7 Questions to Ask in Your First One-on-One With a New Employee (July 2026)
Your first one-on-one meeting is a chance to set the tone for how you'll work with your new employee. This article reviews everything you need to know before your first 1:1. (Plus, an agenda template to get you started!)
Alex Kinsella
The first days at a new company can be exhilarating and overwhelming at the same time. There are laptops to set up, new processes to learn, teammates to meet, the list goes on. As a manager, you play a large role in how those first few weeks go for your new employee.
One critical item that every leader should have on their onboarding checklist is setting up the first one-on-one meeting. It’s your chance to make a positive first impression and set the tone for how you’ll work together moving forward.
In this post, we’ll go through:
TLDR:
- Send your new hire a shared agenda with questions before the meeting so they arrive prepared, not anxious.
- Start with personal questions (hobbies, work style, peak hours) before career goals to signal you see them as a person.
- Agree on 2 to 3 concrete 30-day milestones in the first meeting to give your new hire a clear target from day one.
- Ask about communication preferences early: channel mismatch (direct vs. indirect, Slack vs. email) creates friction fast.
- Spinach can handle note-taking during your one-on-ones, surfacing key decisions and action items so you stay present in the conversation.
Why does your first one-on-one matter?
Hiring is a whirlwind. There’s the lengthy interview process, the offer, preparing for their arrival, phew! But now that they’ve started, where do you begin?
Your first one-on-one is like your first impression. It’s the first opportunity to make your new employee feel welcome, connected and create a sense of belonging in your company. The stakes are real: Gallup employee engagement research found that employees whose managers hold regular meetings with them are almost three times as likely to be engaged as those whose managers do not.
What’s more, it’s a time to set the tone and expectations for future one-on-ones.
How to set up your first one-on-one meeting with a new employee
When setting up your first one-on-one meeting, don’t just send an invite and leave it at that. Throwing a meeting in your new hire’s calendar with no context could make them nervous. And let’s face it, starting a new job is nerve-wracking enough! Before you send out that calendar invite, here’s what you need to do to set up your first one-on-one meeting:
Create an agenda
Agendas are like rudders for meetings: they don’t determine where you’re headed, but they help you find your way there. Before your first one-on-one, create an agenda to guide your conversation and make sure you cover what you need to. Jordan Choo, Managing Partner at Kogneta, explains:
Moving forward, your employee will likely own the agenda for your one-on-ones, but you’ll take the reins on this one. That being said, make sure you still encourage input and, like Jordan said, share it in advance.
Set expectations
This might be your new employee’s first one-on-one meeting. So setting expectations for what you want to get out of it, and what they should plan for, can help get the meeting off to the right start. It’s helpful to include the purpose of the meeting in your agenda, so that your employee has an understanding of what they’re walking into before your first meeting.
Choose an appropriate location
It’s important to choose a location that feels safe and private for your 1:1s. Don’t hold them in the company kitchen or lounge area. Book a meeting room ahead of time that would be a safe space for sensitive discussions. While you may not be covering anything too sensitive in your very first one-on-one, you surely will down the line. Set the stage.
For remote one-on-one meetings, it’s a bit easier as video chat automatically provides a more private space to talk. But, make sure you’re taking the call from somewhere without too many people around. If there is someone around, let your direct report know that. The last thing you want is for them to share something vulnerable only to be surprised that someone else could hear the conversation. That’s a sure-fire way to break trust.
Remove distractions
It’s important to give your new employee your undivided attention. Put Slack on do not disturb, turn your phone over, resist checking emails. Make sure you’re actively listening to your new employee. Taking notes is definitely best practice, but don’t let it come at the expense of truly listening, especially in your very first 1:1. If you are taking notes, let your direct report know that’s what you’re doing so they can feel confident you’re hearing them.
7 Questions to ask your new hire in your first one-on-one
Now that you’ve got your first one-on-one scheduled with your new employee, it’s time to take a look at some questions you can ask for a meaningful discussion.
Psst: We’ve got 121 more questions where those came from.
1. What do you like to do outside of work?
Learning about your new employee’s hobbies, sports, or other activities is a great way to find common interests, form bonds, and build trust.
Work is just part of our lives. Finding out more about what motivates your new employee can potentially give you ideas for everything from motivation to future team building activities (Bowling, anyone?)
