A practical tour of context engineering. One character runs through the whole talk: a brilliant new hire with no memory.
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fleetguru.ai · Context engineering
The model is a given. The context is the craft.
A practical tour of context engineering. One character runs through the whole talk: a brilliant new hire with no memory.
Prepared byAmir Zahedi · fleetguru.ai
Act 1 · Meet the brilliant amnesiac
ironbark·60 people · booking software for clinics
"Write me the Monday update for the leadership team from everything that happened last week."
Big week for the Ironbark team, with strong progress across several key initiatives. We pulled together on some challenges and momentum continues to build. Excited for what's ahead. 🚀
Same request · coldMush.
Two things worth your attention. Saturday's outage was the payments vendor, not us, and buried in their email is the real news: the old API dies in November, so our migration moves up a quarter. New date attached. Second, the signup dip that spooked the group chat is the school holidays, same dip as last July, stand down. Everything else ran to plan.
Same request · right contextSharp.
Same model · same request · same week · only the context changed
02 · Context is the craft
One request, two endings
Act 1 · The character03
in the trade·stateless model
ironbark·ask a stranger, get the left draft
Leila · day one
You've hired a genius with no memory.
Brilliant in general. Her name is Leila. But every morning she walks in knowing nothing about you, your work, or what happened yesterday. That's the model. The whole job is managing her well.
Anthropic say it plainly. Treat the model as "a brilliant but new employee who lacks context on your norms and workflows."
Act 1 · Name the craft
in the trade·the context stack
Prompt engineeringis the words you type.
Context engineeringis everything else the model sees.
Her standing ordersthe ask itselfthe facts fetched for ither toolsnotes on the work so farwhat she keeps long-term…and the shape you want back
Seven things sit in front of her every time she answers, down to the template the answer comes back in. The words you type are one of the seven. That's why prompt engineering is now a subset.
Anthropic have just done this to their own product. For Opus 5 and Fable 5 they cut over 80% of Claude Code's system prompt, with no measurable loss on their coding evals. The smallest set of high-signal tokens is not a slogan. It is a number, and it is getting smaller.
2,686 → 514words of system promptClaude Code, memory offno regressionon their own coding evalsAnthropic, Jul 2026
Jun 2025 Lütke names it→Karpathy amplifies it→Sep 2025 Anthropic formalises it
The words are a sliver · the context is the rest
04 · Context is the craft
"The job used to be picking the model. Now it's designing the context."
Act 1 · The analogy that sticks
CPUthe model · fixed, powerfulRAMthe context window · small, preciousOScontext engineering · decides what loads, and when
The model is the CPU. The context window is the RAM.
Karpathy's framing, and it's the one that sticks. The processor is fixed. The working memory is small and precious. Context engineering is the operating system: it decides what to load into that memory, and when.
Model = CPU · Context = RAM · context engineering = the OS
05 · Context is the craft
Hero analogy
Act 1 · Why it matters06
ironbark·the left draft was starved, not dumb
The skill that lasts
When AI fails, it's usually not too dumb.
It just wasn't told what it needed to know. As models get smarter, the failures stop being about the model and start being about the context. Whatever model you have in front of you, that keeps changing. Building the context right is the skill you get to keep.
3,500developers surveyed, six countriesAtlassian DevEx, 2025#1time drain is finding information, not meetings, not toolscoding never made the list4.4xmore productive when the knowledge is self-servesame survey
Managing the new hire · Don't overload her07
in the trade·context rot
ironbark·the whole week tipped onto one desk
Don't dump the filing cabinet
More context can make it worse.
Tip every document onto her desk on day one and she drowns. So does the model. Anthropic call it an attention budget, and every token you add spends some of it. A bigger desk is not the answer. A tidier one is.
18 of 18frontier models degrade before the window is fullChroma, context rot10k → 100Mtoken comparisons. 100k is 10 billion, a million is a trillionattention is quadraticevery tokenspends the attention budget, earning its keep or notAnthropic, Sep 2025
in the trade·position bias
ironbark·the vendor email sat mid-thread
Managing the new hire · Lost in the middle
She forgets the middle.
Startfound
Endfound
Middle−30% or more
Position of the key fact in the context
Recall
Smaller windowLarger window: deeper sag
Put the key fact at the start or the end and she finds it. Bury it in the middle of a long context and she doesn't. And the bigger the window gets, the deeper the sag.
30%+accuracy drop when the fact sits mid-contextLiu et al.
