One-on-One Questions to Ask Employees

In fast-paced organizations—especially those with 40–70 employees—staying aligned, engaged, and high-performing is no small feat. One-on-one meetings offer a unique opportunity for leaders to connect meaningfully with team members. They help in understanding their challenges and supporting their growth.

But here’s the truth: not all one-on-ones are created equal. To make the most of these meetings, you need to ask the right questions.

Start maximizing your meetings today by signing up for Meeting For Goals at this link. You can also explore our free meeting templates at this link to get started quickly.

One-on-ones aren’t just another calendar item—they’re a leadership superpower. While team meetings focus on group updates and goals, one-on-ones create a safe space for real conversations. They help you:

• Build trust and rapport
• Spot and solve problems early
• Encourage innovation through open dialogue
• Boost morale and employee retention

According to Gallup, employees who have regular one-on-ones are nearly three times more likely to be engaged at work. That’s a big deal in today’s competitive talent market.

The right questions help you:

1. Communicate clearly and transparently
2. Identify challenges and growth opportunities
3. Align individual goals with company objectives

When combined with a structured tool like Meeting For Goals, your one-on-ones become more than conversations—they become strategic levers for performance and engagement.

 

Building Rapport

Before diving into tasks and goals, start by building rapport. This sets the tone for an open, productive conversation.

A little small talk goes a long way. Try:

• “What’s something fun you did recently?”
• “Any new hobbies or side projects you’re excited about?”
• “What’s the best movie or book you’ve enjoyed lately?”

These questions help your employees feel seen as people—not just workers. They also give you insight into what energizes them outside the office.

Trust is the backbone of a great one-on-one. Without it, employees won’t open up. Ask:

• “How are you feeling about your current workload?”
• “Is there anything I can do to make your workday smoother?”
• “How’s collaboration going with the team?”

These questions signal that you care about their experience, not just their output. And when people feel heard, they’re more likely to stay engaged and loyal.

Pro Tip: Use Meeting For Goals to document these conversations and follow up on concerns. It keeps things from slipping through the cracks.

Performance and Development

Once rapport is established, shift the focus to performance and growth. This is where you help your team level up.

Start by understanding how they feel about their day-to-day work:

• “What part of your job do you enjoy the most?”
• “What’s something you wish you could do more of?”
• “Are there tasks you find frustrating or unclear?”

These questions help uncover misalignments between strengths and responsibilities. They also highlight opportunities for support or reallocation.

Goal-setting is where things get strategic. Ask:

• “What are your top goals this quarter?”
• “Where do you see yourself in the next year or two?”
• “What skills would you like to build or improve?”

This not only gives employees direction but also helps you align their personal growth with team and company objectives. With Meeting For Goals, you can set, track, and follow up on these goals easily.

Need help setting goals? Check out our free meeting templates at this link.

 

Feedback Loop

Great one-on-ones are a two-way street. Make space for both giving and receiving feedback.

Employees often have insights that can improve team performance. Ask:

• “What’s one thing we could do better as a team?”
• “Do you feel supported by leadership?”
• “Are there any tools or processes that slow you down?”

These questions show that you value their input. It also helps you uncover issues you might not see from the top.

Feedback should be a conversation, not a lecture. Use prompts like:

• “I noticed X—can we talk about how to improve it?”
• “You did great on Y. How can we apply that to other areas?”
• “What do you think went well on your last project?”

Focus on growth, not blame. And always tie feedback to specific actions or outcomes. With Meeting For Goals, you can document feedback and track progress over time.

Looking for tips on how to give better feedback? Harvard Business Review offers a great guide on the art of constructive feedback: this link.

Aligning with Company Goals

One-on-ones are a great time to connect individual work to the bigger picture.

Help employees see how their work fits into the company’s mission. Ask:

• “Are you clear on what the company’s top priorities are?”
• “How do you think your work contributes to those goals?”
• “Is there anything about our strategy you’d like to understand better?”

When people understand the “why” behind their work, they’re more engaged and motivated.

Your team has ideas. Use your one-on-ones to tap into them:

• “Do you have any suggestions for improving our workflow?”
• “What would help you be more effective?”
• “Are there any tools or resources you wish we had?”

These questions foster ownership and innovation. And they help you make smarter decisions from the ground up.

Want to learn more about aligning teams with strategy? This article from McKinsey offers a deep dive: this link.

Meeting For Goals makes it easy to link employee goals with company objectives, so every meeting drives real results. Learn more at this link.

Career Development and Growth

One-on-ones are also a great opportunity to talk about long-term development.

Help employees think beyond their current role. Ask:

• “Where do you see your career going in the next few years?”
• “Are there roles or projects you’d love to try?”
• “What motivates you to grow professionally?”

These questions show that you’re invested in their future—not just their current output.

Support their development by asking:

• “Are there any skills you’d like to learn?”
• “Would you be interested in mentorship or cross-training?”
• “What kind of training or support would help you grow?”

Use their answers to recommend resources or create a development plan. With Meeting For Goals, you can assign action items and track progress over time.

Well-Being and Work-Life Balance

Performance is tied to well-being. Don’t ignore it.

Show you care by asking:

• “How are you managing your workload?”
• “Are you feeling stressed or overwhelmed?”
• “Is there anything I can do to support your well-being?”

These questions open the door for honest conversations and help you catch burnout before it starts.

Encourage balance with questions like:

• “Are you able to disconnect after work?”
• “Do you feel your time is respected?”
• “Is your current schedule working for you?”

Respecting boundaries leads to happier, more productive teams.

Conclusion

One-on-one meetings are a powerful tool for building high-performing teams. But without the right questions, they can become routine check-ins with little impact.

The questions we’ve shared help you:

• Build trust and rapport
• Uncover challenges and opportunities
• Align individual and company goals
• Foster growth and innovation
• Improve retention and morale

If you’re a Director, VP, or C-level leader, it’s time to elevate your one-on-ones. Use these questions to create more meaningful conversations and drive better outcomes.

And don’t forget—Meeting For Goals is your partner in making every meeting count. Our software helps you:

• Streamline your one-on-one process
• Align conversations with company goals
• Track action items and follow-ups
• Save time and boost productivity

Start now by signing up at this link. Or explore our free meeting templates at this link to get started today.

For more tips and tools to improve your meetings, visit this link.

By asking the right questions and using the right tools, your one-on-ones can become the engine that drives your team’s success—one conversation at a time.