Talks · S Anand AIPL 2026 · Module 5, Session 1 · 18 Oct 2026 · audio, 1:53:02
When Do You Let AI Act? · A workshop that didn't go to plan

The Roll Call

Thirty-three experienced professionals said how far they let AI go. Most said they check everything. An hour later, a question went quiet, and the instructor let AI act on the room. This is the story of that Sunday morning, built from the recording, the live survey and the Zoom chat.

Anand S · AI Product Leadership (AIPL) program, LeadUp Universe with E&ICT Academy, IIT Kanpur
Sunday 18 October 2026, 9:00 AM IST, on Zoom · Session 1 of 3 · about 49 people joined over the morning

Reading the labels: said live the room measured research our reading · 0:43 plays that moment
Nine-panel comic titled 'When Do You Let AI Act?' for AIPL Session 1, 18 Oct 2026. Panels: a workshop opening with a quick survey on Zoom; an autonomy ladder from asking AI for advice, to a first draft, to letting it work with checks, to acting without checking; AI getting smarter while the cost of intelligence falls; Anand holding a phone full of tiny 'pocket professors'; a jagged cliff of tasks AI is amazing at and stumbles on; a locked gate labelled TRUST surrounded by hallucinations, weak context, bad fits and fear of wrong actions; guardrails of multiple agents, benchmarks and rules; Anand celebrating a tax refund found by AI-assisted checking; and a closing panel asking what evidence would make a task reliable enough to act on.

The workshop, as a comic

An illustrated summary of the session's arc: a ladder of autonomy, the falling price of intelligence, the jagged edge, the gate of trust and the guardrails that might open it.

It tells the session the way it was planned. It leaves out the quiet stretch that this page is mostly about.

AI-generated illustration. The refund amounts in panel 8 are invented and are not the real figures. Click to enlarge.

The full session on Zoom, including the breakouts. Download video
The video is a separate recording from the audio this page is built on: it starts at a slightly different time and keeps the breakout, so its timestamps won't match the ▶ links.

Act I · The poll

Nine o'clock on a Sunday

The host finishes the introduction, and Anand skips the usual opening slide. 0:43 “The session is largely interactive… It's more workshop mode than lecture mode.” A link goes into the Zoom chat, a QR code goes up on screen, and he says he'll wait until about twenty of the “20-odd participants” have answered.

The four questions were short, and every one was about delegation.

Q1 · one click
How far have you gone with AI?

In the last 30 days, which is the most you have done?

  • I haven't used AI
  • Asked AI for ideas or answers
  • Used its work, checked everything
  • Used its work, checked only some
  • Let AI do something without checking
33 answered
Q2 · a few words
What is one task you did not ask AI to do last week because you thought it couldn't do it?

It might actually be possible. If none, write “Nothing”.

29 answered · 10 wrote “nothing”
Q3 · two versions
Would you trust this AI?

An AI checks 100 expense claims and decides which can be paid. AIt gets 95 right. BIt gets 5 wrong.

  • Give advice only
  • Decide, but ask before paying
  • Pay, a person checks some
  • Pay, with no checks
31 answered, each saw one version
Q4 · one click
Which AI decisions would you check?

AI makes 100 decisions. You can check only 10. Which 10?

  • The 10 AI is least sure about
  • The 10 where another AI disagrees
  • The 10 where a mistake would cost most
  • Any 10 at random
  • Wouldn't use AI unless I could check more
33 answered

Question wording from the live LiveForm survey (the form ran from Anand's laptop and is no longer open). Q5 to Q7 were added during the session.

The QR code didn't open for Mukul, who unmuted to say so 5:51. The link was posted again, and then again. said live At 9:06: “Okay, we've crossed 20. That's a good sign.”

The answers to the first question make an unusually tidy picture of a room of senior professionals in October 2026. Nobody had avoided AI, and almost nobody had let it act on its own.

Where the room stood on the ladder

the room “In the last 30 days, which is the most you have done?” One dot per respondent, using each person's final answer.

4 · Actlet AI do something without checking
2 / 33
3 · Auditused its work, checked only some
9 / 33
2 · Draftused its work, checked everything
18 / 33
1 · Adviceasked AI for ideas or answers
4 / 33
0 · Nonehaven't used AI
0 / 33
Source: the live LiveForm survey, 33 respondents to Q1, using each person's latest submission; 35 accounts answered at least one question. When the results first went on screen 9:33 there were 23 answers. The rung names follow the four levels Anand showed later 41:14. These are self-reports of the most someone had done, not of how they usually work.

