I start as [ROLE] at [COMPANY] on [DATE]. It is my first civilian job after [YEARS] years
in the [BRANCH].
Prepare me:
1. What to do in the two weeks before I start — what to read, who to connect with, what to set up
2. What to expect on day one and in week one, concretely
3. The civilian workplace norms that most surprise people coming out of the military — be specific,
not general
4. What to ask my manager in our first conversation
5. Things I should NOT do in the first month, even though they would have been right in uniform
6. How to introduce myself to the team — how much to say about my service, and how to read whether
they want to hear more
7. What "good" looks like at 30 days in a role like this
Be concrete. I would rather have ten specific things than a philosophy.11. Your First 90 Days
Congratulations — you got the job. Now comes the part that determines how the next few years go.
A fair number of veterans move on from their first civilian role within a year, and the reason is rarely the work itself. It is that every workplace runs on a set of unwritten conventions, and nobody hands you the manual for this one.
Civilian organizations are built around influence rather than positional authority, around objectives rather than tasks, and around relationships you construct rather than ones assigned to you. These are sensible designs for organizations where people can leave at any time and expertise is spread across levels. They are simply different from the system you know inside out, and the adjustment is a matter of learning local customs rather than changing who you are.
Give yourself the same runway you would give a new arrival to your unit. Watch first, ask a lot of questions, and let the place teach you how it works before you start changing things. The prompts below will speed that up considerably.
If you landed in a federal agency or with a contractor, much of this will feel familiar — and a few things will surprise you precisely because the surroundings look so similar. The building, the acronyms and the customer may be the same while the way decisions get made is quite different. Tell the prompts which market you are in and the advice adjusts.
Before day one
Section titled “Before day one”Build me a 30/60/90 day plan for my new role as [ROLE] at [COMPANY].
What I know about the role: [RESPONSIBILITIES, TEAM SIZE, WHO I REPORT TO, WHAT THEY SAID THEY
NEED]
Structure:
DAYS 1-30 — LEARN
- What to understand about the business, the team, the systems, and the customers
- Who to meet and what to ask each of them
- What to deliberately NOT change yet, and why
- How to document what I am learning
DAYS 31-60 — CONTRIBUTE
- The first things I should own
- How to find a visible early win that does not step on anyone
- Where a new person can add value without political risk
DAYS 61-90 — LEAD
- Where to start taking initiative
- How to propose a change and have it land
- What my manager should be able to say about me at 90 days
For each phase, give me: 3-5 specific goals, how I would know I hit them, and the biggest risk in
that phase.
Also: how do I ask my manager to review this plan without it seeming like I am over-formalizing
something they wanted to be casual?A 30/60/90 plan is also a strong thing to bring to a final-round interview. Arriving with a draft of how you would approach the first three months shows you have already started thinking like someone in the role, and it gives the conversation something concrete to work with.
Decode the workplace
Section titled “Decode the workplace”Help me understand the civilian workplace norms that differ most from military culture. For
each, explain what the military norm was, what the civilian norm is, why it is different, and what
specifically to do instead.
Cover:
1. Chain of command and who you can talk to directly
2. How decisions actually get made when nobody can give an order
3. Disagreeing with your boss, and disagreeing in a meeting
4. Directness — how blunt is too blunt, and how to read when someone is saying no politely
5. Feedback: how to give it and how it is expected to be received
6. Hours, presence, and the difference between being busy and being valued
7. Meetings — why there are so many and what is actually happening in them
8. Email and chat tone, including how much informality is expected
9. Asking for help versus figuring it out yourself
10. Self-promotion and visibility — why nobody will notice your work unless you tell them
11. Saying no, pushing back on scope, and protecting your own time
12. Social norms: small talk, lunch, after-work events, and how much to participate
For each, give me one concrete example of a phrase I could actually use.
Context: I am moving from [YOUR MILITARY ROLE] into [CIVILIAN ROLE] at a [COMPANY SIZE/TYPE].Two of these tend to land hardest. The first is that making your work visible is part of the job here rather than self-promotion — people are genuinely busy and will only know what you tell them. The second is that civilian workplaces often signal disagreement gently, so a phrase like 'let me think about that' frequently carries more weight than the words suggest. Both take about a month to get used to.
Something happened at work that I do not know how to read. Help me interpret it.
WHAT HAPPENED: [DESCRIBE IT — WHO, WHAT WAS SAID, THE CONTEXT, HOW IT ENDED]
HOW I INTERPRETED IT: [YOUR READ]
WHY I AM UNSURE: [WHAT IS CONFUSING]
Tell me:
1. Two or three plausible readings of what actually happened, including ones I have not considered
2. Which is most likely in a civilian workplace, and why
3. Whether this is a military-to-civilian translation issue or a genuine problem
4. What to do next — specifically, including what to say
5. What NOT to do
6. Whether I should raise it, let it go, or wait and watch
Be practical. I am not looking for validation, I am looking to read the room correctly.Working with people
Section titled “Working with people”I have my first one-on-one with my new manager. I have never had a civilian manager and I
am not sure what these meetings are for.
Explain:
1. What a one-on-one is actually for, and what a good one looks like
2. Who drives the agenda — and what happens if neither of us does
3. What to bring to the first one
Then give me:
- 8 questions to ask in the first one-on-one, covering their expectations, how they like to
communicate, how they define success for me, and how they prefer to receive bad news
- A short way to explain my background that gives them useful context without a war story
- How to ask what I should be doing differently, in a way that gets a real answer instead of
"you're doing great"
- What to do in the last five minutes so the meeting ends usefully
My manager's background, if I know it: [WHAT YOU KNOW]I led people in the military where rank carried authority. Now I need to get things done
through people who do not report to me, and some who do but who can simply leave.
Help me adapt:
1. What actually transfers from military leadership, and what does not
2. How to build influence when you cannot direct anyone
3. How to hold someone accountable without the tools I used to have
4. How to motivate people who are not bound by anything beyond wanting to stay
5. How to handle an underperformer as a peer, and as a manager
6. How to run a meeting where I have no formal authority
7. What military leadership habits read as controlling or abrasive in a civilian setting — be
specific, because I will not see these in myself
For each, give me one concrete thing to say or do, not a principle.
My situation: [IC WITH NO REPORTS / TEAM LEAD / MANAGER WITH X REPORTS] at a
[COMPANY TYPE AND SIZE].Sustaining it
Section titled “Sustaining it”In the military, my performance was documented for me. In a civilian job, if I do not track
and communicate my own work, nobody will.
Help me build a system:
1. A simple weekly practice for capturing what I accomplished — 10 minutes, sustainable
2. What to record so it is useful later for a performance review, a raise conversation, or a
future resume
3. How to communicate wins upward without sounding like I am bragging — the specific framing that
works
4. How to make sure my manager's manager knows what I do
5. What a "brag document" is, how to keep one, and how to use it at review time
6. How often to check in about my trajectory, and what to ask
Give me a template for the weekly log with actual column headers.
Also: when should I expect a performance review, and what should I be doing three months before it?Start the weekly log in your first week and keep it going. Two minutes every Friday means that twelve months from now, at review time, you will walk in with specifics while everyone else is working from a vague sense that the year went well. It is one of the highest-return habits in a civilian career.
The job is going okay, but the transition out of the military has been harder than I
expected in ways that are not about work.
What I am experiencing: [DESCRIBE — E.G. LOSS OF PURPOSE, MISSING THE TEAM, FEELING LIKE AN
OUTSIDER, IDENTITY, BOREDOM, RESTLESSNESS, DIFFICULTY RELATING TO COLLEAGUES]
Help me:
1. Understand what is normal about this, and roughly what timeline people describe
2. Separate what is a transition adjustment from what might need more support
3. Find practical ways to rebuild the things I am missing — purpose, camaraderie, structure,
being part of something
4. Identify veteran communities, ERGs, volunteer roles, or other structures that help with this
specifically
5. Know the signs that I should talk to someone, and what the actual options are
Be practical and straightforward with me.Worth knowing what is available: Vet Centers offer free, confidential counselling to combat veterans and their families, with no VA enrollment required and separate from your medical record. The Veterans Crisis Line is there around the clock — dial 988 then press 1, or text 838255 — and you are welcome to call whenever something is weighing on you. The [resources page](/resources) has more.
You have reached the end of the prompt library — but not the end of the transition.
Succeeding at Work goes deeper on the things that determine how the next few years go rather than the next few months:
- Understanding Your Benefits — health plans, retirement, equity, and leave, decoded from scratch
- How Decisions Actually Get Made — influence instead of orders, and how to be assertive and accommodating at once
- Giving and Taking Feedback — the skill that most determines whether you get promoted
- Soft Skills That Carry You — communication, presence, and modern workplace etiquette
- Time, Energy, and Boundaries — managing yourself once the structure is gone
You can also go back to the checklists or the resources page.