The Top 20 Ultimate One on one Questions

by Gabby Davis Apr 16,2022

The People Strategy Leaders Podcast

with Srikant Chellappa, CEO

The relationship between managers and their direct reports is crucial to successfully running a company. And one effective way to achieve a positive relationship between them is through one-on-one meetings. A one-on-one meeting presents an environment to have honest talks on various topics, leading to a less stiff atmosphere between managers and their direct reports. 

A crucial side of this meeting is asking the right questions to make the most of them. Asking the right one on one questions helps stir the conversation in the right and productive direction. This article will discuss the importance of one-on-one meetings and the type of one-on-one questions managers should ask.

Why conduct one-on-one meetings?

People, not robots, make up companies. Therefore, there should be a means to improve communication between employees and management. Fortunately, one-on-one meetings present managers with this opportunity. A study by SHRM found 89% of HR Leaders agree to ongoing check-ins and communication help retain and recruit better. 

In this section, we will highlight the reasons for conducting one-on-one meetings.

  • Builds Trust

It takes effort to build trust, and it’s crucial to build trust between managers and direct reports to run a successful team and, by extension, a successful business. A Human Era at Work study revealed employees who trust their management also respect them. The study also found that when employees trust and value their managers, they were 58% more focused and 63% more satisfied with their jobs.

  • Improves Engagement

To get the best out of employees, they must be engaged. Employee engagement will improve with one-on-one meetings because it allows managers and direct reports to discuss issues they would not otherwise discuss during office hours. Direct reports feedback on the company, career progress, and current projects can help identify and rectify pressing issues. A study by Gallup backs up this point showing employees who have regular one-on-one meetings are three times more engaged and 21% more productive.

Also read: Qualties of a good manager: 10 Skills you need
  • Improves Teamwork

One goal of a one-on-one meeting is to understand your direct reports. It is getting to know them beyond the four walls of the office space or, in recent times, your laptop screens. Engaging with your direct reports as people and not employees helps improve your working relationship, which can help in raising teamwork. One-on-one meetings can also help to diffuse friction between colleagues by the manager becoming a mediator.

  • Reduces Staff Turnover

A study by shows that 23% of employees look for new jobs every day. Another research by Hogan assessment shows that 75% of employees state their direct boss is the worse part of their jobs. Holding one-on-one meetings can help reduce these figures, as one reason employees leave their workplace is due to lack of engagement.

One On One Questions to Ask Employees

When conducting a one-on-one employee meeting, the questions must explore the various areas of the direct report’s life. The questions you ask should cover their personal life, relationship with co-workers, career goals, the working environment, and feedback on management. Touching the various areas that affect your direct reports brings about an open meeting. 

You can have a list of questions divided into separate sections to help you structure it. Also, while timing is essential, flexibility is much more effective because any question can become an issue that needs immediate attention.

This section will discuss the areas to ask questions and the type of questions you should ask your direct reports.

  • Personal Check-in Questions

Understanding the physical and mental health of your direct reports is crucial. Showing genuine concern and empathy can help break the ice and open up the floor for discussions. If this is the first one-on-one meeting, you can ask about their lives outside the workplace. 

Questions about hobbies or what they find fun can help to ease tension. Who knows, both of you may enjoy similar activities.

If this is not your first meeting, you can ask follow-up questions from the previous conversation. 

Questions to ask:

  • 1. How are you feeling today?
  • 2. What do you do over the weekend? / Do you have plans for this weekend?
  • 3. How do you feel about your current work/life balance?
  • 4. Do you have any hobbies you are passionate about?

Depending on the answers you receive to these questions, spend more or less time in this section. If the employee is not doing well mentally or physically, allocate more time to this section.

  • Career Goal and Progression Questions

A study by the Conference Board shows that only 57% of workers show job satisfaction, and for a typical worker who dedicates hours to their job, it’s a low figure. One good way to improve this figure is by understanding your direct reports’ career goals. Asking the right questions will allow you to help with advice, point them to books or other materials they need, and assist them in reaching their goals. 

