First One-on-One Meeting With a New Employee: Questions to Ask and How to Prepare

Optimize team management in minutes with ManageBetter. Start your free trial now and join Uber and Microsoft in boosting performance, gathering insights, and generating reviews—all AI-powered, no writing required.

One-on-One Basics

The purpose of a one-on-one meeting is to check in with employees individually, getting a better sense of their activities and feelings. Most importantly, these meetings are an official yet relaxed way to build and reinforce the vital working relationship between you and your direct reports.

The first one-on-one with a new employee is a great opportunity to set the tone and establish a good rapport. Here are some things to keep in mind:

  • Keep it simple and friendly

  • Watch for anxiety and ease any new-job jitters your employee may have

  • Encourage your employee to share their feelings and experiences so far

  • Reassure them that they are an important part of the team and can come to you with any concerns

One-on-one meetings may be held weekly, as a beneficial tool for managers and employees to keep each other updated. Depending on company size and the number of direct reports, it may make more sense to schedule one-on-ones every other week or monthly. A typical one-on-one should be about 30 minutes long; maybe 45 minutes, if meetings occur less regularly or both parties have a lot to discuss.

Preparing for the One-on-One Meeting

One-on-ones are meant to be more informal get-togethers for you and your direct reports to catch up, but that doesn't mean that they don't require any preparation. Neither you nor the employee will gain much value from a disorganized meeting where you struggle to think of questions or ramble unnecessarily. The day before the one-on-one, take some time to:

  • Think about your new employee’s role, responsibilities and job duties

  • Recall observations you have made about their performance and work style up to this point

  • Keep this background information in mind as you think of questions and topics to discuss during the meeting

You should also expect your new employee to come prepared for their first one-on-one. Remind them a day or two beforehand to think about anything they would like to share or ask questions about. Make sure they understand that this is not a status update or performance review, but rather a chance for the two of you to communicate openly. On your end, be prepared to share the floor and listen attentively.

The One-on-One Meeting Agenda

Not sure what kind of agenda to set for an initial one-on-one? See our template for first-time one-on-one meetings.

Some important areas to cover are:

  • Personal Connection

  • General Overview

  • Issues & Feedback

  • Looking Forward

Be sure to welcome the new employee once again and inquire about how they are adjusting to their role and the company. Connect on a personal level by asking what their interests are or how their family is doing. Once you have broken the ice a bit, you can move into an overview of the agenda and what the format of these one-on-one meetings will be like. Then, the bulk of the meeting can be used to talk about any issues, goals, action items or steps moving forward.

There are many questions that you may want to ask an employee in their first one-on-one. Below, find a list of sample questions to inspire and guide you:

Questions for Your First One-on-One Meeting

How are you doing?

Have you seen any good movies lately?

What activities have you done outside of work this week?

How do you feel about the company so far?

What do you think of the team/company culture?

Do you have any interesting observations you would like to share?

Tell me about something new you have learned.

What has been pleasantly surprising to you about the workplace?

What tasks do you most and least enjoy?

Tell me what you’ve been working on.

What are your major priorities right now?

Where are you on the project right now?

What would you like further training or clarification on?

When do you feel more vs. less productive?

Have you had any concerns or challenges recently?

Do you think there is anything we should consider changing?

What are your long-term career goals?

What are some of the goals you would like to accomplish this month?

What can we do to achieve your goals?

How can I provide support?

What can I help you with before our next meeting?

Is there any feedback you would like to receive?

Do you have any suggestions for me?

Is there anything we missed that you’d like to talk about next time?

Meeting Takeaways

The ideal outcome of a first-time one-on-one meeting is for both manager and employee to establish a feeling of trust and goodwill. Your direct report should walk away feeling reassured and confident about their place in the organization. As a manager, you should gain a few valuable insights into their progress adapting to the workplace and any issues they may be facing. The first one-on-one meeting may not yield any dramatically enlightening information, but at the very least you will successfully set a level of comfort and trust with your new employee, as well as expectations for next time.

Sharpen Your Leadership Edge: Join 3,000+ executives receiving weekly, actionable insights from industry experts. Subscribe free to The Thoughtful Leader and elevate your team's performance.

Previous
Previous

Free Agenda Template for a First Time One-on-One Meeting

Next
Next

Introducing ReviewBuilder’s Phrase Packs