Asking well · for leaders
Asking well as a leader
Leaders often ask AI the way they would ask a senior colleague, in a few words. "Draft the board update" works with a chief of staff who has sat through the last six meetings. A model has not. It fills the gaps with a generic executive voice and invented priorities.
Asking well means stating what an experienced colleague would already know. Who reads this? What decision should it support? What must it not say? What does the reader already believe? Leaders who answer those questions in the request get drafts they can use.
Where it comes up
Preparing for a difficult conversation
You need to tell a long-serving manager that their team is being merged into another. A strong request describes the person’s likely concerns, the facts you can share, the facts you cannot share yet, and asks for the questions they are likely to raise.
A one-page decision memo
Your leadership team must choose between two pricing options. The request should name the decision, the reader, the criteria that matter, and ask for each option’s strongest case and weakest point.
An outline for an all-hands talk
You have ten minutes to explain a change in company priorities. A good request states the audience’s current mood, the three points that must land, and the questions you expect from the floor.
What it looks like at each band
E1 · Foundational
Gets useful drafts on familiar writing tasks with short requests. Requests name the document type but not the reader, the decision, or the limits. Improves results by rewriting the draft by hand rather than by improving the request.
E2 · Proficient
Writes requests that state the reader, the purpose, the length, and what to avoid. Asks for options, such as two framings of a hard message. When a draft misses, adds the missing detail to the request instead of starting over.
E3 · Distinguished
Uses AI to test thinking, not only to draft. Asks it to argue against a preferred option, to list what a skeptical director would ask, or to find gaps in a plan. Splits a large document into a sequence of requests.
E4 · Exceptional
Writes request patterns the leadership team reuses for recurring work, such as decision memos and meeting preparation. Knows when a task needs one precise request and when it needs a short exchange. Direct reports improve their own requests by copying this leader’s approach.
Common mistakes
Asking for a document type and nothing else
"Write a strategy memo" gives the model nothing about your strategy, your reader, or your constraints. It returns a template filled with general advice.
Asking AI to agree with you
A request that states your conclusion and asks for support will get support. Ask for the strongest case against your view as well, so you see it before your board does.
Leaving out what cannot be said
Hard conversations and announcements have boundaries, such as legal limits or undecided details. If the request does not state them, the draft may promise something you cannot deliver.
A worked example
Preparing for a meeting with a direct report whose project you are canceling.
Help me tell my employee their project is canceled. Make it supportive.
The model does not know the person, the reason for the decision, or what can be shared. It will produce general reassurance that may sound hollow or promise things the leader cannot offer.
I need to tell a senior engineer that the project she has led for eight months is stopping. The reason is a change in company priorities, not her performance. I can confirm her role is secure. I cannot yet say what she will work on next. List the five questions she is most likely to ask. For each, suggest a direct and honest answer in two sentences. Flag any answer that would commit me to something I have said I cannot confirm.
The request states the facts, the reason, what can and cannot be shared, and the form of help wanted. It asks the model to check its own answers against the stated limits.
The full study guide for this skill, for every role, is Asking well. The other five skills for leaders are on the AI skills for leaders page. A one-page summary is in the AI prompt checklist.
See where you stand
The free check grades asking well and the other five skills in about fifteen minutes. Nobody sees the grade but you.
Then build the skills and prove it. The three steps for leaders list the courses and templates that fit the work.