New Job Checklist

Congratulations — the offer is signed. This checklist covers the part that comes next.

The first ninety days set up a great deal of what follows: the benefits you lock in for the year, the habits you build, and the impression your new colleagues form of how you work. None of it is difficult, and most of it is easier when you know it is coming.

The deadlines are real

Benefits enrollment windows usually run about 30 days from your start date, and that window is your one chance to set things up properly for the year.

Put every date from this list into your calendar on day one, with a reminder a week ahead. Ten minutes of diary work buys you plenty of time to read the plan documents carefully and make good choices.

Before you start

Between offer and start date

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• Get the offer, the benefits summary, and any negotiated terms in writing before resigning anything or declining another offer.
• Ask HR for the Summary of Benefits and Coverage (SBC) for every health plan option — it is a standardized document designed for comparison.
• Work out your health coverage gap, if any, between losing TRICARE and your employer plan starting. Check CHCBP, a spouse's plan, or a marketplace plan.
• Read Understanding Your Benefits and run the decode prompt on your package.
• Confirm whether the employer offers paid military leave, if you are in the Guard or Reserve.
• Convert SGLI to VGLI if you have not already — there is a limited window after separation to do it without health questions.
• Ask what to read or set up before day one.
• Connect with your manager and one or two teammates on LinkedIn.

Week one

First five days

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• Put your benefits enrollment deadline in your calendar, with a reminder a week before.
• Enroll in health, dental, and vision. Do not default to the familiar-sounding plan — do the arithmetic.
• Set your 401(k) contribution to at least the full employer match. This is the highest-return decision you will make all year.
• Note the vesting schedule for the employer match and any equity, and diarise the cliff dates.
• Open and fund an HSA if you chose an HDHP — and check the VA care interaction first if you use VA healthcare.
• Elect life and disability insurance, including long-term disability, which people skip and later regret.
• If this is a federal job: ask HR about military service credit (buying back your time toward FERS) and creditable service for leave accrual.
• If this is a contractor role: find out the contract's period of performance and recompete date.
• Ask your manager what "good" looks like at 30, 60, and 90 days.
• Start a weekly accomplishment log. Day one, not month six.
• Find the veterans employee resource group and join it.

First month

Learning the place

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• Build a 30/60/90 day plan and walk your manager through it.
• Meet everyone your manager suggests, and ask each of them the same two or three questions.
• Ask someone four years in: "What should I know that nobody is going to tell me?"
• Work out how decisions actually get made here — who really decides, and how proposals get socialized.
• Learn the chat, email, and meeting norms before you assume them.
• Deliberately change nothing yet. Learn why things are the way they are first.
• Find out what the actual working-hours expectation is, versus what is stated.
• Locate your Employee Assistance Program details and save them. Free, confidential counselling and legal or financial consults.
• Set up direct deposit, tax withholding, and emergency contacts.
• Build a civilian budget now that you know your real take-home.

First quarter

Becoming effective

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• Deliver one visible win that does not step on anyone.
• Ask for real feedback using a narrow question, not "how am I doing?"
• Give feedback at least once — to a peer or upward — and notice how it lands.
• Practise saying no once, with a reason and an alternative.
• Block focus time in your calendar and defend it.
• Decline one meeting you do not need to be in.
• Take at least one day off. Establish early that you use your leave.
• Set a stop time for the day and keep it, especially if you work remotely.
• Get a primary care doctor and, if you use it, complete your VA enrollment.
• Rebuild a physical routine now that PT is not mandatory.
• Find one source of purpose outside the job — mentoring, volunteering, an ERG, or something you build.
• Send the follow-up message to everyone who helped you get here, telling them how it turned out.

Ongoing

Each year

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• Review your benefits elections at open enrollment rather than rolling them over by default.
• Increase your retirement contribution when you get a raise, before you get used to the money.
• Update your accomplishment log weekly. It takes two minutes and it changes review conversations.
• Prepare for your performance review ahead of time, not the week before.
• Ask your manager what would constitute a strong year — months before it is assessed.
• Claim the benefits you are entitled to and forget about: tuition reimbursement, certification budgets, wellness stipends.
• Keep your network alive. Thirty minutes a month.
• Keep your resume and LinkedIn current even when you are not looking.