Skip to content
 I Asked Claude the Question I Could Never Ask My Boss
Midjourney/Every illustration.

I Asked Claude the Question I Could Never Ask My Boss

‘Does this mean I'm good at my job?’

Jan 6, 2026 · 8 min readUpdated Jul 30, 2026

Comments7

Was this newsletter forwarded to you? Sign up to get it in your inbox.


I operate on the baseline assumption that I’m about to be fired at all times. It doesn’t matter how many managers tell me I’m doing great or how many positive performance reviews I receive, every piece of feedback gets filtered through my self-doubt.

I had asked AI about my career before, but never about my job performance. So when I finally did, I didn’t expect to believe its answer anymore than I believed when a human said I was doing okay.

It started as routine year-end planning at Every in mid-December. Kate Lee, our editor in chief, asked me to put together 2026 goals based on the performance of my articles. My entire career, I’d been told to use numbers to show results—in performance reviews, in job interviews—but I’d never had the data fluency to do that.

Yet when I fed the fourth quarter numbers on my articles to Claude and ChatGPT and started to see proof that my work was making an impact in terms of driving traffic and sheer output, some dormant part of my brain activated like a sleeper agent, and suddenly I was three hours deep in spreadsheets.

AI helped me do something I’d never managed on my own: believe I’m good at my job. If AI can democratize business intelligence for someone with my particular brand of professional self-loathing, it can probably help you understand your own value, too. Here’s how I ran the analysis.

Yearly review gave me proof of my performance

Step one of my AI analysis: manually exporting data from Every’s content management system into Google Sheets like it was 2009. Not exactly the future we were promised, but a necessary evil.

I uploaded the spreadsheets to Claude with this prompt...


Become a paid subscriber to Every to unlock this piece and learn about:

  1. The exact prompt Katie used to turn raw data into proof of performance
  2. What happened when she ran the same data through a second AI to prove the first one wrong
  3. The AI’s response when asked point-blank: “Does this mean I’m good at my job?
Create a free account to continue reading

The Only Subscription
You Need to Stay at the
Edge of AI

The essential toolkit for those shaping the future

"This might be the best value you
can get from an AI subscription."

- Jay S.

Every ContentEvery Content
AI&I PodcastAI&I Podcast
MonologueMonologue
Every AgentEvery Agent

Join 100,000+ leaders, builders, and innovators

Community members

Already have an account? Sign in.

What is included in a subscription?

Daily insights from AI pioneers + early access to powerful AI tools

PencilFront-row access to the future of AI
CheckIn-depth reviews of new models on release day
CheckPlaybooks and guides for putting AI to work
CheckPrompts and use cases for builders

Related Essays

Comments

You need to login before you can comment. Don't have an account? Sign up!

We use analytics and advertising tools by default. You can update this anytime.