20 questions each to ask in your one-on-one – for manager and employee

What are one-on-ones ? Why Does Your Team Require Them?


“One-on-ones are one of the most important productivity tools you have as a manager,” – Elizabeth Grace Saunders

The foundation of a productive team depends upon the rapport and dynamics between its leaders and team members. One-on-ones work as a cornerstone for both: an effective manager and an employee. Through these meetings, a manger can touch base with his/her team in a more personalized manner. 

They give a chance to the leader so that they can understand their team member’s strengths, weaknesses and potential. Similarly, one-on-ones also give a safe space to the employees for discussing their individual journey, future plans and opinions with their manager.  

one-on-one meeting or weekly check-ins
What a productive one-on-one should look like

One-on-ones are not your regular meeting where you discuss a task and its scope- it’s a window, for both managers and employees, to nurture a talent and derive valuable insights from an experienced authority, respectively. 

The basis of an effective one-on-one depends upon the quality of conversation which ensues in it. Many organizations have adopted a system of weekly check-ins with a stress upon meaningful one-on-ones. However, they fail to see any difference in the attitude and bonding of the teams.


When quizzed about the proceedings of these one-on-ones, it was found out that they failed in building a personal rapport among team members. On top of it, the conversation included work assignment and the project. The managers said that the employees were hesitant to share their feelings with them. While the employees said that they lacked faith in their managers. 


The purpose of one-on-ones is to break the ice between a figure of authority and an employee. It helps people understand the persona behind a designation. This goes a long way in forming cohesive teams that works for one goal.

In order to make these meetings more productive, we have compiled a list of questions from both perspectives that can get the conversation rolling. Let’s have a look.


Questions to ask the employee in a one-to-one :  


If you’re a manager, then, you’re at the right place. Let us introduce you to a few tricks and a set of questions that can increase your one-one-one’s productivity in just a few attempts. 

Not every manager is a leader.
Not every manager is a leader but every leader is a good manager


What brings a leader apart from a manger is their ability to inculcate faith in its followers. The best way to earn team’s trust is by letting them know that you care. If the conversation begins with a work-related topic, it sets the entire tone to be strictly professional. 


The key is to ease them into the discussion. Start by building trust by asking them about their personal life. Don’t just look interested, be genuinely enthusiastic about their response. 

Talk to them about their personal journey and growth plans. This can help you learn more about their skills and how it can be incorporated into your plans. 

To make things simpler for you, we have a list of few questions that you can pose to your team members.

To build trust with the employee: 

  1. What keeps you busy besides work? What are your other passions? 
  2. How do you think your life and work are balanced? 
  3. What do you do for fun? What are your hobbies? 
  4. What drives you and motivates you to get up for work every day? 

To talk about career development: 

  1. What is that you do here makes you feel is in line with your long term goals? 
  2. Who do you admire and why? 
  3. What are your skills and what are the skills that you want to work upon?? 
  4. Is there any role in the company that you want to know about? 

To progress in their growth and career development: 

  1. What do you think we can do to help you move forward with your long term goals? 
  2. Do you like the pace in which you’re growing? If not, where can we help? 
  3. Is there any training you would like to attend to develop your skills? 
  4. Who in this company do you admire? Which quality of their do you find most impressive?

To give and receive feedback: 

  1. How do you think you should receive the feedback? 
  2. Do you feel like you’re getting enough feedback for your efforts? 
  3. Is there anything in work that you still want some guidance upon? 
  4. How much time do you think you feel productive in a day? Is there anything we can do to help you make more productive?

To improve your team: 

  1. Do you think the company needs to improve something to compete better in the market? 
  2. What do you like the most about the work culture in the company? 
  3. What offer can convince you to work somewhere else? 
  4. Do we need to improve something about the team meeting? Why? 


Questions to ask from the manager in a one-on-one or check-in:


If you’re a part of a team and have regular one-on-ones with your leader, this is for you. 

A successful check-on or 1:1
A productive one-on-one should result in better rapport with managers.

No matter what level you operate from, you will always have a senior to report to. From an employee’s perspective, a one-on-one might just look like any other performance-related meeting. But, if you ask the right questions, you can turn it around and make it more personalized.


A one-on-one meeting is not about discussing a project or a task; rather, it is an opportunity for you to share what’s on your mind with your senior. This is your chance to let your leaders know your side of the story. You can make him empathize with your problems and this will help in better performance of the tasks. You have his time and attention; all you need to do is steer the conversation in a way that you get maximum takeaways and learning. 


Never hesitate to strike a conversation about their life and experiences The answers that you get will help you understand your manager’s point of view better. Also, you will be able to work with them more effectively. 


Ask them what their role entails and how you can help them in managing better. Also, these questions will help you get the in-depth look of the practices that your manager follows in his career and how he reached where he is. You will know where he wishes to reach in his career. This way, you will be able to learn from him and know what he expects from your role in the company.

To make this a simple exercise for you, we have made a list of following questions that can help you have a fruitful one-on-one. 


To know more about your manager: 

  1. What is the most important achievement that you hope to accomplish someday in your career and current role? 
  2. What are your goals for your career? How do you plan on achieving them? 
  3. How do you feel when an employee gives you feedback? Can I do the same?
  4. What do you think is okay for me to expect from you?

To know about your manager’s role in the company: 

  1. What does your boss expect from you? 
  2. Can you tell me more about your work and management style?

To receive and give feedback:

  1. Is there anything that I should do differently? How do I do that? 
  2. What is the reason for hiring me? Am I living up to your expectations? 
  3. What is the one thing that I should stop doing at work? 
  4. Would you like to change anything in my position in the company? If yes, why? 
  5. What are the fair expectations for you to have from me? 
  6. How do you think I handled the x project? Could I have resolved it better? 
  7. Is there anything that I can do to make our team more successful? 

To perform better for the company: 

  1. Whom do you consider to be the team’s best performers? Is there anything I can do to emulate them? 
  2. How do you want me to update on the tasks or feedback?

To build a relationship with your manager: 

  1. Do you want to know something about my position in the company? 
  2. How did you decide on the target outcome for the x project? 
  3. What can we do to make our team perform best in the company? 
  4. What do I do that work the most for the company? Can I do it more? 

This was a list of all the questions that can help managers and employees to do their best in 1:1 meeting. Managers will get to know more about their employees and focus more on the team’s performance. Also, by building trust with their employees, they will be able to satisfy their individual expectations. Knowing what the employees aim for in the long run, a manager can help them achieve their goals. 

For employees, these questions will help them to receive the feedback that they need to focus on their skills and gradually improve them. Employees will be able to build a sense of trust and relationship with the manager. Knowing what your manager aspire from their career, you will be able to learn better from them and move forward in your career.