First-Week Question List How-to (20 Minutes)

Sep 10, 2026 | First 90 Days, How-tos

Week one dumps acronyms, access tickets, and well-meaning advice on you at once. “Be curious” is not a plan. You need a short list of high-leverage questions, split by who can actually answer them, and a place to write the answers down before they evaporate.

Time box: 20 minutes to pick questions, book the asks, and set up your capture log. The conversations themselves are separate 10-15 minute chats. This is a timed play, not a pep talk. Pair it with the New Hire hub and first 90 days runway.

When to use (and when not to)

Use this play on days 1-5 once you have basic access and have skimmed the handbook or wiki home. Ideal after your first manager hello, before you invent your own theory of how the team works.

Do not use it before you’ve read the onboarding docs you were given. Do not run it during someone else’s fire drill, on-call incident, or all-hands crunch week. Do not treat it as a substitute for HR policy questions that already live in benefits, leave, or security materials. If your company is in a crisis week, wait until the noise drops, then run a shorter version.

Not every company assigns a buddy. If you don’t have one, use a helpful peer as the “buddy” column, or fold those questions into teammate chats.

Who is involved

You (new hire): pick, ask, capture.
Manager: success criteria, priorities, norms.
Optional buddy / onboarding contact: unwritten rules, tools, “how we actually do it.”
1-2 teammates: workflow reality, handoffs, who to ping for what.

Managers: you can hand this play to a new report so week one isn’t improvisation. Your side of the relationship install is the First 1:1 with a new report play.

Prep (5 minutes before the 20)

Block 20 minutes on your calendar labeled “Week-1 questions: pick and book.”
Open a blank doc or note titled First-week question log.
Paste three columns or sections: Manager / Buddy / Teammates.
Skim your role description and any welcome email so you don’t ask for what’s already written.
Note who your buddy is (if any) and which two teammates sit closest to your work.

Audience-split question picker

Audience-split questions beat a mega-list. Ask the person who owns the answer. Don’t ask your manager for Slack emoji norms, and don’t ask a peer to define your success criteria.

Manager (pick 4-6)

What does “good” look like at the end of week 2 and week 4 for this role?
What are the top 1-2 priorities I should protect if everything else slips?
How do you prefer updates (chat, email, doc, standing meeting), and how often?
Who should I meet in the next two weeks, and can you make warm intros?
What decisions can I make alone vs. bring to you?
What’s already in motion that I should not disrupt?

Buddy or onboarding contact (pick 3-5)

Which tools matter daily, and which can wait?
Where do people actually look things up (wiki, shared drive, tribal Slack)?
What unwritten norms trip new people up (meeting culture, response time, camera)?
Who is the go-to for [tickets / design / data / customers] when I’m stuck?
What’s one thing you wish you’d known in week one?

Teammates (pick 3-4 per person)

How does work enter and leave our team?
What’s a recent handoff that went well, and one that was messy?
When you’re blocked, who do you ping first?
What should I never surprise the team with in a public channel?

Skip policy trivia that belongs in HR docs. Save deep career talk for later. Week one is orientation, not a performance review.

Steps inside the 20-minute box

Minute 0-5: Pick. Circle 4-6 manager questions, 3-5 buddy questions, and 3-4 teammate questions. Cap the total you will ask this week at roughly a dozen across people. Quality over coverage.
Minute 5-12: Schedule. Send short booking notes (script below). Aim for 15-minute slots, not hour-long interviews.
Minute 12-18: Build the log. Create rows: Question | Who | Answer | Follow-up | Date.
Minute 18-20: Park leftovers. Move unanswered items to your first real 1:1 agenda. Don’t force every answer on day two.

After the 20 minutes, run the conversations over the rest of the week. After each chat, fill the log within an hour while memory is fresh.

Script: ask without seeming needy

Chat or email:

Hi [Name], I’m putting together a short orientation list for week one. Could I grab 15 minutes for a few practical questions about [priorities / how we work / tools]? I’ll keep it tight and come with a written list.

In person / Zoom open:

I have five orientation questions, not a fishing expedition. Got 15 minutes this week?

If they say they’re slammed: “No problem. I’ll send the three highest-priority ones async and we can skip the rest.”

Output: first-week question log

Your play output is a living question log, not a vibes journal.

Question	Who	Answer (short)	Follow-up	Date
What does good look like week 2?	Manager	Clear ticket queue + one shipped note	Confirm metrics Friday	Mon
Where do we look things up?	Buddy	Team wiki > Slack search	Bookmark runbooks	Tue

Sample (fictional): Alex joins Ops. Manager Maya says week-two success is “owning intake triage without pinging me for every edge case.” Buddy Priya explains that #ops-help is for blockers, not brainstorming. Teammate Jordan notes that Legal must see refund copy before Eng. Alex writes all three down and carries two open questions into Friday’s 1:1.

Watch-outs

Interrogating people. A list is for you. Don’t machine-gun twelve questions without listening.
Policy questions first. Benefits, leave, security, and expense rules belong in official docs or HR, not a teammate pop quiz. See How HR works for literacy, then your employer’s policy.
Skipping the write-down. If it’s not in the log, it didn’t happen for ramp purposes.
Assuming every company has a buddy. Adapt the columns.
Turning curiosity into a performance. You are learning the system, not auditioning for a TED talk.

Done by end of week 1

You’re done when: you’ve asked your manager the success and priority questions; you’ve captured answers from at least one buddy-or-peer and one teammate; your log has follow-ups parked for the next 1:1; and you can explain in plain language what “good” means for the next two weeks.

Next plays: run the Stakeholder map play once you know who influences your work, and keep using questions to ask in your first week as a deeper menu if you need more prompts. For the broader checklist, see onboarding checklist and mistakes to avoid in your first month.