Sr. Content Developer at Microsoft, working remotely in PA, TechBash conference organizer, former Microsoft MVP, Husband, Dad and Geek.
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One Shot Prompting is Dead

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One shot prompting is dead

I attended one shot prompting’s funeral.

There were no tears. Just a room full of developers quietly pretending they weren’t taking shots the night before. Because if we’re being honest, everyone saw this coming and couldn’t be happier it was over.

Saying “one shot prompting is dead” isn’t revolutionary. It’s just catching up to what builders have been experiencing for months.


The blog post that aged faster than oat milk

Last year, I wrote a post about how to prompt better. I shared tricks, phrasing tips, and even said to add a few “pleases” and “thank yous” and your AI agent would give you the world. At the time it felt cutting edge, because it was. There were livestreams and conference talks entirely about how to prompt better.

Less than a year later, it feels… quaint. Not because prompting stopped mattering, but because prompting stopped being the main character.

The conversation shifted from:

“How do I coach the model better?”

to

“What environment am I dropping this model into?”

That’s a completely different problem, and now it has a name. Context engineering.


The abstraction that broke

One shot prompting worked when agents were party tricks. You crafted a clever prompt, you got a clever answer, and by “clever answer” I mean a fully “working” app, so everyone clapped. But the moment we asked agents to plan, remember, call tools, and operate across multiple steps, the definition of “worked” fell apart.

A single prompt stopped being a solution and became a bottleneck. What matters now isn’t the sentence you type. It’s the system that surrounds it. Prompts didn’t disappear, but they were demoted to one step inside a larger pipeline designed to hold state, plan ahead, and enforce guardrails.

As someone put it in a thread I recently came across:

“The best model with bad context loses to an average model with great context.”

That line explains the shift. Context is now the advantage.

And this isn’t theoretical. You can see it in how serious agent systems are being built. Projects like OpenClaw and Ralph Wiggum loop aren’t chasing clever phrasing. They’re designing environments where context persists, decisions accumulate, and agents can operate across time without resetting every session.

The excitement around these systems isn’t just hype either. It’s relief. Builders have been hungry for real working examples that behave predictably over time.

Which leads to the only question that matters ....


How do I actually do this?

When I started building our skills marketplace, one shot prompting alone couldn't cut it. My normal workflow involved researching in one place and implementing in another, and every time I switched tools I had to re-explain the same decisions. Context wasn’t living inside the system. It was living in my head. The agent would forget, I would remember, and the entire session became an exercise in rehydration instead of progress.

Here’s what that loop looked like in practice:

Even this demo is powered by persistent context.

That was the moment I experimented with RPI. Not because it was trendy, but because the alternative had become tedious.

You don’t have to adopt RPI, or any new pattern, tomorrow to benefit from this. You can simulate the shift in your next session with a small change in how you start.

Before you execute anything, put your agent in chat only mode and run this handoff.

Step 1: Align on the finish line

Tell the agent exactly what counts as done.

“We are shipping: ___
Success looks like: ___”

If the finish line feels fuzzy to you this is the time to flesh it out with your agent, if not your session will drift.

Step 2: Lock in non-negotiables

Define what is not up for debate.

“Constraints: ___
Architecture we are committing to: ___ ”

This prevents the classic agent spiral where it keeps trying to overengineer the project instead of building it.

Step 3: Capture persistent context

Write down the facts that must survive the session.

“Context that must persist:
– ___
– ___
– ___”

This is research, assumptions, domain knowledge, edge cases, terminology, anything your agent will need to pick up exactly where it left off.

Now save it somewhere accessible:

  • a file in the project
  • a context file (goosehints, Cursor rules, etc)
  • a memory extension

Anything that outlives the chat window.

The rule is simple. Context should live in the system, not in your head.


This is good news for people who think beyond code

The interesting part is this shift isn’t just technical. It has a quiet career implication hiding inside it. AI isn’t replacing engineers. It’s replacing workflows that stop at “my code runs, so I’m done.” Context engineering rewards a different mindset, the ability to pick up all these different patterns and utilize them by thinking about how decisions propagate through a system, what persists, and what the downstream effects look like over time.

That’s a muscle I’m actively working on too. And the more I lean into it, the clearer the direction becomes.


The real skill is orchestration

We attended its funeral, but as you can see, prompting isn’t really gone. It just stopped being the workflow.

One shot prompting is still great for demos and exploration. But when the goal is building systems that last longer than a single session, the advantage shifts to how well you design the environment around the model.

The people who thrive in this era won’t be the ones with the cleverest phrasing. They’ll be the ones who know how to orchestrate context so intelligence accumulates instead of resetting.

And honestly, that’s progress.

