2026 4

Case Study

Create a training pack to help analysts (business analysts, data scientists, strategy consultants, forward deployed engineers, etc.) improve their investigative judgment. Success for the analyst is not recovering the hidden truth you designed. It is making the best evidence-based judgment available from the materials. Design and score for that. First, formulate the underlying dynamics - the hidden mechanisms, reasons, processes - e.g. - why the processes are not/poorly/wrongly documented - why the data is stored, structured, and labelled the way it is - why it has the quality issues that it does - what are the underlying unstated organizational dynamics, etc. Discovering some or all of these would be key to the analyst's success in the exercise. Don't state these dynamics directly anywhere the analyst can see. But they may be partly mentioned, disputed, denied, euphemised, or misunderstood by people who each see only a part of it. That is how it works in real-life. For each dynamic, plan two or more independent channels through which an analyst can detect it (a data pattern, a silence in a thread, a timeline that doesn't line up, a form field abandoned mid-year), and at least one innocent explanation that fits any single channel on its own. Also plant anomalies that mean nothing - in real-life, not everything is a clue, and we want to train for the intuition to tell the difference. Create an instructor-only `case.yaml` that includes all of this as the primary context. Include entities, systems, timeline, people, the process (how was it designed, documented, believed to run, actually runs), the dynamics and where and how each dynamic plays a role. Record every anomaly in the pack in case.yaml, marked as: designed and critical / ambient noise / benign quirk / accidental defect. Fix the accidental defects. Generate every artifact below from `case.yaml` to avoid ACCIDENTAL contradictions. Create realistic documents and datasets that an analyst will likely get when investigating a process like below. This includes: - Documents explaining the process. Reflect real-life, where some processes are undocumented, poorly documented, or wrongly documented. - Datasets. - Both structured (spreadsheets, SQL dumps, geospatial, proprietary formats, ...) and unstructured (text, images, documents with a mix, audio, video, ...). - This may include large transactional/reference data as well as smaller datasets, across a variety of realistic formats. - Think about how organizations realistically store data. There are underlying historical and organizational reasons for why their data evolved the way it did. In real-life, datasets have varying quality, based on the process of collecting and processing them. Datasets are often sourced from multiple systems and processes. The nature of gaps / errors / other quality attributes typically reflect the underlying sources. - Use a format only if this organization would likely produce it and it serves an exercise - not just for variety. - For large transactional data, Use a fake data generator skill when available. Write seeded generator scripts rather than static files. - Supporting material. This may include emails, chat logs, meeting transcripts, system logs, people profiles, etc. that are usually passed to an analyst for context. In real-life, these supporting materials are windows into and reflections of organizational structure, politics, constraints, etc. How it is said, and what is unsaid, is often more important than what is said. - People the analyst can question. Add the profiles to `data/`. Include instructor-only notes explaining what each person knows, believes, is wrong about, and would rather not say. Enough for an instructor (or AI agent) to role-play them and answer questions like them. Deciding whom to ask, and what, is a critical skill. That's how analysts go beyond incomplete / incorrect briefs. The same pack can be used for multiple exercises. Include exercises, each containing: - Objective - a page explaining their task. Realistically, these may be loosely, incompletely, or wrongly defined, or unsolvable without additional data or context, etc. This, too, needs to reflect real-life based on a hidden dynamic. Where the brief is wrongly framed or underdetermined, analysts should reframe it, say what's missing, ask for it, and act safely under uncertainty. If they do that, that's a success, not failure. Don't make something wrong in every objective. Deciding whether to dig is part of the training. Mention who the objective is for, how long it should take, which tools (e.g. AI agents) are allowed, and what output to submit. Require an evidence table - claim | source | confidence - and the hypotheses they rejected, with why. Without this, we can't differentiate between judgment and lucky guesses. Some exercises can be small: one artifact, ten minutes, "does anything here smell wrong?" - including some where the answer is no. Intuition comes from many quick exercises with fast feedback, not just from one long case. - Rubric - not shared with the analyst, but explaining to the instructor: - What the analyst needs to discover in order to succeed in the exercise - mentioning the relevant dynamic. - How to evaluate the analyst's work. Share this as a prompt that can be shared with an expert or an AI agent. The prompt will be shared along with the same inputs passed to the analyst (documents, datasets, supporting material, this exercise's objective) as well as the dynamics. The prompt should clearly explain the steps to evaluate the analyst's work and the scoring rubric along with evaluation criteria