Leadership and communication prompts

Your monthly or quarterly all-hands is coming and your notes are a list of metrics and announcements. Use this to turn them into a talk track with a point, honest about misses, and ready for the questions people are already asking.

Act as a chief of staff who writes all-hands talk tracks for leaders who want to be clear, honest, and brief.

What happened this period, with the numbers I can share: [WHAT HAPPENED THIS PERIOD]
Wins and who drove them: [WINS AND WHO DROVE THEM]
Misses, what we learned, and what changes: [MISSES AND LESSONS]
What is next and why it matters: [WHAT IS NEXT AND WHY]
Questions people are asking in hallways and chat: [QUESTIONS PEOPLE ARE ASKING]
Time I have and the format: [TIME AND FORMAT]

Write:
1. A talk track in my voice: open with the one thing I most want people to leave knowing, then the period in three parts (what worked, what did not, what changes), then what is next, then a close that asks something of the audience.
2. Slide headlines only, one line each; no bullet decks.
3. Anticipated questions with honest answers, including the ones I would rather not get, and a way to say 'I do not know yet' that does not sound evasive.
4. Three things not to say: corporate phrases, spin, or anything crediting me for the team's work.

Name the people who drove wins. Keep misses in the same plain tone as wins. No jargon, no rallying cries, no unexplained acronyms.

Tip: Deliver the misses with the same energy as the wins; the team already knows about the misses and is watching to see whether you do. Cut the talk track by a quarter and give the time to questions.

A reorg, a new system, a policy change, or a leadership move is coming and it will land on people who did not choose it. Use this to write the announcement, the manager talking points, and the FAQ, in the order people should hear it.

Act as a change communications lead who has learned that people forgive hard news but not spin.

The change, in plain terms: [THE CHANGE]
Why now, honestly: [WHY NOW]
Who is affected and how, group by group: [WHO IS AFFECTED AND HOW]
What stays the same: [WHAT STAYS THE SAME]
Timeline: [TIMELINE]
Where people go with questions: [WHERE TO GET HELP]

Produce:
1. A sequencing plan: who hears it first, from whom, and how far apart, so no one learns their own fate from a mass email.
2. The announcement, under 400 words: what is changing, why, who is affected, what is not, what happens next, and where to ask. Lead with the change, not with context.
3. Manager talking points: how to open the conversation, the five questions they will get, what they can and cannot promise, and when to escalate.
4. An FAQ of ten to fifteen questions that answers the hard ones directly and says 'not decided yet, expected by' where that is the truth.
5. Anything in my inputs that sounds like spin, with a plainer alternative.

If the change affects jobs, pay, benefits, or working conditions, remind me to involve HR and legal before anything is sent, and make no promises on those topics until they have reviewed it.

Tip: Brief managers at least a day before the wider announcement and give them the FAQ in writing. The change lands through them, and a manager who learned it at the same moment as their team cannot lead the conversation.

A decision is stuck in meetings because nobody has written down the options and the tradeoffs. Use this to put it on one page, make a recommendation, and find its weakest point before the meeting does.

Act as a staff officer who writes decision memos that let a busy leader decide in ten minutes and that hold up afterward.

The decision to be made and by when: [THE DECISION AND DEADLINE]
The options seriously considered, including doing nothing: [OPTIONS CONSIDERED]
The criteria that matter and their rough priority: [DECISION CRITERIA]
What I recommend and why: [YOUR RECOMMENDATION AND REASONING]
What I am unsure about or would change my mind over: [UNCERTAINTIES]
Who is affected and who has weighed in: [STAKEHOLDERS AND INPUT SO FAR]

Write a one-page memo with: the decision in one sentence; the recommendation in one sentence; background in three sentences; an options table scoring each option against the criteria with a one-line rationale per cell; risks of the recommended option and how we would notice them early; whether the decision is reversible and what reversing would cost; what would change my mind; and what I need from the decision maker, with a date.

Then switch sides. Write the strongest case for the option I did not choose, in three paragraphs, as a smart colleague would argue it. Finish with the two questions I should be able to answer before I send this.

Plain language and no advocacy adjectives; let the table do the persuading.

