The Value of Empathetic Questioning in Employee One-on-Ones

Empathetic leadership is essential to creating a psychologically safe workplace—and that has tangible benefits for individuals and businesses alike. Psychologically safe organizations see significantly 76% higher engagement, for example, and 50% greater productivity.

One way to create a psychologically safe workplace is by creating frameworks for feedback—like employee one-on-ones. Of course, it’s not enough to just put those frameworks in place; you want to make the most of them. That means practicing active listening and actually acting on the feedback you receive.

Ten Empathy Building Questions

Simon Sinek has a well-known story about a conversation he had with a barista at a Las Vegas hotel—Noah—who seemed to be exceptionally happy at work. Upon questioning, Noah revealed that he really liked his job and one reason for that was the supportive management, who would often stop by his coffee station and ask, “Do you need anything to do your job better?” That was it. A simple question showed Noah that his managers were supportive, caring, and watching out for him (rather than watching him in a Big Brother-way).

Here are ten questions you can use in a one-on-one that emulate that same spirit of servant leadership:

• What roadblocks are you facing, and how can I support you? Show that you care and are there to help, not judge.
• What motivates you to get up in the morning? Knowing what motivates your employees is key to helping them thrive.
• What project are you most excited about? Odds are that people will excel when doing work they love. Find out what they’re passionate about.
• How do you define success at work? Similar to the above questions, this one can be indicative of what the person is interested in and what drives them.
• Is there feedback you’ve been hesitant to share with me? In case apathy or discontent is brewing, this is a good way to catch it before it festers.
• What would make you more effective in your role? Like Noah’s bosses, you’re showing that your role is to help your team excel.
• How are you managing stress/workload? This is an opportunity to determine if someone is feeling overwhelmed, which they won’t necessarily share proactively.
• What’s something you’re learning right now? Note that this could be on or off the job. Either way, it’s a way to figure out what the person is curious about.
• How can I help you grow professionally? Show that you care about their development beyond the immediate role/company.
• What’s one thing I could do differently as your leader? Feedback goes both ways. Don’t just give feedback—invite it too.

More Than a Checklist

When employees feel heard and valued, they’re more likely to bring their best ideas, take creative risks, and stay committed to the team. The questions above are one way to put empathetic leadership into action—and while they can serve you well in an employee one-on-one, they shouldn’t be rattled off like a checklist. Weave them into conversation naturally and look for other opportunities to explore these topics. And don’t get hung up on asking the perfect question. In the end, it’s simply about showing that you care.