Anand read the spread as a matter of task, not temperament. said live 10:37 “It depends on which task and what level of authority you want to delegate.” He then gave the room its first nudge: if this week you only asked AI for ideas, try one rung higher, “let it fail because you're checking anything anyway. And where it fails, you know this is the limit.” 11:20

The page comes back to that sentence at the end, because the session closed on the same idea. Find the limit by watching where things fail, and write it down.

A thousand professors in your pocket

Next came the reason to bother. Anand opened his LLM pricing chart, which plots cost per million input tokens against capability. The scale he gave was that all the Harry Potter books together come to roughly a million tokens 13:31. In March 2023, GPT-4 charged $30 to read that much. By July 2024, GPT-4o mini read it for 15 cents at about the same level. said live “We have a model that is 200 times cheaper for the same intelligence” 15:40.

Shown live 13:06 · LLM pricing
sanand0.github.io/llmpricingOpen in new tab ↗
The chart Anand walked through: cost per million input tokens against capability, month by month since March 2023. Use the slider to replay the drift toward the top left, cheaper and smarter, that the “200 times cheaper” line describes. Live page; today's models and prices may differ from the session.

“You go to a professor and say, ‘I want you to read this research report which is as big as the entire King James Bible. How much will you charge me for it?’ And they say, ‘15 cents. And I'll have it in the next few seconds.’”

Anand 16:55

That set up the tension that runs through the rest of the session. The chart says capability is now cheap. Yet when asked, more than half the room said they still check every line. Anand put it as a question, not a criticism 17:21: how far would you go with a tenured professor? Would you ask them only for ideas? Check everything they hand back? Or give them the job outright?

What the chart can and can't say

our reading The labels “middle schooler”, “PhD candidate” and “tenured professor” map benchmark scores onto school grades to make them easy to picture. They do not show that a model is equivalent to a person with that degree. The prices are list prices for input tokens at release. The 200× figure ($30 → $0.15) is correct arithmetic for those two prices.

“I've tried this and it works”

The second question asked for something more personal: one task you didn't give AI last week because you thought it couldn't do it. Anand read the answers aloud 18:38: arranging meetings, ABAP syntax, converting Cypress tests to Playwright, deep research “because it mentions some files that don't exist”, booking flight tickets, Workday, legacy systems, high-level design diagrams. the room Ten of the 29 people who answered wrote some version of nothing.

The room's “AI can't do this” list, and who in the room said otherwise

the room The 14 tasks read aloud from Q2. Tap one to see what people in the session said about it.

someone said it worksmixed reportsno one spoke up
Tap a task.
Tasks as Anand read them aloud 18:38. The colours come from what participants said aloud or in the Zoom chat, not from any test.

He pasted the rest into the chat and asked whether anyone had already done one of them successfully 20:10. That turned out to be the liveliest part of the morning. The same task was “impossible” for one person and routine for another.

Mukulnot yet

That “help arrange the meeting” is — it's I who told this… I have not yet gone ahead and given access to AI to help arrange the meetings.

23:42
Vaibhavworks

I wanted to leverage AI to see if I can arrange the meetings and all and it worked very well. Connected to Google Calendar or Outlook, it creates the meeting and sets up the context.

24:29
Akshikafails here

Copilot code reviews on legacy migrations raised comments that weren't valid: it was flagging something which was actually correct. She found Python reviews more trustworthy.

26:15
Ketakiworks, reviewed

Rather than asking AI to fix a sprawling legacy codebase, her team brainstormed with the code itself to plan the new architecture. A solution architect still reviewed it.

28:17
Lakshmiworks

She gives Claude or ChatGPT a long requirements document with many personas and gets back one diagram that turns four or five calls into a single shared picture.

30:27
Mrinmayworks, with context

As a line manager, he asks AI to rate award write-ups for his team. It works if you have a proper transcript and background.

25:39

Mukul had firsthand success with HLDs, LLDs and code reviews 22:12. Saurav pointed out that uploading a video is enough for ChatGPT to summarise it 26:55. Anand drew the conclusion carefully: maybe other people's standards are lower, or their tools, context or connections are different. said live “There may be opportunities for us to extend the capabilities of what we believe AI can do.” 33:10

Then he told a story that shows the difference better than any chart. Two people at organisations that had both deployed Microsoft Copilot gave opposite answers about whether it could book a meeting. One of them had permission only to read the calendar, not to write to it 37:24. Whether a task is “possible” depended partly on a setting someone in IT had chosen.

“When we have to let AI act, we also have to know whether it can act. And that answer changes with time and person.”

