Running Your First One-On-One with a New Direct Report

Learn how to run your first one-on-one with a new direct report, what to ask, and some free templates to get the agenda right.

As a manager, it’s always so exciting when a new employee joins your team.  

Your new direct report likely has a busy first week ahead of them, including their very first one-on-one meeting with you. You want to make sure you and your new report start on the right foot, and to do so, it’s up to you to run an effective one-on-one.

Why one-on-ones are important

If you’re managing many employees, it’s easy to forget just how important one-on-ones are. Whether this is the first one-on-one you’re having with an employee or you’re nearing 50, it’s always a good reminder to consider the many benefits they bring.

Some benefits of one-on-ones are that they:

  • Provide a boost in employee productivity and quality of work. As a manager, this allows you to better coach team members on their priorities and develop a common base of information so everyone is on the same page regarding expectations.
  • Foster positive work relationships. You simply can’t expect to develop a good relationship with your team if you only sit down with them for yearly or quarterly performance reviews.
  • Help better solve problems or challenges as they arise before they get out of control and completely bottleneck a team member.
  • Are a great place to exchange feedback on performance, management style, team morale, attitude, and more.

One-on-one meetings worth showing up to

A well-run meeting can foster communication and collaboration by including an agenda everyone can contribute to. Try using a tool like Fellow!

How to run your first one-on-one with a new direct report

As you run your first one-on-one with a new direct report, follow these steps to ensure the conversation is successful, productive, and stays on topic.

1Create a collaborative meeting agenda

First, take the time to create a meeting agenda that is collaborative. While you likely have questions and action items you want to discuss, your direct report probably does too! Making the agenda a place to collaborate allows your direct report to be a part of the conversation while also making it known that you’d like their input and want them to feel included.

Additionally, this type of agenda, which is easy to create in Fellow, gives you both a heads up on discussion topics before you join the meaning.

2Send the meeting agenda in advance

Be sure to send the meeting agenda out in advance. This ensures your direct report gets the much-appreciated heads up to know what you added to the agenda, but also gives them time to add items to the agenda, too. It doesn’t do either of you much good to send the agenda out less than an hour before the meeting, as doing so would make it difficult to feel prepared and ready to participate in the conversation. 

3Explain the purpose and your expectations

Since it’s your first one-on-one, it’s best to explain the purpose of these meetings and establish expectations. Let your direct report know that these meetings will be where they can come to you with questions, concerns, or general feedback on what they’re working on. It’s also a time when they can ask for help and you can problem solve challenges they’re running into together.

Additionally, make sure to note that not every one-on-one meeting with them will generate action items or tasks to add to their to-do list or be used to set goals. Some meetings will simply be a check-in with one another to build rapport and foster a professional working relationship.

4Start with an icebreaker 

Starting with personal icebreakers before a meeting gets underway is always a fun idea, especially during the first one-on-one you have with a direct report.

There are an endless amount of icebreaker questions you can choose from, but some great options are:

  • What’s the most recent movie you watched and did you enjoy it?
  • Do you have any pets? If so, do you talk to them like they’re a person?
  • If you could have dinner with any real person, dead or alive, who would you choose and why?
  • If you could get up and travel to any country in the world, where would you choose?
  • Would you rather give up sweet or salty junk food?
  • What toppings do you put on your pizza?

5Choose a recurring day and time

It’s a good idea for one-on-ones with direct reports to be on the same day and at the same time every time you meet. Since this is the first one being held, double-check with your new report if the day of the week and time of day is best for them.

Remember that it’s common for people’s productivity to ebb and flow during the day. Some people are most productive in the morning, while others get a burst of productivity in the afternoon. If your direct report feels most productive during the morning, they may prefer to schedule their regular one-on-ones for the afternoon.

6Ask questions to get to know them

A successful and productive working relationship between you and your direct report won’t happen overnight, but your first one-on-one during their onboarding is a great place to start! Be sure to ask questions to get to know them further, personally and professionally.

Find out more about their hobbies outside of work, and ask about their weekend plans. Additionally, find out more about their professional goals, how they like to work, how they stay organized, and how they set their deadlines.

When you have these answers, you can do your part to make sure your new team member can thrive and is set up for success.

7Create alignment on roles

Since this is the first one-on-one you and your new team member have, consider it part of the onboarding process and take the time to create alignment on roles. Let them know you’re there to help them in any way you can, tell them which tasks are typically on your plate, and let them know how you envision their role moving forward. 

If there’s any misalignment or confusion, it’s best to address it as soon as possible.

8Provide and ask for feedback

The best chance to get open and honest feedback on how your team works and operates is by asking a new employee during their first week or two in their role. Ask for their feedback, consider follow-up questions, and learn from what they have to say. This is also a good chance for you to provide feedback, too.

9Ask for meeting feedback afterwards

Once the meeting has come to a close, ask for meeting feedback! 

You can ask questions like:

  • Did the weekday and time of day work for them? 
  • How about the length of the meeting? 
  • Is there anything your new team member felt like they didn’t have time to say?
  • Is there a different cadence they would prefer until they feel more confident in their new role?

If there’s anything you need to change to support your new direct report, consider taking action!

10Be an active listener 

Finally, in every one-on-one, but especially the first one, be an active listener. This means providing your undivided attention to your new team member while they communicate information, feelings, or beliefs.

Active listening communicates empathy and builds trust while demonstrating that the employee has your unconditional and undivided attention. Plus, this ensures that as a manager, you’re making the best first impression possible.

Questions to ask during your first one-on-one with a new direct report 

Not sure what types of questions you should be asking in your one-on-one? Here’s some to put on the agenda!

  1. How has your first week been?
  2. Is there anything surprising or unclear about your role?
  3. Can I provide you with more information or more resources?
  4. Do you have all of the information, and all of the necessary software, to do your tasks?
  5. How can I ensure you’re set up for success in this new role?
  6. Do you feel connected with the team?
  7. Tell me something about yourself! What do you enjoy doing outside of work?
  8. How do you prefer to receive feedback?
  9. What typically frustrates you at work? What are the warning signs that you’ve become frustrated?
  10. What’s your preferred form of communication–email, face-to-face, or instant messaging?
  11. How can I ensure you’re getting the most out of these one-on-ones?
  12. How can our team make sure you’re successful at work?
  13. Do you have any questions regarding our team’s structure?
  14. What are some details of your working style?
  15. Is there anything unclear about your upcoming goals?
  16. Do you have any questions about what’s left to complete during your onboarding?
  17. What types of people have you found easiest to work with?
  18. What kinds of experiences give you the most stress?
  19. Have you ever been burnt out in a past role?
  20. What have you liked or disliked about past managers?

Free first one-on-ones with direct reports agenda templates

When having your first one-on-one with a new hire, take advantage of our free agenda templates to ensure every important detail is part of the conversation:

The art of the perfect one-on-one!

The first one-on-one you have with a direct report will hopefully set the stage for a productive and successful working relationship. Remember that as a manager, this may be the first meaningful conversation you have with this new employee, and you want to make a good impression! Never rush the agenda, be prepared, and don’t be late!

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About the author

Mara Calvello

Mara Calvello, with a Bachelor of Arts in English Language and Literature/Letters from Elmhurst University, is a seasoned Content Marketing Manager. Working at G2, Mara is an expert in software reviews and the tech space. Her expertise in content creation is complemented by her passion for literature.

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