Mastering One-to-One Meetings with Direct Reports: A Practical Guide for Managers

If you're managing direct reports, this guide is made for you!

One-to-one meetings are a crucial tool for encourage open communication, building trust, and ensuring alignment. They create a dedicated space for open communication, building trust and alignment between managers and their team members.

These meetings allow managers to provide personalized feedback, understand challenges, and support their team's growth.

According to Gallup research, employees who have regular meetings with their managers are almost three times more likely to be engaged at work compared to those who don’t.

The research emphasizes that the frequency and quality of these one-to-one interactions can make a major difference in how supported employees feel, impacting productivity and retention. Frequent, high-quality manager-employee communication is a key driver of engagement and performance.

These sessions help address potential issues early, ensure clarity on goals, and build a stronger working relationship. When you as a manager communicate openly, and provide regular feedback, well-structured one-to-one meetings lead to higher engagement, productivity, and job satisfaction. Employees feel heard and supported, which enhances their commitment and performance, driving success both individually and as a team.

1. Establish the Purpose of the One-to-One

In the first on these meeting series, you need to make sure you are clear about the purpose of these one-to-one meetings. What are these meetings about (or even what is not about)

i.e. you might want to make sure you clarify that “those meetings are not happening to control you in any way” or “the purpose of these meetings is to support you on your growth and performance and make sure we both have the space to share ideas and progress on our projects” etc..

But before you share with your direct report the purpose of those meetings take a moment to reflect your self and make sure YOU (as a manager) are clear on what you want from these meetings.

• What are your key goals for these meetings?
• How will you ensure the conversation is focused on support and development, rather than control?
• How can you keep your direct report accountable for their progress?

One-to-one meetings are usually designed for a few key purposes:

• Building the relationship: Understanding your direct report’s motivations, concerns, and goals. This doesn’t mean you need to go personal or ask personal questions. Building the relationship requires you as a manage to listen and coach your direct reports on the job concerns, goals and motivations. Sometimes personal discussions are unavoidable but have in mind that not all people want to go personal on their professional relationships.
• Supporting development: Helping them grow in the role by offering specific regular feedback (positive & constructive) and guidance. Remember “good job” is not feedback, is just a pat on the shoulder. (If you need more feedback tools and info, let’s talk about that)
• Alignment and expectations: Ensuring clarity around tasks, priorities, and team/company objectives. Don’t leave assumptions running the game. Make sure you align on those expectations (from both sides) and you create clarity. Just because you say something, doesn’t mean the other person understand the same.
• Problem-solving: This is a space for them to raise challenges or seek input. Remember not to give all the answers (even if you have them) coach your people by asking them questions to unlock the possible solutions and answers to problems. If you give all the answers you create dependency and you block initiatives.

2. Structure of the Agenda

Below you will find a a suggested structure that balances both short-term and long-term needs, while also focusing on the person, not just the work.

However, feel free to adjust that on your needs and requirements as well.

A. Check-In (5 minutes)

Build rapport: This helps you understand their general state of wellbeing and mindset.

Start each meeting with a personal check-in to help set a relaxed tone. ?Ask how they are doing, both personally and professionally. Ask about their adjustment to the new role. Any challenges so far?

TIP - If you ask a personal question, make sure you keep it short (up to 5 minutes) and you don’t spend half of your one-to-one talking about the kids, the holidays or any other personal topics unrelated to the scope of the agenda. Also make sure this is something the other people want to talk about. Some people they don’t like small-talk while others they find it necessary to begin a good conversation.

Examples:

?"How are things going so far in the role?"

?"Anything outside of work you'd like to share?"

I like to start all my coaching conversations with the question “can you name 1 thing that you are proud of yourself since our last meeting?” That creates a positive tone, relaxes the person and gives us the opportunity to celebrate wins.

B. Role-Specific Discussions / Progress & Updates (10-15 minutes)

This section should cover the core responsibilities, tasks, and role expectations.

Progress Updates: Ask about current projects or tasks.

• "What progress have you made since our last meeting?"
• “What are your top priorities for this week”
• "Are there any blockers or challenges you're facing?"

Clarifying Priorities: Ensure they understand their top priorities.

• "Are you clear on what your priorities are this week/quarter?"

Feedback: Provide feedback on their recent work, be specific and supportive. Make sure you are giving feedback for the tasks/behaviors and not for the person.

• "I noticed how you handled [specific task]—great job! Let's work on improving [ specific area]."

Skills and Learning: Ask if there are areas where they feel they need more training or resources.

• "Is there anything you’d like to learn more about or get help with?"
• "How can I support you more on [X] topic”

C. Open Floor (5-10 minutes)

Give them time to bring up any topics or concerns. This reinforces that the meeting is for them too.

?Challenges or Concerns: Ask open-ended questions.

• "Is there anything you'd like to discuss or clarify?"
• “How do you find those meetings in terms of support”?
• “How can we make those meetings more productive and supportive for you”
• "What’s been on your mind lately?"
• "Is there anything I could be doing differently to support you better?"

D. Action Items and Next Steps (5-10 minutes)

Do not skip this step! This is a very important part of your one to one. You need to make sure you are both on the same page before you dismiss the meeting.

Ensure both you and your direct report are clear on responsibilities for each action item, so there's no ambiguity on who owns what

Ask from your direct report to summarize the key takeaways, action items, and any commitments made on both sides.

• "Let’s make sure we are on the same page before we close this meeting. Would you like to make a recap?”

In this part, you want to make sure you direct report is clear on their next steps – What is the project/tasks they will work, when they have to follow up with you (or you follow up with them)

They need to be clear on WHAT, WHY, HOW, WHO, WHEN.