Anand 40:20

He gave this unevenness its usual name, the jagged edge of AI 36:26: better than humans at some things, useless at others, with a different edge for each person depending on their tools. research The phrase comes from a field experiment with 758 BCG consultants. On tasks inside GPT-4's capability frontier, consultants using AI finished 12.2% more tasks, 25.1% faster. On a task just outside it, they were 19 percentage points less likely to get the right answer than those working without AI (Dell'Acqua et al.; not cited in the session).

Shown live 36:26 · The jagged edge of AI
files.s-anand.net/pages/ai-jagged-edgeOpen in new tab ↗
The jagged edge page Anand used to explain why the same AI can be superhuman at one task and useless at the next, and why each person sees a different edge.

Then he tried an experiment on himself. He pasted the room's list into ChatGPT and asked it to check his own past chats for which of these tasks he had already done, ranked from most to least 37:57. He warned that “This will take ten minutes”, and the session moved on. our reading According to his notes afterwards, the ranking put research, code review and deep research near the top. It found little or no trace of booking flights, Workday, ABAP or a full Cypress-to-Playwright conversion. So even the speaker had an edge, and the room had just helped him find it.

Act II · Trust

Trust is not one thing

At 41:13 Anand drew the autonomy ladder. At the bottom you ask AI for advice. Next it drafts and you rework the draft. Then it does the job and you check periodically. At the top it does the job and you don't check at all. The ladder is the backbone of the comic above. In the session it lasted about a minute, and the next dozen minutes moved it in a different direction.

To show that where AI is good varies by kind of work, he shared his treemap of OpenAI's GDPval results 42:36. Experts set realistic work tasks, models and human professionals both completed them, and other experts blind-graded the results. said live For accountants and auditors, the best model (Claude) won only 24% of comparisons. For personal financial advisors it won 64%. For sales managers, GPT-5 won about 79% 44:25. measured Those figures match the win rates in the data behind his chart.

Shown live 42:36 · GDPval by occupation
sanand0.github.io/datastories/gdpvalOpen in new tab ↗
Box size is roughly total US pay for the occupation; colour is the best model's win rate against human experts (red: humans win, green: AI wins). Hover over accountants, personal financial advisors and sales managers to see the 24%, 64% and 79% discussed live. Click an occupation to read the actual tasks.
Read GDPval narrowly

research GDPval (25 Sep 2025) covers 44 occupations, and each occupation has only a five-task “gold” subset. Experts compared finished deliverables, produced in one shot. It doesn't measure whether an AI can safely take an action, handle private data, or carry liability. A 64% win rate on report-style tasks is not a licence to let AI move a client's money.

He then told a personal story about pushing AI one rung higher. He gave ChatGPT his auditor's draft tax filing, access to his accounts, and a simple question: does this look right? It found a large discrepancy in his favour 46:15. The auditor pushed back with a technicality. He passed her email back to the AI, which came back with a legal argument. The auditor checked with her senior, who agreed, and the refund came through 48:42.

“When I push AI to act on my behalf one step further, I literally make money, or at least literally don't lose money.”

Anand 48:46

our reading Look at what “act” meant there. The AI filed nothing and sent nothing. It read, argued and drafted emails. A professional, and then her senior, checked every step before anything happened. Despite the way it was told, it is a case of the second rung done well, with expert reviewers at each step. The pushing paid off because someone qualified was there to check.

Then the room complicated the ladder. Mukul, who has worked in commodities trading and consulting, pointed out that whether people feel ready is a separate question from whether the model is capable.

“I think it's a trust thing and the explainability which is holding us as humans to a certain extent… degree of trust and degree of confidence probably varies from person to person.”

Mukul 50:21

His own approach is cautious: test low-risk things, and learn from people who have already taken risks and tuned their setup. Ram then split trust in two and moved the discussion away from accuracy entirely.

“That trust is on your data, right? Then there is a trust on the actions.”

Ram 52:34

Ram talked about misuse: people asking AI for deepfakes, or for help breaking into accounts, because “AI doesn't really understand those, I would say, ethical boundaries of the outcomes” 53:35. He also talked about data. Every prompt goes to a company we can't see into, much as phone data quietly made us trackable. “Big tech companies are using this not only as a gold mine, but… as a leverage to control us.” 54:55 None of these worries goes away if a model scores better on a benchmark.

Trust 1 · Correctness

Is the answer right?

Error rates, hallucinations, benchmarks. This is the only one the rest of the session's demos measure.

Trust 2 · Authority

What can it set in motion?