11 of 13models below half their short-context score by 32K tokensNoLiMa, 2025
up to 80%drop with distractors, reasoning models includedLost in the Noise, 2026
buried in the pile"sandbox API deprecated in March"the fact that matters"production API dies in November"Ask which API is going away, and the pattern-matcher answers March.
Strong at the edges · weak in the middle · put what matters where it looks
08 · Context is the craft
Liu et al. · lost in the middle
in the trade·KV cache
ironbark·the house format lives in the freezer
Managing the new hire · The freezer and the stove
Keep a big freezer. Only cook what's new.
The deep freezerStable stuff you keep ready and barely touch: the system prompt, the docs, the examples.
The stoveThe hot part you're cooking right now: this turn's question. Cook only what's new.
Under the hood that's the KV cache. She does the expensive work once for the frozen part, then reuses it: prefix caching. Change one token early and it all goes back on the stove.
Stable stuff frozen · only the new bit cooks
09 · Context is the craft
KV cache · prefix caching
Managing the new hire · The money slide
ironbark·a stamped clock time, full price all morning
90%
cheaper · same tokens · same model
Cached: stable first, query last~10%
Uncached: a changing value at the top100%
10,000-token system prompt, 100 calls across a morning's sessions and agents. Order it right and every call after the first reuses the frozen prefix at about a tenth of the price, replies in milliseconds not seconds. Every serious provider now rewards ordering the context this way. Anthropic's own rule is the long, stable stuff at the top, the question at the end, and it can lift quality by up to 30%.
$0.50 vs $5.00per million tokens, cached against freshOpus 575%off, and on by default, no setupGemini implicit caching50%off cached inputOpenAI
10 · Context is the craft
Order it right
Managing the new hire · The toolkit
ironbark·point her at where the week lives
Five levers. One stack. Not rivals.
Fetch
RAG
What to fetch. Keep bookmarks, not the whole library. Search by word and by meaning. Names, folders and dates are signal too.
Remember
Memory / notes
What to remember. Write it down, reload later.
Forget
Compaction
What to forget. Summarise and move on.
Do
Tools
What it can do. The myth-buster is next.
Divide
Sub-agents
Divide and conquer. Anthropic's multi-agent setup beat a single agent by 90.2%, and token usage alone explained 80% of the difference.
Different jobs, one stack · fetch · remember · forget · do · divide
11 · Context is the craft
You are here
in the trade·function calling
ironbark·Slack, tickets, the churn sheet
Managing the new hire · Tools, the myth-buster
The model never uses a tool. It just asks.
Modelasks for a tool
request
Your systemmakes the actual call
run
Context windowresult flows back in
return
Tools feel like the model "doing things". They're not. She only asks. Your system makes the call and feeds the result back into the context. A tool is really a context-builder.
Pile on too many tool definitions and you hurt her odds of picking the right one, and every schema costs hundreds of tokens before anyone has spoken. OpenAI's own guidance is fewer than twenty. Anthropic's fix is to stop shipping the whole catalogue up front: definitions load on demand, found by a search step, so only the tools this job needs ever reach the window. As they put it, if an engineer can't choose between two tools, neither can she.
72K → 8.7Ktokens of definitions, once they load on demandTool Search Tool49% → 74%tool-choice accuracy, same modelOpus 4, Anthropic evals
Tools build context · the model requests, your system runs it · fewer, sharper tools win
12 · Context is the craft
Request → run → return
in the trade·agent skills
ironbark·the Monday-update runbook
Managing the new hire · Tools and skills
Tools are her hands. Skills are her runbook.
on the desk · one line
monday-updateHow we write the Monday update at Ironbark.
loaded only when the job calls for it
Leadership reads this to make decisions. Lead with anything that changes one.
Give the consequence, not the event. A date is not news. What it moves is.
Everything routine gets one line. Plain and short. Enthusiasm isn't news.
Nobody re-explains the house process to a new starter every Monday. You hand them the runbook once, and they pull it out when a job needs it.
Same with Leila. A skill sits on her desk as one line, a name and a description. The full instructions only land in her working memory when the work actually needs them.
The trade calls this progressive disclosure. Really it's the freezer again, applied to know-how. The runbook costs almost nothing sitting on the shelf, and Monday's draft has its shape before a single fact of the week arrives.
The same trap, one rung up. In Anthropic's own transcripts, one layer said "leave documentation as appropriate" while another said "DO NOT add comments". The fix has a name, the right altitude: firm enough to be useful, loose enough to still be right next week.
