Mastering One-on-One Meetings: Questions and Strategies for Managers & Employees

Many managers and employees look at one-on-one meetings with a little (or a lot) of anxiety—and so too often they avoid them altogether. 

But that means they’re missing the opportunity to give and receive regular feedback, which hurts employee engagement. Research from Gallup shows that when employees strongly agree they received "meaningful feedback" in the past week, they are almost four times more likely than other employees to be engaged.

During these sit-downs between management and employees, you’ll have an opportunity to gather feedback, discuss topics like career goals, and share insights about performance. Plus, setting aside time to connect every week is good for your relationship as two people with goals, lives, stresses, and joys outside of the office as well. Having open discussions about what’s going on in your work and in your life deepens your engagement as people and colleagues too. 

In this guide for managers and employees, we’ll explore important talking points for one-on-one meetings and provide tips for setting actionable goals for these gatherings. By integrating these talking points and concepts into your organization, you can identify productivity challenges, improve performance, and engage with staff.

Introduction to one-on-one meetings

Before shifting your attention to specific communication strategies and questions, it’s important to familiarize yourself with the basics of one-on-one meetings, including what benefits they provide and the types of things you should be discussing. 

What is a one-on-one meeting?

A one-on-one meeting is a direct discussion between two professionals, usually an employee and their immediate supervisor. During this direct sit down, you and your team members will cover topics like current roadblocks, professional wins, and their long-term goals. 

Let’s look at some basic components of one-on-one meetings that you need to incorporate into your own process. These sit-downs should be:

• Pre-planned
• Scheduled with the employee
• Organized
• Limited to a reasonable time (i.e., 30 minutes)
• Private

Don’t just pull someone into your office, virtual or otherwise, and tell them that you are going to have a meeting. This approach can amplify stress levels and make the entire interaction unnecessarily tense. Instead, give them some notice and be transparent about what you are going to discuss. We recommend setting up a recurring one-on-one on the calendar.

Benefits of regular one-on-one meetings

Integrating one-on-one meetings into your management strategy can provide a wide range of benefits. For starters, giving employees a chance to sit down with their direct supervisor can boost morale. During these conversations, staff members can voice their concerns, gather feedback, and provide honest opinions about the direction of the organization. Making employees feel heard goes a long way in improving satisfaction.

Preparing for one-on-one meetings

If you want to make the most of your time, make sure you adequately prepare for every sit-down. This means reviewing the agenda and adding any relevant notes. While you don’t want the meeting to feel rigid, it needs to be structured to maximize productivity. 

Setting objectives for effective one-on-ones

Before you host your first meeting, set some clear objectives. For instance, you may want to learn more about the person’s career goals, long-term plans, and what new skills they’d like to acquire. 

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The best one-on-one meetings aren’t born out of a rigid checklist of the same questions to ask each time. But having a few go-to questions in your back pocket can ease some of the anticipations and make getting into a great discussion easier. Not to mention being intentional by planning your agenda ahead of time is also a great way for managers to improve company culture overall! Here are a few questions we love for both managers and employees to ask in your next one-on-one meeting and why they work so well. 

Download our free One-on-One Meeting Agenda Template to start improving your meetings today!

One-on-one meeting questions for managers to ask employees 

1. How are you feeling?

Knowing what’s going on in an employee’s life, whether it’s at work, at home, or in any other sphere of their world, helps managers gauge what support they need at this moment. It sets an open tone for the meeting ahead as well, which is great because you both might be feeling a little nervous as the meeting kicks off (that’s normal!). Instead of saying the usual "fine" or "good, thanks," encourage your employees to use a few descriptive words from this chart.

2. What are your priorities and plans for this week?

Checking in on your employee’s plans for the coming week helps you see what they’re focused on. It might surface some tasks you didn’t know they were taking on, an opportunity for new projects, or a chance to redirect their focus to a priority you want to make sure is high on their list. 

3. What support do you need from me this week?

As a manager, you’re an enabler of the work your employees do—so what do they need from you right now? It might be removing roadblocks, prioritizing a heavy workload, or doing some exciting career development, but you won’t know until you ask. 

4. What aspects of your job have energized you recently?

Finding what makes your people feel energized, happy, and recharged is one of the best parts of your role as a manager. And it can play a crucial part if you're wondering how to motivate employees. Asking employees this question can help you determine what kind of work makes them feel most empowered and engaged with their work and the organization so you can prioritize it where possible. Plus, the answer may surprise you!

5. What has challenged you in your role or working with others on the team recently?

Uncovering unexpected challenges is just as important as unexpected joys. This question can help you realize issues you might have been unaware of so you can remove roadblocks in an employee’s way, and help them feel supported and seen as well. 

