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Issue 19 · Say What It Is

An agent that hands work back to a person owes them the reason, the evidence and what it could not check.

Hi friend,

Last week I asked what word in your product means two different things to two different people. Hold onto yours, because that was the first of three layers, Design for Meaning, and this issue is the second, Design for Context.

Context has two sides. For the agent, it is what travels from one step to the next. For the person, it is what is on the screen at the moment the work comes back to them, and that second side is where human-centered design lives in an agentic workflow. Most builds spend everything on the first and leave the second to whatever the log happens to say.

I spent the week on that second side, inside Orinyx. I posted one of its failures where developers could pick it apart, merged the first changes that came out of it on Sunday, and did all of it with two AI coding tools at once.

This week

  • 🔨 Built Wrong, an Orinyx failure I posted for developers to pick apart, what they told me, and five moves for designing the handover

  • ⚡ One Slot, why I'm running Claude Code and Codex on one product, each in its own slot

  • 🌎 In the News, three pieces from the last five months that read like a design brief

  • ✅ Before You Ship, the ten-second return test

  • 💻 Prompt for Productivity, read your own handback as a stranger

  • 🗓 Open Calls, my Clock In to AI class, eight online and US-wide events, three Kansas City rooms, three hackathons and five startup calls

🔨 Built Wrong

The build I see most treats human-centered AI as keeping a human in the loop, which usually means an approve button at the end. Anthropic showed what that button is worth in August. Users approve 97% of permission prompts in Claude Code, and in a test with 1,053 paid professional testers, people caught 13.6% of the clearly dangerous commands slipped in among them. Those are Anthropic's figures for its own product, from testers who knew they were being evaluated, so hold them loosely. Read it

The end of the line is the last place to start. Human-centered design starts before the interface, with four questions. What does nobody want to do anymore? Automate that. What does the person do that nothing else can? Amplify that. Where does the automation run out? Design that handover on purpose. And who owns the system once it is running? Name them.

I wrote up the full approach on DEV, which starts from your role and what you want to keep doing, hands off what you don't, then points the AI at the biggest pain point in the work you kept. Designing Around What You Want to Keep

I learned how much this matters from one of Orinyx's own failures. In testing last week we sent it an order for acetaminophen at 1,500 mg every four hours, and six doses in a day is 9,000 mg. Orinyx missed the total, lost the frequency along the way, and still answered in reassuring language when its checking was incomplete. A confident output looked exactly like a verified one.

So I posted the failure in two developer communities on Reddit and asked people to help test it. The answers ranged from skeptical to precise.

  • A model can look like it checked the numbers without checking the logic that connects them, which is the acetaminophen miss in one sentence.

  • Where a rule already exists, nobody needs a probabilistic model to apply it. One developer laid out the split, interpret the order into normalized fields, then verify with reproducible calculations, explicit uncertainty and regression cases checked against clinically appropriate expected outcomes.

  • Another said to stop hand-writing scenarios. Generate every combination of dose, frequency, unit and boundary value, implement the calculation twice independently, and treat any disagreement as a finding.

  • One described an internal agent that started reading the wrong database tables after deployment. The answers stayed plausible, so it took a while to notice, and development and operations argued over whose problem it was. The bad output was only half of it. Nobody owned the monitoring. Another argued that every production agent needs a registered identity, a named human owner, execution traces and documented policy decisions.

  • Some pushed back hard, asking whether informal testing belongs in healthcare at all and what reference standard Orinyx checks against. Fair questions. Reddit gave me informal technical feedback on synthetic data, the physician group is in design sessions, and formal clinical validation is a separate undertaking that neither of those replaces. A verification tool owes people a stated scope, its reference standards and its limits.

  • And one developer volunteered to try to break it.

Letting the people who will use a thing, and doubt it, challenge it while it is still soft is participatory design. It also gave me five moves, and none of them belongs to healthcare alone.

Decide who judges before you build. For every decision in the workflow, pick its owner, a person's expertise, a deterministic rule or a model's interpretation. Use a model where interpretation is needed and a rule where a rule already exists. In Orinyx the arithmetic and the label rules are deterministic, and no language model takes part in a verdict.

Make "I can't verify this" a real answer. On Sunday we merged the changes that stop the reassurance. The acetaminophen order now gets an answer that leads with not verified and says why. An order written in millilitres with no concentration names the missing fact. Each result from the engine carries a coverage line saying, drug by drug, whether Orinyx had a dose rule to check against, and a number the parser could not place is listed as unread instead of disappearing.

