Looking To Make One-On-One Meetings More Productive? Nine Questions To Ask Your Employees

One-on-one meetings can be powerful opportunities for employees and managers to connect on goals, reassess tasks and brainstorm ideas, but they can also turn into wasted time if not leveraged properly. If there’s no agenda to follow or neither party is sure what to discuss, the meeting may end early and without any real progress made.

By asking the right questions, however, managers can gain better insights from their team members, discovering what truly motivates them and what’s holding them back from achieving their goals. To help, nine members of Young Entrepreneur Council share some of the questions they like to ask during one-on-one meetings and why they think these questions help improve the quality of their conversations.

1. ‘What are your personal, financial and professional goals?’

I always ask my employees what their goals are—professionally, financially and personally. That way, we can align their careers with the outcome they are dreaming of. The question itself shows them that you care and positions you as a team member on their side, supporting their own individual success, which naturally reciprocates more loyalty and support for your company. I think many business owners are afraid to ask open-ended questions like this because their employees might expect too much from the company, but we’ve had the opposite effect. Our employees are better able to understand where our company is now and where it’s headed. They strive to make the company successful. All of our goals are aligned. – Jonathan Sparks, Sparks Law

2. ‘What’s the most difficult work you’ve done this week?’

This question helps me, as the leader, understand how my employees are feeling about their work, whether they are feeling overwhelmed and if they need additional support. It also helps them identify what’s going well for them, which helps in gauging their happiness at work. – Kristin Kimberly Marquet, Marquet Media, LLC

3. ‘What have you done in the last week to improve the company?’

One question I ask during my one-on-one meetings with my employees is: What have you done in the last week to improve the company? I believe this question helps make our conversation more productive because it encourages employees to learn, be creative and think long term. In addition, it is a great habit to learn something new every day. – Vikas Agrawal, Infobrandz

4. ‘What do you need from me?’

This is a simple question that opens the door for an employee to easily ask for help. It allows their guard to drop so the employee can now ask for help in an area they may have otherwise wanted to ask for help in but couldn’t. It always shows them that you are on their side and that you both are working together toward a shared goal. – Mary Harcourt, CosmoGlo

5. ‘How do you feel about your work-life balance?’

This is the question I usually ask during my one-on-one meetings with my employees. I believe that work-life imbalance affects employee productivity in a lot of ways. Open communication about obstacles and roadblocks, especially anything relevant to their productivity and goals, will help businesses create better working conditions. Are you satisfied with your current work hours? Can you better manage your family life or life situation while fulfilling your work targets? How could that be made better? These sub-questions help you get more information about areas where your business can further address individual productivity. – Brian David Crane, Spread Great Ideas

6. ‘What are you thinking about now that we haven’t discussed?’

Employees have many thoughts about how things can or should be done but often don’t say anything because they think they won’t be heard. Asking this question opens the door for them to express these ideas. In a sense, it permits them to speak their mind about any number of things that you may need to know. An employee may have a gem of an idea or could have noticed a concern they wish they could share. As an employer, you may find out some useful information after permitting them to speak freely. It also creates a bond with them where they understand that you welcome ideas and concerns. – Baruch Labunski, Rank Secure

7. ‘Can you describe your dream job?’

I ask employees to describe their dream job, regardless of what they are doing and regardless of what I am offering. This makes the conversation more productive because I get to learn what fuels my people. I give them permission to talk about more money, a flexible schedule, a different skill set or anything that gets them excited. Then I try to figure out if there’s something mutually beneficial there. I see if there is a place where the vision that fuels them can work with the needs of my company. More often than not, the answer is “yes” or at least “not yet,” but it is rarely a straight “no.” You get better results when your people are passionate about what they are doing. Channel that energy wherever your company needs it most. – Tyler Bray, TK Trailer Parts

8. ‘How can I make your workday a little easier?’

During one-on-one meetings with my team members, I always ask if there’s anything I can do to support them and make their workday a little bit easier. This question is an excellent way to get feedback on your leadership skills and find creative ways to make your team happier and more productive. I find that asking this question also helps you find employee pain points that are not always immediately visible. I believe this has a positive effect because people are more likely to speak up about issues they’re facing if asked directly. – Chris Christoff, MonsterInsights

9. ‘What kind of help do you need?’

Your biggest responsibility as a leader is to create a safe and thriving environment for your team and help them succeed. I always ask how they are doing and what kind of help they need. It’s very important to check in with your team from time to time and offer assistance directly because people are different. More extroverted employees have no problem asking for support whenever they need it, while more introverted ones tend to keep this need to themselves and just persevere. – Solomon Thimothy, OneIMS

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