6. How are you progressing toward your long-term career and life goals?

One-on-ones should definitely focus on an employee’s career goals, but it’s also a good idea to check in on life goals too. After all, work is a critical part of a well-rounded life. Asking employees about both kinds of goals, and their current progress gives you a better understanding of how their work fits into that bigger picture. If you really want to be a good manager, you can help them achieve both!

7. How is everything going with the people you work with, or on the team?

Peer relationships are a vital part of workplace culture, so don’t forget to check in on them from time to time. This question can uncover positive collaboration opportunities, colleague conflicts, and also simply how connected your employee feels to the rest of the team, which is key to their happiness and engagement. 

8. Do you have any questions about the recent organizational changes?  

If your company has recently made any major announcements, organizational changes, or shifted processes or policies that might affect your employees, check in with them to see how they’re feeling and if they have questions. While changes may seem straightforward or clear to you, ensuring your reports feel informed and alleviating any anxiety they have is a good leadership practice. 

9. Do you have any feedback for me?

Feedback is a two-way street! Ask your employees if they want to share any constructive, upward feedback to help you become a better manager—even if there’s nothing at the moment to say, the act of asking for their feedback regularly builds openness and trust. 

10. Is there anything we didn’t cover that you’d like to discuss?

If your employee is on the quieter or more introverted side, or simply doesn’t know how to approach a tricky topic, this open-ended question can get them to open up. This is a good question for the end of the meeting to close out the chat.  

Get our free, customizable one-on-one meeting agenda template that includes a proven structure for effective and productive one-on-ones.

One-on-one meeting questions for employees to ask managers

1. How are you feeling?

Emotional check-ins go both ways—don’t be afraid to ask your manager how they’re feeling too! If you sense your manager is feeling tense or stressed, this question can be a great way to let them know you’re open to appropriate sharing and can be supportive with anything work-related. 

2. What’s your highest priority right now? How can I help?

Knowing what your manager considers a high priority can help you organize your workload at busy times to focus on what truly matters to reach team goals. Asking this question will also show your manager that you’re willing to proactively help the team to succeed and help you manage up. 

3. Is there anything I should be doing differently? 

Even great managers can fail to give feedback regularly if there’s a lot on their plate. Asking for constructive criticism or advice can open up that discussion so you know where you're meeting expectations and where you might have some room for growth. If you’re struggling to understand the answers, asking a follow-up question like “Do you have examples?” can clarify the feedback. 

4. What should I consider adding to my growth plan?

Your career development plan is a constant work in progress, and your manager is your partner and ally in your growth strategy. So don’t be afraid to ask if there’s anything missing from your current plan! 

5. What are your long-term goals for the team?

Knowing how your manager envisions the team’s future can help you create a plan for your own future as well. It gives you the chance to explore new skills and opportunities and consider your career direction, whether it continues with your current team or somewhere else. 

6. What are you most hopeful for and worried about in the team or organization’s future?

The answer to this question can offer insight into your manager’s thinking about what lies ahead for your team or company. It may alert you to organizational challenges or opportunities you weren’t aware of, industry trends, or simply some team dynamics you should know about. 

7. What part of my job would you like more visibility into?

Your manager might not have as much visibility into your role or day-to-day tasks as you imagine, so asking them this question can allow you to shine a light on any gaps and keep them up to date on your hard work and accomplishments. 

8. Is there anything I should prepare for our next one-on-one?

Proactively asking your manager about your next one-on-one does a few great things: it ensures the meeting cadence stays on track, lets you prepare ahead of time for any larger conversations like upcoming opportunities, and ensures you have a productive meeting. 

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During the one-on-one meeting: tips

One-on-one meetings are meant to be unmissable. You should set a time for this discussion, read up on each team member beforehand, and review any information that is pertinent to your conversation. Remember: you should focus on connecting with your team and their professional journey. 

These meetings represent a great opportunity to build rapport, strengthen team chemistry, and let your employees know that you are in their corner. 

Conducting the meeting: A guide for both parties

If you are conducting the meeting, listen as much as, if not more than you speak. Give your team members a chance to be open and honest. Also, balance constructive feedback with positive feedback. 

As the employee, it’s important to answer questions thoroughly and take advantage of this opportunity to elaborate on any concerns or frustrations you’ve experienced. Be respectful but transparent. Remember, this meeting is a great opportunity to get to know your boss and align their management strategy with your personal goals. 

Enhancing one-on-one meetings

With the right approach, you can use meetings to enhance staff and team productivity. You’ll have an opportunity to share insights into the big picture and explain how each person’s efforts contribute to overall organizational success. You can also address any concerns that staff members have before those worries fester into bigger problems.

