One to Ones

This guide is for managers within Mad to use for their one-on-one sessions.


These are critical to maintaining communication in the workplace. Management can make a big difference by having regular, structured yet informal One-on-One conversation with their team members. This is a simple yet powerful practice that takes just 30 minutes every month, bi-weekly if possible. The goal is for each team member to have an informal conversation around engagement, workload, team dynamics, performance, learning and development.

Although it’s a time-consuming effort, the returns on One-on-Ones are huge. Most people like to speak about their accomplishments and concerns. As a manager, have an open ear and actively listen to everything your team members have to say. You can guide the conversation to understand even better what is meant and provide immediate guidance and feedback.

Effective One-on-Ones need preparation and structure. You need to discipline yourself to prioritize them, despite any conflicting demands for your time. Losing engagement with your staff has a compounding impact on both your effectiveness and workload. One-on-Ones are important to preventing this. The following guide demonstrates how to have effective One-on-Ones that engage team members and give managers a better understanding of how their teams are operating. One-on-Ones also provide insight into the team’s morale; such has happiness or motivation.


It is important to prepare for a One-on-One. While planning, take into consideration: the mindset, the schedule and the agenda.


Don’t overthink the meeting, the conversation should be informal and somewhat free flowing. There is no need for a rigid agenda or meeting minutes; however, as the manager you need to track and follow through on any actionable discussion that results from the meeting. Put yourself in the mindset that this conversation is happening in a relaxed and very natural manner.

Most important is that the focus is on the team member – not the manager. It’s more important to ask open-ended questions and listen rather than explaining and justifying recent decisions. Be open to step back and listen to your teammates as much as you possibly can. Come in with a clear mind and no bad feelings. As a rule of thumb, a manager shouldn’t really talk more than 25% of the meeting. You should certainly guide it, asking the right questions, but then listen to sense the team member’s motivation or concerns.

Recurring Schedule

During the first One-on-One you should briefly explain the purpose and set the tone right. Make sure to establish this is going be an informal and recurring meeting that doesn’t require much preparation but a certain openness, trust and honesty to share whatever is on top of mind. The first few meetings might be a little dry – it takes time to build trust and communication. Each person is different – the key is keeping cadence to ensure the communication remains open. Rapport will build naturally over time with each consecutive conversation. Therefore, it is imperative that these meeting commitments are kept and not pushed to the side.

You need to put your One-on-One appointments directly into your calendar as a recurring meeting and be sure to invite the relevant team members. This way you and your team have already committed to having a regular conversation. Stay disciplined and consistent. These conversations should not be a surprise. Speak to each team member prior to sending the invite so that they know what it is about and why it is valuable—for both you and them.

Sample invite:

This is our time as previously discussed to start doing one-on-ones in our team. Just informal conversations to get more feedback from you. We can talk about anything. What is bothering you? Your progress? Or whatever else that you find important. This will happen every two weeks. Let me know if you have any questions.

Do not cut meetings short if they end early that is ok, but don’t start double booking over. Remember, this is their time and you should take it away. Always allow the team member to speak first. It is advisable that you schedule an hour. If you find in the beginning that content is light at the conclusion of your session spend the remaining time reflecting specifically on that person and how you can assist them in their development. By focusing on the team member, your assistance will be tailored to the individual and will increase productivity as a result.

Try not to skip any meeting. Should an unavoidable conflict arise, make every effort to reschedule the One-on- One, not cancel it. Others who have already incorporated one-on-ones into their schedules have shared some of their solutions: Some approach scheduling a specific day to dedicate it to One-on-Ones. Some use Fridays because they can directly recap the week and it lets people go more motivated into the weekend. Others kick- off the week with One-on-Ones on Monday when the mind is fresh and everything being said can directly have an impact on the days ahead. The day isn’t as important as consistently doing them without fail. When the conversations happen regularly, they have a beneficial side effect of keeping the “do you have a minute” – daily interruptions reduced. If team members have confidence and trust that they have a scheduled time to bring non-time-sensitive issues to your attention, they will utilize that time instead of feeling as though they need to create that time during the day.

