ali khan
Ali Khan
Published On
April 30, 2024
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25+ Vital One-on-One Meeting Questions to Boost Employee Engagement

Hello there! Do your one-on-one meetings feel like they could be better? You’re not alone. 

Traditional employee feedback sessions often miss the mark, leaving both leaders and employees feeling unfulfilled. This disconnect is more than just a missed opportunity—it's a call to action for improving how we communicate and connect in the workplace.

That’s why I’m excited to share over 25 essential one-on-one meeting questions that 

  • can change your meetings from routine check-ins to engaging discussions. 
  • are perfect for anyone leading teams.
  • are designed to cut through the usual chatter and get down to what really matters.

With my years of experience in team management, I'm here to guide you through turning those routine one-on-ones into engaging and productive conversations.

Whether you’re new to managing people or just want to improve, the tips in this blog will help you make every meeting more effective.

Let’s dive in and make each conversation not just productive, but genuinely engaging! 

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Why Are One on One Meetings Important?

While you might be familiar with some of the key benefits of one-on-one meetings, I'll touch on the most recognized ones first. 

  • Personal Connection: Strengthens bonds between managers and employees.
  • Tailored Feedback: Offers specific, actionable feedback for growth.
  • Employee Engagement: Shows employees they are valued, boosting satisfaction.
  • Problem Resolution: Provides a private setting to solve sensitive issues.
  • Career Development: Discusses future opportunities and career paths.
  • Direct Updates: Keeps both parties aligned on projects and goals.

Now, let’s look at the subtler, yet impactful, benefits one-on-one meetings can offer:

  1. Innovation Encouragement: Encourages sharing of creative ideas in a safe space.
  2. Reduction of Workplace Conflicts: Addresses potential conflicts early on.
  3. Enhanced Team Dynamics: Builds a collaborative and supportive team atmosphere.
  4. Adaptability to Change: Provides a forum to discuss organizational changes.
  5. Retention Improvement: Makes staff feel heard and respected, improving retention.
  6. Leadership Development: Hones essential management skills like empathy and resolution strategies.
  7. Feedback Loop Creation: Establishes continuous improvement through regular feedback.

25+ One on One Meeting Questions to Transform Your Manager-Employee Dynamics

These questions are grouped by topic to help guide your chats, but feel free to mix and match or add your own!

1️⃣ Assessing Employee Needs and Satisfaction

  1. What are your biggest challenges or roadblocks right now?
  2. How can I better support you in achieving your goals?
  3. Do you feel your workload is manageable?
  4. Is there anything about your current role that you'd like to change?
  5. What are your long-term career aspirations within the company?

2️⃣ Acknowledging Feedback and Challenges

  1. What accomplishments from the past month are you most proud of?
  2. What challenges have you faced recently, and how have you addressed them?
  3. How do you feel about the feedback you’ve been receiving? Is it helpful?
  4. What support do you need from me to make your job easier or more fulfilling?

3️⃣ Fostering Development and Growth

  1. What skills or areas of knowledge would you like to develop further?
  2. Have you identified any training opportunities that interest you?
  3. Do you feel comfortable taking on more responsibilities?
  4. Is there something we can do to improve our team's efficiency?

4️⃣ Promoting Communication and Alignment

  1. Do you feel comfortable communicating with me openly and honestly?
  2. Are there any concerns you have about the team or the company?
  3. Do you understand the team's current goals and priorities?
  4. How can we improve communication within the team?
  5. Is there anything you'd like to discuss from previous meetings?

5️⃣ Encouraging Openness

  1. What can I do better as your manager to support you?
  2. Do you feel your ideas and contributions are valued?
  3. What are you most excited about working on right now?

6️⃣ About their Job Satisfaction

  1. What do you enjoy most about your job?
  2. What do you enjoy least about your job?
  3. What has motivated you recently, and what has been demotivating?

7️⃣ Knowing Company Direction

  1. How do you feel about the direction the company is taking?

8️⃣ Managerial Support and Policy

  1. What can we do to make this workplace better for you and your colleagues?
  2. Do you feel you can talk openly about concerns and suggestions?
  3. What do you think about your career progression at this company?

9️⃣ Additional Insights

  1. Do you have any concerns or suggestions you feel have not been addressed?
  2. What can we collectively do to enhance our workplace culture?

How do you Prepare for a Productive One on One Meeting?

  • Set Goals & Agenda Together: Know what you both want to get out of it.
  • Review Past Stuff: Briefly skim emails, notes to refresh your memory.

🌟 For the Employee: Plan what to discuss (workload, challenges, goals).

🌟 For the Manager: Review employee performance, projects, areas for support.

