Your biggest AI challenge.
100+ support leaders shared what's keeping them up at night
Welcome back! This week I want to share two things with you:
- The top 10 AI challenges support leaders are facing right now
- My first impressions on Anthropic's new Claude Cowork (Claude Code for non-technical folks)
Let's start with what you told me.
Straight from the source
When you requested access to Field Notes, you shared your top AI challenge with me. I read every single response.
Some of you wrote one word ("Hallucinations!"). Others wrote paragraphs about budget constraints, team adoption, and trust issues from past AI failures.
Now that I can see the patterns, here's what I'm learning (countdown edition!):
10. Training & Role Changes
AI is changing what support work looks like. When AI handles all the tier 1 tickets, how do new hires learn? What does career progression look like? One manager put it clearly:
"Getting the buy in to spend time optimizing our product documentation, onboarding new hires when the AI bot answers all the entry level support tickets."
These aren't hypothetical questions anymore.
9. Customer Experience Concerns
Everyone has opinions about AI, even your customers. Sometimes really strong opinions that might break the relationship with your company.
The question isn't whether to use AI. It's how to use it without breaking trust.