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MY TINKERING

I built a Leadership OS to help me lead with better context

I lead a multidisciplinary design team. A normal day can move from a 1:1 to strategy, product design, a technical question, and hands-on building. The context I needed was there, but scattered across meetings, Slack, GitHub, and my own memory.

My main work surface

I built a private Leadership OS with GitHub Copilot, GitHub, and Markdown to keep the context connected. Copilot is the conversation layer. The files are the memory. Together, they help me pick up where I left off without starting over every time.

Most of my work is not code. I use Copilot to prepare consequential conversations, turn meetings and messages into decisions and artifacts, shape product direction and move design work toward implementation, make sense of technical systems, run work in parallel, and occasionally code.

The GitHub Copilot app has become my main work surface because it keeps conversation, repository context, skills, artifacts, and parallel sessions together. That is the product story I find most interesting: Copilot can be shaped around the work you need to do, whether you are leading, designing, or building.

What changed

I no longer need to treat every meeting like a note-taking exercise or spend as much time getting back up to speed.

The bigger shift is how fluidly I can work. I can move something forward, step into a completely different kind of conversation, and come back without losing the thread.

What this looks like

  • Preparing conversations and communication

    Bring together past discussions, commitments, and evidence, then turn them into talking points, a response, or a clear next step.

  • Turning context into an artifact

    Combine meetings, messages, research, and issue history into a plan, update, brief, or guide.

  • Shaping product direction

    Move from research and earlier decisions into a clearer direction, prototype, critique, and implementation-ready handoff.

  • Running work in parallel

    Give separate sessions bounded jobs, review their output, redirect when needed, and bring the work back together.

  • Starting the next day

    Review what changed, update the context that matters, and bring forward what may need my attention.

How it works

Raw history preserves what happened. Living digests keep the current state clear. Focused skills help me apply that context to weekly planning, manager coaching, product design, technical sensemaking, and system health.

Each night, it checks the day's meetings, Copilot sessions, Slack, and GitHub work. It updates what matters, surfaces what may need attention, and keeps missing sources visible.

  1. Capture

  2. Distill

  3. Apply

  4. Act

  5. Write back

What I designed

The files are simple. I designed how the context is organized, how it stays current, how each skill uses it, and how useful outcomes get written back. I built clear boundaries too: Copilot can retrieve, organize, draft, and update safe files, but it cannot silently change my priorities, make sensitive people judgments, or act outside the repository without my approval.

For me, this is design and design engineering: deciding how people and agents should work together, then building enough of the system to use it in my real work.

What makes it different

It is not trying to remember everything or act on my behalf. The memory lives in files I can read, correct, and change. The skills have clear jobs. The judgment stays with me.

A portable starting point

My working system contains private context about people and the organization, so I cannot publish it. I published the reusable architecture as a clean, Markdown-first starter that other leaders can adapt without any of my private context.

Explore the Leadership OS starter

BUILT WITH

  • GitHub Copilot
  • GitHub
  • Markdown