Tools are her hands · skills are her runbook · written once, picked up on demand
12b · Context is the craft
Agent skills · progressive disclosure · the right altitude
Managing the new hire · Forgetting on purpose13
in the trade·compaction
ironbark·four hundred messages, one long session
Forget on purpose
Every so often: summarise, and start fresh.
Claude Code auto-compacts at 95% of the window. In plain ChatGPT or Claude you get no view of how full it is, so be the harness yourself: once a chat gets long, ask for a handover note in three lines, the plan, the findings, the open questions, and paste it into a fresh chat. It is lossy. The chatter dies; those three survive.
Managing the new hire · How to forget well
There's a right way and a wrong way to forget.
Naive
Drop the oldest tokens
Cheap. But it bins the start of the context, and we just saw the model reads the start best.
Better
Keep the edges, summarise the middle
The direct fix for lost in the middle. Protect the edges, compress the sag.
State of the art
Clear the noise
Strip the old tool calls and results the model no longer needs, keep the reasoning. You trim the context without losing the thread.
91.6% vs 71%last five tool calls plus a running summary, against the full historyLess Context, Better Agents, 202637%of the tokens, for the better scoreGPT-5, 50-task enterprise benchmark
Forget on purpose · keep the edges, cut the noise
13b · Context is the craft
The compaction spectrum
Managing the new hire · Model collapse13c
in the trade·model collapse
ironbark·summaries of summaries end in mush
The photocopy problem
A copy of a copy of a copy.
Compact from the source, not by re-compressing your own compressions.
in the trade·persistent memory
ironbark·same dip as last July
Managing the new hire · The notebook that compounds
The fix for amnesia is a notebook that compounds.
Give the new hire a notebook they keep and re-read, one that gets richer every day instead of being rewritten from scratch.
RAG rentsre-derives knowledge every query, forgets after.
The wiki ownscompiled once, cross-linked, contradictions flagged.
Layer themAnthropic don't pick a side: some context up front, the rest fetched at runtime, and no stale index to keep warm.
It's just a git repo of markdown. Three layers: raw sources, the wiki, the schema. Three moves: ingest, query, lint. She does the filing. You decide what matters.
RAG rents, the wiki owns · compiled once, kept current
14 · Context is the craft
The LLM wiki
Managing the new hire · Divide the work14b
in the trade·sub-agents
ironbark·Bea reads engineering, Marcus reads sales
Divide the work
She sends the messy jobs out.
A job too big for one desk leaves Leila's desk still sealed. Meet Marcus and Bea, each with their own fresh, clean desk.
Managing the new hire · Divide the work14c
ironbark·her desk gets engineering, his gets sales
Divide the work
The mess stays on their desks.
Forty documents, dead ends, false starts. All of it happens over there, in their own context, not hers.
Managing the new hire · Divide the work14d
in the trade·context isolation
ironbark·two facts come home: November, and the dip
Divide the work
Only the answer comes home.
A short digest lands on a clean desk. That is a sub-agent: its own context, the mess quarantined, a digest handed back, never the pile.
Anthropic put numbers on it. A sub-agent can burn tens of thousands of tokens exploring, and hand back a digest of one to two thousand. All of the mess, one line home.
Act 2½ · The war story15
Not in a paper. On my screen.
A big refactor. And the further it went, the worse it got.
A while back I was running a large refactor across a big codebase. Quality held early, then drifted. Near full, the tell was unmistakable: no fresh plan, just old findings rehashed, the same mistakes on a loop. That's context rot. Live, on a real job.
LOCA-bencha 2026 benchmark built to measure exactly thisHKUST-NLP, Feb 2026measuredcontext rot under controlled, agentic context growthso it isn't just me holding it wrong
Act 2½ · The fix
So I built a loop that never lets the context rot.
01
Chunk
The plan into phases, each with clear acceptance criteria.
→
02
Fresh context
A harness spawns a brand-new session per phase, so no single window rots.
→
03
Exit gate
It only signals done when criteria verify, otherwise it retriggers fresh. Circuit breakers stop it spinning.
→
04
Distil findings
A lighter model harvests verified patterns into a compounding skillbook, promoted only after seen twice, and feeds later phases just the relevant slice.
findings loop back in
Fresh context each phase · a skillbook carried forward · no rot
16 · Context is the craft
The smart Ralph loop
Act 2½ · The punchline
I'd hand-built the entire textbook. By accident.
What I builtThe official name
Fresh context per phase→Sub-agent isolation (+90.2%)
The skillbook→Structured note-taking · the LLM wiki
Lighter model distilling→Compaction
Relevant-slice injection→Just-in-time RAG
"Seen twice before it's kept"→The guard against a wrong fact getting cemented in
I built every lever because the quality was rotting and I had no choice. Months later, most of these are shipped with harnesses. This isn't theory. It's what you reach for when it breaks.