Check the work, not the presentation. The result now quotes the whole label sentence it was checked against, never a slice. And the next change, decided on Sunday, does the daily arithmetic for plain fixed schedules, says the assumption it made, round-the-clock dosing and the total it reached, and flags anything above the label's daily maximum. As-needed orders, ranges and "while awake" still abstain, because there the arithmetic would be a guess. It lands in a later release, once the as-needed handling is airtight.

Keep people in the whole build, not the last meeting. Developers testing, physicians designing and a named owner watching once it runs each catch a different failure, and an approval meeting at the end catches almost none of them.

Treat feedback as architecture. The boundary cases, the duplicate calculation and the regression set from those threads are going into the test plan I am building with Codex, which is where One Slot picks up.

My reason for the arithmetic decision was simple when I gave it. "Orinyx should never drop the ball. It should say what it is." Human-centered AI means giving the people around a system the information, the authority and the chance to make their part count. A stated assumption gives them something to push back on, and a reassuring silence gives them nothing.

⚡ One Slot

The One Slot Rule is that every job gets one slot, and a new tool has to take it from whatever holds it now. This week I am holding myself to it, because I am running two AI coding tools on one product, and the only way that works is if each one has its own slot.

Claude Code, running Claude Fable 5.1, holds the engine. I have used it for a long time, it has all the context, and it does the orchestration and builds the main components. Codex, in ChatGPT and running GPT-6 Astra, holds the Arena, the part of Orinyx being built around what developers told us they want from an evaluation tool, and there is more to come on that. Codex also fills in the blanks, brainstorming with me, go-to-market research, and helping me write the test scripts. The four changes above came from tests Codex helped me script and Claude Code built into the engine.

What is the job. Two jobs, kept apart. Claude Code builds and orchestrates the verification engine. Codex builds the Arena and helps me plan what we test.

Can it do that job, not can it do more. This is the first time I have used Codex for real work rather than a quick test, and I picked it for a plain reason. The classes I teach can only use Codex or Gemini, so if I am paying for one, I want to know how it holds up on a real build. The part I did not expect to love is talking to it. I went through the feedback from my survey questions with it out loud and planned test questions around it, and it felt like collaborating with a person.

What does it touch that is hard to undo. Each other's work, if I let them. Claude Code has everything and Codex has a slice, so they work in separate places, Codex on its own branch, and nothing reaches the engine until I have read it and merged it myself. I am in the middle, carrying messages between the two.

What would have to be true to let it run unwatched. More than is true now, so I watch both. It is my own version of an AI judge, with one model helping write the test, the other changing the code, and me deciding whether either of them is right, which is the only arrangement the developers above would trust. Inside the product, no model judges anything. Would I recommend two tools on one build? Maybe, depending on the build. Right now the orchestration is doing a good job, I do not have agents set up in Codex the way I do in Claude yet, and eventually Stellar Agents will fit in there. More to come as it runs.

🌎 In the News

Three pieces from the last five months that read like a design brief for the same problem. I could not find a fresh agent-oversight story from the past seven days that I could trace to a primary source, so I would rather give you these than pad.

  • 🧩 What oversight actually needs
    Data & Society argues that "human in the loop" names who is responsible without the conditions that make oversight possible. The person has to know what to look for, see the relevant part of the work, be able to decide and act in time, and a long action log can show every step without saying why. Read it

  • 🧠 Oversight skills fade
    A position paper from Margaret Mitchell, Avijit Ghosh and Samir Passi argues that the way agents are built and deployed makes human oversight harder, and that heavy use of automation weakens the very judgment oversight depends on. It has no experiments, and it is a design argument worth arguing with. Read it

  • 🔎 How developers actually review
    Microsoft researchers interviewed 17 experienced developers, mostly at one large company, and found they rarely watched an agent while it worked. They reviewed afterwards, leaning on shortcuts like treating the agent's plan as a stand-in for its work and treating passing tests as proof. The authors read those as reasonable responses to time pressure, which makes it a design problem more than a discipline problem. Read it

✅ Before You Ship

Run the ten-second return test on one workflow you already have. Find the last thing your agent handed back to a person, whether that is a notification, a summary, an approval request or a queue item, and open it the way the recipient sees it, with nothing else on the screen. Start a timer. In ten seconds, can you answer five questions without opening anything else?

  1. What happened?

  2. What is being asked of me?

  3. Which part is urgent, and which part can wait?

  4. What did the system check, and what is it only claiming?

  5. Why did this come to me and not get handled?

Any question you cannot answer in the time is a missing fact in the handback, and it is a fact the agent had and did not pass along. Add the most useful one first, which is usually number five.

