One Question Great Leaders Ask

One-on-one debriefs with your team members are one of the most underutilized leadership tools. Not because leaders don’t have them, but because they don’t use them to their potential. Most one-on-ones turn into status updates, but the best leaders don’t just manage work in a one-on-one; they uncover what’s really going on beneath the work. Today, we discuss one of my favorite questions to ask in a one-on-one and how you can use it to help your employees thrive: What’s getting in your way right now?

Why Asking “What’s Getting In Your Way Right Now” Is So Powerful

1. It Surfaces Hidden Friction

Your team rarely tells you what’s actually slowing them down unless you ask. And even then, you have to ask the right way. Sometimes the barrier isn’t the work; it’s confusion, fear, misalignment, or even another person.

2. It Builds Trust Fast

When you ask this question consistently, your team starts to see that you aren’t just checking in on them, you are advocating for them. The more you can help people feel this way, the more they will open up.

3. It Shifts You From Manager to Leader

Managers track progress; leaders remove obstacles. Asking, “What is getting in your way right now?” forces you into the right role.

Q: Has anyone ever asked you this question? How did you respond?

Where Leaders Get This Wrong

Leaders who ask this question and get limited responses often…

• asked it once, not consistently

• asked it but didn’t act on the answer

• or asked it, but their team didn’t feel safe enough to answer honestly yet

How to Ask It the Right Way

1. Ask It Every Time

When you ask questions inconsistently, people think every question is an attack. If you ask it consistently, you build safety, and you prove that you are not looking for a problem; you are looking to be a solution. 

2. Be Comfortable With Silence

You don’t have to move on or prompt responses. Let people think and process the information. You will get better answers if you make it clear you are not rushing through the meeting. 

3. Follow Up With Curiosity

• “Tell me more about that.”

• “How long has that been an issue?”

• “What would help remove that?”

Q: When was the last time someone on your team told you what was really getting in their way? Do your one-on-ones feel like conversations or reporting sessions? Why?

Application Activity:

1. If you have not already, integrate one-on-one meetings with your team. Schedule 20-30 minutes with each direct report and ask one question: “What is getting in your way right now?” You don’t have to overcomplicate the meeting. One-on-ones are less about what you talk about and more about creating the opportunity to hear what your team is really thinking.

2. Make your one-on-ones better! The Weekly Engagement Playbook - 52 Weeks of Connection Questions to Elevate Your Leadership Influence is designed to help you get to know your employees, give meaningful feedback, and help them reach their goals. This playbook can be used digitally or printed and includes 52 sets of 5 engaging questions you can use during your weekly one-on-ones. Take the guesswork and planning out of your one-on-ones and focus on the connection you are building instead. You can purchase this resource at jeffhancher.com/products