Necessity first · the textbook caught up
17 · Context is the craft
Homemade → official
Act 2½ · The good news18
Harness engineeringthe manager running her day
Promptthe words you type
Contextwhat she sees
The hard part is done
I had to build the operating system. For you, it's already in the kernel.
Auto-compaction, sub-agents, a memory tool, built-in context management. It ships now. You just have to switch it on.
state, next steps, learningswhat compaction writes down by default. The morning handover note.Anthropic, server-side compaction97%fewer critical errors, cost and latency both down 30%+Rakuten, Anthropic case studyno beta headermemory is generally available on the Messages APIswitch it on today
Act 3 · The honest bit
ironbark·one wrong number rides every future update
Be honest about the limits.
Wiki cites sources accurately~52%
RAG cites sources accurately~5%
But the wiki cost 21× more per question and ran 6.6× slower. Small sample, directional.
Contamination. A wrong fact, once written, gets read as truth by everything after. My "seen twice" gate helps. It isn't free.
Scale wall. Lovely at 50 to 100 sources. At thousands it's a knowledge base with no editors.
Vibe thinking. The understanding forms while you do the filing. Outsource that and you get a tidy wiki you never learned.
The rot, the blind spot, the photocopy, the poisoned notebook. The trade has a name for each, and you've watched all four tonight.
It's not free · trust, cost, scale, and the thinking you skip
Every version died on the same rock: maintenance is a chore humans abandon. The model is the first tireless librarian.
Act 3 · One more thing
18of20flagged the same problem
I didn't just talk about the five levers tonight. I used every one of them to build this.
The panel of twenty that reviewed this talk. Eighteen flagged the same problem. They were right, and what you just watched is the fix.
Fetch. Research agents read the 2026 papers, so each slide only carried the facts it needed.
Remember. What I learned went into notes and a notebook the next session could read. I never argued the same point twice.
Forget. When a session filled up it wrote a handover note and started fresh. The morning handover from the war story, on this deck.
Do. The skills did the real work. One narrated this whole script. One drew every photo of Leila, the same face every time, on purpose.
Divide.53 agents worked on it; a panel of 20 reviewed it, because I didn't trust my own opinion on its own.
I argued with a focus group of twenty about my own talk, and I lost. Very 2026.
Every one of them did the filing. Not one could tell me what the talk was about, which joke to keep, or that she should be Leila, a person with a name.That part stayed mine.
20½ · Context is the craft
One more thing
Act 3 · The thesis
The machine can do all the filing. It can't tell you what matters. And that was always the point.
Context is the craft
Big week for the Ironbark team, with strong progress across several key initiatives. We pulled together on some challenges and momentum continues to build. Excited for what's ahead. 🚀
Two things worth your attention. Saturday's outage was the payments vendor, not us, and buried in their email is the real news: the old API dies in November, so our migration moves up a quarter. New date attached. Second, the signup dip that spooked the group chat is the school holidays, same dip as last July, stand down. Everything else ran to plan.
21 · Context is the craft
The close
Act 3 · Over to you
ironbark·whatever your Monday update is
Try it tonight.
Anyone
Before a big ask, give the context first. Paste the brief, the goal, the constraints. And start a fresh chat when it drifts. Watch the answer change.
No compaction button? Be the harness.
"Summarise this chat for a fresh version of you that can't see this history: the plan, what you've learned, and what's still open."
Paste it into a new chat.
Hands-on
Point Claude Code or Codex at one folder, ingest five things into a markdown wiki, ask one question. That's a wiki, and you didn't have to build a Ralph loop.
Give context first · start fresh often · build one tiny wiki
22 · Context is the craft
A move you can make tonight
fleetguru.ai
Thank you.
The talk
The model is a given. The context is the craft. A practical tour of context engineering.
Prepared by
Amir Zahedi · fleetguru.ai
Sources
Anthropic, context engineering (Sep 2025) · Anthropic, new rules of context engineering (Jul 2026) · Chroma, context rot · Karpathy · Liu et al., lost in the middle · Lütke (qmd) · Bush, Memex · Luhmann, Zettelkasten · Forte, Second Brain · LOCA-bench (2026) · Lost in the Noise (2026) · Wu et al., position bias (MIT, ICML 2025) · Anthropic, server-side compaction + Memory for Managed Agents (2026).