns in my “Game within the Game” and “Do Nothing” strategies?
I have emerged from this 100-day debiasing session with a clearer understanding of how I can help enterprise sales professionals in 2026.
It will shape my newsletter going forward.
For example, Gemini responded that AI agents now handle prospecting, lead qualification, and basic Q&A.
But it goes on to share that as AI handles the execution layer, human reps are left with the most emotionally charged parts of the sales cycle.
The successful enterprise technology salesperson must have High-EQ “human” skills:
Adaptive Storytelling
Empathetic Negotiation
Radical Transparency.
So I fed “High-EQ” “human skills”, and “Adaptive Storytelling, Empathetic Negotiation, and Radical Transparency” back into Notebook LM and asked it to search my content for examples.
Good news.
It loved what it found.
I was especially pleased that it found two examples in particular.
“You effectively bridge the gap between unrelated worlds to drive a point home. You used the animated film Ratatouille and the food critic Anton Ego to explain how sensory details (like food) trigger emotional memories that influence behavior.” (The Summer of '71)
“You even used a 6th-grade basketball rivalry to explain ‘home-court advantage’ and competitive strategy.” (Full Court Press)
And finally: “Your archives confirm that your ‘brand’ is not just about sales tactics; it is about the human element of business.”
I think that Notebook LM does a better job of providing insights into my content than I do.
I’m looking forward to sharing more with you in 2026.
Lessons…
1) Don’t fall victim to the illusion of explanatory depth when it comes to sales.
2) Emotions are part of every sales cycle - humans with High-EQ skills are better than AI in this area.
3) Remember to use Adaptive Storytelling to engage.
Thank you for reading,
Jeff