Pay a claim, send an email, book a meeting. What are the limits, and can it be undone? This is Mukul's meeting invite and Ram's “trust on the actions”.

Trust 3 · Data

Where does what I give it go?

Confidentiality, retention, who profits. This was Ram's main worry, and several written answers echoed it.

Trust 4 · Reliance

Do people accept the right answers and reject the wrong ones?

Explainability and calibration. This is Mukul's “degree of confidence varies from person to person.”

our reading This split comes from this page, not the session, though each card is grounded in something said in it. Compare NIST's AI RMF Generative AI Profile, voluntary guidance that treats privacy, security, reliability and accountability as separate risks. On reliance, Cao, Liu & Huang (2024) found that showing calibrated uncertainty was not enough on its own to make people rely on AI appropriately.

Anand agreed, said live “And trust does form an important part of this” 55:33, and before going on he posted one more question to the same form. It was the most interesting question of the morning, and the hardest:

Q5. Why do you think people didn't ask AI to do that task in Q2? What made them think that this is not possible with AI?

He said he would wait until he had about twenty-five answers.

Act III · The wait

Eighteen minutes

The first answer to Q5 came in about ninety seconds after it was posted. “Just seeing, we have five responses so far. I'll wait till we have about 25” 58:29. Lakshmi wrote in the chat to ask whether the audio was working. Someone confirmed it was. “Eight responses so far” 59:12. A participant who had dropped out and rejoined asked what they had missed, and Anand answered honestly: “We were completely silent for one or two minutes. We're just waiting for people to fill out…” 61:35

“We have a dozen responses so far. I'm waiting until we get to 25” 62:13. The next eight minutes are the hardest part of the recording to sit through. About four-fifths of that time is silence, broken only by the count: “We're kind of stuck at 14 responses” 63:42, a thank-you to “the 15th person”, “Stuck at 18” 66:36, “20 responses so far” 68:17.

If you want to feel what that was like, press play on 63:00 and keep reading.

Two questions, two climbs

Cumulative respondents, by minutes after each question was posted. Dashed lines show roughly how many people were in the Zoom room at the time. Times come from the form's submission timestamps, matched to the recording to within about 20 seconds.

Q1 · “How far have you gone with AI?” (one click)Q5 · “Why do you think people didn't ask AI…?” (written answer)
5 answers “I'll wait till we have about 25.” 58:29
A dozen, then eight minutes of mostly silence. Answers kept arriving the whole time. 62:13
The roll call, at 21. “I'm going to do something little more dramatic.” 70:37
25. “This is the first workshop where I've actually had to do this.” 73:47
Source: LiveForm submission timestamps (first submission per person), aligned to the recording using the counts Anand read aloud at 9:18, 58:29, 59:12, 62:15 and 72:44, which match to within about 20 seconds. Headcounts: “20-odd participants” 3:32 and “47” 57:18, both as said live. One more Q5 answer arrived after the breakouts, for 28 in total.

The chart tells a slightly different story from the room's mood. The quiet on the recording didn't mean nothing was happening. Between the counts, Q5 answers went from 12 to 21. People were typing. Q1, a single click, reached 20 in seven and a half minutes. Q5 asked for a reason, in writing, an hour into a Sunday-morning session, and it took about twelve and a half minutes. The real difference is the share of the room: Q1 reached roughly everyone who was there, while Q5 levelled off at about half of a room that had more than doubled.

our reading Nobody knows why the other half didn't answer, and this page doesn't guess. A question that asks people to explain other people's hesitation is harder to answer than a multiple-choice one. People who join late, step away, or plan to watch the recording later all look the same on a response counter.

The roll call

At 70:37 Anand changed tack.

“Okay, we are at 21 responses still, so I'm going to do something little more dramatic. What I'm going to do is ask ChatGPT who are the people who have responded to some of the other questions.”

Anand 70:37

ChatGPT compared the form's responses and listed thirteen people who had answered earlier questions but not Q5. Anand read the names aloud and gave everyone a way out: you may be in the process of answering, that's fine… you refuse to answer is also perfectly fine. We don't repeat the names here. Replies came into the chat: “answering”, “answered”, “submitted”, and one that said “I answered.. I think”. Within about three minutes the count reached 25.

“This is the first workshop where I've actually had to do this, take attendance so to speak, like ever. I'm going to need one minute to think about that.”

Anand 73:47

our reading Look again at what just happened, in a session called When Do You Let AI Act? For an hour the talk had been about delegating to AI in the abstract: claims, contracts, meetings. The first time AI output was acted on immediately, publicly, and in a way that affected people, it was this list of names. Measured against the morning's own questions, it was a reasonable call. A wrong name costs a moment of awkwardness and is easy to correct. Anand hedged every name, and the room could, and did, answer back. That is the third rung, letting AI act while people check some of it. “I answered.. I think” is that check in action: a person in the loop, gently unsure whether the machine's list was right.

