You are a career strategist helping me identify 
the most strategically sound development target 
from a specific set of emerging professional roles.

My current professional profile:
Role and function: [describe what you actually do]
Industry and sector: [describe your context]
Years of experience and seniority level: [be honest]
Current AI capability level: [1 to 10, with specific evidence]
Domain expertise depth: [where you are genuinely strong]
Career objective for the next two to three years: 
[be specific about what advancement looks like for you]

The six roles I am evaluating:
1. AI output evaluator
2. AI workflow architect
3. AI communications specialist
4. AI ethics and governance professional
5. AI training data specialist
6. AI-augmented domain expert

For each role, please assess:
1. How accessible is this role to me given 
   my current profile, on a scale of 
   near-term, medium-term, or not currently relevant
2. Where the fit between my existing strengths 
   and the role's requirements is strongest
3. The single most significant gap between 
   my current profile and a credible claim 
   to this role

Then recommend one primary role to target 
in the next ninety days with a specific 
rationale grounded in my profile, not 
in which role sounds most appealing.

Also identify the role I am most likely 
to choose for the wrong reason, and why.

You are helping me conduct a precise gap analysis 
between my current professional profile and 
the specific role I am targeting.

My current profile: [paste from Prompt 1]

My target role: [from Prompt 1 recommendation]

The specific requirements of that role as I 
understand them from the role mapping: 
[paste relevant description from Issue #41]

Please identify:

1. The capability gaps between my current 
   profile and the role requirements, 
   listed in order of their significance 
   to someone hiring for this role today
2. For each gap, assess whether it is 
   closeable in ninety days with focused effort, 
   closeable over a longer period, 
   or structural in a way that requires 
   a different approach
3. The single gap whose closure would most 
   change how a hiring manager or senior 
   colleague evaluates my candidacy for 
   this role
4. The gap I am most likely to underestimate 
   because it does not feel like a gap 
   from the inside, with your reasoning

Be precise. A gap analysis that identifies 
general areas for improvement is not useful. 
One that identifies the specific capability 
whose absence is most visible to the people 
evaluating for this role is.

You are helping me set a ninety-day development 
objective that is specific, measurable, and 
grounded in what is actually achievable with 
the time and resources I have available.

My target role: [from Prompt 1]
My primary gap: [from Prompt 2]
My realistic weekly development time: 
[be honest, not aspirational]
My professional context constraints: 
[travel, high-demand periods, competing priorities 
you know are coming in the next ninety days]

Please:

1. Propose a ninety-day objective for closing 
   or significantly reducing my primary gap, 
   stated specifically enough that I will be 
   able to say unambiguously at day ninety 
   whether I achieved it
2. Break it into three thirty-day milestones, 
   each building on the previous one and each 
   assessable with the same unambiguous standard
3. Identify the most likely reason this objective 
   will not be achieved, based on what I have 
   told you about my constraints
4. Propose a modified version that accounts 
   for that failure mode, one that is still 
   meaningful but more robust to the specific 
   risk you have identified
5. Tell me what achieving this objective will 
   specifically demonstrate to the people 
   evaluating me for the target role

The objective that requires perfect conditions 
to achieve is not a plan. It is a wish. 
Build me a plan.

You are helping me design a weekly practice 
that will compound toward my ninety-day 
objective through consistent, structured effort.

My ninety-day objective and milestones: 
[from Prompt 3]

My realistic weekly development time: 
[from Prompt 3]

My working week structure: 
[describe when you have focused time, 
when you are in meetings, what your 
energy levels are like at different 
points in the week]

Please design a weekly practice that:

1. Fits within the time I have actually available, 
   not the time I would like to have
2. Is structured around application to real work 
   rather than exercises disconnected from 
   my actual professional context
3. Includes a deliberate practice component: 
   the part where I am working at the edge 
   of my current capability rather than 
   doing what I already do well
4. Includes a reflection component of no more 
   than fifteen minutes, structured around 
   three questions: what worked, what did not, 
   and what I will do differently
5. Is attached to a specific existing routine 
   in my week so it does not require a 
   separate decision to begin

Make the practice simple enough that I will 
actually do it on a week when everything 
else is demanding. Complexity is the enemy 
of consistency and consistency is what 
produces compound returns.

You are helping me conduct an honest 
milestone review at day [30 / 60 / 90] 
of my ninety-day development plan.

My original objective and this milestone's 
specific target: [paste from Prompt 3]

What I actually did in the past thirty days: 
[describe honestly, including weeks where 
the practice did not happen and why]

The output or evidence of progress I have 
produced in this period: [describe specifically]

Please assess:

1. Progress against the milestone target: 
   achieved, partially achieved, or not achieved, 
   with the specific evidence for that assessment
2. The most important thing I learned about 
   my capability development in this period 
   that I did not know at the start of it
3. Whether the original plan's assumptions 
   about my available time and the practice 
   design are holding up or need revision
4. One specific adjustment to the practice 
   for the next thirty days based on what 
   this period revealed
5. Confidence level in achieving the ninety-day 
   objective from here, and what would 
   need to be true for that to change

Be honest. A milestone review that confirms 
everything is on track when it is not produces 
a false sense of progress that makes the 
day ninety assessment more painful than 
it needed to be.