and clear definitions of what constitutes a good/bad response, with an emphasis on the hidden dynamics that the analyst needs to discover. Because the evaluator is handed the dynamics, say explicitly: score the evidence and reasoning first, THEN the conclusion. A well-supported alternative conclusion can score as high as the intended one. But the intended conclusion asserted without evidence should not score high. You can use the tone, omissions, timing, and other "non-verbal" aspects of the response as a signal, but treat that as hypotheses needing proof. - Write behavioural anchors for each score level. - Then write test submissions for this exercise, as an analyst would write them - not as someone who knows the answer. For example, if a "good" submission clearly states the dynamic, that's unrealistic. Recommended submissions: 1. Strong: real evidence, traced to files, calibrated, some things still open. 2. Polished but shallow: confident, well written, restates the brief, no evidence. 3. Right conclusion without evidence - a lucky guess. 4. A different conclusion that the evidence actually supports. 5. Says the evidence is insufficient, and asks for the right things. 6. Treats a decoy as a finding. Target what this rubric is most likely to get wrong. - For each submission, write what the evaluator should return: its expected rank against the others (a band for each dimension, not an exact score), and the specific text in the submission it must cite for that score. We'll test the evaluator based on whether it gets the right rank using the cited reasons. Exact numbers vary between evaluators and are not a fair check. Generate this pack as a set of files with this structure: - `README.md` - for the instructor, containing a full overview of the case, including the underlying dynamics, explanation of the data. An instructor reading this for the first time would understand everything they need to know about running this training exercise. Layer this. Begin with an overview, an explanation of the dynamics, a walkthrough of the data, a list of exercises and what they uncover and how to evaluate them. Then go into the details of how each dataset was generated and what dynamics it reflects. - `case.yaml` - instructor-only source of truth. Everything else is generated from it. - `data/` - for the analyst, containing all documents and datasets to be shared with the analyst. Nothing here (including metadata, hidden sheets, comments, ...) should reveal the dynamics DIRECTLY - `src/` - generator scripts and seeds, so the pack can be rebuilt and re-seeded for the next cohort. Not all `data/` needs to be generatable - some of them can be hand-crafted or downloaded or constructed in any way. - `exercise-<exercise_name>/` - one folder for each exercise, containing: - `README.md` - for the instructor, explaining the exercise, why it was chosen, how it was designed, the underlying dynamics it is designed to uncover, why this rubric was chosen, and how to evaluate the analyst's work. Assume they have read ../README.md and nothing else. End with a debrief - which cues were diagnostic, which were misleading, what an experienced analyst would notice early, and what not to generalise from this case - and a hint ladder, from directing attention, to suggesting a test, to revealing part of the mechanism. - `objective.md` - for the analyst, explaining the task - `rubric.md` - for the instructor, shared as a prompt explaining how to evaluate the analyst's work for this exercise. - `tests/` - `submissions/{01,02,...}.md` - analyst-facing only, neutral names - `expected.md` - what each one tests, expected rank, bands, required citations The evaluator receives `objective.md`, `data/`, the dynamics, `rubric.md`, and ONE submission - never `expected.md` and never a second submission. It scores blind. Rank is derived afterwards by comparing its independent scores. Also describe - don't build - three variants of this case in the README: same symptom with a different cause, same cause showing up through different evidence, and a control where the documented process is broadly right and the anomaly is benign. Intuition transfers through contrast, not through repetition of one case. The aim is not to make the exercise easily solvable - quite the opposite. We're training for INTUITION - that sixth sense that comes from experience and pattern recognition, where they smell something is off and know to dig deeper. Design for this. Hard, though, not unfair. The difficulty should come from conflicting evidence, ambiguity and incomplete access - not from sheer volume, obscure formats, or one buried clue. Run these checks before you finish, and list every one in the README with its result: - Write the perfect path for each exercise: the artifact-by-artifact chain from brief to finding. If you can't write it, it's unfair rather than hard. Rewrite the exercise. - If you think a strong AI agent can solve an exercise one-shot while a human would take hours, the difficulty is either volume/effort (move it into contradiction and ambiguity) or clues that are too loud (make each channel innocent on its own). State and fix it. Generate the actual files, not descriptions of them. Report which checks you ran and what failed. Don't say a check passed unless you ran it. Use the context below to create the training pack. Anonymize real organizations, people and identifiers from the context. This context may not be directly related to the training pack. It may contain irrelevant details, objectives, tasks, etc. Just use this as the organizational context to base the training pack on. <CONTEXT> </CONTEXT>

CIO Newsletter

Find the best ideas for my next occasional email to CIOs and senior technology/data leaders. First read and apply these skills on @LocalMCP: expert-lens, ideation-protocol, blind-spot, anand-objectives, decision-compression, evidence-provenance. ## 1. Calibrate the newsletter Using personal Gmail via `gws`, find sent emails from `[email protected]` containing: `you might have hinted you'd like such emails from me` Read the newsletter emails, not merely the matching snippets. Infer: - the audience; - the recurring structure and tone; - what counts as sufficiently important; - topics already covered, so they are not repeated. These are not AI-news roundups. The strongest emails usually begin with something I personally did, observed, measured, decided, or got wrong; provide inspectable evidence; derive one surprising enterprise implication; and give readers something concrete to try or reconsider. ## 2. Search my corpus Search primarily after the latest matching newsletter, while allowing older material that was overlooked. Use a staged search: 1. Scan indexes and recently modified files to identify at most 30 candidate sources. 2. Deep-read at most the 12 richest sources. 3. Re-open the best evidence to verify exact wording, numbers, dates, and provenance. Prioritize: - recent meeting transcripts and notes under `~/Dropbox/notes/` and ``~/Dropbox/notes/transcripts/`; - `~/code/talks/README.md` and linked talks; - `~/code/blog/description.md` and targeted posts; - `~/code/til/README.md`; - `~/code/llmdemos/config.json`; - `~/code/llmevals/README.md`; - email or chat only when it supplies a firsthand incident, reaction, decision, result, or failure. Do not let public AI news become the core idea. Public sources may corroborate my evidence, but cannot substitute for it. ## 3. Gate every candidate Keep an idea only when most of these hold: - **Firsthand:** I did, observed, measured, decided, or materially shaped it. - **Surprising:** it challenges a reasonable CIO assumption. - **Consequential:** it could change an enterprise decision within the next 6–12 months. - **Evidenced:** there is a concrete incident, number, artifact, failure, or audience reaction. - **Exclusive:** a well-read CIO is unlikely to learn most of it from ordinary AI media. - **Emailable:** it supports one focused story: incident → implication → practical move. - **Shareable:** it is public, can be safely anonymized, or is clearly marked as requiring approval. Reject generic trends, secondhand frameworks, routine project updates, unsupported opinions, thin rewrites of earlier newsletters, and impressive claims whose provenance cannot be recovered. Explore broadly before ranking. Include 2–3 `IDEA`s: rich sources that may not yet support a finished thesis but are likely to provoke a better idea. ## 4. Output Return 8–12 ideas, prioritized. For each: 1. **Working title and one-sentence thesis** 2. **Opening incident or evidence** 3. **Why a CIO should care** 4. **Why this is uniquely me** 5. **Sources:** exact path, date, and useful line range or section; mention any public artifact available in the source 6. **Shareability:** PUBLIC / ANONYMIZE / APPROVAL NEEDED 7. **Missing evidence or weakness** 8. **Verdict:** WRITE NEXT / STRONG / IDEA / SKIP Then provide: - the top three in order, explaining why each narrowly beats the next; - one attractive but generic idea rejected; - one strong idea rejected because it is not sufficiently me; - any important corpus area that could not be inspected. Do not draft the newsletter. Be concise, skeptical, and specific. Never invent a result or imply external approval. 27 Jul 2026: Created. ChatGPT

White Pebble Black Pebble

When I was in class 8 or 9, our English teacher told us a story I’ll never forget. There was a poor farmer who lived in a village. He owed the zamindar (landlord) of the village a lot of money. The zamindar had an eye on his daughter. “Marry your daughter to me, and I’ll forgive your debt,” he said. The farmer was reluctant. “Please, sir, what will the village say about your marrying such a young girl?” he asked. ...