What he asked ChatGPT next, live, on screen 74:28

“I'll tell you my problem and once I maybe narrate the problem, it will get resolved.”

You know that AIPL session that we were discussing? It was planned for two and a half hours. The first 45 minutes I was monologuing… when I introduced question 5, it was a struggle. It took about 15 minutes to get 25 people to answer the question and I for the first time had to ever almost do a roll call, call people by name, and ask them to fill it in. That tells me that the workshop format is not really working. Maybe it is the time, that is the duration, or the timing that it is morning on a Sunday or whatever… one is it's getting recorded, so people can just turn it on and listen to it later on, which is a perfectly reasonable way of learning… But in that case I also need to have some metrics of calibration so that I can tune it accordingly. So help me with this. Frankly I don't really know even how best to ask this question, but you have a reframe question skill, so reframe my question accordingly…

What came back paraphrased from his private chat log

ChatGPT reframed the problem as how to make one session work both for the people taking part live and for the people who will watch the recording, and how to tell whether either group learned anything. It said the evidence did not yet show that the workshop had failed. It suggested he stop chasing participation and stop the roll calls. It proposed checking whether Q5 had simply been harder or easier to miss, and measuring three things separately: participation, learning (the same decision problem before and after) and application (what people actually delegate a week later).

It ended by asking whether the quiet majority learned less than the active minority. Nothing collected that morning can answer that.

There is something funny about this: an instructor who teaches people to use AI treats his own engagement problem as one more AI task, out loud, in front of the class. It is also the most honest moment in the recording. He goes from a conclusion (“the workshop format is not really working”) to an admission that he doesn't know how to ask the question, and the answer he gets back pushes him further: a response count is not evidence of learning.

The answer arrived while the session moved on. Anand didn't call the roll again. When he returned to the Q5 answers 77:10, it was to read what they said.

What the room said was holding it back

Q5 asked people to explain why others hesitate, which is a polite way of asking about yourself. Here are all 28 answers, sorted by what they blame. Fewer than a third of the reasons were about the AI getting things wrong.

Why people don't hand a task to AI, in their own words

the room 28 written answers to Q5, grouped by theme. our coding One answer can fall under two themes. Treat the groups as rough, not exact.

About us · what people know and how they work · 12

Don't know what AI can now do
5
Don't know how: context, connectors, prompts, which model
5
Not worth the effort, or a hybrid is better
2

About consequences · what could go wrong if it acts · 9

Confidential data, privacy, compliance
4
Money, production systems, side effects
4
Guardrails and misuse
1

About the AI · it might be wrong or can't do it · 8

Hallucinations, can't verify, bad past results
5
A real capability gap (negotiation, taste, judgement calls)
3
Source: the latest Q5 answer from each of 28 respondents. The coding is this page's own, not the session's. ChatGPT's live coding of the same answers ranked “reliability” first, by a margin too small to matter. No individual answers are reproduced.

Two answers stand out. One respondent suggested that “our mental model is evolving much more slowly than AI's actual capability”. In other words, people judge today's AI by yesterday's experience. That fits the pricing chart better than anything Anand said about it. Another pointed out something no accuracy test would catch: ask an agent to check flight prices too many times and the fare may go up. Simply acting has side effects, even when every answer is correct.

Anand picked out the answer most suited to the next demo: said live “some people say it's because there's hallucination” 77:41. That's a fair way into the second half. The chart above is a reminder that hallucination was only one item on the room's list of worries.

Act IV · Earning autonomy

Five models, one answer

Anand's first answer to hallucination came from a support-desk problem. said live He described it as a client with lots of calls and chats who wanted AI to sort them into queues, cheaply and accurately 78:51. One example was “What do I need to do to register?” Some models filed it under Create account. The right queue was Registration problems. About half the models got it right.

The useful finding was not that models make mistakes. It was that they make different mistakes. In his correlation grid, most pairs of models barely agreed on which messages they got wrong 80:28. So he asked several of them and accepted an answer only when they all agreed.

What “99.3% accurate” actually costs

1,000 incoming messages. Choose how many independent models must agree before an answer is accepted automatically. Messages where they disagree go to a person.

