高階主管與幕僚長的最佳 Claude Skills（2026）

Ryan - Chief of Staff AI Skill ($29) for board packs, OKR drafts, all-hands scripts and one-page decision memos. Pair it with Diane - Executive Assistant ($29) if the daily inbox and meeting load is the bigger problem. Rule of thumb: 'we need to decide' is Ryan, 'nobody knows how we do this' is Owen (Operations Manager, $29).

No. None of them connect to your inbox, calendar, Slack, CRM or drive. You paste the thread or attach the file, and the skill processes what you gave it. Diane's inbox-triage workflow means pasting a block of email and getting back an action list, not the skill fetching anything on its own. Any article describing an AI chief of staff that reads your mailbox is describing a different category of product.

It can structure one - headline, the numbers that moved, the approval you are asking for, and risks with owners against them - but it cannot supply the figures. Give it a topic without data and it will format invented placeholders that read exactly like real results, so check every number before the pack leaves your desk. Your name goes on the output, not the model's.

Skills need code execution enabled, which you switch on as 'Code execution and file creation' under Settings then Capabilities. If the Skills menu is greyed out, that switch is usually why, and on Team and Enterprise it may be controlled by an organisation owner rather than by you. Anthropic's help centre currently lists Skills on Free, Pro, Max, Team and Enterprise, while its Academy tutorial lists Pro, Max, Team and Enterprise, so if you are on the free plan check Settings then Capabilities for your own account rather than trusting either page. Where there is no Skills menu, paste the SKILL.md contents into the conversation and it works the same way, without automatic triggering.

Each is a ZIP with SKILL.md at the root of the archive, not inside a nested folder. In the Claude desktop app go to Customize, then Skills, then the plus button, upload the ZIP and toggle it on. Claude reads the SKILL.md and shows you a summary before you enable it. You can keep several installed and switch them on and off independently.

Yes. Open SKILL.md in a text editor and paste its contents into custom instructions or a project's instructions. You lose the on/off toggle and the automatic triggering, but the behaviour is the same. The ZIP upload flow is specific to Claude.

A skill configures the role and waits for you to direct it: you decide what to ask for and in what order. An agent bundles the same role with an activation prompt that runs the workflow, asking for one input at a time until the artefact is done. William is $32 against Diane's $29, so the three dollar gap is not really the decision. The question is whether you would rather drive or be driven.

Five things. They have no access to your email, calendar, Slack, CRM or drive. They do not know your numbers, so a board pack is only as good as the figures you paste in. They have no read on your internal politics, and anything they say about a named colleague's motivation is fabrication. They do not remember between sessions unless you keep the context in a project. And your name goes on the output, which makes an unchecked confident sentence the expensive failure mode.