Scepticism and Humility

High Scepticism + High Humility = Scientist. Editor. Indecisive. “Let’s test it.” Good for high-stakes, irreversible decisions. System 2 thinking is slow and effortful. But if you do this too often or too long, you miss the window or other opportunities. High Scepticism + Low Humility = Critic. Troll. Red Hat. “You are wrong.” Good for stress-testing and auditing. To prevent/anticipate failures. But it’s toxic and demoralizing if you do it too much. ...

2024 1

Things I Learned - 03 Mar 2024

This week, I learned: You can use slots to stream HTML out of order! Shane Parrish. Short-term patience podcast have a frame of reference to relate EVERY experience to. That helps you evaluate (measure) and learn. That’s part of what Charlie Munger’s lattice of frameworks is about when there is a very high or very low interest scenario, low interest scenario then go ultra long term. Issued hundred years when the interest rate regime was very low short term optimal is rally long term optimal. So you need to learn to take a loss and look like an idiot to play the long-term game grit is a behavior that enables long-term thinking. Short term success gives you the luxury to think about long term #IMP power is about optionality. It’s about being in a position where you have the options that can affect the positive change rather than circumstances controlling you. Read Robert greene’s book on the 48 laws of Power low leverage enables that begin with the end in mind. Always how do you think about risk? Well, things do happen. It’s as simple as that autonomy and decentralization helps derisk do more and more of what works. That’s a powerful way of compounding long-term investments are better than frequent trading because you get to reinvest the tax you otherwise would have paid. So unless the alternative is super compelling, stay invested if you need to be the person who DOES the thing, you delegate less, leverage list, compound less, because you have to DO. BE A PERSON WHO SETS THE FIELD INSTEAD. The coach, the chess master, the director, patient strategist who Waits for the good hit Being in Control motivates #Lesson. my cycle tires were flat. I thought it was someone pulling out the air and felt very demotivated. But once I carried my cycle pump, I felt so much more in control and power and felt a whole lot better SourceGraph is the default platform for private code completion & search MetaVoice 1B offers voice cloning on American & British accents with 30s training Qwen 1.5 72B appears to outperform Mistral Medium, making it one of the top non-proprietary models Llava 1.6 is a substantial improvement over Llava 1.5 and slightly better than CogVLM, Qwen-VL AI scams are growing. Deepfakes scammed $34m. But voice fake for kidnapping is scarier. Buildspace’s demo is a great demo of how voice and actions can be used effectively. demucs does an EXCELLENT job of splitting songs into drums, bass, vocals and others