You are helping me build a visibility plan 
that makes my ninety-day development visible 
to the people whose assessment of my capabilities 
affects my career trajectory.

My development objective and milestones: 
[from Prompt 3]

The people whose assessment matters most 
and their current awareness of my development: 
[describe each person and their current 
level of awareness honestly]

Please:

1. Identify the most natural point in my 
   ninety-day plan where the development 
   produces an output worth sharing, 
   one that demonstrates capability 
   rather than just announcing effort
2. Propose one specific visibility action 
   for each thirty-day milestone, grounded 
   in the actual output that milestone produces
3. Identify the audience member whose awareness 
   of my development is most important and 
   propose how to ensure that awareness exists 
   by day ninety
4. Identify the visibility action I am most 
   likely to avoid because it feels like 
   self-promotion, and the cost of that avoidance
5. Write the one-sentence description of my 
   development focus that I could use in any 
   professional conversation without overclaiming 
   or underclaiming

The visibility plan should be an output of 
the development, not a performance of it. 
The people you most want to impress are 
the ones most likely to notice the difference.

I am going to describe three scenarios that 
commonly derail development plans at different 
stages. For each one, give me a specific protocol 
for responding that takes less than fifteen minutes 
to execute and does not require starting over.

Scenario 1: I missed the weekly practice for 
two consecutive weeks because of a high-demand 
work period and the habit has broken.

Scenario 2: I am completing the practice but 
my outputs are not improving at the rate I 
expected and I am questioning whether the 
approach is working.

Scenario 3: Something significant has changed 
in my professional context and the target role 
or the primary gap from the original plan 
may no longer be the most relevant focus.

For each scenario, give me a decision tree: 
the two or three questions to ask and 
the specific action each answer leads to.

The protocol should distinguish between 
plans worth adjusting and plans worth stopping. 
Both are valid outcomes. Continuing a plan 
that should be stopped is not persistence. 
It is sunk cost thinking.

You are helping me build an accountability 
structure for my ninety-day development plan 
that is robust to the pressures that derail 
most development plans.

My plan summary: [objective, milestones, 
weekly practice from above prompts]

My specific risk factors for non-completion: 
[be honest about past patterns, upcoming 
high-demand periods, and the competing 
priorities most likely to crowd this out]

Please:

1. Propose a specific accountability mechanism 
   for each thirty-day milestone: who will I 
   tell, how will I document it, and what 
   will I do if I miss it
2. Design a format for weekly documentation 
   that takes under five minutes to complete 
   and produces a record useful for the 
   thirty-day milestone review
3. Identify the moment in the plan where 
   I am most likely to consider abandoning 
   it and propose a specific protocol 
   for that moment
4. Identify what success looks like at 
   day ninety in terms I can assess 
   without anyone else's validation: 
   the internal standard that tells me 
   the plan worked regardless of whether 
   external recognition has yet followed

Accountability structures that depend on 
external validation for their motivating 
force are fragile. The most robust ones 
are grounded in internal standards the 
professional genuinely cares about.

You are helping me design the first week 
of my development plan in enough detail 
that I can begin without any further 
planning decisions.

My plan: [summary of objective, milestones, 
weekly practice, and existing routine trigger]

Please give me a day-by-day schedule for 
week one that:

1. Starts on the first working day 
   after I run this prompt
2. Includes every specific action required 
   to begin the practice I have designed
3. Takes no more than the time I have 
   committed to each day
4. Ends with a five-minute reflection 
   that tells me whether week one is on track

Make the schedule specific enough that 
I do not need to make any decisions 
to follow it. Every decision made now 
is one that does not have to be made 
under the pressure of an actual working week.

Design the day ninety review I will run 
at the end of this plan.

The review should:

1. Assess the objective honestly: achieved, 
   partially achieved, or not achieved, 
   with the specific evidence
2. Identify the most important thing I learned 
   about my capability development that I 
   did not know at the start
3. Assess whether the target role is still 
   the right one to continue developing toward, 
   or whether what I learned in ninety days 
   points toward a different direction
4. Produce the input for the next ninety-day 
   plan: where my current position sits relative 
   to where I was targeting, and what the 
   most important next step is from here
5. Identify the one thing I would do differently 
   if I were starting this plan again with 
   what I now know

The day ninety closer is not the end of 
the process. It is the baseline assessment 
for the next cycle. Design it accordingly.