Chapter 5
Asking Good Questions

Everybody knows how to ask good questions, right?

Wrong. In fact, the question you just read isn’t very good, because it implies its own “right” answer, the answer you’re supposed to give. It’s also a trick question because the “right” answer turns out to be wrong.

To illustrate how carefully questions must be worded to get useful information, let’s take an example. Let’s suppose that, as you’re shopping at the mall on a Saturday afternoon, you’re approached by a smiling person carrying a clipboard. You’re about to be interviewed by an opinion pollster.

Here’s the question you’re asked: “Do you feel that a person who has been caught engaging in an immoral activity can be trusted to serve in high elected office?”

Your opinions about politicians and public servants really aren’t the issue here. But you will learn the three reasons that public opinion polls don’t really tell us anything about public opinion.

1. You’ll deliver an opinion—whether you’ve got one or not. Suppose you really don’t care what may have gone on behind the closed doors of an elected officer. Maybe you haven’t been keeping up with the situation in Afghanistan, either, or spending much time fretting over our trade imbalance with China. But you don’t want to look stupid in front of the man holding the clipboard, pencil poised, waiting for your insightful comment.

So you give an answer.

Whatever answer you give, it may not really be your opinion. More likely, the pollster gets the opinion you gave because you felt you had to give one. This isn’t useful information.

2. The question means everything and thus doesn’t mean anything. In the context of the example question, what does “immoral activity” really mean? That all depends on who’s doing the moralizing. The phrase means different things to different people. Because it can mean anything, it really means nothing. How can the pollster evaluate your “yes” or “no” response without knowing your definition? Context is key.

Take a look at another part of that question: “who has been caught engaging.” Does that mean “caught in the act”? Or does it mean “suspected” or “accused”? Maybe it means “convicted.” How you interpret the wording affects how you respond to the question.

3. The question implies that there is a “right” answer. Look at the question again: “Do you feel that a person who has been caught engaging in immoral activity can be trusted to serve in high elected office?”

Notice that you’re given a binary, closed choice: your answer should be “yes” or “no.” There’s no room on the pollster’s chart for “maybe” or “that depends on what you mean by ‘immoral activity’” or “‘caught’ in what way?” or even “which high elected office?”

You’ve got to fit your response into one of two extreme slots.

Your definition of “immoral activity,” if you buy into the concept at all, probably carries a negative connotation. “Immoral” is bad. “Caught” is also bad.

On the other hand, “trusted” is good. So the wording of the question and the yes/no choice oversimplify a complex situation. You’re asked if you would give something good (trust) to a bad person (someone caught engaging in immoral activity).

You know, then, that the “right” (socially approved) answer—the one the smiling pollster with the clipboard expects from a fine, upstanding citizen like you—is “no.”

That doesn’t mean you’ll say “no,” of course. You might say “yes” simply to defy social expectation. Either way, you’re reacting to the way the question is worded and not necessarily its content.


Why Ask Questions?

Asking your staff questions and looking for feedback offers two immediate benefits—regardless of what answers you get.

When you’re listening, you’re learning. No matter how useful the answer is in practical terms, it reveals information about the person who gave it. You’ll discover a lot about workers’ attitudes as well as aptitudes by listening to their responses.

When you’re asking, you’re expressing respect. Workers may not thank you for asking, but they’ll feel good about it. You wouldn’t have asked if you didn’t want to know. You’ve brought them into the decision-making process and shown your respect for their knowledge and experience.

You win just by the very act of asking.


The Qualities of Effective Coaching Questions

It isn’t easy to ask a question that doesn’t fall into one or more of the traps we just discussed—or any others. You’ll need to ask effective questions if you really intend to get useful information from the people who work with you and support them in their growth. That’s why you need to learn the qualities of effective coaching questions. Good questions are

Image brief

Image clear

Image focused

Image relevant

Image constructive

Image neutral

Image open-ended.

Let’s look at each of these qualities.

An effective question is brief. So is an effective speech, marriage proposal, or court brief, and for the same basic reasons.

Image Your listener’s attention span is limited. (That depends a lot on interest and engagement. You probably have a little more latitude for a marriage proposal.)

Image Words written on the wind tend to blow away. If your question is long or convoluted, by the time you get to the end, your listener may have forgotten the first part.

Image The longer the question, the more likely you are to confuse your listener. Short sentences aren’t only easier to understand; they’re also easier to say.


An effective question is clear. “Do you think we should veto the proposal to discontinue the policy of rejecting parts that haven’t successfully gone through the nonmandatory inspection?”

That question is almost good enough to qualify as a referendum in the next election—one of those ballot initiatives that needs an explanation: “Note: A ‘no’ vote on this proposal indicates your support for continuing to reject parts that haven’t passed inspection. A ‘yes’ vote means you’re in favor of changing the current policy.”

If you veto a proposal to stop doing whatever it is you’re doing now, you would be agreeing to continue doing what you’re doing, right? So ask, “Should we keep rejecting parts if they haven’t passed inspection?”