2023 1

Things I Learned - 24 Dec 2023

This week, I learned: DPO is a simpler alternative to RLHF for fine-tuning. Several HuggingFace models use DPO for training Name2Vec is a potential embedding for names. Google Knowledge Graph ID powers the Knowledge Graph. If it begins with /m/ it’s the same as the FreeBase ID. This is now available as WikiData. e.g https://www.wikidata.org/wiki/Property:P2671 I tried running Mixtral-8x7b locally (via Llamafile) and on together.ai. It’s good, but far from GPT 4. Generic computate-intensive algorithms eventually beat domain-specific tuning, because of Moore’s law. Ref The hidden brain podcast. the mystery of beauty Evolution drove us to beauty as an efficient survival mechanism. Understanding the world is one such mechanism. Hence we enjoy maths and chess ⭐ This leaderboard included paid models like GPT4 and Claude and compared them with open models on HUMAN + system benchmarks Lez Friedman Podcast: Jeff Bezos Build stuff that is is ubiquitous that other people take it for granted. The initial idea needs to be that obvious and easy. Like one click purchase or customer reviews Build stuff that other people can build on. Internet makes startups possible. Infrastructure is about enabling others at scale Decision making approaches: single person decides on two way doors. Deliberate as a team on one way doors Conflict resolution: disagree and COMMIT. NO sniping, I told you so, malicious compliance. Avoid compromise. Avoid decision by attrition (most persistent wins). People are inherently biased towards hierarchy. So the senior most person should speak last We have a happiness bias. Contracted by choosing the unhappier options first The map is not the territory. The metric is not the objective. We need metrics. But make sure you know why See the world through the eyes of the customer. Use your own product. It’s living their lives that makes customer obsession real. Jeff Bezos called their own customer care to see how long the actual wait time was. It was much longer than the metric reported How to prioritize. whatever problems customers will still face in 10 years are the big problems. These are worth putting time into because they are stable in time People working on big problems will never get down to the small problems. So have a dedicated team that works only on the paper cuts. It should be a dedicated team We co evolve with our tools. We build tools and then our tools change us. It reprograms our brains Cut out 10 minutes to the beginning of each meeting for people to read the material. They never reread anyway. This makes the meetings more productive Powerpoint is designed for persuasion, not truth seeking. It is also easier for the author than for the reader. Prefer narratives that are focused on finding the truth and are easier for the audience though tougher for the author ⭐ whisper-standalone-win provides a Windows binary for Faster-Whisper. It just needs CUDA and cuDNN installed. Then whisper-faster.exe video.mkv --language=English --model=medium generates the transcript. LLM use cases by Benedict Evans “Every text box on the internet will get an LLM” “Infinite interns” “Every UNIX function has become a company.” “Every ChatGPT suggestion…” llm360 publishes models along with training datasets. In The Age of AI has begun, Mar 2023, Bill Gates says, “In my lifetime, I’ve seen two demonstrations of technology that struck me as revolutionary.” The GUI (1980) and ChatGPT (2022). Rubeus is a HTTP proxy for multiple LLMs with load-balancing, fallbacks and retries. GPTRouter is a Python interface for multiple LLMs with fallbacks and retries. ⭐ Token Tally has an LLM Cost Tool that estimates GPU memory required and token cost across cloud providers.

2010 1

A sense of proportion

A quote from David Heinemeier Hansson: So the problem is, a lot of business managers and especially business owners, they have no sense of probability. They can’t fathom that concept. So They treat the probability of 1 to 10 trillion as the same as a 1 to a 100. And like, “We’ve got to deal with this 1 to a trillion probability, because, what if it happens?” No! Doesn’t matter! I mean, don’t care. ...

2009 1

A flaw in rationality

I found this piece from “The Happiness Hypothesis” pretty interesting: In the 1990s, Damasio found that when certain parts of the orbitofrontal cortex are damaged, patients lose most of their emotional lives. They report that when they ought to feel emotion, they feel nothing, and studies of their autonomic reactions (such as those used in lie detector tests) confirm that they lack the normal flashes of bodily reaction that the rest of us experience when observing scenes of horror or beauty. Yet their reasoning and logical abilities are intact. They perform normally on tests of intelligence and knowledge of social rules and moral principles. ...

2008 1

Resolving the Prisoners Dilemma

If you’re ever taken a course in Economics, and it discussed Game Theory, you may be familiar with The Prisoner’s Dilemma. Roughly, this is the problem. Assume you possess copious quantities of some item (money, for example), and wish to obtain some amount of another item (perhaps stamps, groceries, diamonds). You arrange a mutually agreeable trade with the only dealer of that item known to you. You are both satisfied with the amounts you will be giving and getting. For some reason, though, your trade must take place in secret. Each of you agrees to leave a bag at a designated place in the forest, and to pick up the other’s bag at the other’s designated place. Suppose it is clear to both of you that the two of you will never meet or have further dealings with each other again. ...

2007 2

Wisdom and Intelligence

Paul Graham pens another brilliant essay on Is it worth being wise? It’s mostly about the difference between being wise (right most of the time) versus being smart (being right where few others are). If you’re picking between options, being wise is useful. There is a best option, and you’ll pick it most of the time. If you’re doing something creative, there’s no finite set of options. Then it’s worth being smart. Increasingly, tasks are asking for more creativity, so it may be better to be smart.

