One-on-One Meeting Questions

Ruth Hadari
Ruth Hadari
Agile Advocate, Engineering Ops Expert
Posted on
Feb 25, 2022
Updated on
May 23, 2022
Table of Content

One-on-one meetings are very important for employees, just as they are for managers. A one-on-one is a reflective and insightful meeting between a manager and an employee. There are plenty of different ways managers might conduct such a meeting, and there is not a lot of consensus as to how often it should take place, what should be talked about, and all the different details that can make or break a  one-on-one.

Importance of one-on-ones

One-on-one meetings establish employees’ trust and help them realize that they work for a company that genuinely cares about their personal development. While such meetings are easier to conduct in small-scale companies, the reality is that companies grow, and as hard as it may be, not holding one-on-ones can be an indicator of bad management, bad company culture or lack of transparency and communication.

Having a consistent one-on-one structure requires a template to follow to the T. To create a template, you need to sort out the most important one-on-one questions you will ask your employees. There are different types of questions that you can align when creating a template; knowing about each type of question and what change they can potentially bring helps address them fairly well.

Types of Questions to ask in one-on-ones

Checking-in questions

The questions that fall under the checking-in umbrella are not only good for the manager, but also for team members during a direct report session. In fact, these may be some of the most integral one-on-one questions to ask a manager. As an employee, you must ensure that your manager is satisfied with your contribution to the company.

If your performance does not meet expectations, you need to be notified so that you can make immediate and necessary changes. Your manager is often tied up fulfilling other duties and making big decisions; you can’t expect them to keep regular tabs on your performance and hold your hand.

You need to take responsibility and put forward self-check questions to make sure that the manager is happy with your work. You can accomplish this by asking a series of checking-in questions that also work as self-accountability checks. Initiating this type of evaluation requires you to ask the following one-on-one meeting questions:

  • Are you satisfied with my performance?
  • What am I doing well, and why?
  • What part of my performance are you not happy with, and why?

Icebreaker questions

Icebreaker questions are integral for generating a meaningful conversation. They help cut through all the mundane conversations and smalltalk and get to the more important topics. If you as an employee are good at icebreakers, then you will be able to get the most value out of your one-on-ones. The best icebreaker connects people and also establishes the purpose of having the personal session in the first place.

Icebreaker questions that help two individuals align their experiences, perspectives and ideas are the best ones. Icebreaker questions also help change mindsets from knowing to learning.

Typically, when managers and employees partake in a meeting and they have worked with each other for a very long time, then are each likely to go in with a knowing mindset. This type of mindset infers that you already know the person for such a long time and you do not need to learn about them any further. Therefore, questions to ask in one-on-ones must be impactful and work towards a knowing mindset.

Questions to ask steam members

Managers need to be very careful with the questions they ask the team during a one-on-one session. Managers can benefit from both open-ended and close-ended questions: Open-ended questions allow employees to jog their memory and reveal crucial details that need to be addressed. An example of such an open ended question is “What has been on your mind this week?”

The answer to this question does not have to be related to their work, and it can extend past work life to more personal matters. Sometimes a personal matter can weigh down on an employee and impact their productivity. Talking about the issues can be a great way for them to unwind and unburden their stress.

Another question can be along the lines of “How happy and productive did you feel this week/month and when?” This is a really good question for managers who are not closely connected to the day-to-day achievements of the employees. Questions like this can help managers get a glimpse of the good moments they might have missed. Another similar question could be “Where did you feel friction in the previous week/months?”

Answers to this question can reflect even the smallest of problems. Friction does not have to necessarily pertain to their team’s process, but can also be moments of interpersonal tension. Overall, similar thought provokers such as these are great one-on-one questions.

Questions for your first one-on-one meeting

When conducting the first one-on-one meeting, you and your employee have to understand why you’re having one in the first place. The point is not to address an ongoing issue or solicit business operations; A one-on-one meeting is instead an opportunity to connect with your staff from an individual standpoint. Keeping this in mind, you can create effective templates for first one-on-one questions for meetings with employees.

Final Thoughts

One-on-one check in questions, along with others, help open up your agenda and convey it to the other person without being too imperative. Even though feedback is important, that is not the sole purpose of these meetings. When done right, your one-on-one meeting template can flow seamlessly into a conversation that encourages teamwork and productivity.

About the author

Ruth Hadari
Agile Advocate, Engineering Ops Expert

Highly experienced in leading multi-organizational teams, groups, in-shore as well as off-shore. The go-to person who is able to simplify the complex. An agile advocate, experienced in all common methodologies. Responsible for the entire software development lifecycle process from development, QA, DevOps, Automation to delivery including overall planning, direction, coordination, execution, implementation, control and completion. Drives execution, and communicates on status, risks, metrics, risk-mitigation and processes across R&D.

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