Make a genuine, non-forced effort to also connect personally. Build a strong relationship with your team members to create an environment of trust, respect and honesty. Sometimes it’s good to share some personal happenings to make the atmosphere more relaxed and less tied to actual work. This way team members will be more likely to open up as well if they have any problems today or in the future. The key is to be genuine – we care about our team members and giving them the opportunity to grow is one our most important investments.

An Agenda is Optional

You can ask your teammates to shortly share with you what they would like to talk about so you have the chance to prepare critical topics like promotions or performance discussions. However, this is really up to the team member to set the direction of the meeting if they want.

If there’s no agenda it may be helpful to set one overarching topic that the One-on-One could be about. Some examples include the following:

  • General engagement and motivation

  • Team dynamic

  • Learning and development

  • Your leadership style

  • Future ambition and past performance

  • Ideas and requests for change

During the One-on-One Meeting

As the manager, you should take the lead to set an informal tone for the meetings. Focus on asking questions and listening attentively to understand the feedback. Don't forget to wrap up each meeting and prepare for the next.

Be on Time.

The 1:1 is really not your time, it’s their time. Being late is disrespectful. Constantly prioritizing “something else” – email, other meetings, etc. suggests that this particular 1:1 meeting is not as important to you as these other things. Remember, as a manager, in many ways, you represent the company to the team member. Think about the message that you and the company are sending to someone that their time is not that important to you.

Keep It Informal

Keep your One-on-One informal, but private. It is best to find a relaxing place where you can hold the conversation. These are best when not done with a desk between each other. Also try to avoid using a manager’s office– while this may be your comfort zone, it is not necessarily comfortable for the team member. Use shared meeting space when available. They can be done over a walk, coffee or breakfast. It’s really simple. Also, never include any one else prior to the meeting. If it isn’t truly One-on-One – it isn’t the right format.

Ask Questions

To get the most out of your time together, a good practice is to prepare some questions in advance just in case the team member is reserved at the start. A well-asked question is a powerful tool because there are so many things one does not think of sharing until asked to do so. When conversations come to a certain topic, such as work habits or personal learning, you can use the questions to get the more feedback from your team. One- on-ones can be about almost anything. However, there are some common topics that managers like to cover.

Work Habits

As a manager you want to understand how each of your team members operates. Once you learn their productive modes, you can support them to work more efficiently. Here are some questions regarding work habits:

  • Which part of the day do you feel most productive?

  • When do you feel that your energy and focus at the lowest level?

  • What are the changes that can be made so you can take the best out of a work day?

  • What were your biggest time wasters or roadblocks in the last couple of weeks?

  • What do you do when you stuck on something?

  • What is your process of getting unstuck?

  • Who is the team member you turn to for help?

Team Collaboration and Relations

Opportunities to increase team productivity by improving the interpersonal relationship amongst team members. Ask the right questions to uncover the hidden challenges and opportunities. Some examples:

  • Who in your team inspires you?

  • Whose opinions do you respect?

  • What have they done to earn it?

  • Is there anybody in the team that you find it difficult to work with?

  • Can you tell me why?

  • What do you think about the amount of feedback in our team?

  • When do others give feedback to you?

  • Would you like to hear more feedback from other team members and me?

  • What do you think would help us work together better?

  • Any suggestions for improvement in the way we work together?


Personal happiness has an undeniable impact on productivity and engagement. Here are some questions you can use to promote the discussion:

  • Are you happy working here?

  • Are you happy with your recent work?

  • Why or why not?

  • What keeps you engaged with your daily work?

  • What can I do to help make daily tasks more engaging?

  • What kind of projects do you enjoy working on?

  • What motivates you to work on a project?

  • Can you name three things we can do to help so you can enjoy your job more?

  • What is the best accomplishment you had since you are here?

  • Do you feel appreciated for it?

  • What are the things that worry you?

  • Anything on your mind?

  • Have you ever felt undervalued here?

  • Why?

Short-term Goals

Your team’s feedback on their short-term goals will keep you aligned with their progress as well as their frustrations on the projects. It is healthy to address frustrations in a timely manner. Ask some questions, like:

  • How is the project going?

  • What can we do to help?

  • What are the main bottlenecks?

  • Can we do anything to move it along?

  • What are the projects you would be interested in working on next?

