There is a good reason for the order. A template asks you to describe the job you held. What a
hiring manager is actually buying is the value you bring, and those two things are related but they
are not the same. Working out the second one first makes everything downstream easier and better.
These prompts do that work. They pull out the raw material — what you were responsible for, the
scale you operated at, the decisions you owned, the outcomes you produced, and the things you turn
out to be genuinely good at. Give them your real detail and you will finish with a document you
will use for months.
You are a career coach who has spent 20 years placing veterans into civilian roles. You are
good at hearing what someone did and recognizing the civilian value in it — including the parts they
have stopped noticing because it was "just the job."
Interview me to build a complete inventory of my experience. Ask me ONE question at a time and wait
for my answer before asking the next. Ask follow-ups when an answer is vague or when you sense there
is more scope than I am claiming.
Cover these areas over roughly 12-15 questions:
1. Each assignment/duty station and what I was actually responsible for day to day
2. People: how many I led, trained, evaluated, or mentored — directly and indirectly
3. Money and materiel: budgets, equipment value, inventory, contracts I touched
4. Systems, tools, platforms, and software I used or administered
5. Decisions I made without asking permission, and what was at stake if I got them wrong
6. Problems I solved that nobody assigned me
7. Things that got better because I was there — even if nobody measured it
8. Crises, deployments, inspections, or high-pressure periods and my role in them
9. Training, schools, certifications, and collateral duties
10. What I was repeatedly asked to do because I was good at it
Start with my background:
- Branch: [BRANCH]
- Years: [YEARS]
- Final rank: [RANK]
- Job(s): [MOS / RATING / AFSC AND WHAT IT ACTUALLY INVOLVED]
- Assignments: [BRIEF LIST]
When the interview is done, produce:
A) A "Scope Summary" — one paragraph a hiring manager could read to understand my level
B) 10-15 accomplishment statements in plain civilian English, each with the concrete detail attached
C) A list of 8-12 transferable skills, each with the specific evidence from my answers
D) A list of numbers I should go find in my records, and exactly where to look for each
Do not invent anything. If I gave you a vague answer, say "needs a number" rather than filling it in.
Set aside fifteen to twenty minutes, and answer the way you would talk to a friend over coffee rather than the way you would write an evaluation. Ramble a bit. Include the detail that feels too small to mention. The messiness is exactly what this prompt is built to sort through, and the tool will pull the structure out at the end.
I am going to paste text from my [NCOER / OER / EPR / FITREP / EVAL / AWARD CITATIONS].
For each one:
1. Pull out every concrete fact: numbers, scope, scale, dollar amounts, people counts, timelines
2. Translate each achievement into civilian business language
3. Note which of these would be most impressive to a hiring manager outside the military, and why
4. Flag any claim that sounds impressive in military writing but would read as empty to a civilian
("consistently exceeded standards", "an invaluable asset")
5. Identify what is missing — what a civilian reader would want to know that the document does not say
Present the results as a table: Original Phrase | What It Actually Means | Civilian Version | Strength (High/Medium/Low)
Here is the text:
[PASTE YOUR EVALUATION OR CITATION TEXT — REMOVE ANY NAMES, UNIT IDENTIFIERS, OR OPERATIONAL DETAIL FIRST]
Your evaluations and award citations are full of concrete figures you have long since stopped thinking about — headcounts, dollar values, percentages, timelines. Pull your records from milConnect or your service record before you run this, and you will be surprised what is in there.
Based on everything I have told you so far, help me separate three different things:
1. THINGS I AM GOOD AT — skills I have real evidence for
2. THINGS I ENJOY — work that energized me rather than drained me
3. THINGS I WAS JUST ASSIGNED — competent but indifferent
For each item in list 1, give me the specific evidence from my own answers. Do not assert a strength
I have not demonstrated.
Then answer these:
- Which items appear in BOTH "good at" and "enjoy"? Those are my leverage.
- Which items am I good at but dislike? Warn me if I am likely to get hired into them anyway.
- What is the pattern across the things I enjoyed? Name it in one sentence.
Finally, give me three sentences I could say out loud in an interview that describe my strengths
without sounding rehearsed or arrogant.
Service members routinely undervalue capabilities that are rare in the civilian workforce
because everyone around them had the same ones.
