Strategy and OKRs with AI as your sparring partner

I'm [role] at a company that does [industry, size, type of
customers].
Our vision statement is: [vision statement].
Current situation: [3-5 sentences on where the company stands —
revenue, customers, team, main pain point].

Don't write me goals. Do one thing: translate that vision into
a picture of the company three years from now. Describe what
would have to be measurably different from today, across five
areas: customers, product, people, processes, money.

For each area, write:
- what it looks like today (based on what I gave you)
- what it would look like if the vision were fulfilled
- in one sentence, what the gap between the two actually is

Where you're missing information, write QUESTION: [what you
need to know], instead of guessing.

Here's the picture of our company three years out, and the
list of areas where we need to move forward:

[paste the output of the previous prompt, or your own list]

The upcoming quarter is [Q4 2026]. Capacity: [number of
people, main constraint — e.g. two dev teams, one person on
marketing].
What's hurting us most right now: [description].

Propose 4 different strategic bets for this quarter. A bet =
one thing we commit capacity to, at the expense of everything
else.
For each one, write:
1. What we're betting on and why now
2. What we're consciously deferring or sacrificing
3. How we'll know in three months whether the bet paid off
4. What happens if we push it out a quarter
5. Why this bet might be the wrong choice

The bets must be mutually exclusive — not four variations on
the same thing. Don't recommend which one to pick.

Here's our strategic bet for the quarter: [describe the bet
in your own words, 5-8 sentences].
Company: [industry, size]. Team it affects: [description].

Write 6 Objective variants (a qualitative goal, no numbers)
that capture this bet. Vary the level of ambition and the
angle — two cautious, two ambitious, two framed from the
customer's point of view.

Rules:
- one sentence, 12 words max
- no numbers, no deadlines
- a verb that expresses a change of state, not an activity
- no corporate filler (“synergy,” “excellence,” “take it to
  the next level”)

Under each variant, write one sentence on what that phrasing
implicitly promises, and what it rules out.

Objective for this quarter: [Objective wording].
Team: [who, how many people, what they do].
Data we actually measure today: [list the metrics you have
in your systems, including where they live].
Metrics we'd have to start measuring: [list].

Propose 12 Key Result candidates for this Objective.
Split them into three groups:
A) outcome (lagging) — measures impact, shows up later
B) leading — measures the behavior that drives the impact
C) qualitative — measures a shift where no direct number
   exists (e.g. share of customers who mention [thing] in
   an interview)

For each candidate, give:
- exact wording as “from value X to value Y by end of
  quarter” (leave the values as [BASELINE] and [TARGET] if
  you don't know them)
- where that number comes from and who can pull it
- how often it can be measured
- how it could be hit dishonestly, without anything actually
  improving

Don't fill in numbers I didn't give you.

I want to set this Key Result: [KR wording].
I don't know the current value, or I'm not sure of it.
Data sources I have: [systems, exports, spreadsheets].
Time I can spend finding out: [e.g. 3 hours].

Write me a plan for finding the baseline in that time:
1. Exactly where to pull that number from and how
2. How to calculate it — an exact definition (what counts,
   what doesn't, over what period, how to handle duplicates
   and missing data)
3. Who at the company has the fastest access to it
4. What to do if it turns out this was never measured — the
   cheapest fallback metric, and what I give up by using it
5. How to write down the definition so it's calculated the
   same way three months from now

Write the definition so it can be pasted straight into the
OKR document.

You're a seasoned COO who's seen hundreds of OKR sets over
your career and can't stand goals written for reporting.
Be harsh, blunt, and specific. Don't compliment anything.

Here are our OKRs for the quarter:
[paste the Objectives and all Key Results, with numbers]

Context: [industry, team size, what the company does].

Go through them and answer four questions:
1. Which of these Key Results can be hit without anything
   actually improving? For each, describe the specific
   scenario of how I'd do it if I wanted to look good without
   working hard.
2. Which KRs measure activity instead of outcome? Rephrase
   them.
3. Which KRs is the team unable to influence through its own
   work?
4. Which Objective wouldn't surprise or unsettle anyone at the
   company on reading it — and is therefore probably empty?

Finish by saying what you'd cut first, and why.

It's the end of [Q4 2026]. Our strategic intent for this
quarter was [Objective wording], with these Key Results:
[paste the KRs and their target values]

It failed. Not by a little — we finished under 30%, and it
cost the company a quarter.

