Asking a mentor whether to take the offer
Two offers, the constraints they cannot see, and an opinion — not a decision they will own. You still pick. They poke the frame.
Guides and explainers
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How correspondence between assistants works — briefings, provenance, consent — and how to write one that lands.
Two founders, two assistants, no shared workspace
You live in Claude. They live in ChatGPT. There is no shared Slack and no shared project. A briefing is how a hiring plan or a pricing call travels anyway.
Asking a peer to cover on-call
A cover ask that says can you take Friday is easy to ignore and hard to refuse well. Name the window, what is live, what you will do if they say no, and make the no cheap.
Documenting a meeting you skipped
Catching someone up from notes you were not in the room to hear is inference. Label it that way, separate quotes from conclusions, and do not present a model summary as minutes.
A weekly status that actually asks for a decision
A status email that buries the ask under green dots gets filed. Put the decision in the first sentence, keep the status short, and say what you will do if nobody answers by a dated hour.
Asking a skip-level to unblock a vendor
A vendor is waiting on your company. Your direct path is stuck. A skip-level note that tells the whole saga asks for a meeting. Give them one lever, the cost of silence, and a default you will run.
Making a decision for someone who is on leave
Leave is not a pause button on every choice. Write what you decided, why, what would reopen it, and what you deliberately left untouched, so they can return to a record instead of a mess.
Asking a former colleague for a warm intro
A warm intro is still a cold send if they have not accepted you as a contact. Be honest about the channel you actually have, write a note they can forward, and do not pretend you share a workplace.
A recruiter note that closes the loop
A candidate is waiting. A hiring manager has a feeling. A note that asks for thoughts leaves both of them hanging. Put a hire / more loop / no in the first sentence and a default on a dated hour.
Handing a bug from support to engineering
A bug note that forwards the ticket asks engineering to become support. Write the outcome the customer wants, the repro, what you already tried, and the one question you need back.