Tool for the Field: Developing Better Questions Over Time 


If we are teaching something, we ought to value students’ thoughts, right? In fact, when we ask students for their thoughts and listen carefully to what they say, we show them that we value their thoughts. Indeed: students are more likely to value our thoughts as well!


The purpose of this tool for the field is to introduce a set of questions—and question types—you can use again and again to help students think and learn better. And there are tips for developing the skill and art of asking better questions. There are also activities that will help you to develop the skill and art of questioning with on-the-job practice.

List of Better Questions

This list is intended to provide you with the “flavor” of a good question by letting you see some examples (other examples appear in the webinar). Also notice that good questions don’t always have to have the form of a question (see the second “question” in this list). The point is to get students talking about their thoughts about the math problem.

  • How could you start this problem?
  • Tell me what you know and what you don’t know about this problem (or topic).
  • Does this problem remind you of any you’ve done before?
  • Can you rephrase what (another student or the textbook) said?
  • What questions do you have about this topic?
  • How could you check whether this answer is reasonable?
  • What do you need to know how to do in order to be able to solve this problem?
  • Why?
  • How do you know that?
  • How did you get that answer? (This is a good question even when the original answer was correct, especially if it appears that the student guessed!)
  • Can you explain that a bit more for me?
  • What steps did you take to get that answer?

List of Not-So-Good Questions

These questions are the most common in math classrooms. Of course, there are indeed times when a quick drill-type question makes a lot of sense. But, then, it is also helpful to follow up most of these questions with a more open-ended question. Good questions elicit thinking. That’s what we want in math.

  • What’s the answer to number five?
  • Here’s where you’d use the Pythagorean Theorem, right?
  • This one’s an easy one. You know the answer, don’t you?
  • Is this a right triangle? (This might actually be a good question if used as a hint. For example, it could be asked if the student is trying to use a right triangle rule on a non-right triangle.)
  • Do you want me to go over that another time?

Developing the Capacity to Ask Better and Better Questions

Using better questions on the job will be an adventure! Don’t be too hard on yourself. You will improve. Paraprofessionals are in a good spot to ask good questions since, in a one-on-one or small-group setting, students will not worry so much about what their classmates might think of their answers!

Here are a few tips to help you improve the skill and art of asking better questions.

Working on the Skill of Asking Better Questions

  • Any skill takes a lot of practice. Otherwise it’s not a skill!
  • Like most of us, you too probably just naturally think up questions of the sort that Mr. Samson asked.
  • We’ve all been there. We can learn not to do it!
  • How? Pause and think some before asking. Give yourself “wait time”!
  • It takes practice to break the unproductive question-asking habits that we’ve formed in the past. Been there, done that.
  • Practice—don’t give up! Become skillful!

Developing the Art of Asking Better Questions

  • Skillful questioning leads to artful questioning.
  • Why? Conversation about thinking requires a series of good questions.
  • You have to choose which questions to ask to help a good conversation move along.
  • Make the choice based on what you learn about the challenges the lesson has for students’ thinking. Making such a choice is where the art comes in.
  • What is “art”? Art involves inspiration, insight, and improvisation—on top of skill.
  • Fortunately, many of the better questions in the “better questions” list can be sequenced in just this way.
  • Becoming artful requires practice.

Putting it All Together

Developing the skill and art of questioning probably seems overwhelming.

It’s difficult for anyone who teaches—teacher or paraprofessional—(1) to know when to ask which good question, (2) how to craft a follow-up question that will take a student to a deeper level of understanding, and (3) how to recognize when a student is emotionally in need of some hints or reassurance rather than another good question.

It’s tricky, isn’t it? Asking a good question at the wrong time can make it a bad question in the sense of not being productive for the student!

But, really, you are already doing much better than average as soon as you start asking some better questions.

Mr. Samson would do better if he could read the material and listen to the webinar in this unit. After all, he really cared about his students’ performance. He did care what they thought—he just didn’t know how to get there. Or even how to start. You know how to start.

And you can get started immediately. Practice with your own kids or grandkids or children in the neighborhood. It’s an adventure in thinking! It’s fun!

Remember to ask questions of yourself, as you think about what happened after the conversation is over. Make changes based on your reflections, and make them at your own pace. Your skillfulness and artfulness will improve over time.


  • Re-read the list of better questions. For each question, ask yourself, “Why is this a good question to ask?”
  • Re-read the list of not-so-good questions. For each question, ask yourself, “Why is this not a very good question to ask?”
  • Come up with three good questions and three not-so-good questions of your own. Explain (to yourself or to a small group) why your questions are good or not as good.
  • Why is the second list of questions titled “Not-so-Good Questions” instead of “Bad Questions” or “Stupid Questions”? See this link for some thoughts: