The best onboarding programs don’t just tell new hires what to do — they ask the right questions to set the relationship up for success.
Most companies treat Day 1 as an information dump. Here’s your badge. Here’s your desk. Here are 47 policies to read. Sign here, here, and here.
But the most effective onboarding programs flip this around. Instead of only talking at new hires, they ask questions. Questions that surface expectations, learning styles, and potential issues before they become problems.
Here are 10 questions every new hire should answer on Day 1 — and what to do with the answers.
1. “What does a great first month look like to you?”
Why ask this: New hires arrive with expectations — some realistic, some not. Understanding what they think success looks like lets you align (or reset) expectations early.
What to listen for: If they say “I want to close a deal in the first week,” they may need a reality check on ramp time. If they say “I just want to not bother anyone,” they may need encouragement to ask more questions.
What to do: Compare their answer to the 30-60-90 day plan. Where there’s alignment, reinforce it. Where there’s a gap, discuss it openly.
2. “How do you prefer to receive feedback?”
Why ask this: Some people want direct, in-the-moment feedback. Others prefer written feedback they can process privately. Giving feedback in the wrong format doesn’t just fail — it backfires.
What to listen for: Pay attention to both format (verbal vs. written, public vs. private) and frequency (real-time vs. scheduled). Cultural background often influences preferences here.
What to do: Share the answer with their manager and onboarding buddy. Adjust your feedback approach accordingly for the first 90 days.
3. “What’s the best onboarding experience you’ve had? What made it good?”
Why ask this: Past experience reveals what matters to this person. Someone who valued a structured first week needs a detailed schedule. Someone who valued autonomy needs space to explore.
What to listen for: The specific elements they mention — structure, social connections, early responsibilities, clear documentation, or something else entirely.
What to do: Where possible, incorporate their preferred elements into their onboarding plan. If their ideal onboarding doesn’t match your program, explain what you do differently and why.
4. “What’s the worst onboarding experience you’ve had? What went wrong?”
Why ask this: This tells you what to avoid. People remember bad experiences more vividly than good ones, so their answer will be specific and instructive.
What to listen for: Common answers include “nobody talked to me for the first three days,” “I had nothing to do,” and “I got thrown into work with no context.” Each of these points to a specific failure you can prevent.
What to do: Explicitly address their concern. If they dreaded being ignored, introduce them to their buddy and schedule extra check-ins. If they hated being idle, front-load meaningful work.
5. “How do you learn best — by reading, watching, doing, or discussing?”
Why ask this: Training effectiveness drops when the format doesn’t match the learner. A hands-on learner won’t absorb a 50-page manual. A reader won’t get much from a shadowing session.
What to listen for: Most people have a primary and secondary learning style. “I prefer doing, but I like having documentation to refer back to” is a common and useful answer.
What to do: Adjust training delivery where possible. If they’re a hands-on learner, replace documentation reviews with guided exercises. If they’re a reader, provide written guides before training sessions so they can come prepared.
6. “What tools and systems are you already familiar with?”
Why ask this: Don’t waste time training someone on a tool they’ve used for five years. And don’t skip training on a tool they’ve never seen.
What to listen for: Both what they know and how deeply they know it. “I’ve used Slack” might mean “I send messages” or “I’ve built custom workflows with the API.”
What to do: Skip introductory training for tools they know well. Add extra support for tools that are new. This alone can save hours in the first week.
7. “Is there anything about your work setup that we should know?”
Why ask this: This is an open invitation to share needs that might not come up otherwise — ergonomic requirements, accessibility needs, schedule constraints, or remote work preferences.
What to listen for: Some people will share specific needs (standing desk, screen reader, flexible hours for childcare). Others will say “nothing” now but may bring something up later once they’re comfortable. Keep the door open.
What to do: Act on whatever they share, quickly and without making it a big deal. Responsiveness to early requests builds trust.
8. “Who do you think you’ll need to work with most closely?”
Why ask this: This reveals how well the new hire understands the role and the organization. It also highlights relationship-building priorities for the first month.
What to listen for: If their answer matches reality, they’ve done their homework. If it’s off, you have a chance to correct misunderstandings about the role before they solidify.
What to do: Prioritize introductions with the people they’ll work with most. Schedule working sessions, not just meet-and-greets. People build real connections through collaboration, not small talk.
9. “What questions do you have that you haven’t had a chance to ask yet?”
Why ask this: By Day 1, new hires have accumulated questions from the interview process, the offer stage, and pre-boarding. Some questions feel too small to ask formally. Others feel too risky.
What to listen for: The questions they ask reveal what they’re actually thinking about. Compensation questions suggest they’re still evaluating. Culture questions suggest they’re trying to adapt. Technical questions suggest they’re ready to dive in.
What to do: Answer honestly. If you don’t know the answer, say so and follow up. The goal is to establish that questions are welcome and will be taken seriously.
10. “What should we check in about at the end of your first week?”
Why ask this: This question does two things — it tells the new hire that a check-in is coming (accountability) and lets them set part of the agenda (ownership).
What to listen for: Their answer reveals their priorities and concerns. Someone who says “whether I can access all the tools I need” has different needs than someone who says “whether I’m meeting expectations.”
What to do: Actually check in at the end of the week. Use their answer as one of the agenda items. Following through on this builds trust and shows that their input matters.
How to Collect These Answers
There are several ways to gather Day 1 responses:
In a 1:1 conversation. The manager or buddy asks these questions during a dedicated Day 1 check-in. Best for building rapport.
In a digital form. Send the questions as a task in your onboarding tool. The new hire can answer thoughtfully at their own pace. Best for introverts and remote employees.
In a team setting. For cohort onboarding (multiple hires starting the same day), these questions work well as icebreakers in a group orientation. Best for building peer connections.
OnboardFlow supports adding custom questions as onboarding tasks — new hires answer from their phone, and responses are visible to HR and the hiring manager in monday.com.
What Not to Ask on Day 1
Avoid questions that create pressure or feel like a test:
- “Where do you see yourself in 5 years?” — Too much, too soon. Save it for a later 1:1.
- “What would you change about our company?” — They’ve been here for 4 hours. They don’t know enough yet.
- “Can you start on [project] today?” — Day 1 should be about orientation, not output.
- “Why did you leave your last job?” — They answered this in the interview. Bringing it up again feels like a redo.
The Bottom Line
Day 1 sets the tone for the entire employment relationship. The companies that ask good questions on Day 1 don’t just get better information — they signal that they care about the individual, not just the role.
These 10 questions take about 30 minutes to cover in a conversation. That’s a small investment for the clarity, alignment, and trust they create.
Ask the questions. Listen to the answers. Act on what you hear.
OnboardFlow lets you build custom onboarding tasks — including Day 1 questions — that new hires complete from their phone. HR sees everything in monday.com. Try it free.