Tip: Send the memo 48 hours before the meeting and ask people to comment in writing. Decisions read cold and argued in the room go better than decisions presented on slides, and the argue-against-it section is where your credibility comes from.

Someone you do not manage is doing something that costs you or the work, and you have been avoiding the conversation. Use this to plan what to say, how to open, and what to do when it gets awkward.

Act as an executive coach who helps people give feedback sideways and upward, with no authority to fall back on.

Who they are to me (a peer, my manager, a leader elsewhere): [WHO THEY ARE TO YOU]
What happened, with two or three dated examples: [WHAT HAPPENED]
The effect on me or the work: [IMPACT]
What I want to be different: [WHAT YOU WANT TO CHANGE]
Our history and how they take feedback: [RELATIONSHIP HISTORY]
What I worry will happen if I raise it: [YOUR WORRIES]

Give me:
1. A one-sentence way to ask for the conversation that signals it is about the work, not them, and lets them choose the time.
2. An opening of three or four sentences that names the pattern using my examples, states the impact without exaggeration, and shows I want to solve it together.
3. Two questions to ask before proposing anything, so I hear their side.
4. Likely responses (surprise, defensiveness, a counter-complaint, agreement with no change) and what to say to each without escalating.
5. A specific request to end on, with a check-in date.
6. If they are senior to me, a version of the core message that respects the power difference without softening the point into nothing.

Then offer to role-play it as the other person.

Tip: Do it in person or on video, never in writing, and within a week of the last example while it is still concrete. If the AI's opening lines sound like a script, say them out loud until they sound like you.

You have a weekly one-on-one and your notes are a scroll of half-finished threads. Use this to pull out what to follow up on, what to recognize, and the topics you keep postponing.

Act as a leadership coach who helps managers run one-on-ones the other person finds worth their time.

My notes from the last few one-on-ones with this person, with names and anything sensitive about third parties removed: [PASTE YOUR RECENT ONE-ON-ONE NOTES]
Their current goals and what they said they want to develop: [THEIR GOALS AND DEVELOPMENT INTERESTS]
What I have noticed lately, good and concerning: [WHAT YOU HAVE NOTICED]
Topics I keep meaning to raise and have not: [POSTPONED TOPICS]
Meeting length: [MEETING LENGTH]

Give me:
1. Open threads from my notes: commitments either of us made, with what happened or 'no update recorded'.
2. One specific thing to recognize, tied to an example from the notes.
3. An agenda that gives the first half to their topics and reserves time for one postponed topic of mine, with a plain way to open it.
4. Three questions beyond status: what is in their way, what they want more or less of from me, where they want to be in a year.
5. Anything in my notes that suggests a pattern I might be missing, phrased as a question, not a conclusion.

Keep it to half a page. This is a working conversation, not a performance review; do not draft ratings or judgments.

Tip: Share the agenda an hour before the meeting so they can add to it. The postponed-topic slot is the point of this prompt; managers who skip it for four weeks running end up having the conversation as a performance problem instead.

Your strategy exists as a slide of pillars and nobody below the leadership team can explain it. Use this to write the story: where we are, what we believe, what we are choosing, and what we are giving up.

Act as a strategy writer who turns leadership decisions into a narrative a new employee could retell.

Where we are today, honestly, including what is not working: [WHERE WE ARE TODAY]
Where we want to be in two to three years, concretely: [WHERE WE WANT TO BE]
The bets we are making and the belief behind each: [THE BETS AND BELIEFS]
What we will stop doing to make room: [WHAT WE WILL STOP]
Evidence or signals supporting the bets: [EVIDENCE AND SIGNALS]
Who will read this: [AUDIENCE]

Write a narrative of about 800 words in these movements: the situation (what is true now, including the uncomfortable parts); the insight (what we believe about customers, the market, or ourselves that others miss); the choices (each bet, why it follows from the insight, and what we give up); what it means for each major team, in a sentence or two; and how we will know it is working, as observable signs rather than a scorecard.

Then, separately:
1. The three weakest points in the argument and what a skeptic would say.
2. Any bet that is really a goal in disguise, with no belief or tradeoff attached.
3. Sentences that could appear in any company's strategy; rewrite or cut them.

Plain language. No pillars, no acronyms, no slogans.

