The sharpest leaders aren't the ones with the best instincts.
They're the ones whose instincts are best informed.
The system is only as good as what you put into it. Start with the context files. Everything else runs on top of them.
Three documents that tell the system who you are, how you work, and how you think. Without them, you have a generic AI assistant. With them, you have something that sounds like you and thinks about your actual situation.
Quick Desktop is where most of you will start — it's straightforward and connects to your existing tools. Instructions are below.
Skills are workflows you save once and reuse. Three are ready to copy below — morning briefing, team coaching prep, and executive meeting prep. Start with one. The morning briefing is the one that changes your day fastest.
Open any LLM. Paste the prompt for each file. Answer honestly. Save the output. These three documents become the foundation everything else runs on.
Your core values, beliefs, and principles. The system uses this to understand what you stand for, how you make decisions, and what matters to you when the answer isn't obvious. This is the one that takes you somewhere you didn't expect.
Paste this prompt into your AI assistant:
A foundational reference that gives the system deep understanding of your org, your number, and the environment you operate in. The more specific you are, the sharper every output becomes.
Paste this prompt into your AI assistant:
How you write: your sentence structure, vocabulary, punctuation habits, and the patterns you never use. This is what makes AI output sound like you, not like a generic assistant. Build the profile first, then use the editing checklist below every time you review AI-drafted content.
Step 1 — Build your profile
Paste this prompt + 2–3 of your own emails or messages into any LLM:
Step 2 — Remove the AI tells
AI-generated text has recognizable patterns. Readers are getting better at spotting them. Run every AI draft through this checklist before you send it.
Context files tell the system who you are. The steering file tells it how to act on that. Without it, you have a well-informed generic assistant. With it, you have something that operates like a chief of staff.
Create a file called steering.md in Quick Desktop. Paste the base template below. Edit the sections marked CUSTOMIZE before you start using it.
# Steering File ## Who I Am I am a senior leader at [your company]. I run a large org accountable for significant business outcomes. I operate in a matrixed environment with high political complexity. My time is predominantly meetings. My solo work happens in short, focused bursts. [CUSTOMIZE: add your org size, your number, the VP you report to, and what they care about most] ## Communication Rules Default to my email register: direct, point-first, no preamble, ends with a concrete ask or next step. Never use hyperbole or filler transitions. Never hedge. Use active verbs. Write like a senior operator, not a consultant. [CUSTOMIZE: load your writer-profile and add 2 rules specific to how you write] ## Context Application Rules Strategic work and org decisions: pull from org-context.md first. Any written output: apply writer-profile.json. Decisions with values or ethics dimensions: apply personal-constitution.md. Meeting notes: save to Obsidian with date and meeting name. Flag decisions and commitments at the top. ## Hard Stops Never send any communication without showing me the draft first and receiving explicit confirmation. Never fabricate org details, performance data, or leadership dynamics. If information is missing, ask me rather than filling the gap. [CUSTOMIZE: add at least two hard stops specific to your role]
Two tools do most of the work. Start with Quick Desktop — it's the fastest path to a working system.
Where you talk to the system. Reads your context files. Connects to your tools. Start here.
Where everything lives. Every briefing, meeting note, and context file. Gets smarter every day. obsidian.md
Free · Local · Your data stays yours
Browser extension. Save any article or page directly into your vault in two clicks. obsidian.md/clipper
2 min to install · You'll use it constantly
~/[your-cloud-folder]/Obsidian/These are workflows you save as skills in Quick Desktop. Once saved, you invoke each one by name or by typing its trigger phrase. Copy the prompt text exactly.
Pulls today's calendar, unread email, Slack mentions, and your weekly focus file. Delivers a prioritized briefing: flags that can't slip, schedule with context, email requiring action, and this week's priorities. Saves automatically to a dated file.
Pull today's calendar, check unread email (top 10), check Slack mentions, read your Weekly-Focus file, and deliver a briefing covering: — Top flags that can't slip today — Today's schedule with context on each meeting — Email that requires action — Slack mentions — This week's priorities Save the briefing to a dated file.
What this gives you: clarity about your day before anyone else has shaped it for you. This one can also run as a scheduled agent, so the briefing is waiting for you before you ask.
Pulls their goals and recent performance data, surfaces the pattern across recent conversations with that person, flags any commitments you made that you haven't followed through on, gives you the right questions to ask — and tells you what this conversation probably is before you walk in.
When prepping for a 1:1 or coaching conversation with someone: pull their goals and recent performance data, surface the pattern across recent conversations with them, flag any commitments you made that you haven't followed through on, give the coaching questions to ask (not a script — the right questions), and tell the user what this conversation probably is.
What this gives you: clarity about your people — including what you promised and forgot.
Pulls what was committed last time and whether it was delivered. Surfaces what's changed since the last conversation. Anticipates the hard questions. Tells you what you want to walk out with — and what not to do. Works for customer calls, stakeholder meetings, and ambush conversations with direct reports.
When prepping for a customer or stakeholder meeting: pull what was committed last time and whether it was delivered, surface what's changed since the last conversation, anticipate the hard questions, tell the user what they want to walk out with, and tell them what not to do.
What this gives you: clarity about your most important conversations — including exactly where to stop talking.