Great Mid-Year Review Questions for Human Centered Leaders

Mid-Year Review Questions: A Human-Centered Guide to Inspire and Grow

Mid-year reviews are your halftime huddle in the performance Super Bowl. It’s that moment where you catch your breath, revisit the playbook, and decide what happens next. Whether your company requires them or not, don’t skip this chance to pause and reflect.

If your boss doesn’t have one scheduled, here’s your moment: ask for it. Proactive reflection isn’t about checking boxes—it’s about investing in your growth and building stronger connections.

Mid-year reviews are the perfect time to summarize, celebrate, challenge, and inspire. And one of the most powerful ways to do that? Great questions. The kind that spark insight, not just answers. The kind that say, “I see you,” and “I believe in what you can become.”

Below are some of my favorite mid year review questions, organized by purpose. Whether you’re the one leading the review or you’re preparing for your own, these prompts will help bring the conversation to life.

Mid-Year Review Questions to Reflect on Performance

• How are you feeling about the year so far?
• How would you describe what’s happening with this project?
• What are you most proud of this year?
• What lessons have you learned?
• How are you different now than you were 6 months ago?
• What new skills have you developed?
• Where are you stuck?
• What new relationships have you fostered?

Questions to Challenge and Turnaround

• Have you ever had an experience like this before? Can you describe what you did you do that helped at that time?
• What patterns do you see?
• What do you think we should do?
• Which habits would you like to change?
• What’s the most important thing you can do to turn this situation around?
• What additional resources do you need?
• How can I best support you?

Mid-Year Review Questions to Encourage

• What would it look like if?
• What would happen if?
• Or you can use our BECOME tool to inspire deeper encouragement conversations.

Questions to Solicit Feedback

• If you were in my shoes, what would you be doing differently?
• What can I do to better support you and the team?
• What have I done this year that most ticked you off?
• Can you describe what I’m doing that is most helpful to you?

Mid-Year Review Questions to Gather Ideas

These sessions are also a great time to invite team members to share their best ideas to improve the business.

You can simply ask a courageous question or two. Or, invite them to prepare for their mid-year review by bringing you one idea to improve the business.

• What’s one policy that just sucks (and how would you change it)?
• Can you think of one idea that would help you provide a better customer experience?
• What’s one change you could make that would improve your productivity?
• What’s your best idea to improve teamwork and collaboration around here?
• If you could make one change to improve our team huddles what would that be?

If you’ve been using our one-on-one meeting tools on a regular basis, preparing to conduct or receive a review should be that much easier.

 Mid-Year Review Q&A: What Leaders Are Asking

Q: What if my company doesn’t require mid-year reviews?
A: Do one anyway. This isn’t about bureaucracy—it’s about leadership. Taking the initiative to reflect and connect signals that you care about development, not just deliverables.

Q: How do I make mid-year reviews meaningful with remote or hybrid team members?
A: Presence matters more than place. Turn on your camera. Eliminate distractions. Lead with connection: “I know we haven’t had as many face-to-face moments—how are you really doing?” Remote team members often feel out of the loop. Use this time to reinforce that they’re seen, valued, and heard.

Q: What if the person I’m reviewing is already crushing it—do they even need this?
A: Absolutely. High performers crave challenge and recognition. Use this opportunity to stretch them. Ask: “What would it look like to take this to the next level?” or “Where do you want to grow next?” Celebrate their impact, and explore how they can mentor others or lead something bold. You can also use this time for a career conversation about what’s next with this career conversations tool. 

Q: What should I do if the person shows up emotionally guarded or quiet during the review?
A: Go gently. Sometimes, silence is self-protection. Try a low-pressure opener: “I know these conversations can feel a little formal. No pressure—let’s just talk about how things are going for you.” Give them space. And if they stay closed? Follow up later with: “I’d love to keep the door open if anything bubbles up.”

Q: How do I document the conversation without killing the vibe?
A: Jot a few shared takeaways at the end. Say, “Mind if I capture a few of the things we talked about so we can revisit?” Better yet, co-create the notes during the chat. It builds ownership.

Bonus: Preparing for Your Own Mid-Year Review with Your Boss

Mid-year reviews aren’t just something you give—they’re also something you receive. And if you want the conversation with your boss to go beyond “you’re doing fine” or a vague “keep it up,” you’ve got to show up ready to lead the dialogue too.

Here’s how to walk in clear, calm, and ready to grow:

Do Your Homework

Don’t rely on memory. Come in with:

• A short list of key accomplishments since the beginning of the year

• Metrics, milestones, or testimonials that show impact.

• A story or two that highlights how you’ve demonstrated growth or leadership.

Bonus points if you bring an example of how you’ve helped others succeed too.

Ask for What You Need

If your manager tends to be vague or noncommittal, guide the conversation. Use prompts like:

• “I’d really appreciate specific feedback—what’s one thing I’ve done well, and one area I could improve?”

• “Looking at the next 6 months, where should I focus most?”

• “What does success look like for me at the end of the year?”

Handle Tough Feedback with Grace

Sometimes the review brings up surprises or even frustrating feedback. If that happens, pause, breathe, and use the opportunity to learn, not defend.

📺 Watch: What to Do When You Get Frustrating Performance Feedback

This quick video will help you stay grounded, turn frustration into insight, and respond with credibility—not combativeness.

Close the Loop

At the end of your review, try this:

• “Just to confirm, here’s what I heard… does that match your perspective?”

• “Here are three things I’m taking forward from this conversation.”

• Even if your boss doesn’t show up fully prepared, you can lead by example. The more intention you bring to the process, the more value you’ll take from it.

See Also: How to Hold an Effective Mid-Year Review in a Pandemic

Your turn.

What are your favorite mid-year review questions?