Based on my background, identify the things I probably consider unremarkable that are actually
uncommon and valuable outside the military. For each one:
- Name the capability in civilian terms
- Explain why it is rarer than I think
- Give me a specific example from my own experience that demonstrates it
- Name two or three civilian roles where it is a genuine differentiator
Consider areas like: operating under time pressure and incomplete information, accountability
culture, security and compliance discipline, working with people from every background, training
and developing others, documentation and process rigor, briefing senior leaders, logistics and
resource planning, risk assessment, and the ability to be dropped into an unfamiliar situation and
be useful within a week.
Be specific to MY experience. Do not give me a generic "veterans are disciplined" list.
This one surprises almost everyone who runs it. Details that felt entirely routine at the time — briefing a colonel every week, holding a clearance for eight years, training every new arrival in your section — carry real weight in a civilian hiring conversation, precisely because they are uncommon outside the service.
Help me figure out what kind of civilian work environment I would actually thrive in, so I
do not take the first offer and hate it in four months.
Ask me about:
- How much structure and clarity I need versus how much ambiguity I can tolerate
- Whether I do better with a clear chain of command or a flat, negotiate-everything culture
- How I feel about pace: steady and predictable versus constant change
- Solo deep work versus constant collaboration
- How much I need the work to matter to me
- Travel, hours, on-call, and what I am done with
- Remote, hybrid, or in person — and honestly why
- Size of organization: 50 people, 5,000, or 500,000
Ask one question at a time. Then give me:
A) A short profile of my ideal work environment
B) Three types of organization that tend to fit that profile, with examples
C) Two or three environments that would likely frustrate me, and the warning signs to watch for in
a job posting or interview
D) Five questions I should ask in an interview to test whether a company is really like that
Based on my inventory, my strengths, and my work-style profile, suggest 10 civilian career
paths I should consider.
For each one give me:
- The common job titles (entry point and where it leads in 5 years)
- Why my specific background maps to it — cite my actual experience, not generalities
- The realistic salary range for someone with my experience, in [CITY/REGION]
- What I am missing and roughly how long it takes to close that gap
- Typical employers, including at least one I would not have thought of
- An honest difficulty rating for me to break in: Easy / Moderate / Hard, and why
Include a mix across all three employment markets, not just commercial:
- 3 obvious paths that directly use my military specialty
- 2 paths in federal civil service, noting the likely GS grade
- 2 paths with government contractors, noting whether a clearance is required
- 3 adjacent or unexpected paths in the commercial private sector
Do not assume "civilian job" means "corporate job." Federal agencies and contractors are often
where a military background is worth the most, and I want them weighted properly.
Rank them by a combination of fit, realistic accessibility, and earning potential. Be honest about
the hard ones rather than encouraging.
Ask for specific salary figures, then confirm them against BLS, Levels.fyi or Glassdoor before you rely on them. Compensation data is the area where these tools most often work from an out-of-date picture, and it takes about two minutes to check.
I am considering moving into [TARGET ROLE / FIELD].
Play devil's advocate. Do not encourage me. Give me:
1. The three strongest reasons someone with my background would fail or wash out in this field
2. What the day-to-day actually looks like, including the boring and frustrating 70% that the job
description does not mention
3. Where my military experience will be a liability, not an asset — habits or expectations that
will not translate
4. Who I will be competing against for these jobs, and what they have that I do not
5. The realistic timeline from today to a first offer, assuming I work at it consistently
6. Two or three adjacent roles that would be a materially easier entry point with 80% of the upside
Then, separately, tell me the strongest honest case FOR me pursuing it.
Be direct. I would rather hear it now than in eight months.
Help me write down my non-negotiables before I start getting offers, so I am not making
these decisions under pressure with a number in front of me.
Walk me through, one question at a time:
- What is the lowest total compensation I could accept without resenting the job?
- What is my hard limit on commute, travel, and hours?
- What do I need from the mission or the work itself, if anything?
- What did I promise my family about this transition?
- What would make me quit within a year?
- What am I willing to trade for the right opportunity, and what am I not?
Then produce a one-page "decision card" with:
- My three absolute non-negotiables
- My three strong preferences (would trade for the right role)
- My three nice-to-haves
- A single sentence I can read when I have an offer in hand and I am tempted to ignore my own list
Print this one and keep it somewhere you will see it. Deciding what matters to you while you are calm is far easier than deciding it with an offer letter and a deadline in front of you, and the version of you that wrote it down will make the better call.
