Stupid questions are annoying. But the right questions can make a huge difference.

I’m suggesting five questions that you should ask your employees each month. These aren’t stultified performance review questions. These are real questions that can dramatically improve an employee’s morale, output and quality of work.

Questions To Ask Employees

For managers, asking the right questions is perhaps the only way to be a truly effective manager. No one likes the proverbial my-way-or-the-highway boss, the control freak, or the micromanager.


What will keep you from turning into one of these managerial freaks?

It’s about asking the right questions.

How do you ask the right questions?

Just as important as asking the right questions is asking them in the right way. These questions will be as useless as soundwaves disturbing the ether unless you ask them in the right way.

Here are three tips for asking the right questions in the right way.

  1. Ask sincerely. Ask these questions with realness. You really want to know the answers. You’re not reading a form. You’re engaging with a person. Ask with authenticity.
  2. Ask humbly. One asks questions in order to get answers. In other words, we ask to learn. Be prepared to hear answers that you may not like. This isn’t a time to protest answers with a no-can-do attitude. This is a time to listen — openly and honestly. Be patient, and hear them out.
  3. Ask frequently. I’m suggesting that you ask these questions monthly. Totally transparent answers may not be forthcoming the first time you try. But as your team members are reminded of these questions, the gears begin to turn, and the thoughts begin to flow. Ask regularly.

Now, let’s ask the questions.

1. What is your biggest accomplishment this month?

There are other ways to restate the 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 helps provide a sense of forward motion and progress. A worker needs to know that things aren’t just the same-same humdrum, but are moving along, going forward, getting better.
  • When a worker relates positive information, it gives them a sense of personal accomplishment. By communicating positive information, they are setting an upbeat context for any further discussion.
  • As a manager, answers to such questions give you both oversight power and improvement potential. You have a measurable way to track the employee’s work, and to see if they are actually contributing in the ways that you need them to.

2. What’s your biggest challenge right now?

The flip side of the biggest accomplishment question is the “biggest challenge” question. This question doesn’t have the same psychological uptick as question number one, but it is a very good question, nonetheless.

Why the Question Is Effective

  • First, you get to understand where the worker is struggling. You may have no idea that the software is malfunctioning, that her coworker is slacking, or that the office chair is putting his back out. As a manager, you’ve got to be aware of any pinch points in an employee’s process, work, or the company culture as a whole. Once you know about the problems, you can nail them.
  • This question also puts your conversation into problem-solving mode. First, of course, you’ve got to understand the problem. Then, you solve it. A problem-solving conversation is a productive one. You’ve gone beyond small talk and office chit chat, and you’re actually working on things that have ROI.
  • You get to improve processes, eliminate barriers, and enhance productivity. When you know where your team member is struggling, you can do something about it. For most challenges, there is a solution. Challenges are good things, because they make us better.

There are things you can do to solve problems, but you have to first know that there’s a problem to solve. In other words, you have to ask the question — “What’s your biggest challenge right now?”

3. What things should we do differently?

Every team member has a different perspective on the company. Your designer is going to look at things in a very different way from your programmer. Your content writer is going to have a vastly different approach from your administrative assistant.

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 their performing a strictly-defined job title. They can provide value by sharing their own managerial insights.

One question that 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 question is there — improvement, progress, betterness.

Why the Question Is Effective

  • The team member understands that things can be done differently. A good company is one that is dynamic, adapting to workers’ needs, adjusting to the shifting market, and accommodating industry trends. By introducing “do different” terminology in your discussions you are entertaining the possibility of change. Being open to “what can we do better?” is invaluable both for worker satisfaction and company change.
  • The team member recognizes the value that he or she can provide beyond his or her 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 for improving the company as a whole.
  • You get to introduce changes that will improve the company. Again, you gain information that allows you to 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?

This question gives you concrete actionable information that can help a worker do better, do more, or do it right. By using the word “resources,” you’re leaving the door open to a wide variety of things. She may need a virtual assistant, a larger desk, a better computer, more meetings, fewer hours, a vacation, whatever.

Why the Question Is Effective

  • You may be surprised by the answers you get. Sometimes, what we managers think our employees need is different from what they actually need. We 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.
  • This question should be tempered, of course, by a mutual understanding that you can’t deliver anything or everything they want. You have limitations. However, let your employee know that if you can do anything to help, you’re prepared to do so.

5. Is there anything I can help you with?

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

You can spin the question in a more specific way, to guide them toward answers:

  • Perhaps you know that your employee and his wife recently had a miscarriage. “How’s your family doing? Is there anything I can help you with?”
  • Or, they had water damage in their basement. “You guys had some damage from the flooding? Is there anything I can help you with?”
  • Maybe she is participating in a community volunteer project. “You’re heading up the Main Street Cleanup this week. Anything you might need help with?

You’re more than just a company-minded manager. You’re available to improve their work/life balance.

Why the Question Is Effective

  • Such a question may reach beyond strictly professional needs, allowing you to understand any personal factors that may influence their work.
  • This question truly demonstrates your concern. You’re a real human, regardless of the caricature of pointy-haired Dilbert bosses who lack souls.
  • By communicating your interest in their life and improvement, you’re helping to improve your working relationship with them.


Being an effective manager is about understanding. You won’t understand unless you listen. The best information to listen to is answers to the right questions.

Questions are one of the manager’s most powerful tools. Knowing how to wield them with precision is your key to becoming a better manager. Like asking your team the right questions, it’s crucial to choose the right project planning tools. Try TeamGantt’s free project management software, complete with all the team collaboration tools you’ll need to lead a successful project.

Planning Your Projects Can Be Easier

Thousands of people from over 60 countries use TeamGantt to plan, track, and manage their projects! Join them in making project planning an easier part of your life.

Learn More

Try TeamGantt

Create a beautiful project plan completely free, forever.

Try Free