Questions your new hires are afraid to ask before their first day

June 14, 2022

Have you ever had a burning question you wanted to ask, but you either felt silly or didn’t know who to go to? Many of us probably have - and as a new hire, that’s often the case.

Starting a new job at a new company is exciting! But along with that often comes some uncertainty about the first day. It’s pretty likely that your new hires have some questions they really want to know the answer to but might shy away from asking.

If I’m going into the office, where do I park? What time do I show up? What do most people do for lunch?

If I’m remote, what apps should I sign into to get started? Will I have an agenda or any meetings on my first day? Will my manager or someone else be my first point of contact when I start?

All questions that most of us write off as silly when we want to ask them, but are actually pretty important.

Shifting from interview to first day mindset

When a candidate signs their employment contract, they’re most likely not thinking about the logistics of their first day. At that moment they’re excited to sign the offer and are still winding down from the interview process, where their focus was on demonstrating who they are and why they’re the right fit for the job - not what to do for lunch.

Cut to the week before their scheduled start date, though, and all of the logistical questions start flooding in. They’ve switched from an interview mindset - “Is this company the right fit for me?” - to a pre-start date mindset - “What will my first day be like?”. But where do they go to get answers (and do they feel comfortable asking)?

Create an open dialogue

One way you can get ahead of the anxiety your new hires might be feeling is by assigning them a point of contact - before their first day - to answer their questions and assure them that no genuine questions are too silly to ask. You can also start to anticipate some of the things they might be wondering, like what they should wear, if they’re expected to be busy and productive all day on their first day, and what time they’re expected to start and end.

Every new hire has a different level of confidence when it comes to asking questions before they’re comfortable with the team. To those who might be a little more introverted or shy, we want to encourage them to ask questions - and let them know no one will be judging them!

Not sure where to start?

You’re probably sending a lot of emails to communicate a lot of need-to-know items. But maybe send one that isn’t about communicating action items or standard pre-start-day tasks, and more about making sure your new hire's needs are taken care of. Ask how they’re doing and if they have any questions, big or small.

Take a survey of your current employees to see what questions they had before their first day that they felt uncomfortable asking. Incorporate their responses into an email to your new hires that encourages them to ask questions and reassures them they’re not alone!

Once you open the door to give them a safe and comfortable space to speak openly, your new hires will be even more excited about their first day with you. They’ll be more likely to continue that open communication with their team, which will encourage them to learn and grow without fear of judgment. They’ll also always remember how you welcomed them into an environment where they could be themselves, and that positive impression goes a long way. 

Questions your new hires want to ask


  • What is the remote work policy?
  • Do I have any remote work stipends (and if so, how do they work)?
  • What do I do if I have an issue with my laptop or need help from IT?
  • When will I get access to all of the tools I need?
  • What materials should I have?
  • What time should I sign in on my first day?
  • How do people usually connect with each other?
  • Does everyone work the same hours or is there a flex policy?

Office Logistics

  • How does the coffee machine work?
  • What’s the fridge or snack situation?
  • What’s the lunch situation like? Should I bring lunch? Will we go out?
  • Is there a cafeteria?
  • What’s the best local coffee shop?
  • What time should I show up on the first day?
  • When do people normally leave?
  • If I drive my car, where can I park?
  • Is there an office map?
  • Where are all of the meeting rooms?
  • Where do different people sit?
  • Am I expected to sit at a desk or are there co-working spaces?
  • Will someone meet me at the door?
  • Who should I contact if I have an emergency and need to leave?
  • Will my manager show me around?
  • Does the team know I’m starting?


  • What should I accomplish on my first day?
  • How should I dress?
  • Is there anything I should bring?
  • Will I be introduced to the team?
  • How do my stock options actually work?
  • Is there a tool I should use to see my benefits and payroll info?

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