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Working with AI: Lessons from software’s head start • Jack Damon

Source: https://jackdamon.org/blog/working-with-ai/

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Working with AI: Lessons from software’s head start

October 27, 2026

On Monday, October 26, I gave this talk at a dinner hosted by With Coverage. It explores parallels between AI adoption in software engineering and financial knowledge work, using Excel as finance’s equivalent of the IDE to map four stages: AI assists, collaborates, executes, and coordinates. These are broad generalizations, but software’s head start offers useful clues about where non-programming knowledge work workflows may be headed and how to prepare as an individual and organization.

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![Image 1: Working with AI: Lessons from software’s head start. Title slide, October 2026.](https://jackdamon.org/assets/images/working-with-ai/slide-01.webp)

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[![Image 2: Parallel timelines for software engineering and financial knowledge work introduce the deck’s estimated 12–18 month adoption lag.](https://jackdamon.org/assets/images/working-with-ai/slide-02.webp)](https://jackdamon.org/assets/images/working-with-ai/slide-02.webp)

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![Image 3: Timeline adds stage 1, AI assists: copying code and Cursor’s March 2023 launch.](https://jackdamon.org/assets/images/working-with-ai/slide-03.webp)

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![Image 4: Spring 2023: Cursor’s inline code editing illustrates AI assisting within the existing programming workflow.](https://jackdamon.org/assets/images/working-with-ai/slide-04.webp)

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![Image 5: Timeline adds stage 2, AI collaborates: Cursor Agent launches in November 2024.](https://jackdamon.org/assets/images/working-with-ai/slide-05.webp)

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![Image 6: Fall 2024: Cursor Composer’s code diffs and chat illustrate AI collaborating within the programming workflow.](https://jackdamon.org/assets/images/working-with-ai/slide-06.webp)

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[![Image 7: Timeline adds stage 3, AI executes: highly capable coding models and mainstream Claude Code adoption in late 2025 and early 2026.](https://jackdamon.org/assets/images/working-with-ai/slide-07.webp)](https://jackdamon.org/assets/images/working-with-ai/slide-07.webp)

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[![Image 8: Winter 2025: Claude Code, an Anthropic headline, and an Andrej Karpathy post illustrate a shift toward agents executing independently.](https://jackdamon.org/assets/images/working-with-ai/slide-08.webp)](https://jackdamon.org/assets/images/working-with-ai/slide-08.webp)

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![Image 9: Timeline adds stage 4, AI coordinates: Cognition and Factory cloud agents and swarms in 2026.](https://jackdamon.org/assets/images/working-with-ai/slide-09.webp)

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[![Image 10: A rising monthly usage chart and Cognition and Factory headlines illustrate the 2026 shift toward autonomous cloud workforces.](https://jackdamon.org/assets/images/working-with-ai/slide-10.webp)](https://jackdamon.org/assets/images/working-with-ai/slide-10.webp)

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![Image 11: Timeline adds Excel’s first stage: copying and pasting formulas from ChatGPT during 2023–2025.](https://jackdamon.org/assets/images/working-with-ai/slide-11.webp)

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[![Image 12: Timeline adds Excel’s collaboration stage, showing Shortcut’s July 2025 demo and Claude in Excel in October 2025.](https://jackdamon.org/assets/images/working-with-ai/slide-12.webp)](https://jackdamon.org/assets/images/working-with-ai/slide-12.webp)

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![Image 13: Excel’s Cursor Agent moment: side-by-side screenshots of Shortcut and Claude in Excel.](https://jackdamon.org/assets/images/working-with-ai/slide-13.webp)

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[![Image 14: Four-stage timeline comparing software engineering and Excel AI, marking financial knowledge work at the transition toward independently executing agents.](https://jackdamon.org/assets/images/working-with-ai/slide-14.webp)](https://jackdamon.org/assets/images/working-with-ai/slide-14.webp)

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![Image 15: Is Excel approaching its end-to-end agent moment?](https://jackdamon.org/assets/images/working-with-ai/slide-15.webp)

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![Image 16: How long until spreadsheet users spend most of their work without the actual spreadsheet open?](https://jackdamon.org/assets/images/working-with-ai/slide-16.webp)

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[![Image 17: Timeline adds a possible 2027 coordination stage and asks what a Cognition or Factory equivalent for knowledge work will look like.](https://jackdamon.org/assets/images/working-with-ai/slide-17.webp)](https://jackdamon.org/assets/images/working-with-ai/slide-17.webp)

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[![Image 18: Cloud agents are independent, proactive, and scalable: they work without an open laptop, respond to triggers, and delegate across workers.](https://jackdamon.org/assets/images/working-with-ai/slide-18.webp)](https://jackdamon.org/assets/images/working-with-ai/slide-18.webp)

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![Image 19: A two-column table pairs lessons from software teams with ways finance teams can prepare.](https://jackdamon.org/assets/images/working-with-ai/slide-19.webp)

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[![Image 20: First lesson: bottlenecks shift from producing work to reviewing it, increasing the importance of reviewing AI outputs.](https://jackdamon.org/assets/images/working-with-ai/slide-20.webp)](https://jackdamon.org/assets/images/working-with-ai/slide-20.webp)

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[![Image 21: A second lesson: institutional knowledge becomes infrastructure, so firms should document implicit knowledge and make it accessible.](https://jackdamon.org/assets/images/working-with-ai/slide-21.webp)](https://jackdamon.org/assets/images/working-with-ai/slide-21.webp)

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[![Image 22: A third lesson: delegation becomes a core skill; train managers on AI tools and individual contributors on delegation.](https://jackdamon.org/assets/images/working-with-ai/slide-22.webp)](https://jackdamon.org/assets/images/working-with-ai/slide-22.webp)

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[![Image 23: Screenshot of Cognition’s article on allocating AI spending by efficiency, with guidance to reward efficient users and coach others.](https://jackdamon.org/assets/images/working-with-ai/slide-23.webp)](https://jackdamon.org/assets/images/working-with-ai/slide-23.webp)

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![Image 24: A green callout beside the article says efficient AI users should receive more AI spending.](https://jackdamon.org/assets/images/working-with-ai/slide-24.webp)

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![Image 25: A blue callout says less efficient AI users should receive coaching to improve.](https://jackdamon.org/assets/images/working-with-ai/slide-25.webp)

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[![Image 26: The preparation table adds a fourth lesson: greater individual capability changes team design, so reconsider team composition.](https://jackdamon.org/assets/images/working-with-ai/slide-26.webp)](https://jackdamon.org/assets/images/working-with-ai/slide-26.webp)

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