How To Make The Most Of One-On-One Meetings

By Amanda Covaleski - Jan. 20, 2021

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We know, one-on-one meetings with your boss can be nerve-wracking. Maybe you were called in unexpectedly, and you think you’re about to get bad news. Or perhaps you need to report on your latest project to your manager.

No matter what kind of individual meeting you’re having, you can prepare ahead of time to get the most out of it.

Whether you love your boss or you’re a little less enthusiastic about them, meetings can be an excellent opportunity for growth and learning. Knowing how to navigate these one-on-one meetings can be a great skill and asset to your career.

We’re going to give you some tips on making the most out of an individual meeting and wowing your boss. Leaving a meeting feeling productive, positive, and inspired is always a good thing, so let’s look at how to make every meeting feel like that.

Employee’s Guide to Better One-on-One Meetings

Mastering meetings is a key skill for anyone in the workforce. Meetings can take many forms and offer opportunities for individual feedback, sharing your work, or even just acclimating to a work environment.

Being able to attend and participate in meetings effectively will show off your skills to your coworkers and help you be a great employee as you build upon constructive feedback and share your ideas.

This is especially true for one-on-one meetings. Whether you’re meeting with your supervisor, a colleague, or an executive at the company, there are a few things you can do to prepare and stay on track during your meeting.

While the bulk of the responsibility falls on your manager to make one-on-one meetings successful, you can always contribute to the effort. Our guide will prepare you for any meeting scenario and help you make the most of your conversations:

  1. Lock down a meeting time. If you’re having a one-off meeting, make sure you block that time off and have your supervisor block it off too. Respecting each other’s time is an essential part of holding a successful meeting, and that starts with honoring the time you set aside to meet.

    It’s not unusual for bosses to want to cancel meetings if they think there’s nothing to go over, but you should always try to reschedule instead of cancel.

    That will still allow you to talk to your boss and find a touchpoint for discussing any projects, assignments, or worries that you have.

  2. Make it weekly. If possible, try to create an opportunity for a weekly one-on-one meeting with your supervisor.

    While you might need extra one-off meetings to cover things you don’t get to in your weekly meeting, having that time to connect once a week will improve your workflow, rapport with your boss, and create opportunities to act on your feedback.

    Creating a time to check in with your manager, even if it’s for 15 minutes a week, will pay off in the end as you get to know them better and get more guidance from them.

  3. Create an agenda. After you settle a time for your meeting, you should draft an agenda. It doesn’t have to be super thorough with detailed points you want to raise; even just a rough outline of what you want to discuss will be helpful.

    A plan can keep you on track, so you don’t lose time or get distracted. It can also help you remember all of the things you want to talk about with your boss. They can be extra helpful for long meetings where you’ll cover lots of topics.

    Feel free to send the agenda to your boss ahead of time to show them you prepared and give them some idea of what you’ll be bringing to the table. You should also expect your boss to have their own agenda, so leave some room for the things they want to bring up.

  4. Discuss relevant topics. While drafting your agenda, make sure you’re keeping everything pertinent to the meeting. It’s tempting to use sessions as a time to catch up and debrief, but that can actually lead to meetings getting canceled.

    Of course, you should use meetings to give status updates when relevant, but don’t make the whole meeting one big debrief. You can always send an email to your boss to provide a status update or check in, but meetings should be used to dive into any questions you have about your performance or get guidance from your boss.

  5. Create timelines together. When you have your boss’s undivided attention, you can use the time to create timelines and verbally commit to getting things done.

    It might be difficult to get your boss to do whatever you need them to do in order to progress in your work, but one-on-one meetings are a great place to remind your boss of their to-do list and have them commit to getting something done by a specific time. The same goes for you, too.

    You can commit to timelines with your boss and give them an idea of when you’ll be able to turn in a project or a task on your to-do list. Working together on a timeline helps your boss understand your workload and adjust as necessary, so you’re not overloaded.

    It’s a great way to prioritize your work and figure out what needs to get done and when.

  6. Take notes. Taking notes is a great way to make sure you remember everything you discussed and what you committed to doing. It can also show that you’re engaged in the meeting and participating, even if your boss is doing most of the talking.

    You should encourage your boss to take notes, too, so neither of you loses track of what’s being discussed after the meeting ends.

  7. Discuss challenges. Did you have any sticking points during your week? What’s going to prevent you from getting things done this week? Thinking of questions like this can help you bring up any challenges you’re facing in your projects.

    Maybe your boss won’t be able to help you troubleshoot, but letting them know where you’re stuck can help them create a new deadline for you, tap a colleague who might be able to help you, or provide feedback on your problem-solving process.

  8. Bring questions. When you’re planning your agenda, and actually in the meeting, you should be thinking of questions to ask your boss. They can be small clarification questions about your work, or you can guide the conversation to a bigger topic, like your career opportunities or personal growth.

    This is also a good way to bring up any concerns you might have, like your workload, anything in your personal life that might be bleeding into your work life, any issues with coworkers, or asking for advice from your manager.

    Just like an interview, you want to make sure you have questions to contribute to the meeting.

  9. Get into your goals. The most successful meetings cover a wide range of topics, but flow well between everything you discuss. You should make sure to cover your career goals, organizational goals, or anything long term headed your way.

    It doesn’t have to be years out; you can even talk about something you want to do next month.

    Letting your boss know your goals is one of the best things you can do for growth. If they know your goals, like you want to manage a team and lead a project, they can help put you in positions where reaching your goals is possible and encourage employee performance.

    Your boss can put you in charge of a project if they know that it’s something you want to achieve, so make sure they have some idea of your long term goals.

  10. Consider your boss. It’s a good idea to always keep your manager’s point of view in the back of your mind. Try to see things from their perspective when you’re preparing and participating in the meeting.

    Just like you’d like their compassion and empathy while working together, putting yourself in their shoes is a great way to build that relationship. You might need something from them to get your project done, but what else do they have on their plate?

    Thinking like this will also help your boss think in this way to create a working relationship founded on trust and respect.

  11. Build rapport. When you’re ready to wrap up your meeting, don’t be afraid to turn the meeting a little more personal.

    Having a good professional and personal relationship with your boss can help you feel more comfortable at work and create a great workplace environment. Don’t pry too much, but ask them how their week has been or what their weekend plans are.

    Volunteer some of your personal life to share, but always keep it appropriate. Getting to know your boss and making a strong personal connection is always good for your professional work.

  12. Follow up. Sometimes you forget to mention something or realize you have a question after your meeting is finished. Don’t hesitate to reach out to your boss with a clarification question or quick text so you can feel good about whatever you’re doing next.

    This is a good way to keep an open and clear line of communication between you and your manager. You’ll feel more comfortable and supported if you know you can follow up with your boss and check in, even outside of meetings.

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Amanda Covaleski

Amanda is a writer with experience in various industries, including travel, real estate, and career advice. After taking on internships and entry-level jobs, she is familiar with the job search process and landing that crucial first job. Included in her experience is work at an employer/intern matching startup where she marketed an intern database to employers and supported college interns looking for work experience.

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