Tips to improve the quality of discussions 

After you’ve mastered the basics, tailor your objective and talking points based on who you are meeting with. If you are meeting with the current sales leader, commend them on a job well done and find out what steps they are taking to be so productive. 

Conversely, if you are speaking with a newer employee, it might be a good idea to ask about their initial impressions of the company. If they’ve worked at a similar organization before, find out how your business stacks up. Ask pointed questions about what you can do better and what’s going well.

By approaching each meeting as a strategic opportunity for growth and improvement, you can maximize the value of this important management tool.

Advanced strategies for one-on-one meetings

One-on-one meetings are a great way to build stronger connections with your staff. It’s important that they understand who you are and your communication style. Likewise, you need to know how each person works, how they find motivation, and what will bring out their full potential. 

Beyond the basics: deepening engagement 

During a sit down with individual employees, you can clear the air and address any underlying issues that may be causing tension in the workplace. For example, if someone has been struggling with performance, talk to them about what’s contributing to their issues and offer suggestions and actions for remedying the problem. 

The key here is to customize each meeting to align with the unique needs and goals of your staff members. Personalized one-on-one discussion is the pinnacle of relationship building. 

Creating better one-on-one conversations: template

One-on-ones aren’t just another item on your weekly to-do list: they’re a very valuable way for employees and managers to communicate and connect. These questions are a way to start initiating more productive and helpful conversations on both sides, but don’t be afraid to get creative with them!  

Looking for more ways to make your next check-in even better? See our guide to improving one-on-one meetings for managers!

Download our free PDF, Google, or Word Doc one-on-one meeting agenda template to take these meetings to the next level.

The template includes:

🗒️  A proven structure for effective and productive one-on-ones.
✅  Fillable form fields to record agenda and action items.

📄  Customizable Word and Google doc templates to fit your needs.
💡  One-on-one meeting best practices.
📘  Additional resources to help you improve your one-on-ones. 

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Watch: How managers drive performance

In this on-demand webinar, we explore the vital role managers play in crafting and sustaining high-performance cultures while addressing burnout prevention strategies. We aim to equip managers with practical insights for optimizing team performance, nurturing employee well-being, and creating a thriving work environment. We also dive into the specific challenges managers face in maintaining high-performance cultures, emphasizing the importance of addressing toxic behaviors and their impact on employee engagement.

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Frequently asked questions

What is a one-on-one meeting for?

A one-on-one meeting is a dedicated time for two individuals to connect and discuss topics relevant to their relationship, work, or collaboration. These meetings serve various purposes depending on the context:

1. Relationship Building: One-on-one meetings provide an opportunity for colleagues or team members to build rapport and strengthen their relationship. They can help foster trust, understanding, and empathy.
2. Feedback and Coaching: Managers often use one-on-one meetings to provide effective feedback. This could involve discussing performance, addressing challenges, offering guidance, and setting goals for professional development.
3. Problem Solving: Individuals may use one-on-one meetings to brainstorm solutions to specific challenges or problems they are facing. This could involve seeking advice, sharing ideas, or collaborating on strategies to overcome obstacles.
4. Alignment and Communication: One-on-one meetings are also valuable for ensuring alignment and clarity on goals, priorities, and expectations. They provide an opportunity for individuals to discuss projects, deadlines, and any updates or changes that may impact their work.
5. Career Development: Employees can use one-on-one meetings with their managers to discuss their career aspirations, growth opportunities, and development needs. This could involve exploring potential career paths, seeking guidance on skill development, or discussing future opportunities within the organization.

Overall, one-on-one meetings are a versatile tool for fostering communication, collaboration, and professional growth within teams and organizations. They provide a dedicated space for individuals to connect, communicate openly, and work towards common goals.

What do you talk about in a 1 on 1?

In a one-on-one meeting, the topics of discussion can vary depending on the relationship between the participants and the purpose of the meeting. Here are some common topics that are often discussed in one-on-one meetings:

1. Current Projects and Work Updates: Participants may discuss the progress of ongoing projects, share updates on tasks, and provide status reports on their work.
2. Challenges and Obstacles: Individuals might talk about any challenges or obstacles they are facing in their work and brainstorm potential solutions or strategies to overcome them.
3. Feedback and Performance: Managers may provide feedback on the individual's performance, offer praise for achievements, and address any areas for improvement. Likewise, employees may provide feedback to their managers or peers on their performance or on specific projects.
4. Career Development and Goals: Participants may discuss their career aspirations, goals for professional development, and any opportunities for advancement within the organization.
5. Personal Development: Individuals may talk about areas where they want to grow personally or professionally, such as acquiring new skills, improving time management, or enhancing communication abilities.

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