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Team Productivity

Five Questions to Ask Your Team Members Every Month

Daniel Threlfall
February 18, 2014

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

Why the Question Is Effective

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

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

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

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:

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

Why the Question Is Effective


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.

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