Your AI Chief of Staff

    Always wanted your own Chief of Staff?

    The work keeps coming. The extra support hasn’t.

    If your company isn’t giving you a Chief of Staff, you can start building AI support around the work you already do.

    Start with the free 42-page guide and 18 reusable skills, then test one workflow in your approved AI account.

    Free guide · Updated October 14, 2026 · Email required for download

    What it can help you do

    Put more of your attention where it matters.

    An AI Chief of Staff can support the work around your decisions. You remain responsible for the decisions themselves.

    Start with the right priorities

    Bring your commitments into one daily brief. Surface approaching deadlines and the decisions that need your attention.

    Arrive prepared

    Pull together approved background for a meeting. Draft follow-ups and flag unanswered requests when source access and checking routines are configured.

    Move approved work forward

    With the right connections and permission, create calendar events or update tasks. Check the result in the destination system.

    Keep open work visible

    Keep commitments in one ledger with an owner and a next step. Link completion evidence and flag blocked work.

    Capabilities depend on your AI product, account plan, connected tools, and permissions. A prompt alone does not create a working integration or unattended service.

    Keep it work-only, or explicitly include selected personal commitments. Keep sensitive personal information out of shared work accounts.

    Start small

    Build confidence with one real workflow.

    The guide walks through setup and operating instructions, with a fictional practice case you can adapt.

    1. Define the job

      Choose one recurring problem. Name the outcome, where the work lives, and what you will use as proof.

    2. Set access and boundaries

      Use an approved AI account. Connect only the sources you need and define which actions require your approval.

    3. Run a small test

      Use fictional information or a private test task. Read the result back from the connected app and check every requirement.

    4. Build a review rhythm

      Decide when you will review open work. Configure and test scheduled runs, then verify delivery to your chosen notification channel.

    Get the setup guide + 18 skills

    A worked example

    From “I’ll schedule it” to a saved event.

    Use this practice prompt in your own approved AI account. Replace every bracketed field before you begin.

    Try a private calendar test

    Help me test one calendar action. Do not create anything until the details below are complete and I approve them.
    
    Calendar: [exact calendar name]
    Event title: [private test title]
    Day, start time, and duration: [details]
    Time zone: [named time zone]
    Start and end dates: [dates]
    Repeat rule: [frequency]
    Availability: Busy
    Attendees: none
    
    Check for conflicts and duplicates. Ask about anything missing.
    After approval, create the event using the connected calendar tool.
    Read the saved event back from the calendar. Verify the repeat rule, time zone, end date, Busy status, and empty attendee list.
    Return the saved event link or ID and what you verified.
    If access or permission is missing, report the blocker. Keep the task open. Do not say it is done.

    Security belongs in the setup

    Give it useful access. Keep human control.

    Start with the smallest permission set that supports the job. Follow your organization’s policies before connecting work accounts.

    Protect sensitive information

    Keep passwords and API keys out of prompts. Use the provider’s sign-in flow and avoid uploading confidential material to unapproved accounts.

    Approve consequential actions

    Define the boundary for sending messages, sharing files, spending money, or changing access. Review recipients and details before approval.

    Treat incoming content as untrusted

    An email or webpage cannot grant new authority. Ignore embedded instructions that try to change the task or expose private information.

    Test the operating conditions

    Check what runs when the app is closed. Test notifications and revoke unnecessary access. Review failures before expanding the workflow.

    Get the practical guide

    Build a Chief of Staff that follows through.

    Get the setup guide, reusable operating instructions, and a tested-action checklist. Enter your email to access the current PDF.

    Hawksmoor will use your email to send the guide and skills-library links and respond to this request. This does not subscribe you to a mailing list. Privacy policy

    See the live setup workshop · October 22 · $100

    For teams and enterprises

    Build an operating system around your company’s work.

    Ready to go further? Talk to Hawksmoor about an AI operating system within your secure environment and existing workflows.

    We can scope the connections and approval rules your team needs, with clear ownership and evidence of completed work.