On Meeting Day:

  • Small Talk (Optional): Briefly connect on a personal level.
  • Review Agenda: Be flexible based on what comes up.
  • Ask Open-Ended Questions: Spark deeper conversation.
  • Listen Actively: Prioritize active listening to show respect and encourage open communication.
  • Take Notes: Document key points, action items for future reference.
  • Plan for Follow-Up: Decide how you’ll monitor progress on any action items discussed.
  • End Positive: Acknowledge contributions, express appreciation.

💡Bonus Tips:

  • Be on time, avoid distractions, follow up with a quick email summary.
  • This sets the stage for impactful one-on-ones that benefit everyone.

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How to Craft Effective One-on-One Meeting Questions?

Choosing the Right Questions:

  • Focus on "Why" and "How":  Move beyond "what" questions (e.g., "How's the project going?") and delve deeper with "why" and "how" (e.g., "What challenges are you facing?" or "How can I better support you?").
  • Variety is Key:  Mix up question types to keep the conversation flowing. Use open-ended questions for in-depth discussion, but also include clarifying and closed-ended questions for specific details.
  • Align with Goals:  Tailor your questions to the meeting's agenda and the employee's role.  

Tailoring Questions by Role and Experience:

  • New Employees:  Focus on onboarding, understanding their role, and identifying any initial roadblocks. (e.g., "How are you settling in?" or "Is there anything unclear about your responsibilities?")
  • Experienced Employees:  Discuss career development, skill growth, and opportunities for taking on more challenges. (e.g., "What are your long-term career goals?" or "What skills would you like to develop further?")

Safe Space for Honesty:

  • Be Approachable: Smile, make eye contact, and listen actively.
  • Keep it Confidential: Assure them sensitive talks stay private (unless safety risk).
  • Work Together: Approach challenges as a team, finding solutions together.
  • Start Positive: Build trust with compliments to encourage open talk.

What Are the Common Pitfalls in One-on-One Meetings and How to Avoid Them?

❌ One-on-One Meeting Don'ts:

  1. Winging It: No plan, no goals = wasted time.
  2. Chatterbox Boss: You talk too much, they get unheard.
  3. All About Tasks: It's not just a status update, focus on growth!
  4. Forgotten Follow-Up: "We'll talk next time" (never happens).

By avoiding these, you'll have productive one-on-ones that benefit everyone.

✔️ Do This Instead:

  1. Plan Together: Set goals & an agenda beforehand.
  2. Quick Refresh: Briefly skim past notes to catch up.
  3. Listen Up: Pay attention, ask questions, show you care.
  4. Growth Mindset: Discuss challenges, goals, and development.
  5. Notes & Follow-Up: Write down key points & next steps for both of you.


One-on-one meetings are more than just checking boxes. They're a golden opportunity to connect with your team, understand their needs and aspirations, and ultimately, unlock their full potential. 

But effective communication is key, and the questions you ask play a pivotal role.

🌟 The Power of Powerful Questions:

By incorporating well-crafted questions into your one-on-ones, you can achieve several key benefits:

  • Spark Deeper Conversations: Thoughtful questions can unearth valuable insights you might have missed otherwise. They encourage employees to share challenges, roadblocks, and untapped potential.
  • Fuel Growth and Development: Effective questions can spark conversations about career goals, skill development, and opportunities for advancement. This empowers employees to take ownership of their growth and become more engaged.
  • Build Stronger Relationships: Asking the right questions demonstrates your genuine interest in your team members. It fosters trust, open communication, and a more positive work environment.

🌟 Continuous Improvement:

The one-on-one process is an ongoing journey. As you have these conversations, pay attention to what works well and what doesn't. 

Here's how to ensure continuous improvement:

  • Gather Feedback: Regularly ask your team for feedback on the one-on-one process. Are the questions helpful? Are the meetings productive? Their input will help you refine your approach and make adjustments as needed.
  • Adapt and Experiment: Don't be afraid to experiment with different question formats or topics based on the employee's role, experience level, and current focus.
  • Embrace New Ideas: The best questions can come from anywhere. Be open to suggestions from colleagues, industry experts, or even your own team members.

🌟 Take Action and See the Results:

The suggestions and questions outlined in this blog are a starting point. The most important step is to take action! 

Put these questions into practice, listen actively, and engage in open conversations. You'll be amazed at the positive impact effective one-on-ones can have on your team, your company, and your own leadership skills.

Remember, one-on-one meetings are an investment in your team's future. By mastering the art of asking thoughtful questions, you can create a space where employees feel valued, empowered, and ready to achieve great things. 

By following these tips and using the questions provided, you can transform your one-on-ones from meetings to engaging conversations.

So, grab a cup of coffee, schedule your next one-on-one!

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More Articles From Ali Khan

Ali is a co-founder of Wrenly known for his innovative thinking and exceptional drive to create value for every Wrenly customer. His dedication, mentorship, and leadership skills have not only shaped various careers but have also made him an invaluable asset to the Wrenly team.

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