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Engineers have Cursor; leaders play “Calendar Tetris.” This case study shows how to build a personal AI assistant using commercial tools. Learn to automate toil, manage high-volume context, and reclaim time for strategic impact.
The AI market is currently obsessed with the Individual Contributor. Tools like Cursor and Cloud Code have revolutionized the IDE, allowing engineers to ship features and crush complexity at record speeds. But as Engineering Leaders, we have been largely left out of this revolution. Our “IDE” isn’t a code editor; it is a fragmented ecosystem of calendars, documents, and messaging apps.
While our teams move faster, we find ourselves bogged down, playing “Calendar Tetris” and drowning in context switching. Since the release of ChatGPT 2.5, I have been on a mission to fix this imbalance. I wanted to answer a simple question: Can I build a personal AI assistant that actually understands the context of engineering leadership?
In this session, I will walk you through the architecture of my personal AI system built using existing commercial tools. We will move beyond basic chat prompts and look at how to automate the “heavy lifting” of management. We will cover how to use AI to:
- Streamline meeting preparation and context gathering.
- Stay on top of a high volume of conversations across multiple teams and projects.
- Reduce the manual toil required for operational data analysis.
- Act as a “strategic coach” to help you prioritize between short-term fires and long-term goals.
You will leave with a blueprint for building your own assistant—one that handles the noise so you can focus on the signal, the strategy, and your people.
Key takeaways
- The “”Leader’s Stack””: A walkthrough of the specific commercial tools and integrations used to build a low-maintenance, high-impact personal assistant.
- Managing Scale: How to use AI to summarize and track context across dozens of concurrent streams without losing the details.
- The AI Coach: Techniques for using LLMs to analyze your schedule and tasks, helping you enforce prioritization between the urgent and the important.
- From Toy to Tool: How to move past the novelty of LLMs and make it into a centralised IDE that help you become a more impactful leader?
