Delegating with AI: assignments that don't boomerang back

I want to delegate a task. Here's what's in my head, written
the way I'd say it on the way out the door:

[paste your sentence or a few sentences]

Who's doing it: [role, experience, what similar work they've
already done].
When I need it: [deadline and why it's that specific date].

Convert this into an assignment with these five fields:
context / output and acceptance criteria / deadline /
boundaries / escalation.

Rules:
- don't make anything up; where you're missing information,
  write QUESTION FOR ME: [what you need to know] instead
- phrase acceptance criteria so they can be checked off, not
  as “handled well”
- in boundaries, list what's out of scope too, so nobody does it
- propose escalation with a concrete trigger, not “if there's
  a problem”

Write it in language I can send unchanged.
Don't send this anywhere — just give me the text back.

Here's a task assignment I wrote:

[paste assignment]

Write acceptance criteria for it — a list I can use to
unambiguously check off that the output is done and usable.

Requirements:
- 4 to 7 items, each verifiable yes/no
- no subjective words (quality, careful, sufficient); where
  you'd use one, replace it with a measurable description
- split them into: must meet / would be nice
- at the end, add 3 things that often get overlooked for this
  type of task, and ask whether I want them added to the
  criteria

Finally, rewrite it as a short checklist I can send along
with the assignment.

Read this assignment as [a junior who's been at the company
3 months and has never done this type of task before].

[paste assignment]

Answer in four blocks:
1. What's unclear: specific sentences or terms I'd need to
   ask about. For each, write exactly what I'd ask.
2. Where I might fill in the gap wrong: places that allow
   two different readings — list both and say which is more
   likely.
3. What's missing from the assignment for me to be able to
   start without a single question.
4. What I'd do as the first three steps based on this
   assignment.

For point 4, describe it exactly the way I'd actually dive
into it — so I can tell whether the assignment would steer me
in the right direction.

You're someone who just received this assignment. Don't
critique it. Answer the way I would if I were the one
taking it on:

[paste assignment]

1. Summarize in your own words what I'm asking for (5
   sentences).
2. Write what output I'll hand you back, and in what form.
3. List the decisions I'll have to make on my own along the
   way.
4. Write 3 questions I'll ask you before I start.
5. Estimate how long this will take me, and explain what the
   estimate is based on.

Don't add anything extra and don't improve on it. I want to
see what I actually communicated with this assignment.

Help me choose the level of delegation for this task.

Task: [description]. Who's doing it: [role, experience, how
similar tasks turned out in the past — add what you know].
What happens if this goes badly: [impact, reversibility, who
sees it].

Go through the three levels (do it / propose / decide) and
for each, write:
- what it would mean in this specific case
- what the risk is if I choose it
- what I'd have to add to the assignment for it to work

Then tell me what I should ask myself before deciding.
Don't give me a clear-cut recommendation — choosing the level
is my decision, you just lay out the consequences for me.

I've delegated a task: [description]. Deadline: [date].
Estimated effort: [hours/days]. Delegation level: [do it /
propose / decide]. Risks I'm worried about: [what could go
wrong].

Propose a plan of check-ins:
- how many there should be and exactly when (specific dates)
- what should be done by each one — a partial deliverable,
  not a percentage
- 3 questions for each check-in that ask about the OUTPUT,
  not the process or how much the person has gotten through
- a signal that tells me, at a check-in, that this is heading
  in the wrong direction, and what to do about it in the
  moment

Don't propose daily status reports or progress tracking.
The goal is to avoid a surprise at the end, not to supervise.

Here are the acceptance criteria I assigned, and here's the
output I got back:

Criteria: [paste]
Output: [paste]

Compare them point by point and return a table:
criterion | met yes/no/partially | based on what specifically
in the text.

Then, separately, write:
1. What's missing and needs to be added before this can be
   used
2. What's different from what I assigned but actually works
   better — and why
3. What I should specify more precisely next time so this
   ambiguity doesn't happen again

Don't evaluate the person and don't write feedback for them.
Give me material I'll use to write it myself.

I got this message from someone I delegated a task to:

[paste message]

The original assignment was: [briefly].
Delegation level: [do it / propose / decide].

Break this down for me:
1. What are they concretely asking for — information, a
   decision, approval, or for someone to just solve it for
   them?
2. Which part is legitimately mine (only I have the access
   or authority for it) and which part is theirs?
3. Based on this message, who takes the next step if I reply
   the normal way?
4. What are they missing to answer this themselves —
   information, authority, or confidence?

Answer briefly, four paragraphs.

I want to hand a decision back to the person who sent it to
me, but I don't want it to sound like I'm refusing to help.

Situation: [description]. What they want from me: [what].
What I think they already know: [what].
Their experience and confidence with this type of task:
[description].

Give me three versions of a reply:
a) when the answer is within their authority and they just
   don't trust themselves
b) when they genuinely lack information that only I have
c) when this decision really is mine to take back

For each version:
- the exact wording of a message I can send
- the question that hands the ball back to them (for
  version a)
- what this signals about them and how they'll most likely
  read it

Write it in my normal tone, not corporate-speak. No empty
“I believe in you, you've got this” with nothing behind it.

Here's my workload for the last month: a list of meetings
and activities with a time estimate (names replaced with
roles).

[paste list]

My role: [position]. Team: [number of people, roles]. My
main responsibility that nobody else has: [description].

Sort all the activities into four groups:
1. Must be done by the manager (decisions, evaluations,
   personnel matters, representing the team externally)
2. I do it out of habit or history, but someone else could
3. Someone else could do it after training — say how long
4. Nobody needs to do it — cancel or simplify

For groups 2 and 3, for each item write: which role should
do it, what I need to hand over along with the task, and how
many hours a week it frees up for me.
At the end, rank the top 5 delegation candidates by the ratio
of time freed to how hard the handoff is.

Don't recommend specific people — that's my call.

I want to hand off this recurring responsibility: [description,
how often, how much time it takes, what it involves].
Taking it over: [role, experience]. Time I have for the
handoff: [how much].

Propose a [3]-month handoff plan:
- phase 1: I do it, they watch — exactly what I should show
  them
- phase 2: they do it, I check — what I check and how often
- phase 3: they do it alone, report the result — what I keep

For each phase, write what has to be true before moving to
the next one (a concrete criterion, not “once they feel
confident”).

Separately, list:
- what's unwritten in this responsibility and I have to say
  out loud
- decisions I need to keep for myself even after handing off
  the rest
- what happens if I hand it off without training

Here are three assignments for the same type of task that
I've written over the last few months:

[paste assignment 1]
[paste assignment 2]
[paste assignment 3]

Build one template out of them:
- the common part that stays the same every time (context,
  boundaries, escalation, standard acceptance criteria)
- mark the variable parts with brackets describing what to
  fill in
- add whatever was missing from all three but should have
  been there

At the end, write a short “before I send” checklist: 5
questions I can use to check the assignment in a minute.