Tip: If you cannot fill in the 'what we will stop' field, you do not have a strategy yet, and the AI will tell you so politely. Test the narrative by having three people at different levels retell it to you a week later.

Your project update is due and the honest status is 'yellow, trending red'. Use this to write a short update that states the situation, what changed, and what you need, in versions for executives and for the working team.

Act as a program manager whose status updates executives trust because the bad news is at the top.

Project and its goal in one sentence: [PROJECT AND GOAL]
My raw status notes: [PASTE YOUR STATUS NOTES]
Overall status and whether it changed: [STATUS AND TREND]
Decisions, resources, or help I need, from whom, by when: [WHAT YOU NEED AND FROM WHOM]
Risks and what we are doing about each: [RISKS AND MITIGATIONS]

Write two versions:
1. Executive update, under 200 words: status and trend in the first line with the reason; what changed since last update; the top three items with dates; what I need from the reader and by when; risks in one line each. No history, no activity lists.
2. Team update, under 350 words: finished, in progress, blocked and who owns unblocking it, decisions made, decisions pending, and what to expect next week.

Rules: if the status is yellow or red, say so in the first sentence with the cause. Turn every 'we are working on it' in my notes into what is being done, by whom, by when, or mark it as needing an owner. Do not add optimism I did not give you. Flag any item in my notes that reads like a problem I have not acknowledged.

Tip: Send the executive version as the body of the email, not as an attachment, and keep the same structure every week so readers know where to look. A status that was green for ten weeks and then turns red destroys more trust than an honest yellow in week three.

Leadership made a call, you had little say in it, and now your team wants to know what you think. Use this to communicate it honestly, without undermining it and without pretending you made it.

Act as a leadership coach for the manager in the middle: carrying decisions from above to a team that will read your face, not the memo.

The decision: [THE DECISION]
What leadership said about why, and how much I can share: [THE STATED REASONS AND WHAT YOU CAN SHARE]
What my team will worry about: [TEAM CONCERNS]
What I personally think, disagreement included: [YOUR OWN VIEW]
What I can still influence and what is fixed: [WHAT YOU CAN INFLUENCE]

Give me:
1. Talking points that state the decision and reasons plainly, own the delivery, and neither pretend it was mine nor distance me with 'they decided'.
2. Honest answers to 'do you agree with this?' that do not lie, undermine the decision, or leave the team feeling managed.
3. A response to each team concern, separating what I can commit to, what I will raise upward, and what will not change.
4. What to take back to leadership from the team's reaction, and how to say it so it lands as information, not resistance.
5. Phrases to avoid: anything that sounds like a hostage note or a press release.

Keep it conversational; this is a team meeting, not an announcement. If my disagreement is serious, tell me whether to resolve it upward before I talk to the team.

Tip: Your team will remember how you carried this long after they forget the decision. Have the argument with your boss first, then deliver the decision as someone who was heard, even if you lost.

You need a yes, a no, or a budget from someone who reads email on their phone between meetings. Use this to turn your long explanation into a message that can be decided in one read.

Act as an executive communications advisor who writes emails senior leaders answer the same day.

Who I am writing to and how well they know the topic: [RECIPIENT AND THEIR CONTEXT]
What I need them to decide or approve, exactly: [THE DECISION YOU NEED]
Why it matters to them, in their terms: [WHY IT MATTERS TO THEM]
The options and my recommendation: [OPTIONS AND RECOMMENDATION]
Background they might need, pasted in full: [PASTE THE BACKGROUND]
The date I need an answer by and what happens if I do not get one: [DEADLINE AND CONSEQUENCE]

Write an email under 150 words that:
- Puts the ask in the subject line and the first sentence, with the deadline.
- Gives the recommendation and the one-sentence reason.
- Lists the alternatives in one line each, so a different answer is easy to give.
- Ends with a question they can answer with one word or a single line.
- Puts any necessary background below a line that says 'details if useful', in at most five bullets.

Then give me a two-line version for chat, and tell me which parts of my background to leave out entirely. If the ask is really two asks, split it and tell me which to send first.

Tip: If the leader can reply 'yes, option B' from a phone in ten seconds, you wrote it right. Send it in the morning rather than at the end of the day, and resist adding a paragraph about how hard the team worked.