the approval · the interrupt list · the shape of a reply · the whole message · the handover
Most advice about working with an assistant covers what you type. Almost none covers the rhythm of your exchange — who decides when, what is worth stopping for, and what has to come back to you. Get the rhythm wrong and your ten-minute job takes ninety, with everybody polite the whole way.
None of these are about prompting. Each one settles who is deciding, and when — the part that turns a good assistant into a slow one.
Every habit here looks like care from the inside, which is exactly why yours survive for months before anybody names them out loud.
People look for: working with an AI assistant, session management, when to approve AI work, AI progress reporting, and delegation to AI tools.
Read the middle column. Every behaviour there looks careful from the inside, which is why yours survive so long before anybody names them.
| The habit | What it looks like when it is missing | What to say once |
|---|---|---|
| The approval | Permission asked at every obvious next step. A ten-minute job takes ninety and reads as sharing the blame rather than carrying the work | Approve the plan once, then run to the end and report as you go |
| The interrupt list | Either constant check-ins or total silence, and both cost you the same afternoon | Stop only for real spend, destruction, or a genuine fork. Otherwise decide it and tell me |
| The shape of a reply | Five bullets at equal weight, so you do the sorting. Or two options when one is obviously right | Rank it. The simplest route first, alternatives clearly after, findings last |
| The whole message | Part one answered, parts two and three ignored, and you repeat yourself | Read all of it, list every requirement, address each one |
| The handover | A wall of summary and no way to open the thing that was built | End with the live link and the full path of everything changed |
Every behaviour there is a virtue slightly out of place. Asking permission is careful. Listing options is thorough. A full summary is generous. None of the three reads as a fault from the inside, so all three persist for months — and naming yours once is usually enough to end them.
The assistant carries out work that was approved once; the decision to spend, to destroy, or to change direction remains with the person.
Asking before every step feels like respect and lands as a refusal to carry your work. You approved the plan; the next twelve decisions were the ones you delegated. What you want instead is a line every few minutes saying where the work has reached, with the work still moving.
A or B, asked up front, costs you five seconds and shapes everything after. The same question halfway through interrupts something you already agreed, and reaches you once you have moved on. Same words, and your timing is the whole difference.
A question followed by four more tool calls means your answer was never really wanted, and you now untangle work built on a guess. Needs your decision, stops at your decision. Does not need you, should never have asked.
A long-running task was launched detached, so no progress could be reported and no interruption could reach it. The rule that replaced it was a progress line every few minutes with the work continuing.
A request to fix one page returned a plan covering a hundred and eleven, each item defensible. Counting the plan against the request caught it in one glance.
A completed piece of work was reported in prose with no link and no paths, so reviewing it meant hunting for it. Every deliverable now ends with both.
With a short progress line every few minutes, and the work continuing while it reports. The rule is do not go silent - never stop and ask. Constant permission requests cost as much of your day as silence does, and train you to stop reading the output.
Three cases: real money about to be spent, something about to be destroyed or overwritten, and a genuine fork where two readings of your request produce different work. Everything else gets decided and reported in one line.
Because sorting them was the job you delegated. One thing that matters, then the rest, in that order. A flat list hands your triage back at exactly the point you expected an answer.
Only when a real choice exists. If your stated goal already implies the answer, a manufactured second option is padding, and sometimes reintroduces the problem you were solving. Your simplest honest route comes first, alternatives clearly after.
The live link to see the work running, and the full path of every file that changed. A path tells you where the source lives; the URL tells you where to watch the work. You need both, without asking.
You set the rhythm once, and never have to ask for any of it again.