Models that must agree:
719
accepted automatically
281
sent to a person because the models disagreed
≈5
accepted, but wrong. 0.7% of the accepted ones
measured Published results from Double Checking Hallucinations: 11 LLMs (one consistently weak model dropped) classifying Kaggle's public Customer Support Intent Dataset. Error among accepted answers: 14.1%, 3.7%, 2.2%, 1.5%, 0.7%. Share sent for review: 0%, 12.6%, 18.5%, 23.0%, 28.1%. The grid applies these rates to 1,000 messages, rounded. It is one classification benchmark, not a promise of accuracy for any other task.

Live, he gave the client's side of the deal 81:09. With five models agreeing, “I could go to the client and tell them I'll get you 99.3% accuracy. But that is only if all the models agree. 28% of the time the models won't agree.” 82:14 That means 72% of the work is done automatically, and the cost of five models is, by his rough estimate, about 2% of one person's cost.

Then came the line that reframes who should be doing this work:

“Managers are much better equipped to make AI more reliable than engineers because engineers are working with deterministic systems, managers are more experienced with indeterministic systems.”

Anand 83:39

Banks use maker and checker roles. Elections rely on many voters rather than one. “Humans are not reliable.” The processes we already use to manage unreliable people carry over to models. For a room of people who manage teams for a living, this was probably the most useful sentence in the session.

Four things to keep straight
  • 0.7% is the error among the 72% that were accepted, not across everything. The other 28% still need someone to decide them.
  • Reviewing 28% of the messages isn't the same as 28% of the work. The disagreements are probably the harder cases.
  • The published experiment uses a public dataset. The client story is how the speaker framed it. We haven't seen any client's data, savings or costs, including the “2% of a person”.
  • Agreement only helps if the errors are independent. Models trained on similar data, a shared bad prompt, or inputs unlike the test set can make five models wrong in exactly the same way.
Shown live 78:51 · Double Checking Hallucinations
sanand0.github.io/llmevals/double-checkingOpen in new tab ↗
The write-up behind the grid above, with the per-model accuracy chart, the model-correlation matrix Anand showed (yellow means two models agree), and the effort-versus-error table.

A good tip that failed its test

The second technique was simpler: before you adopt a piece of advice, test it. Anand's example was a popular prompting tip from Andrew Carr: tell the model to report only in ASD-STE100 Simplified English, the controlled language used in aircraft maintenance manuals, so its answers are easier to follow 84:20.

Andrew Carr on X · 27 Jul 2026
“The fix for this is to say: only report to me in ASD-STE100 Simplified Technical English”
Quoting a post that complained: “me, begging, crying, on my knees: ‘Please just use plain english, I don't understand what you're saying.’” followed by a dense paragraph of Claude jargon.
~2,100 likes · ~844,000 views when checkedView on X ↗

“The question of is AI reliable is something that I often ask of humans as well.”

Anand 84:58

So he ran six real prompts with and without the instruction. He had separate ChatGPT windows judge each pair for correctness, mechanisms, caveats and calibration, and skimmed the results himself. said live The simplified versions lost almost everywhere 86:09. They won once on correctness and once on calibration. His new habit: let the model think in its own way first, and only then ask it to restate the answer simply.

How far the result goes

measured The write-up (1 Aug 2026) covers six tasks on one model (GPT-5.6 Sol). Pairs were judged in both orders by a model from the same family. That is a small test with an LLM judge, not a general law about simple English. “Think first, simplify later” is sensible advice, but the experiment didn't test it directly. The more general point stands: a tip that sounds obviously right can still make things worse, and it costs about an afternoon to find out.

Shown live 84:20 · Simple Writing Hurts Thinking
www.s-anand.net/blog/simple-writing-hurts-thinkingOpen in new tab ↗
Anand's write-up of the test, with the per-dimension scores for each of the six tasks and the prompts used.

Contracts that compile

The third technique gives prose the main advantage of code: an automatic signal for whether a result is correct. said live “Iterating as a human is time and effort. A compiler has the advantage that it can provide a correctness signal automatically” 88:45.

His first example was an InsurLE demo. InsurLE is a controlled language in which a motor-insurance policy becomes rules like a driver is fully eligible if they are age-eligible, license-compliant and have an acceptable driving history, down to age > 21 and months of experience > 12 90:07. An agent then checks a claim against each clause. For a sample claim filed in June 2024, the license was fine, the vehicle was authorised, and the blood alcohol was 0.14 against a limit of 0.08. The claim is rejected, and the record shows which clause failed 92:19.