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alvinashcraft
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Export Your ML Model in ONNX Format

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When building machine learning models, training is only half the journey.

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alvinashcraft
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A Beginner’s Reading List for Large Language Models for 2026

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  The large language models (LLMs) hype wave shows no sign of fading anytime soon: after all, LLMs keep reinventing themselves at a rapid pace and transforming the industry as a whole.

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Daily Reading List – February 10, 2026 (#718)

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I’m heading to India on Friday and will be in Delhi and Bengaluru all of next week. Trying to prepare for that—demos, logistics, packing—while doing full days of “regular” work is quite the juggling act. “Smart Richard” would have taken a day off work to prepare, but alas, he rarely makes an appearance.

[article] What keeps AI-generated pull requests from getting merged into production? It’s not documentation gaps that are the biggest blocker. Seems to be testing and security concerns in AI-generated code submissions.

[article] Is AI killing open source? Provocative title, but thoughtful piece from Matt. There are conflicting forces at play and the future isn’t clear.

[blog] How we cut Vertex AI latency by 35% with GKE Inference Gateway. Big improvement, especially for this product’s scale.

[blog] You’re Not Taking On Enough Tech Debt. Haven’t seen this point of view before, but there’s at least some merit to it!

[article] Survey: Java Developers Wrestling With Massive Amounts of Technical Debt. Meanwhile, Java devs seem to be crushed under tech debt right now.

[blog] Write-Only Code. I need to update my own thinking on this, as Joseph is right about something here. We’re not going to need to review or even skim every line of generated code.

[blog] Decoded: How Google AI Studio Securely Proxies Gemini API Requests. This is a smart solution for these types of apps. Although a properly hardened production solution would be even more rigorous, as Guillaume points out.

[article] AI Doesn’t Reduce Work—It Intensifies It. Some of this is self-inflicted, according the research, and some is mismatched expectations.

[article] The first signs of burnout are coming from the people who embrace AI the most. The hunger to do more with better tools is making us ignore that internal alarm that says we’re doing too much.

[blog] Agentic Engineering. A better phrase than “vibe coding.” It’s more professional, and accurate. Related.

[blog] Go 1.26 is released. Many updates, including some difference-making performance improvements in garbage collection.

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Former GitHub CEO launches new developer platform with huge $60M seed round

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Thomas Dohmke. (Entire Photo)

Thomas Dohmke, who helped scale GitHub Copilot during his tenure as CEO at GitHub, is back with a new startup that’s coming out of stealth with a hefty $60 million seed round.

Silicon Valley venture firm Felicis, which led the round, called it the largest seed investment ever for a developer tools startup. Other backers include Seattle-based Madrona, Microsoft’s VC arm M12, and Basis Set, along with individuals such as Yahoo co-founder Jerry Yang, Y Combinator CEO Garry Tan, Datadog CEO Olivier Pomel, and developer community voices such as Gergely Orosz and Theo Browne.

Entire, valued at $300 million, is betting that existing developer tools aren’t built for the rise of AI coding agents. Its platform is designed for teams that increasingly manage fleets of AI coding agents rather than writing every line themselves.

Entire is shipping its first open-source project, a command-line tool called Checkpoints. The software records the reasoning and instructions behind AI-generated code and saves that information together with the code itself, so teams can see how and why changes were made. The goal is to make AI-written software easier to review and audit.

Checkpoints is launching with support for Anthropic’s Claude Code and Google’s Gemini CLI, with plans to add other popular agents over time.

“Just like when automotive companies replaced the traditional, craft-based production system with the moving assembly line, we must now reimagine the software development lifecycle for a world where machines are the primary producers of code,” Dohmke said in a statement. “This is the purpose of Entire: to build the world’s next developer platform, where agents and humans collaborate, learn and ship together.”

Entire enters an increasingly competitive market for AI coding tools, with companies such as Google, OpenAI, Anthropic, Microsoft, Cursor, and others offering their own platforms and services.

Dohmke moved from Germany to the United States after selling his startup HockeyApp to Microsoft in 2015. He took over as GitHub CEO in 2021, several years after its acquisition by Microsoft, and led the unit for nearly four years. Dohmke, who is based in Bellevue, Wash., left in August to work on Entire.

Entire has 15 employees and operates as a fully remote company, with team members who previously built developer tools at GitHub and Atlassian. The startup plans to expand its headcount as it works toward a broader platform launch later this year.

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It’s Time to Redesign How Product Teams Work

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Three months ago, I started using Claude Code to handle the repetitive, day-to-day work of product management.