Many companies have lost excellent employees due to not understanding how their goals align with employees. Identifying the career goals of your direct reports can also help you assign projects they are interested in working on or projects that will help them develop their skill set.

Sample 1 on 1 career goals and progression questions to ask include:

  • 5. What are your career goals? Have you put much thought into your career goals?
  • 6. What can I do to help you achieve them?
  • 7. What do you enjoy most about your work?
  • 8. What skills do you think you need to develop? Do you feel you need more training?
  • 9. Do you feel your current job role contributes to achieving your career goal?
  • 10. Do you feel you can achieve your career goal with this company?

These one-on-one employee meeting questions will help you and your direct report clear the air regarding their career goals and progression. Their answers will highlight what you can do to help them progress in their career.

  • Workplace Environment and Condition

The workplace environment is vital in ensuring the success of a company. Employees are a significant source of feedback since they spend most of their time working and interacting in the office environment. A poor office environment can impede productivity, so it’s best to have feedback by asking one-on-one questions from your direct reports. Chances are you would receive a few.

Sample one on one workplace environment and condition questions to ask:

  • 11. Are you happy with the current working environment?
  • 12. What changes would you make to the current work environment?
  • 13. Do you feel you can be more productive if we make changes to the work environment?
  • 14. What distracts you in the office environment?
Also read: Benfits of employee career development program
  • Company Culture and Relationships

In a study by Gallup, managers determine how great or lousy a workplace turns out. The study states managers have a variance of 70%, suggesting they are vital in dictating the company culture. A positive atmosphere helps to foster teamwork and healthy work relationships. When managers promote a healthy culture, it improves employee retention and productivity.

One good way to determine if managers lead by example is by asking questions in one-on-one meetings with employees.

Sample 1 on 1 company culture and relationships questions to ask:

  • 15. Is there any aspect of the company work culture you would want to change?
  • 16. Do you feel the team works well together?
  • 17. Is there anyone in the team you notably work well with? Why is this?
  • 18. Is there anyone in the team you dislike working with? Why is this?
  • Managers Feedback

Managers need feedback from their direct reports. According to Gallup, managers provided with strength feedback showed a 12.5% increase in productivity and a 14.9% increase in turnover rates compared to those who didn’t receive such feedback. In short, managers also need feedback to improve, and a one-on-one meeting presents an opportunity for the managers.

Sample 1 on 1 managers feedback questions you can ask:

  • 19. Do you feel I give enough feedback?
  • 20. What can I do to support you better?

The aim is to make sure the employee is comfortable with your management style and get feedback on what you should do more or less. In this section, take the words of your direct reports in friendly spirit. If they are giving constructive criticism or observations they have made, it’s because they also want to see you grow. They could easily have kept quiet, spoken behind your back, or given a written complaint to HR.

Bonus  1 on 1 Questions

Managers and employees are busy individuals, and therefore they need to make every moment in the workplace count. On average, managers spend 23 hours in meetings during the week. That’s a lot of time spent in meetings, and because of this, it’s best to ask your direct reports about the effectiveness of your one-on-one sessions.

  • Do you feel these meetings are a good use of your time?
  • How as these one-on-one meetings helped you?
  • What do you think I should change about my approach?


Asking the right one on one questions in meetings with your direct reports is essential in getting the best from these meetings. The success of the one-on-one sessions is dictated by how well you can break the ice and have simple conversations, leading to more complex ones. As you question your direct reports, remember the aim is to understand your employees better, to provide adequate support.

Want to know how Engagedly can help you mange your remote employees better? Request us for a demo.

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Gabby Davis

Gabby Davis is the Lead Trainer for the US Division of the Customer Experience Team. She develops and implements processes and collaterals related to the client onboarding experience and guides clients across all tiers through the initial implementation of Engagedly as well as Mentoring Complete. She is passionate about delivering stellar client experiences and ensuring high adoption rates of the Engagedly product through engaging and impactful training and onboarding.

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