Struggling to Keep Your One-on-Ones Productive? Try These 15 Questions Today!

If you’ve ever found yourself struggling to keep your one-on-ones meaningful or productive, you’re not alone. As a leader, you know how crucial these conversations are for your team’s success, but without structure, they can sometimes feel like just another task. The key to making these sessions impactful is having a consistent agenda and asking the right questions.

In the military, we held monthly counseling sessions (One-on Ones) with a standard document, asking the same questions and discussing key topics each time. This ensured we reviewed performance and set goals for growth. It was essential that my soldiers knew the questions in advance, so they could come prepared with thoughtful answers. This not only made our discussions more productive but also set a tone of open communication and reflection from the start. Over time, the routine fostered a culture of accountability, where the process became second nature.

Just like in the military, private companies can benefit from a structured framework for one-on-ones. A consistent agenda ensures that performance, challenges, and goals are always addressed, keeping the conversation focused and fostering accountability. When employees know what to expect, meetings become more productive and meaningful.

Here are some questions you can ask during a counseling session to foster open communication, accountability, and growth:

Performance and Feedback:

1. How do you feel about your performance this month? (Encourages self-assessment and reflection.)

2. What challenges did you face, and how did you overcome them? (Promotes problem-solving and perseverance.)

3. Do you feel like you’ve met the expectations that were set? If not, why? (Helps identify areas where clarity might be needed.)

4. What feedback would you give yourself based on your performance? (Encourages self-evaluation and accountability.)

Goal Setting and Improvement:

5. What goals have you set for yourself, and how are you progressing? (Ensures alignment with company or team goals.)

6. Is there an area where you feel you need more support or resources? (Opens the door for support or guidance.)

7. What skills or training would you like to improve upon? (Encourages growth and professional development.)

Communication and Team Dynamics:

8. How has communication been within the team, and do you feel heard? (Focuses on teamwork and communication effectiveness.)

9. How can I, as your leader, better support you? (Demonstrates willingness to adapt leadership style.)

10. Are there any issues you’re facing with colleagues that may affect your work? (Provides an opportunity for conflict resolution.)

Accountability and Ownership:

11. Can you identify an instance where you took ownership of a situation or task? (Promotes responsibility and accountability.)

12. How do you manage your workload, and are there any areas where you feel overwhelmed? (Helps identify areas for support in prioritization or time management.)

Future Outlook:

13. What are your goals for the upcoming month? (Encourages forward planning and focus on success.)

14. What steps will you take to improve or address areas we’ve discussed today? (Establishes a roadmap for improvement.)

15. What does success look like for you in the next few months? (Aligns long-term vision with immediate actions.)

Having structured, open conversations like these helps build stronger communication and accountability, just like it did in the military. By staying consistent and having senior leadership check-ins, companies can ensure that one-on-ones are happening regularly and driving both individual and team performance.

Call to Action: If you’re a leader looking to elevate your team’s performance, start using these questions in your next one-on-one. Consistent, private conversations with active listening can transform your organization’s culture and success. Your team's growth starts with the right questions why not start today?

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