• Set the date for the next One-to-One and confirm any follow up topics to address.

?3. Key Tips for Success

Here are some tips to make your one-to-one meetings more effective:

Be consistent:

Schedule these regularly, whether weekly or bi-weekly. Regularity builds trust and ensures issues are addressed in a timely manner.

The ideal frequency for one-to-one meetings with direct reports depends on the context, such as the employee's experience level, the nature of their work, and the team's goals.

However, a common recommendation is weekly or bi-weekly meetings.

• Weekly: This is especially useful for new employees or those in dynamic roles where priorities shift quickly. Regular check-ins allow for ongoing support, faster feedback loops, and timely guidance.
• Bi-weekly: This can be a good balance for more experienced employees or teams with steady work. It offers enough regularity to address issues without becoming overwhelming.

For new team members, starting with weekly meetings can help build rapport, address early challenges, and offer more hands-on support. As they settle into their role and gain confidence, you might move to bi-weekly meetings.

Listen actively:

Use these sessions to truly listen to your direct report’s needs. Avoid dominating the conversation; let them share their experiences and concerns. Make sure you don’t speak more than 20% in total. This means you must ask a lot of open-ended questions and coach your direct report according to their needs. Be curious in those meetings and try not to make any assumptions. Judgment will not support your direct report from sharing all they have in their mind for their progress.

Accountability:

Keep your direct report accountable first by doing what you promised and them by asking for what was agreed. Reinforce the idea of holding both parties accountable to the notes and action items. Suggest reviewing the previous meeting's notes at the start of the next session to ensure progress is being tracked effectively. Make sure you double check the deadlines, and conflicting priorities. Sometimes people might become over-optimistic on their schedule leading them to make promises they cannot keep.

Offer support, not just oversight:

These meetings aren’t just about checking in on progress. They should feel like a space where they can ask for help, offer suggestions, or discuss development needs.

Stay flexible:

While it’s good to have an agenda, don’t be too rigid. Sometimes urgent topics or concerns may take over the meeting, and that’s okay. On the other hand make sure this does not turn into a bad habit that harms accountability. Having a shared agenda for these meetings is important.?

Keep it short and specific – (but not too short)

The best duration for a one-to-one meeting is typically around 30-60 minutes based on the context the relationship and the experience of the direct report.

• 30 minutes: This is usually enough time for a focused check-in, covering progress updates, challenges, and any immediate concerns. It works well for more experienced employees or when the agenda is straightforward.
• 45-60 minutes: A longer duration is helpful if there are complex issues to discuss, if the employee is new and needs more guidance, or if you're working on development goals. It gives more time for a deeper conversation without feeling rushed.

The key is to ensure the meeting is long enough for meaningful dialogue but not so long that it feels inefficient. Starting with 45 minutes is a good default, and you can adjust based on the needs of the discussion.

Take notes – Nobody can remember their commitment

If your direct report is not taking notes that means they will probably forget some of the topics you have discussed. Make sure your direct report and you keep notes in an easy way that you can go back to previous meetings and next meetings’ agenda.

Although some people prefer the traditional note taking pads you might also find useful to have a shared folder with your direct report to ensure transparency, alignment and accuracy in the note taking.?

Bellow i give you some suggestions but feel free to make your own research as well.

• For Microsoft: Microsoft OneNote - OneNote is integrated with the Microsoft ecosystem, making it ideal for users who rely on Outlook, Teams, and other Microsoft tools. You can create shared notebooks, collaborate in real-time, and link directly to meeting invites and tasks in Outlook.
• For Apple: Apple Notes - Apple Notes is built into macOS and iOS, making it a natural choice for Apple users. It’s easy to create shared notes, collaborate in real-time, and organize meeting agendas. Integration with Apple’s Reminders and Calendar apps makes it easy to set follow-ups and tasks.
• For Cross-Platform: Google Docs - Google Docs works seamlessly across both Apple and Microsoft platforms. It allows real-time collaboration and can be accessed from any device with a web browser, making it perfect for teams using a mix of devices. Plus, it's simple to set up, and users can track agendas, notes, and tasks.

4. Extra tips for “new kids on the block”

If your direct report is new in the role, pay extra attention to the following:

• Onboarding feedback: Ask how they’re finding the onboarding process. Are they getting the information and support they need to succeed?
• Role clarity: Ensure they understand their role and what success looks like. Misunderstandings about expectations are common early on.
• Align on expectations: Happiness is reality minus expectations, make sure you align on your expectations (from both sides) you don’t want them to have expectations that you don’t know about or having no idea about your expectations as their line manager.
• Mentorship and guidance: Offer more support in the early stages by providing mentorship or pairing them with others in the team. As the time passes make sure you reduce the number of answers and you replace them with more questions to empower your direct report come up with the answers.

5. Sample Agenda Template

1. Check-In (5-10 min)

2. Progress & Updates (15-25 min)

• Current tasks/projects - progress
• Wins - what is working well
• Challenges - what is not working as well as we expected (and why)
• Feedback

4. Open topics (5-10 min)

·??????? Concerns

·??????? Skill building

·??????? Ideas / Thoughts

5. Next Steps & Action Items (5-10 min)

In conclusion, effective one-to-one meetings are more than just check-ins—they are a vital tool for building strong, engaged employees. By creating an environment where open communication, personal development, and problem-solving are prioritized, you can empower your direct reports to grow, take ownership of their work, and thrive in their roles.

Remember to stay consistent with your meeting schedule, actively listen, and always leave room with the next steps clear from broth sides. With a clear purpose, well-structured agenda, and commitment to your team's growth, one-to-one meetings can transform the manager-employee relationship and drive meaningful progress.