Shown live 89:17 · InsurLE demo
mynkpdr.github.io/insurle-demoOpen in new tab ↗
Try the demo Anand used: a motor-insurance contract, its InsurLE rules, and sample claims. Check the claim from June 2024 and watch the blood-alcohol clause fail.
A correction

In the session InsurLE was described as coming from Cambridge. research It comes from work associated with Imperial College London: Cummins, Dávila, Kowalski & Ovenden, an insurance extension of Robert Kowalski's Logical English. The demo itself is a separate open-source project.

The second example was Policy as Code 93:55. An agent reads a pile of regulatory guidance on financial promotions, breaks it into atomic, testable rules, and then checks marketing material against each one. (It was described live as European and US guidance. The demo's configuration actually uses the UK FCA's social-media and Consumer Duty guidance.) An SMS promotion failed. It highlighted the returns prominently and buried the “capital at risk” warning.

Shown live 93:55 · Policy as Code
sanand0.github.io/policyascodeOpen in new tab ↗
Ingest a policy, extract atomic rules, validate documents against them. This is what Anand ran live on the financial-promotions guidance. It needs your own LLM key to run.

“Obviously the regulator will spot the same error. So don't.”

Anand, speaking for the agent 97:23

Notice how responsibility is split. When the agent finds a violation, you can reject the material. When it finds none, a person still reviews it 97:49. our reading That is a delegation policy in its own right. The AI gets to act only where a wrong decision is cheap: wrongly rejecting a draft costs a rewrite, while wrongly approving one could cost a fine.

What the rule engine can't check

our reading A rule engine can check the rules it was given. It can't tell you whether those rules mean what the original contract or guidance meant. Turning prose into rules introduces a semantic fidelity problem: a clause that was missed, an exception that was flattened, or a judgement call (“balanced view of risks”) forced into a yes/no test. The InsurLE paper names this as part of its motivation. Running the check is the easy part. Making sure the rules faithfully capture the text still needs someone qualified to spot-check them.

Which ten would you check?

Anand summed up his three techniques 97:54: agreement, benchmarking and checkable rules. “Once you have agents more reliable, then you will be able to let them act more autonomously.” 98:24 But the room had already answered a related question, at 9 a.m., before any of this was shown. It wasn't discussed in the session. It is perhaps the most revealing result in the data.

“AI makes 100 decisions. You can check only 10. Which 10?”

the room Q4, final answers from 33 respondents. The option shown in teal is the one the five-model demo is built on.

21
Where a mistake would cost the most
9
Wouldn't use AI unless I could check more
1
Where another AI disagrees
1
Where AI is least sure
1
Any 10 at random
Source: LiveForm Q4, latest answer per person, n = 33. A self-reported preference, not a test of which policy works better.

The demo and the room were answering different questions. Model disagreement points to the decisions most likely to be wrong. The room wanted to check the decisions that would be most expensive if wrong. Twenty-one of 33 chose cost. One chose disagreement. Nine said that checking 10% wasn't enough to let AI decide at all.

our reading Neither approach is enough on its own. A cheap decision the models disagree on wastes a reviewer's time. An expensive decision they all agree on can still be wrong in exactly the way that matters, and five-model agreement can't see that. A sensible review queue would rank decisions by roughly how likely an error is × how much it would cost, and then add the cases that need human sign-off whatever the probability, for privacy, legal rights or reversibility. The session didn't test this, and neither did the survey. It is simply where the room's instinct and the demo's maths meet.

Q3 had its own small experiment. Half the room read about an expense-claim AI that “gets 95 right” and the other half about one that “gets 5 wrong.” The performance is the same, only the wording changes. see the split The results didn't go the way you'd expect: only the “5 wrong” group let the AI pay claims on its own, with spot checks, and that was 3 people out of 16. Nobody in either group allowed payment without any checks. With groups this small, this is a curiosity, not evidence of a framing effect.

“95 right” · 15
213
“5 wrong” · 16
583
advice onlydecide, ask before payingpay, spot-check somenobody chose “pay, no checks”
Every time AI did something in this session, by rung

our reading Tap an item. The top rung is nearly empty: nothing in the session got to act with nobody checking. The only examples are two survey respondents.

Tap an item to see what the AI did, who checked it, and when.
Placement is this page's judgement, using the four levels Anand drew 41:14.
Act V · The question nobody could answer

Eleven rooms

The breakout brief was simple 99:08: “take one real-life task and answer the question: how can you or what would it take for you to make it reliable enough that you can have it run autonomously?” Two new questions were added to the form while he talked. Mukul, speaking for a room that had been sitting for close to two hours, asked for a five-minute break first 101:52. Anand's reply showed how he had come to see the session: “please take breaks whenever and wherever you want.” The session, he added, was being recorded 102:04.

