Four requests in one message? Number them so none gets dropped

You send one message with four requests tucked into it. The reply arrives quickly, is friendly and covers two of them. The other two were not refused. They simply disappeared into the paragraph, and a week later you are still waiting on something nobody remembers being asked. (A hypothetical scene, for illustration.)

When several requests share a paragraph, the first and the last tend to get answered and the ones in the middle get lost. Numbering them takes about a minute and works with any helper, whether a colleague, an agency or an AI assistant. Five habits make a numbered message do its job:

  1. One request per number, and one action per request. "Confirm the room for the 14th" is one request. "Confirm the room and tell the caterer" is two. If you cannot give a request a number of its own, it is not finished yet.
  2. Put them in the order you need the answers, not the order you thought of them. If number three has to happen before number one, say so or move it up.
  3. Mark which requests depend on which: "needs 1 first". Independent requests can be done in any order and chained ones cannot, and saying which is which saves a round of questions.
  4. Ask for the reply by number: "Please answer by number, even if the answer is 'not yet'." A reply that mirrors your numbering makes a gap obvious at a glance, and a gap is exactly the problem you are solving.
  5. Quote the number when you follow up. "Any news on 3, the final headcount?" is clearer than "any news on the other thing?", for the helper and for you a week from now.

Keep the list short. Past five or six requests you are sending a small project, not a message, so split it by topic or by deadline and say how many messages to expect.

Keep the numbers stable. When you think of something later, call it 5 instead of squeezing it in as "2b" and shifting everything else. A request that keeps its number can still be found in a long thread a month from now.

Close each number, too. A line such as "1 done, 2 done, 3 waiting on me, 4 dropped" helps everyone, and "dropped" matters: a request you cancelled on purpose should say so, or it looks like one that was lost.

The habit works in both directions. When a helper writes to you with several questions, answer by number as well. It cuts down the back-and-forth for both of you.

A hypothetical message to a helper preparing a small workshop: "1. Confirm the room for the 14th. 2. Send the draft agenda to the three speakers (needs 1 first). 3. Ask each speaker whether they need a projector. 4. Tell me by Friday how many people have signed up. Please answer by number." The reply reads: "1 confirmed. 2 sent. 3 two of three have replied. 4 forty-one so far." Number 3 is visibly incomplete, so the follow-up writes itself.

Octuo is a personal assistant and one starting point for work across AI, tools and specialist services. It operates external solutions on your behalf, and it reports back when a job is done. A numbered list of requests is an easy brief to hand over and an easy report to check against. Public beta on macOS: https://www.tutuo.ai/en/octuo/

— The Octuo team at Tutuo, Inc.

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