💻 Prompt for Productivity

Read your own handback as a stranger.

I'm going to paste what one of my AI workflows hands to a person
when it needs them: a notification, a summary, an approval
request, or a queue item.

[paste the handback exactly as the person sees it]

Pretend you are the person receiving it. You have ten seconds
and no memory of the earlier steps. Then answer:

1. What do you think happened?
2. What do you think is being asked of you?
3. What would you do first, and what makes it feel urgent or not?
4. What would you need to know that is not on the screen?
5. What does it say the system verified, and what does it only
   claim?

Mark every answer you are guessing at. Do not rewrite the
handback yet. When you finish, list the three missing facts in
the order you would add them, and ask me one question about the
workflow behind it before you answer.

WHEN TO USE IT. Before you add a second agent to a workflow that already hands work to a person, and any time a teammate says "I just click approve."

WHAT IT DOES. It turns the handback into something you can argue about, one missing fact at a time, from the seat of someone who was not in the room.

TIP. "Mark every answer you are guessing at" is the line that matters. Where the model guesses is exactly where a tired human will guess too.

Lex

🗓 Open Calls

My class

  • Thursday, November 12, 6 to 7:30pm Central. Clock In to AI, my live 90-minute working session on Google Meet, $95. There are plenty of free ways to learn about AI, and the way that sticks is doing it, so this class is hands on. You get access to Thinkific before we meet, with prework and custom prompts, then in the session you build one reusable brief for a task you do at work and learn to spot a confident wrong answer. Bring one task you find tedious. Signing up gives you a credit toward the full Working 9 to AI course, starting January 2027, dates to come. Save your seat for Clock In to AI

This week, online and across the US

  • Today, October 19, 2pm Central. Carina Hong on AI that can prove its work, Stanford Digital Economy Lab, Zoom or in person. Details

  • October 20 and 21. PyTorch Conference keynotes, livestreamed from San Jose with a free Linux Foundation login. Livestream

  • October 21, 7:30pm Central. Microsoft Reactor, Beyond Vibe Coding, formal verification for AI-generated code. Register

  • October 22, 11am Central. Product School, Beyond Technical Evals, measuring trust, control and understanding in AI. Free with an account. Register

  • October 22 and 23. AGNTCon and MCPCon North America, the AI agents conference, San Jose. Paid. Details

  • October 25, 1pm Central. Keys You Shouldn't Hand Your Agent, which agent actions should always need a person's approval. Online. Luma

  • October 27 and 28. ODSC AI West, free virtual pass, limited spots. Details

  • October 29, 9am Central. All Tech Is Human's Responsible Tech Summit, free livestream. Details

Kansas City

  • October 21, 9am. 1 Million Cups KC, Kauffman Foundation. Free. Details

  • October 29, 5 to 9pm. Let's Build It. Kansas City, from Intuidy and Startland News at Spark Coworking, hands-on breakouts with people who have shipped. Free. Register

  • November 5, 6pm. DevDay Exchange KC, a community recap of OpenAI's DevDay. Luma

Hackathons

  • October 19 to 25. DEV's Hacktoberfest Open-Source AI Challenge, Week 3. Build something new with open-source AI at its core, theme revealed at launch, and a new challenge opens every Monday through October 31. Details

  • October 26, 11:45pm Pacific. OpenCV AI Competition 2026. Rules

  • October 30, 10:45pm Central. Qloo Agentic Hackathon, 18 and over. Rules

Startup calls

  • October 31. IV Accelerator, pre-seed and seed AI healthcare startups in the US or Canada, $25,000 on acceptance. Details

  • November 2. Y Combinator Winter 2027. Apply

  • November 17. Tory Burch Foundation Fellows, women-owned businesses. Details

  • December 1. MedTech Innovator 2027, $15,000 program fee if accepted. Apply

  • Rolling. Digital Sandbox KC, up to $20,000, no equity, KC metro. Details

Tool verdicts, templates and reference material live on the site at charmthirteen.com.

🔭 Next From Me

Next week is Design for Trust, the last of the three layers, and the one that decides whether anyone gets to rely on the other two.

💌 One Ask

Software engineering is still here (and so are Python developers, shout out to my fellow Python devs), and like everything else, the role is changing shape. One new shape is the forward deployed engineer, who can walk into any industry, understand why a business problem exists, and build the right fix, which is often not an agent. That is what Houston We Have a Build teaches, a hackathon bootcamp I am running with SOTV Creators Collective for middle schoolers, high schoolers and early college students, enrolling for 2027.

Know a young person who would want it? Email [email protected] or pass my information along.

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