Communication makes or breaks the employee experience. We often hear about what companies think they’re doing right—open-door policies, team meetings, surveys—but real, intentional one-on-one conversations still go missing. At Tru Art HR, we believe the best managers are the ones who talk with their employees, not just to them.

Here are five conversations that shouldn’t be optional—they’re must-haves.

1. How’s it going… really?

This isn’t a performance check-in or a quick “How are you?” in passing. This is a genuine, sit-down conversation where you give someone space to open up. What’s going well? What’s frustrating? Are they feeling supported? You’d be surprised what you learn when someone feels safe enough to be honest. It’s the foundation of trust—and trust drives retention.

2. Where do you want to go from here?

Too many people leave jobs because no one ever asked about their goals. Career development doesn’t have to mean promotions or huge changes—it can be skill-building, cross-training, or just getting better at what they love. Make time to ask employees where they see themselves in six months or two years, and how you can help them get there.

3. What’s getting in your way?

This one’s about clearing obstacles, not assigning blame. Employees often deal with roadblocks they don’t feel empowered to fix—inefficient systems, unclear expectations, or even interpersonal friction. Asking this question signals that you care about their day-to-day and are willing to remove the clutter so they can do their best work.

4. How do you prefer to work and receive feedback?

We’re all wired differently. Some people want direct, real-time feedback. Others need time to process. Some like detailed instructions; others prefer autonomy. Having this conversation helps avoid frustration and makes your communication more effective. It also shows respect for individual work styles—which is a big morale booster.

5. What keeps you here—and what might make you leave?

Yes, it’s a bold one. But it’s one of the most important. If you wait until the exit interview to find out what’s broken, it’s too late. Regular check-ins about engagement, satisfaction, and potential deal-breakers can help you course-correct before someone walks out the door. And when someone shares what does make them stay, you’ll know what to keep doing.

Conclusion

These conversations don’t need to be formal or scripted, but they do need to happen consistently. They build connection, improve clarity, and create a culture where people feel seen and heard.

How Tru Art HR Can Help

If you’re not sure where to start, Tru Art HR can help you or your managers build the confidence, tools, and structure to make these discussions part of your culture—not just one-off events. Want to talk more about this? Let’s connect.

Author: Oksana Day, SHRM-CP