September 23, 2026
Hi Everyone,
The promise of AI is that your team gets more done without growing. Whether that's happening on your team right now is surprisingly hard to know. People who talk a lot about AI aren't always the ones using it well.
Today we're sharing five 1:1 questions that show you where each team member stands, and what to do with the answers.
Five AI questions for your next 1:1
Use them in your normal 1:1s, one or two per meeting.
1. "Show me something that went out with AI's help."
You're listening for a finished piece of work: a proposal a client received, an analysis your leadership team used, code that's running.
At Shopify, a sales rep with no coding background built a small tool that pulls a prospect's website data, compares it against Shopify's speed benchmarks, and writes the talking points for the call. Site audits that used to take hours of manual work now run on their own.
2. "What did you stop doing?"
You're listening for a task that disappeared: a status report that writes itself, a first draft nobody types anymore. In BCG's survey of 11,749 employees this year, the biggest time savings came from companies that changed the process itself. Where AI was added on top of the old process, the savings were far smaller.
3. "Where has AI let you down?"
AI makes mistakes and hallucinates. People who use it every week have run into these issues and can tell you about a task they've stopped trusting it with. Someone with only praise for AI hasn't given it anything difficult yet — or they’re not using it critically enough.
4. "What did you check before it went out?"
A strong answer describes what they fixed before sending.
Sending AI output as-is just moves the work to someone else. Researchers at Stanford and BetterUp call this "workslop": it looks finished, but whoever receives it has to do the thinking. In their survey, each piece of workslop cost the receiver nearly two hours of checking, correcting, or redoing it.
5. "Where does the saved time go?"
In the same BCG survey, 42% of frontline employees who use AI regularly saved a full day or more per week. Two-thirds said they get little or no guidance on what to do with that time.
If they don't have an answer, that's not on them. It just means nobody has said what the extra time is for. Pick something together before the meeting ends.
What to do with the answers
When someone shows you good work, help the rest of the team learn from it. Give them 15 minutes in a team meeting you already run to walk through one piece of work from start to finish.
Credit from you, in front of the team, is what makes it safe to talk openly about using AI.
When someone is still practicing, give them a concrete next step. Pick one recurring task from their week, pair them with a colleague who's further along, and let the two build the AI version of it together. Then, follow up in a few weeks to check on their progress.
And if nobody on the team has much to show, the problem may not be the people. Ask whether anyone ever identified the tasks AI should handle. If the answer is no, pick one recurring process, decide together where AI helps, and run the questions again next quarter.
This only works if it's safe to answer
The questions will feel like a test if people sense their answers count against them. So go first: answer the five questions about your own week before you ask anyone else, including where AI let you down. In the Atlassian experiment, the stigma around admitting AI use nearly disappeared at companies where leaders talked openly about it themselves.
Go deeper
👉 Atlassian: New research shows honesty about AI use at work is backfiring — read this before your next team meeting to understand why your most capable AI users may be the quietest about it.
👉 First Round Review: From memo to movement: Shopify's cultural adoption of AI — see the kinds of shipped work you're listening for in question one, from people with no technical background.
👉 Axios: AI "workslop" is crushing workplace efficiency — a five-minute read on the Stanford numbers behind question four, worth forwarding to anyone who pastes and sends.
👉 BCG: AI is reshaping jobs faster than companies are reshaping work — use this when you're deciding where your team's saved hours should go.
Coming up tomorrow
In tomorrow’s issue, we’ll cover the three questions to ask before you welcome a former employee back.
P.S. If you find someone with great answers to all five, you may have found your AI champion. We wrote about what to do with that person here.