It was an immediate improvement over standard chatbots I have been using for the past few years for handling core PM tasks:

  • Deep market, competitive and technical investigations  
  • Turning raw customer input into structured change requests  
  • Generating high-fidelity specs for the SDLC and user docs

I soon moved from simple tasks to rapid prototyping.

Having coded early in my career (if you know MFC, you know how long ago), it felt natural to create interactive mockups for feature ideas. When ChatGPT came out, I prompted it for Python and JavaScript, copied the code into an IDE, and fed back errors for fixes. This time, it was a different experience: I could get a working prototype in hours and initial feedback within a day.

A dream of autonomous coding, directly applied to my product

Prototyping worked well, but it made me wonder: Could a coding agent take my specifications and produce full, working features?

Answering this would mean a major shift in my workflow.

I would stop generating piles of specifications for the product team to convert into working features and start managing “executable intent” for agentic coding.  My job was no longer overseeing a list of tasks; it was to architect the specific goals, guardrails, and project context an AI needs to turn a requirement into a production-ready feature.

My ultimate vision was autonomous coding applied directly to my product. The transition would start with small, scoped increments and bug fixes to learn the agentic system’s nuances and build trust. Once we prove success on isolated components, we can scale to larger cross-domain features and multi-agent setups.

So I went searching for design patterns that promised HOOTL (human out of the loop, no ongoing human intervention), and soon the name Ralph Wiggum came up (see the side note).

What is the Ralph Wiggium Loop?

Named after the lovably persistent Simpsons character, the Ralph Wiggum Loop is an orchestration pattern for autonomous AI agents.  Popularized by developer Geoffrey Huntley in mid-2025, it shifted AI from “reactive chat” to “autonomous worker.”

Unlike typical one-off prompts, the Ralph Loop runs an agent repeatedly (like a “while loop”) until a task, such as a complex software refactor, is fully complete. It’s become popular because it solves “context rot”: each iteration starts fresh, so the AI doesn’t get tripped up by its previous errors and can keep working for hours without human oversight.

Ralph showed me how, but being naturally skeptical, I wanted to test it first – a “sandbox” to see if the workflow actually worked in a real project before rolling out full autonomous coding in production.

AI built 90% of a feature, I finished the rest

I picked an open-source framework called NiceGUI (a Python framework for building web UIs) as my playground. 

The idea was to implement a new component, an enhanced data table with inline editing, inheriting from the existing table. It had to be a repeatable process enabled by the agentic coding loop, so I decided to build one.

First, I used Claude Code to scout the repository and extract “institutional knowledge” – the specific tech stack, coding patterns, and standards of the project. I fed this context and a detailed feature request into a custom Ralph PRD Factory. This turned my requirements into a JSON-formatted PRD file that the Ralph loop is driven by and that serves as the “executable intent.”

After one day of prep work, I turned the agent loose. In under four hours, it completed the task autonomously – or so it told me.

In reality, I spent a few more hours weeding out UI bugs and minor quirks until it finally felt complete. Still, having the agent take me to 90% was a clear success. The autonomous coding worked.

Redesigning how our product team works

In traditional development, ideas often get lost in translation, passing from PM to designer to engineer to QA, each handoff can dilute or distort the original intent.

When AI builds features from scratch, the old handoff-heavy workflow falls apart. To succeed, teams need to shift from doing manual work to orchestrating the system:

  • The PM as Intent Architect – The PM’s output is no longer a ticket; it is the “brain” of the feature. By owning the context engine, the PM ensures the agent has the exact data and guardrails needed to execute. Success is measured by the precision of the context, not the volume of tasks.
  • The Engineer as Architectural Oversight – Senior developers can stop spending 80% of their time on boilerplate. They become guardians of the system, focusing on high-level architecture, security, and complex logic that agents cannot yet handle.
  • The Designer as Real-Time Reviewer – Instead of static handovers, designers review live agent output as it is generated. They move from static creation to dynamic orchestration, adjusting the visual intent on the fly.
  • The QA as Quality Architect – Testing moves from manual bug-hunting to designing “self-healing loops.” They build automated systems to catch failures early, allowing humans to focus on strategy and edge cases.

Let the AI orchestration games begin

This experiment wasn’t just about building a feature in hours, it offered a glimpse into a bigger shift in how we create products. Autonomous agents building features are becoming reality. It’s not a magic solution, we still have a lot to learn about using agentic AI effectively and guiding it toward the results we want.

This shift doesn’t eliminate specialized roles, it moves us away from manual “doing” and toward orchestrating and designing systems.

To succeed, we all need to level up and expand our roles – moving from doing manual tasks to guiding and orchestrating AI. I’m excited about this shift. It’s time to stop just managing backlogs and start shaping the future.

The post It’s Time to Redesign How Product Teams Work appeared first on ShiftMag.

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