One-on-one meetings can be powerful opportunities for employees and managers to achieve goals, reassess tasks, and brainstorm ideas, but they can also become wasted time if not used properly. If there is no agenda to follow or if neither side is sure of what to discuss, the meeting can end early with no real progress being made.
However, by asking the right questions, managers can gain better insights from their team members, discover what really motivates them and what prevents them from achieving their goals. To help, nine members of Council for Young Entrepreneurs share some of the questions they like to ask during one-on-one conversations and why they think these questions help improve the quality of their conversations.
Members of the Young Entrepreneur Council share tips to make face-to-face meetings more useful.
Photos courtesy of individual members.
1. ‘What are your personal, financial and professional goals?’
I always ask my employees what their goals are: professionally, financially and personally. In this way we can tailor their career to the result they dream of. The question itself shows them that you care and puts you on their side as a team member, supporting their own individual success, which of course means more loyalty and support for your business. I think many entrepreneurs are afraid to ask these kinds of open-ended questions because their employees may be expecting too much from the company, but we have had the opposite effect. Our employees have a better understanding of where our company is now and where it is going. They strive to make the company successful. All our goals are aligned. – Jonathan Sparks, Spark law
2. “What’s the hardest work you’ve done this week?”
This question helps me as a leader understand how my employees feel about their work, whether they feel overwhelmed, and whether they need additional support. It also helps them identify what is going well for them, which helps measure their happiness at work. – Kristin Kimberly Marquet, Marquet Media, LLC
3. ‘What have you done in the past week to improve the company?’
A question I ask during my one-on-one conversations with my employees is: What have you done in the past 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 good practice 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 decreases their vigilance so that the employee can now ask for help in an area where they might otherwise have wanted to ask for help but couldn’t. It always shows them that you are on their side and that you are working together towards a common goal. – Mary Harcourt, CosmoGlo
5. ‘What do you think of your work-life balance?’
This is the question I usually ask during my one-on-one conversations with my employees. I believe that work-life imbalance affects employee productivity in many ways. Open communication about obstacles and roadblocks, especially anything relevant to their productivity and goals, will help companies create better working conditions. Are you satisfied with your current working hours? Can you better manage your family life or life situation while fulfilling your work goals? How could that be better? These sub-questions will help you learn more about areas where your company can further address individual productivity. – Brian David Crane, Spread great ideas
6. “What are you thinking about now that we haven’t discussed it yet?”
Employees have a lot of thoughts about how things can or should be, but often don’t say anything because they don’t think they are being heard. Asking this question opens the door for them to express these ideas. In a way, it allows them to voice their opinion on some of the things you might need to know. An employee may have a gem of an idea or have noticed a concern that they would like to share. As an employer, you can learn useful information after letting them speak freely. It also creates a bond with them where they understand that you welcome ideas and concerns. – Baruch Labunskic, Rank Safe
7. ‘Can you describe your dream job?’
I ask employees to describe their dream job, no matter what they do and what I offer. This makes the conversation more productive because I learn what drives my people. I give them permission to talk about more money, a flexible schedule, different skills, or anything else that gets them excited. Then I try to find out if there is something that is mutually beneficial. I see if there’s a place where the vision that fuels them can work with the needs of my business. More often than not, the answer is “yes” or at least “not yet”, but it is rarely a direct “no”. You get better results if your people are passionate about what they do. Channel that energy where your business 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 I can do anything to support them and make their workday a little easier. This question is a great way to get feedback on your leadership skills and find creative ways to make your team happier and more productive. I notice that asking this question also helps you find employee pain points that are not always immediately visible. I think this has a positive effect because people are more likely to give their opinion about problems they face when asked directly. – Chris Christoff, MonsterInsights
9. “What kind of help do you need?”
Your greatest 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 help they need. It is very important to reach out to your team from time to time and provide immediate assistance because people are different. More extroverted employees have no problem asking for support when they need it, while more introverted employees keep this need to themselves and just push through. – Solomon Thimotheus, OneIMS
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