Last week I spilled the sauce on the most investable use cases for AI, so you can advance your career or business.
Students & Job Seekers - Jobs in high demand
Business Leaders - Where to invest in AI
Knowledge Workers - Where to nudge your team, or improve your skills

Shocker! AI Skills increase your value
(by 64%, across industries)
My research points to customer support automation as the #1 use case for AI in 2025+…….
So let’s hear from the chatbots themselves in this week’s episode!
*Chatbots are not just for customers!
Many will be used to power your team as internal resource helpers!
3 Chatbots Walk Into a Bar…
Table of Contents
Bot #1: The Context Know-It-All
I perform best when my human teammate trains me.
My human trainer is an office admin who claimed, "I know exactly what our customers ask every day. Let me train our chatbot."
My human trainer isn’t technical, but years of answering emails means she knows customer issues cold.
What I Handle:
Internal resources & proceduresl
Account status checks
Service or policy questions
Scheduling and availability
My Training:
I need context!
I perform best when my human trainer feeds me real data. I learn from call transcripts, past support tickets, and even her carefully polished FAQs.
I get better each week, thanks to my human teammate’s dedication.
🧠 Takeaway: Empower your frontline team. They know your customers better than any vendor or VP ever will.
Bot #2: The 80/20 Expert
I know what matters.
I’m not trying to be everything to everyone. Company data showed me the truth: 80% of support queries cover the same 5 topics.
Pareto’s Law:
According to Vilfredo Pareto, this is the nature of how things work, in almost any given area. Pareto, an Italian, first noticed that about 80% of the wealth belonged to a mere 20% of the population.
Solving high-frequency issues helps improve customer experience.
What I Handle:
Daily surges
Basic info collection
Payment questions
Recurring tasks
My Resource Allocation:
The 80/20 Rule helps me direct resources to what matters most.
My trainers provide carefully chosen CRM notes, past support tickets, and authentic chat transcripts.
This context helps me understand the inquiries I’ll see most often.
Now the business owner is proud of me, while customers praise quicker resolutions.
📊 Takeaway: Chatbots need precision, not perfection. Identify and train for the 80% that really moves the needle.
Bot #3: The Escalation Specialist
I know when to tap out.
I’m smart enough to recognize when I need human help.
Meet my human counterpart - The Escalation Specialist - a new role gaining traction in customer experience circles (even Zendesk lists it as a breakout role).
My Specialist monitors escalations, serving a critical role as the Human in the Loop.
What I Escalate:
Urgent issues
Churn signals
High-stakes, sensitive moments
My Training:
My job isn't to resolve. It's to recognize and route.
Routing, routing, routing.
If confidence dips or frustration surfaces, I alert my human teammate.
My seamless handoffs help my Specialist turn challenging customer interactions into opportunities to build loyalty and trust.
Takeaway: Build graceful handoffs into your chatbot strategy. Great AI knows exactly when to step aside.
Get your free Human In The Loop Sticker

free laptop sticker ‘when and how to use AI’ (first 50 subs)
Happy Hour: Who’s the Best Chatbot?
Spoiler alert: It isn’t a competition. Each ‘chatbot specialty’ can be rolled into 1 or multiple solutions at your business.
Your chatbot doesn't need to be perfect at everything.
It needs to be excellent at recognizing what type of conversation it's having - then respond accordingly.
Six-Pack: Questions to Ask Before Deploying a Chatbot
What issues do we handle repeatedly?
What training data is most valuable?
Which scenarios require immediate human intervention?
How will our chatbot route and escalate seamlessly?
Who is best suited to train and oversee our chatbot?
How will we measure chatbot effectiveness?
Remember, a chatbot’s success relies heavily on human collaboration.
Role: Handle chatbot escalations, improve AI training, customer satisfaction.
Key Responsibilities:
Real-time monitoring of chatbot interactions
Rapid human intervention for critical cases
Weekly review and retraining of chatbot responses
Analysis and reporting on escalation trends
Skills Needed: Empathy, decisiveness, pattern recognition, communication
If you know someone who would enjoy this content,
Here’s what’s coming next :
Thursdays: We’ll cover LLM and AI concepts for business leaders. (Don’t worry. I put the cookies on the lower shelf, where anyone can reach ‘em.) I teach complex ideas in simple chunks anyone can understand.