Write a post-mortem of how it happened:
1. The five most likely causes of failure, ranked by
   likelihood, not by drama
2. For each: the first warning sign, and in roughly which
   week of the quarter it would have shown up
3. Which causes were within our control and which weren't
4. What I should concretely do right now, in week 0, to head
   off the three most likely causes in advance
5. Which of those steps is cheap enough that there's no reason
   to put it off

Company context: [description]. What didn't go well last
quarter: [brief summary].

Company Objective for the quarter: [wording]
Company Key Results: [list, with values]

Our teams and what they do:
- [team A]: [what it does, how many people]
- [team B]: [what it does, how many people]
- [team C]: [what it does, how many people]

For each team, propose:
1. In one sentence, how it can contribute to the company
   Objective using what it's good at (not by splitting the
   company number into pieces)
2. Two to three candidate team-level Key Results — measurable,
   within its reach, phrased as “from X to Y”
3. Which company KR(s) that supports
4. What the team would have to stop doing to have the
   capacity for it

Call out separately:
- where two teams' proposals overlap so much they'd end up
  doing the same work twice
- where there's a gap between the company goal and the team
  proposals that nobody covers

Here are the team Key Results the teams set for themselves:
[paste, by team]

Company Objective and KRs:
[paste]

Run a cascade check. For each team KR, write:
- If it were hit 100%, how much would it move the company KR?
  If that can't be estimated, write “no defensible link.”
- Is it a result, or a renamed task?
- If this KR vanished, would anyone outside the team notice?

At the end, give three lists:
1. KRs whose link to the company goal is only asserted
2. KRs that are basically business-as-usual dressed up as a
   goal
3. Company KRs that no team is actually aiming at

Prepare material for our biweekly OKR check-in.

Current state:
[for each KR: wording, baseline, target, value today, value
two weeks ago, one sentence on what happened]

Give it back to me like this:
1. A stoplight color for each KR (green / yellow / red) and
   one sentence why — based on pace, not gut feel: compare
   progress against where we should be at [week] of 13
2. At most 3 things that actually need to be decided at the
   check-in, each phrased as a question with answer options
3. What's just information that can be sent in writing and
   doesn't need airtime in the meeting
4. One question someone should ask and nobody will, because
   it's uncomfortable

No summary, no intro — go straight to the points.

Our Key Result [wording] is red.
Baseline was [X], target [Y], today we're at [Z], [number] of
13 weeks remain.
What's happened: [brief description, including what we've
tried].
My read on the cause: [your opinion].

Draft a message for [leadership / the team], 10 sentences,
structured:
1. Where we stand (the number, no dressing it up)
2. Why — separate causes we controlled from external ones,
   and don't hide the first kind
3. What we've learned that we didn't know before the quarter
4. The decision I'm recommending: push through / cut scope /
   stop — and what that means for the rest of the quarter
5. What I need from you to make that decision

No hedging language, no “unfortunately.” Don't try to make it
sound better than it is.

We're closing the quarter. Here are our OKRs and the results:

[for each KR: wording, baseline, target, final value, 2-3
sentences on how it went]

Give me a quarterly review:
1. A score for each KR (0.0-1.0) and one sentence of
   assessment
2. For KRs under 0.7: was the cause performance, a badly set
   target, or a shift in external conditions? Keep those
   separate, don't blend them.
3. For KRs above 0.9: was the target set too low? How would
   you tell?
4. Which KRs turned out impossible to evaluate because we
   defined them badly — and how to phrase that better next
   time
5. Three lessons for next quarter's goal-setting, specific to
   our company, not generic advice
6. Which of these goals should continue, and which should
   definitely end

Work only from the numbers I gave you. Where data is missing,
say so instead of estimating.

You're an auditor looking for signs that goals are being
written for reporting, not for management. Be skeptical.

Here are our OKRs from the last two quarters, their results,
and the check-in notes:
[paste]

Find the signs of OKR theater:
1. Goals that are business-as-usual described in goal form
2. Goals whose wording shifted during the quarter toward
   whatever turned out achievable
3. KRs whose status got reported in words instead of numbers
4. Decisions that were actually made because of the goals —
   list them. If you can't find any, say so plainly.
5. Goals that keep reappearing quarter after quarter with no
   movement in the numbers

At the end, list three concrete process changes that would
curb this, and for each one, what it would cost.