Fabian Camargo, Management Coach at Camargo Consulting, explains that he likes to start off the meeting with more personal questions to get across these messages:
- I’m interested in getting to know them as a person
- I’m willing to be vulnerable and open up about myself
- I want to respect their boundaries
- This meeting isn’t all about work
- This meeting isn’t super formal
2. How do you like to communicate?
In the old days (the 90s), you phoned someone to get a hold of them. In the less old days (the 00s), you could call or email. Today, we’ve got texting, Slack, Zoom, phone, email, Teams, WhatsApps, Signal, and more to choose from.
Whether you’re in an office, remote or hybrid workplace, you’ll find that everyone has a preferred method to communicate. Your first one-on-one is the time to figure out what works best for you and your new employee. We’ve set up a hierarchy of what channels we use for how important something is and what can be done async vs. real-time communication:
Channel | Response Expectation | Best For |
|---|---|---|
✉️ Email | Can wait a day or two | Non-urgent updates, documentation, async communication |
💬 Slack | Sometime today (unless flagged urgent) | Day-to-day questions, quick check-ins, team coordination |
📞 Phone | Immediate response needed | Urgent issues, time-sensitive decisions, escalations |
Slack: sometime today, but not major unless noted
Phone: we need you right away!
But beyond the actual method of communication itself, it’s also important to understand communication styles. Jordan Choo presents an example of why your first 1:1 is an important time to get a grasp on your team member’s communication style:
3. What time of day do you do your best work?
We’re not all morning people, even with copious amounts of coffee. Use your first one-on-one to learn about how and when your employee works best. Some people get their best work done late at night. Others are power workers right after a nutritious breakfast.
This is a great question to find out when your employee needs focus time too. Setting expectations for when you need them to respond can help them block time to get work done.
4. What kind of projects are you most excited to work on?
Your one-on-one is a chance to find out what projects inspire creativity and energy in your new employees. Use this question to find out what motivates them, and what types of projects they might need help on. It’s a great way to set them up for success with tasks and projects that they’re jazzed about.
5. What are your 1-year, 3-year, and 5-year career goals?
Understanding your new employee’s desired career path provides you with opportunities to help them set milestones. For example, if they’re interested in advancing as a leader, you might find ways for them to exercise leadership skills.
6. What does success look like for you in 30 days?
Understanding what success looks like for your new employee can help you create a plan for the first month as they try to find their place in the company. Decide on 2 or 3 milestones your employee could realistically accomplish in their first 30 days. These milestones could be a first project or simply setting up meetings with people on other teams (especially in larger organizations).
This is also a great time to learn more about where their anxieties lie and how you can mitigate them so they’re set up for success from the very start. Meg Murphy, Manager of Product Marketing at Visual Lease, explains:
7. When and how frequently would you like to have one-on-ones?
The only thing worse than a poorly planned one-on-one is skipping them altogether. If you or your new team member start canceling at the last minute, it could be a sign to the other person that the meetings aren’t valuable. Plan out a schedule that works for both of you and stick with it.
Seven questions cover the ground that matters most: what they enjoy outside work, how they prefer to communicate, when they do their best work, what projects excite them, their 1-, 3-, and 5-year career goals, what success looks like in their first 30 days, and how frequently they want one-on-ones. Starting with personal questions before moving to professional ones signals that you see them as a person, not just a new hire.
Send a shared agenda with your questions in advance so your new hire has time to think rather than being put on the spot. Frame the meeting around them — their goals, their working style, their anxieties — and set expectations for what the conversation is for before it starts. That preparation shifts the dynamic from manager-questioning-employee to two people figuring out how to work well together.
Yes, but tell your direct report you’re doing it so they know your attention is on the conversation, not somewhere else. The bigger risk in a first one-on-one is that note-taking pulls your focus away from actually listening — so if capturing everything manually feels like a distraction, an AI meeting assistant like Spinach can handle the notes and surface key decisions and action items automatically, leaving you free to be present.
Two or three realistic milestones work better than a long list — a first project completed, key cross-team introductions made, or a specific process learned. Agreeing on those milestones in your first one-on-one gives your new hire a clear target and a way to measure their own progress, which directly reduces the first-week anxiety that shows up in almost every new hire.
There’s no single right answer, which is exactly why you should decide together in the first one-on-one rather than defaulting to a cadence the new hire had no say in. The more important rule is consistency — a one-on-one that gets canceled repeatedly signals the meetings aren’t valued, which erodes trust faster than the wrong frequency ever would.
What to do next
You made it to the end of this article! Here are some things you can do now:
- We have a massive (& free) collection of meeting agenda templates all designed to help you run more effective meetings.
- Check out Spinach to see how it can help you run a high performing org.
- If you found this article helpful, please share it with others on Linkedin or X (Twitter)
