1. What’s your biggest accomplishment this month?

Everyone likes talking about their wins, so why not start with that? Here are a few ways you might phrase this question:

• What have you been working on recently?
• Is there any work you’re proud of?
• What are some highlights of your recent work?
• Any good success stories?

Why the question is effective

• This question provides a sense of forward motion and progress. A worker needs to know things are moving along and getting better.
• Relaying positive information gives your team member a sense of personal accomplishment. By communicating positive information, they’re setting an upbeat context for any further discussion.
• The answer can give you both oversight power and improvement potential. You have a measurable way to track your employee’s work and to see if they’re contributing in the ways you need them to.

2. What’s your biggest challenge right now?

Challenges are good things because they make us better. While this question may not have the same psychological uptick as the first one, it’s important to ask nonetheless.

Why the question is effective

• First, you get to understand where your team member is struggling. You may have no idea the software is malfunctioning or a coworker is slacking. As a manager, you’ve got to be aware of any pinch points in an employee’s process, work, or even the company culture.
• This question also puts your conversation into problem-solving mode. And a problem-solving conversation is a productive one. You’ve gone beyond small talk and office chit-chat and are actually working on things that have ROI.

You get to improve processes, eliminate barriers, and enhance productivity. When you know about a problem, you can fix it. Thankfully, most challenges have a solution.

3. What should we do differently?

Every team member has a different perspective on the company. Your job as a manager is to synthesize all this information and improve the company.

Everyone can add value—and not just the value that comes from performing a strictly defined job title. Your team can provide value by sharing their own managerial insights.

One question my CEO asks me is, What processes can we improve? Every week. Same question. I don’t always have any improvements to suggest, but at least the opportunity is there.

Why the question is effective

• It shows your team things can be done differently. A good company is dynamic—adapting to workers’ needs, adjusting to the shifting market, and accommodating industry trends. Introducing “do different” terminology in your discussions opens up the possibility of change and improvement. That’s invaluable for both worker satisfaction and company growth.
• Team members recognize the value they can provide beyond their job description. As mentioned above, everyone has a larger role to play in the company. You’ve got to harness this contribution. Your workers need to understand their role in improving the company as a whole.
• You gain insight that enables you to introduce changes that make the company better. Sure, you may not always act on every suggestion. But now and then, you’re going to discover some things that truly need to change.

4. What resources would be helpful to you right now?

Using the word resources leaves the door open to a wide variety of things—whether it’s a virtual assistant, a larger desk, a better computer, more meetings, fewer hours, or even a vacation. Just be sure there’s a mutual understanding that you can’t deliver anything or everything they want.

Why the question is effective

• This question gives you concrete, actionable information you can use to help a team member grow and improve and lets them know you’re prepared to do anything you can to help.
• You may be surprised by the answers you get. Sometimes, what you think your employees need is different from what they actually do. You may be prepared to throw more people or money at a project, whereas the real need is a small, inexpensive tweak. You won’t know unless you ask.

5. Is there anything I can help you with?

Finally, provide a connection that lets your employee know you’re a human. This is the broadest question of all and can transcend the office, the work, and the business.

Feel free to spin the question in a more specific way based on things you know are going on in your team member’s life:

• Perhaps your employee had water damage in their basement. “You guys had some damage from the flooding? Is there anything I can help you with?”
• Maybe she’s participating in a community volunteer project. “You’re heading up the Main Street Cleanup this week. Anything you might need help with?

Why the question is effective

• This question reaches beyond strictly professional needs, allowing you to understand any personal factors that may influence their work.
• Communicating your interest in your team member’s life and improvement helps build trust and strengthens your working relationship.
• This question truly demonstrates your concern for your team member’s success and well-being. You’re more than just a company-minded manager. You’re available to improve their work-life balance.