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Questions people ask before they say yes

Seventeen short answers in five groups, each ending with a link to the page that goes deeper.

THE DIRECT ANSWER

Before you say yes to a request, ask two questions: one for a fact you are missing and one for who decides. Treat what you offer as a proposal until the person who decides confirms it. The answers below are practice material with fictional cases, not advice about a real situation.

What should I ask before I commit to a request?

What are the two questions to ask before I say yes?

Ask “What don't I know that someone here does?” to find a missing fact, and “Who decides this, and what do they need from me first?” to find the owner. Keep both short and answerable: how much, which, when, who. A scoped yes or a proposal stays a proposal until the person who decides confirms it.

Go deeper: the request-clarification checklist →

What do I ask when someone gives me a deadline?

Ask what must happen by that time, who needs the work, and what would be affected if it arrived later. Then compare what must be ready with the hours that are really free: in the fictional Fixed Deadline case, five hours are free before Friday noon, and the core work (3 hours) plus the handoff (1 hour) fits in four of them. The polish takes 3 more hours, so the full version is seven hours of work in five hours of time.

Go deeper: how to ask for the real deadline (guide) →

What do I ask at the start of a new piece of work?

Pick from the project kickoff question bank: 100 questions in eight scenarios, including scope, deadline and capacity, decision rights and AI-produced work. Each question is tagged with the one of the two questions it serves, a fact or an owner, and you check up to ten for one kickoff. It is a shelf to pick from, not a checklist of everything to ask, and it is a draft template.

Go deeper: the project kickoff question bank (draft) →

How do I clarify a request, push back politely and find out who decides?

How do I clarify requirements with a manager?

Ask what comes off your list if this goes on it, what done looks like in one sentence, and whether the date is yours to set or someone above you sets it. If the requirements keep changing, summarize the current baseline, list the proposed changes and ask the authorized owner to confirm one version. A summary on its own does not create approval, so keep anything unresolved visibly unresolved.

Go deeper: how to confirm requirements that keep changing (guide) →

How do I push back on a request politely?

Start with the request itself, then say the fact you hold first: a number, a time or a record. Then offer a scoped yes that says what is in and what is out, for example core work and handoff by Friday noon, with the polish decided separately. A pushback script asks for a fact or an owner, not for winning an argument, and a scoped yes stays a proposal until the person who decides confirms it.

Go deeper: the pushback script builder →

How do I find out who can approve a change?

Name the exact decision first, such as a date, a scope, an access or a record, and ask who can approve that one change. The people who know the facts, who explain the options, who approve and who carry out the plan are often different people. Record the name of the one who decides and the next step, and if authority is unclear, ask for a named route for clarification instead of treating the loudest response as approval.

Go deeper: how to clarify who can decide (guide) →

What is a decision-rights sheet?

It is a one-page sheet where each decision gets one name in Decides, plus who is consulted first, who is told after and who does the work. Consulted people give input before and people who are only informed are told after, but only the name in Decides decides, and if you do not know the name you write Unknown, never two names. You fill it in on the site, copy a plain-text summary or print one page, and nothing is saved or sent.

Go deeper: the decision-rights sheet →

Can an AI tool be the one who decides?

On the decision-rights sheet no tool or bot is written as the one who decided: a tool can describe the work but cannot approve it. In the fictional case “It says it’s done,” Otto, a fictional AI research assistant, reports that all 20 sources are summarized, and Dana decides which sources may be cited. Ask what the tool actually checked and what it assumed, then ask who can sign it off.

Go deeper: the scenario “It says it’s done” →

What should I write down before a handover or a meeting?

What should I put in a handover?

Say what is handed over, to whom and when, and point to the one current source with its version or date. Mark each part as verified or open, and for each open part write what is missing, who can close it and by when. Then say what the receiver can use now and what the receiver should hold off on, and check off the seven lines before you send.

Go deeper: the handover checklist (draft) →

What should I put in my prep for a meeting?

Write what you know, what you are missing and who holds it, and the one fact you will share. Then write the two questions you will ask, who decides and your next step, which is a proposal, not a promise, until the person who decides confirms it. If the other side is an AI tool, add what it actually checked, what it assumed and what you will verify before you rely on it.

Go deeper: the two-question prep card → Or fill it in on this site: the meeting prep (draft) →

What if a request touches several people?

List each person or role in a stakeholder map: what they decide, what they need to hear from you, what you need from them, how and when you will ask, and your next contact. A row that says Unknown has a question in its ask box, and that question is your first move. The map is a draft template with a fictional example, and you can copy it, export a CSV file or print the pack version.

Go deeper: the stakeholder map (draft) →

How do I practice?

How do I practice the two questions?

Play one of the eight free cases: read your half of the brief, ask up to two questions, and you learn only the answers to what you ask. Then choose a plan, check it, and write a next-step card you can copy or download. Every case is fictional, there is no sign-up, and you can replay the same facts with an AI tool as the counterpart.

Go deeper: the free cases →

What is the branching simulator?

It is eight short branching scenarios, about three minutes each, where you choose what to say, ask for the missing half and see where each path ends. In every scenario each ending can skip ahead to a later moment the case points to (Friday noon in Fixed Deadline) and says what the case does not give. The scenarios are Fixed Deadline, Scope Swap, Credit Repair, A short overlap for an eight-file package, Two role windows around a one-page brief, It says it’s done, The vendor’s bot said Friday and The brief the client’s AI rewrote. After an ending where you asked something, you can try again with what you now know: the answers you asked for stay in a list at the top, labeled as learned earlier, and the new run starts fresh so you can ask different questions. Your choices stay on the scenario page and are not saved or sent anywhere, and the scenarios need JavaScript.

Go deeper: all eight branching scenarios →

How does the 30-day practice tracker work?

Pick one short practice from the site, do it, check that day and add a one-line note: a free case, a simulator scenario, the self-check, a pocket-card question or a two-question message. A picture of 30 pieces fills in one piece for each checked day, the days do not have to be in a row, and a skipped day costs nothing. It counts days practiced, not skill, it promises no result, and it is a draft template that clears when you close the tab, so copy or export first.

Go deeper: the 30-day practice tracker (draft) →

What is free, who is Otto, and is this advice?

What is free, and what is a draft?

The free cases, the branching scenarios, the self-check, the prep card, the fill-in templates and the fifteen guides are free to use, with no sign-up. Some of the fill-in templates are marked as draft templates and are still free to use, and the template packs, the question card deck and the team workshop facilitator deck are drafts for review, not finished products. The e-book Before You Say Yes is a draft edition: chapters 1 and 2 are a free sample, and the full book is not published, not for sale and not offered as a download. Membership is planned but not open, and nothing on this site is for sale.

Go deeper: the resources page →

What is Otto?

Otto is a fictional AI assistant, a character in the practice cases that only knows what the case says it knows. Otto’s replies are written for each fictional case, so they are not a prediction of how any real AI product behaves. In most of the free cases you can replay the same facts with Otto as the AI counterpart, and in the others with another fictional AI.

Go deeper: the cases and their fictional cast →

Is this advice or coaching?

No: it is practice material with fictional cases, not advice about a real situation, and the planned membership will not include coaching. The materials have not been validated as a training intervention, and the site claims no client results, accredited credentials or guaranteed workplace outcomes. A rehearsal is preparation, not permission or a guaranteed solution.

Go deeper: what we have not established (about) →

Every case on this site is fictional, and Otto is a fictional AI. Nothing on this page is advice about a real situation, and none of it promises a result.

Try the two questions yourself.
Play a short fictional case, ask for the missing facts and see what changes.

Play a free case ↗

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