The program coordinator split the 44 people still present into 11 groups of four 102:54. The recording skips most of the breakout. After a few seconds of overlapping crosstalk it cuts to the regroup 103:39, so the half hour of group discussion is missing. The Zoom chat shows some confusion about whether every member or one person per group should fill in the form, and two people gave opposite answers.

the room Eighteen people described a task. Most of them picked jobs that involve people: interview screening and candidate evaluation, a meeting-prep or scheduling assistant, monitoring regulatory and risk updates, KPI outlier alerts, triaging medical cases as emergency or not, and a voice bot that sells health insurance from greeting through to payment. The reliability plans (16 people) mentioned richer context, verified sources, deterministic checks, human review at set stages, monitoring, and autonomy granted in steps. These are proposals, not anything anyone deployed, but they apply the morning's techniques to the room's own work.

The homework was the important part 106:55: “Pick a real-life task, see if you can get AI to act autonomously. Write down your experiences. What is working, what is not working?… That cataloging itself is one of the most useful exercises.” Then, a little later: “the trying is important.” 107:57

What was planned and didn't happen

The preparation notes describe a more elaborate exercise. Groups would all get the same case, each with a different packet of evidence (accuracy, confidence, model agreement, error severity), commit to a delegation policy, and then be scored against a hidden test set. That exercise wasn't run in Session 1. What happened instead was discussion, the survey, three demos and the breakout proposals described above.

“When do we generally say stop?”

With three minutes left, Anand asked for questions about anything AI-related. One participant asked about the opposite of everything the morning had covered. Not when to let AI start, but when to make it stop.

“Many a times we try to do some R&D, try to do some research. It keeps on going on with AI… I keep on pushing it to its limit, keep on pushing, but I do not get the exact answer. I, in fact, keep roaming into places where I don't want. In that, where a human should actually say stop?”

A participant 109:43

Anand didn't have a rule, and he didn't make one up. He admitted to a small quirk: “I don't like interrupting people, so I don't click on the ‘stop’ icon on ChatGPT also. That's silly, right? It has no feelings.” 110:36 He said he gives up on AI the way he gives up on people: try once, and if it doesn't work out, find someone else. Then he said that habit is probably the wrong model for agents 111:16, and instead of advice, he offered an experiment.

“Every time you feel like stopping AI, just write it down… Just log, maybe 10 times. That log will give you a good reflection when you go back and say, ‘When am I feeling like I should stop it? When am I actually stopping it?… Should I have stopped it?’”

Anand 111:44

Then he said the thing most speakers leave out:

“I have not done this myself. Thanks to your input, I'm going to try it this week.”

Anand 112:26

our reading The ending answers the roll call. At 70 minutes, the instructor measured what was easy to count, which was answers. Then he caught himself, and an AI told him that a count is not evidence of learning. At 112 minutes, given a question he couldn't answer, he proposed measuring what matters: your own decisions, written down when you make them and checked afterwards. That is the same benchmarking habit he used on the Simplified English tip, applied to his own judgement this time. It may not work. He said himself that it hadn't been tried.

A workshop called When Do You Let AI Act? ended on its mirror image, when do you make it stop?, and on an experiment nobody had run yet. That seems the right place to stop.

Your ten stops

The experiment proposed at 111:44, as a notebook page. Note what you were doing and whether you stopped the AI. In a week, mark whether stopping was the right call. Your entries stay in this browser.

    0 of 10 logged

    What to take away

    01 · Per task, not per person

    Delegation is a decision you make for each task. The same “impossible” task was routine for someone else in the room. Ask which tasks you would trust AI with, not whether you trust AI.

    02 · Can it act?

    Whether AI can act depends on access as much as intelligence. Calendar permissions, connectors and context decided what was possible as often as the model did.

    03 · Four kinds of trust

    Correctness, authority, data and reliance are separate problems. Mukul and Ram raised concerns that a better accuracy score won't settle.

    04 · Likelihood × cost

    Disagreement finds likely errors; the room wanted to check costly ones. Five agreeing models cut accepted errors to 0.7% on one benchmark, with 28% sent to people. Rank reviews by both.

    05 · Test the tip

    Benchmark the advice before you adopt it. A sensible prompting tip made answers worse in a small test. Turning policies into checkable rules helps, as long as the rules stay true to the text.

    06 · Measure the right thing

    Response counts aren't learning, and gut feel isn't a stopping rule. Write the decision down when you make it and check it later. The speaker hadn't done this yet either.

    Shown in the session

    Not shown live: further reading

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