You Can’t Put Lipstick on a Pig: 10 Questions Every Business Owner Should Ask Their Team

Let’s be honest.

You can’t decorate your way out of bad team dynamics.

Not with free coffee.
Not with a ping pong table.
Not with “fun” Friday socials.

If your team relationships are strained, unclear, or dysfunctional, none of that matters. Strong teams don’t happen by accident — they happen through regular, honest conversations.

These 10 questions are designed to help you reconnect with your employees, understand what’s working (and what’s not), and catch small issues before they turn into bigger problems like disengagement or turnover.

Pro Tip: Set the Tone First

Before you start, let your employee know this is simply a check-in, not a performance review. Keep it relaxed and conversational. You don’t need a script or perfect wording; the goal is to show up as yourself, be present, and create space for an honest conversation.

You might say:

“I just wanted to check in and get a sense of how things are going for you right now — both at work and outside of work — and see if there’s anything I can do to better support you.”

You don’t need to ask all these questions at once. Pick 4–5 that feel right and let the conversation flow naturally.

1. How are things going for you right now — at work and outside of work?

Show you care about the whole person, not just the job.

2. What does a really good week at work look like for you?

Understand what success and satisfaction look like from their perspective.

3. What part of your job do you enjoy the most right now?

Identify what energizes and motivates them.

4. Where do you feel you add the most value right now?

Encourage them to reflect on their strengths.

5. What personal or work goals are important to you right now?

Understand what they’re working toward in life and career.

6. What would you like to learn or get better at this year?

Open the door for growth and development.

7. What’s been the most frustrating part of your job lately?

Create space for honest feedback about challenges.

8. Is there anything slowing you down or making your job harder than it should be?

Identify tools, processes, or obstacles that may need fixing.

9. What’s something you’re proud of from the last few months?

Recognize wins and build confidence.

10. What’s one thing I could do that would help you succeed more?

End the conversation by showing you’re willing to support them.

The Takeaway

No amount of perks, posters, or ping pong tables will fix broken relationships. You can’t put lipstick on a pig.

But these questions? They start the real work. Honest conversations build trust. Trust builds engagement. Engagement builds strong teams.

Need help building a stronger team? I help small business owners improve retention, strengthen their teams, and create workplaces where people want to stay. Reach out any time at emarriott@iris-hr.com.