Ask it like you would ask a person.

Fifty things worth saying to a program manager that never sleeps, grouped by who is asking. Things to ask it, things to tell it to change, and rules to set once and never repeat. The highlighted words are the parts you swap for yours.

SAMPLES · NO SYNTAX TO LEARN

Sponsor or executive

You are accountable for it, you do not run it, and you read about it once a week.

8 prompts
Ask

Are we going to make [date]? Give me the honest answer, not the polite one.

It answers with the chain that decides it, not with a colour.

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Ask

What would embarrass me if the board asked about it today?

Finds the thing that is true, unowned, and not in anyone’s deck.

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Ask

What changed since I last looked, and what should I actually care about?

Written for someone who reads the program once a fortnight.

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Ask

What decisions are waiting on me, and what does each day of waiting cost?

Turns your inbox into a number instead of a nag.

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Ask

Show me the three risks most likely to move the date, and who owns each.

Three, not thirty, ranked by effect on go live rather than by severity.

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Change

I have approved [thing]. Record it, redate what it unblocks, and tell the owner.

One sentence closes the decision, moves the rows, and sends the note.

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Change

Move go live to [date] and show me everything that breaks.

Proposed with the full ripple attached, before you accept a single row.

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Set up

Send me five lines every Monday at 7am and nothing else all week.

Sponsors get one message, not a dashboard login they will never use.

Program director or PMO

You own the plan, the governance, the reporting, and the argument about the date.

10 prompts
Ask

What is on the critical path this week, and what is sitting behind it?

The chain, in order, with the first thing that has to move.

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Ask

Which rows have no owner, no date, or neither?

The audit that normally costs a PMO analyst a day and a spreadsheet.

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Ask

Where are two workstreams assuming different things about the same date?

Contradictions between plans, which is where slippage is born.

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Ask

Build the steering pack for Thursday.

A deck from live rows, not last month’s deck with the dates typed over.

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Ask

What did we agree in the last three steering meetings that has not happened?

Decisions have a half life. This is the list of the ones that expired.

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Change

Re-baseline against [date] and mark what moved, by how much, and why.

A baseline you can defend, because every move carries its reason.

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Change

Add a stage gate before cutover with these exit criteria: [list].

Governance you described in a sentence, wired into the plan.

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Change

Close [risk or issue id]. The mitigation landed and the evidence is [where].

Closes it with the evidence attached, not just the status changed.

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Set up

Chase anything with no update for five working days, then escalate to me on the eighth.

Your follow-up rhythm, running every morning without you.

Set up

Our RAG rules are [rule]. Use ours and stop using yours.

It reports in your language, against your thresholds.

Technical program manager

You own the systems, the interfaces, the environments and the cutover sequence.

9 prompts
Ask

What depends on [system or interface], and what happens if it lands late?

The blast radius of one component, counted in outcomes and days.

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Ask

Show me the fit gap items with no decision, sorted by how much they block.

The gaps that matter, ahead of the gaps that are merely open.

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Ask

Walk me through the cutover sequence backwards from go live.

Backwards is the only direction a cutover plan survives.

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Ask

Which environments are needed by when, and is anything double-booked?

The clash that usually surfaces the week you need the environment.

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Ask

What is being built that nothing in the plan actually asked for?

Scope that arrived without a requirement behind it.

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Change

Add a dependency: [A] cannot start until [B] is signed off.

Adds the edge and redates everything downstream of it.

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Change

Split [process area] into the sub areas that genuinely have different owners.

For when one area is really three and one person is carrying all of it.

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Change

Mark [requirement] as a gap, give it to [name], and date it against the build freeze.

A gap with an owner and a date, which is the only kind that closes.

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Set up

Treat anything touching [integration] as high risk until data migration passes.

A standing rule, applied to rows that do not exist yet.

Delivery or workstream lead

You own one slice of it, and you are being asked when it will be done.

7 prompts
Ask

What is mine this week, in the order I should do it?

Sequenced by what it unblocks, not by whoever asked loudest.

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Ask

What is blocked on me, and who is waiting?

Names attached, so you know whose week you are holding.

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Ask

Am I going to hit [milestone]? If not, by how much?

A number of days, before somebody else discovers it.

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Ask

What did I say last week that has not happened?

The quietly honest one. Ask it on a Friday.

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Change

[Task] is done. The evidence is in [link].

Closes the row the way you would say it out loud.

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Change

I need two more days on [thing]. What does that hit?

The cost of the slip, before you ask anyone to accept it.

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Change

Hand [item] to [name] from Monday, they have the context.

Re-owns the row and tells both people, in one line.

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Business or process owner

You own the process after go live, and the team who has to work in it on day one.

6 prompts
Ask

What is changing for my team, and when does it actually land?

Your slice of the program, in plain language and real dates.

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Ask

Which of my processes still have no tested design?

What is on paper versus what somebody has actually run.

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Ask

What am I on the hook for before go live?

Your commitments, pulled out of a plan you did not write.

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Ask

What happens to my team on day one and in week one after cutover?

The part everyone plans last and feels first.

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Change

Sign off [process area]. We tested it on [date].

Signs it off with the date and the evidence, in one sentence.

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Change

We cannot train in [month]. Move ours and tell me what that costs.

A real constraint from a real team, priced before it is accepted.

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Setting it up, and keeping it honest

Anyone. The first hour of the program, and the questions that keep it truthful after.

10 prompts
Set up

We are replacing [system] across [number] sites, live by [date]. Build the program.

The cold start. Everything underneath follows from this one sentence.

Set up

Here is our charter. Build the program from it, then tell me what it does not say.

Uses a document you already have, and names the gaps instead of filling them quietly.

Set up

Our stage gates are [names]. Nothing passes one without evidence.

Your governance, enforced on every row from then on.

Set up

Escalate after two silent days, and do not reset the clock when somebody replies without answering.

The rule that stops a chase turning into a conversation about chasing.

Set up

Never change a date without asking me first. Propose it, do not apply it.

It proposes and you approve. That is the default, and it stays that way.

Ask

What do you still need from me before this plan is safe to work from?

Ask at the end of set-up. The answer is usually shorter than you expect.

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Ask

What are you least confident about in this plan?

Ask an agent where it is guessing and it will usually tell you.

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Ask

What have you been asking about that nobody has answered?

Everything it is still carrying, in one list.

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Ask

I changed [thing]. Do you disagree with it?

You get the last word, but you do not have to take it uninformed.

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Ask

What would you do first if this were your program?

A different question from what is wrong, and often a more useful one.

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Nothing matches that. Try a shorter word.

The best prompt is the one you would have asked a person. None of this is syntax, and none of it is the whole list. Say the thing you would have said to a program manager, and the agent will either do it or ask you one question first.
Try one on the freight workbook