Long-term Goals

Long-term goals are important to a person’s sense of fulfillment and happiness. Your team members like to see that they are making progress toward their big life goals. You want to learn about their goals, and whether their current job fits into those goals. Here are some questions you can use:

  • What do you want to achieve in the next 3 years?

  • How do you think about your progress on your big goals?

  • What needs to be done to move towards the goals?

  • What can we do to help?

  • Which part of the work here do you feel as most relevant to your long-term goals?

  • What kinds of projects do you want to take part in to move toward your goals?

Personal Development Plan

You want to find out if your team members take learning and development the same way as you do. Some of the following questions can help you learn more about their motivation.

  • Do you feel like you are learning at work?

  • What are the new things you learned lately?

  • What are the areas you want to learn about?

  • Whom in the team do you want to learn from?

  • Whom do you get valuable feedback from?

  • Do you think that you receive enough feedback?

  • Is feedback helpful for your personal development?

  • What can I do to help you get the feedback you want?

  • Would you like more coaching?

  • What aspect of your job do you like more help and coaching on?

Manager Improvement

It is crucial for you to know how your team thinks about you and your management style. It is challenging to get honest feedback specifically about you from a direct report. Set the right tone and choose your questions wisely. Here are some examples:

  • What can I do as a manager to make your work easier?

  • What do you like about my management style?

  • What do you dislike?

  • What is the percentage of my involvement in your daily tasks?

  • Would you prefer more or less?

  • How can I support you better?

  • What is something I could have done better?

  • What are the situations that I could have helped more but didn’t?

Listen Actively

Listen to your team member’s insight carefully. It is important to remember that you don’t just listen to be polite. You listening to understand what is being shared. Active listening involves:

  • Asking clarifying questions, something like: "Let me know if I got you right. Do you mean that you would rather see me being less involved in your daily task?"

  • Paraphrasing giver’s view, such as: "So you are saying that I should give you more autonomy in making decision regarding your daily tasks."

  • Acknowledging their feelings, for example:" I understand your strong feeling about your independence at work."

  • Clarifying questions and reaffirmation bring you closer to what is being expressed. By showing your recognition and respect toward one's feeling, you are to build a stronger relationship with your team.

Wrap Up & Suggest Next Moves

At the end of the meeting, you should wrap up the talking points. It is also essential to suggest an action plan till the next meeting. Be careful to set proper expectations at the conclusion of the session. While the team member has the right to bring any suggestion or idea to the meeting it does not mean the manager can solve them all immediately or even to the team members ultimate desired result. Building trust and confidence doesn’t mean saying yes to every request. It does however require listening and responding back timely.

General Tips

  • One-on-One’s with remote team members should be conducted with webcam’s when possible. Day to day interactions should never substitute for an team member’s session.

  • Remember a focused time is a critical component for these meetings being successful. One-on-One’s are not project or deadline reviews.

  • Each team member will have a slightly different approach that works for them.

  • Manager’s must be careful to not be too rigid in the structure to account for this individuality.

  • Always thank the team member for their time at the conclusion of a session.

  • Show up on time.

  • Showing late even by a minute demonstrates you don’t respect the time seriously.

  • Demanding excellence is only possible when a leader demonstrates it first.

  • Start with a positive point.

  • Even if a tougher conversation is to take place – no one likes being greeted with negative talk first.

After the One-on-One meeting

Make notes about the discussion points and the action plan. If you have done this already during the meeting, log it on your note system. You want to make sure you can easily review the items and act on what is needed. Make sure you do the legwork before the next meeting. Also, remember to make it happen for the next meeting! Your credibility as manager depends on this step.


One-on-ones are a great tool for managers and team members. The weekly sessions are for you to check in with the team’s morale. They are also about getting to know the people you are working with better. You can also save one-on-ones for higher-level things like career development and continuous learning. Each team member’s feedback is extremely important for managers. Effective one-on-ones are one of the best ways to seek feedback, as well as opening a two-way dialogue through which to give feedback that is tailored the specific team member’s motivations and needs. Learn to do one-on-ones the right way so you can get your team members engaged and let them know that you value them. These conversations will have a huge impact on your whole team.

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