Knowing less is better

Malcolm Gladwell argues that knowing less can be an advantage. This is based on a study in which kids in the US were asked which was a bigger city: San Antonio or San Diego. Many didn’t know. Kids in Germany were asked the same. Most knew: San Diego was bigger. Why? Because they’d heard of San Diego, but not of San Antonio. P.S: A comment mentions that the actual difference in population between these cities is only 2%. So maybe the US kids were right to be unsure… ...

2006 5

Filtering vs weighting

I am selecting a CRM package for a bank. I asked my colleagues how they’d gone about it, and got 8 responses. Every single one of them had the same weighting approach: Take a huge list of criteria, assign weights, score each package, calculate a weighted-average score, pick the highest one. As I mentioned earlier, I think weighting is a lousy method. (See Errors in multicriteria decision making.) You can’t say “I picked this package because it has X, Y and Z features, which the others don’t.” You can only say, “Oh, overall, it has the highest score…” ...

Errors in multicriteria decision making

I talked about my approach for multicriteria decision-making, and mentioned that it was fundamentally flawed. Here’s why. The charts above compared two industries. The bigger the area, the more favourable the industry. The underlying assumptions being: The criteria are comparable. (Points at the same level are of comparable importance. Twice as large is twice as important.) All (and only) relevant criteria have been included. In this particular example, I know for a fact that both these assumptions are invalid. And in every case I used this methodology, the assumptions fail. ...

Knowing when to stop

Mathematics, marriage and finding somewhere to eat has a simple solution to all these problems. Whether you’re hiring someone, or picking a partner, or finding a house – or any problem that requires you to pick the best among N choices – here’s the rule. Scan the first 37% of choices. Then pick the first one that’s better than anything you’ve seen so far.

How I buy gadgets

I’m a cautious gadget freak. I love buying gadgets, but think a lot before buying them. Invariably, I use spreadsheets to help me decide. I try to buy only those gadgets that are right for me at the cheapest possible price, and I look at two things: features based on usage and breakeven. Usage-driven buying I pick the features I want based on my usage. For example, when I bought my first mobile, I listed the my most likely uses for the phone: ...

Demand draft fees

Once, we were looking at whether banks made money on demand drafts (DDs). DDs are costly. 90% of a bank’s costs are people-related, and it takes a fair bit of time (hence people) to process DDs. If you pay for DDs in cash, it costs even more because the teller has to count the notes. To recover this cost, banks charge a fee. The fee increases with the size of the DD. A DD for Rs 10,000 may cost Rs 50, while one for Rs 100,000 may cost Rs 200. ...

2005 2

Herbert Simon on Information

Quote by Herbert Simon on Information: What information consumes is rather obvious: it consumes the attention of its recipients. Hence a wealth of information creates a poverty of attention, and a need to allocate that attention efficiently among the overabundance of information sources that might consume it. It sounds quite like the Scientific American article The Tyranny of Choice which says that after a point, more choice causes unhappiness. The satisfaction of picking the best choice is less, because the second best is almost as good. And you’re more likely to not pick the best – because there are so many choices – and will regret it more often. ...

Acts of commission rather than omission

Thinking, a book by Hardman and Macchi, says people would much rather let bad things happen, than take a risk to stop them: Decisions with identical outcomes are judged as worse when they result from acts of commission than acts of omission. For example, most people are reluctant to vaccinate children against a potentially lethal flu when side effects of the vaccine can cause death. Faced with a flu epidemic that is expected to kill 10 out of 10,000 children, most people are not willing to accept a 9 out of 10,000 risk of death from vaccination, and the median acceptable maximum risk is 5 in 10,000. Apparantly, killing a child with a vaccination (that is, an act of commission) is perceived as worse than causing its death by failing to vaccinate (that is, an act of omission). ...

2002 1

We can make better decisions sub-consciously

A neurological experiment indicates that we can make better decisions sub-consciously, even if we can’t explain why.