The 5 Questions You NEED to Ask in Every 1-on-1

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One-on-one meetings aren't just routine check-ins, they're opportunities to build stronger relationships, boost productivity, and foster growth within your team. The key to transforming these meetings from obligatory calendar items into meaningful conversations lies in asking the right questions.

Let's explore five essential questions that can revolutionize your one-on-ones, plus a bonus question that could change how you lead.

1. "How are you doing—really?"

This seemingly simple question sets the foundation for authentic dialogue. The emphasis on "really" signals that you're looking for honest communication, not just a surface-level response. When asking this question:

  • Give space for a genuine response
  • Listen actively without rushing to solutions
  • Pay attention to both positive and negative signals
  • Follow up with empathy and understanding

If they share something positive, use it to build momentum. If they express challenges, resist immediate problem-solving and focus first on understanding and empathy.

2. "What are you working on?"

While you might track projects through standups or team meetings, one-on-ones provide space for deeper discussion about priorities, challenges, and alignment with broader goals.

This question helps:

  • Uncover insights that don't surface in group settings
  • Identify potential roadblocks early
  • Connect daily tasks to career development goals
  • Create opportunities for targeted support

Pro tip: Acknowledge existing context while inviting elaboration: "I know we touched on this in standup, but I'd love to hear more about how it's going for you personally."

3. "What are your biggest wins?"

Celebrating achievements, whether major milestones or small victories, is crucial for maintaining motivation and building confidence. This question:

  • Reinforces team members' value
  • Builds confidence through recognition
  • Creates a culture of celebration
  • Identifies patterns in successful performance

When discussing wins, ask follow-up questions like "What made this win meaningful?" or "What did you learn from this experience?" to extract deeper insights and learning opportunities.

4. "What are your biggest challenges?"

Creating space for honest discussion about challenges builds trust and enables proactive problem-solving. When addressing challenges:

  • Foster a judgment-free environment
  • Collaborate on solutions rather than dictating them
  • Follow up consistently on discussed issues
  • Use challenges to identify growth opportunities

Remember: Your response to shared challenges shapes future openness. Validate experiences before jumping to solutions.

5. "What's one thing I can do to make your job easier?"

This question transforms you from manager to partner in your team's success. It:

  • Demonstrates active commitment to support
  • Uncovers hidden operational friction
  • Creates accountability for improvement
  • Builds trust through action

Be prepared for answers ranging from simple process tweaks to significant operational changes. Whatever the response, follow through with clear action steps.

Bonus Question: "Is there anything we should be doing differently?"

This open-ended question invites innovative thinking and constructive feedback about processes, communication, and leadership approaches. It signals your openness to change and commitment to continuous improvement.

Making It Work

The power of these questions lies not just in asking them, but in how you handle the responses. Create psychological safety, demonstrate genuine interest, and follow through on insights and feedback received.

Remember: Regular one-on-ones using these questions build stronger teams, improve communication, and create an environment where both individuals and the organization can thrive. By incorporating these questions into your one-on-ones, you'll transform routine check-ins into powerful tools for leadership, growth, and team development.