Clear questions avoid:

Image Passive voice. A passive construction like “the offer is to be evaluated” or “the work is to be completed on time” often fails to specify something important—the person or people responsible for the action. Who’s going to be evaluating that offer or completing that work?

Image Fog. Sometimes big words and jargon happen to get in the way of communication. That’s fog. (If the confusion is intentional, as part of a smoke screen, it’s called smog.) For example, what does the phrase “managerial compensatory alternatives” mean? Is it ways to make up for some deficiency? By managers or to managers? Or is it choices of payment? Again, is the payment by managers or to managers? If managers make the payment, is the choice up to them or to whoever receives the payment?

Image Multiple negatives. We don’t mean only to avoid asking questions like “Don’t nobody here know nothing?” (What your fourth-grade teacher told you about grammar may be right, but it’s not enough to ensure good questions.) Consider our question “Do you think we should veto [negative] the proposal to discontinue [negative] the policy of rejecting [negative] parts that haven’t [negative] successfully gone through the nonmandatory inspection?” No wonder it defies understanding!

An effective question is focused. Target a single subject and a particular aspect of that subject per question. Otherwise you may render any answer meaningless.

Suppose you ask, “Do you think that a simplification in the development process, specifically eliminating the initial discussion, the storyboard, or the focus group, or any two of those steps, would result in a reduction in the quality of the final editorial product, if we also brought in an outside coder to beta-test all programs before release?”

The response is likely to be “Huh?” or “Could you repeat the question?” Even if you get an answer of “yes” or “no,” it won’t be much more useful, because you won’t know what it means—which you’ll find out as soon as you echo that answer.

“So you think we ought to get rid of the focus groups?”

“I didn’t say that. I like the focus groups.”

“Well, then, you want to drop the storyboarding?”

“No, we need the storyboarding. Why would I want to drop it?”

“But you said …”

You can imagine how the discussion goes on from here.

Break questions into their component parts, and ask them sequentially.

Q: Do you think we could eliminate the initial discussion without hurting the quality of the program?

A: Sure. Those discussions are a complete waste of time.

Q: How about the storyboard?

A: No way. That’s where we figure out how to make the program flow properly.

Q: What do you think of the focus group?

A: It doesn’t seem necessary, at least as part of the routine process.

Q: What if we hired a freelance coder to beta-test everything after we’re done with it?

A: An outsider wouldn’t catch the kind of mistakes I’m talking about. Q: Can you give me an example?

Now you’re getting useful feedback, without the frustration and confusion your multipart question would cause.

An effective question is relevant. Have you ever been “blindsided” by an irrelevant question? The surprise question might work for attack journalism and in TV courtroom dramas, but it doesn’t do much good in the office. Be clear about your purpose and honest about your motives. Keep your questions on subject and on target. If an answer strays off the point, tactfully refocus.

Suppose you ask, “What if we hired a freelancer to edit our documents after we’re done with it?” The response might be, “First we hire a bunch of consultants to tell us how to run the production process, and now you want to bring in an editor to hack up our copy! Why don’t we just can the editorial staff and ship the whole thing out?”

The mention of “consultants” sounds an alarm in your head. Maybe you were against hiring them from the start, but you got voted down. This is a perfect chance to vent your spleen and let somebody know that the resulting mess wasn’t your fault.

Don’t do it. You’ve got another problem on the table, and there may be no connection between the production consultants and the potential editorial freelancer.

Instead, reply, “I share your concern about consultants, but we need to talk through the editorial process right now. I really need your feedback on this.” You will use your coaching skills of being focused to keep the conversation on track.

An effective question is constructive. Accentuate the positive in your approach to questioning, not because it makes you seem nicer but because your questions will be more effective. It will open up possibilities for change and growth, rather than looking to point fingers and assign blame. Let’s look at the difference between asking a question with a negative slant or wording and asking a similar question in a positive way.

Negative: “How can we get people to stop skipping the meetings?” [“What should we do to punish people who don’t come to meetings?”] (Notice how this focuses on “skipping” and punishment.)

Positive: “How can we get people to attend the meetings?” “How can we make the meetings better, so everyone will show up?”



It’s more than just a matter of phrasing. You’re asking two different questions, and you’ll get two different answers.

Admittedly, discussing the negative question could be a lot more fun, but discussing the positive question will be much more productive, leading to genuine improvements—which may even mean eliminating an unnecessary meeting.

Sometimes, even when you ask a positive question, the person will have a negative response. You could ask, “How could we improve communications between the sales department and the public relations department?” Imagine the person replies, “I don’t know, but what we have now just isn’t working! PR doesn’t respond to e-mails, and Sales never seems to have any good suggestions!”

Some people go straight to the negative and need a little prodding to think about the positive. You can follow up with, “Okay, so if e-mail isn’t working, what would work?” Stay persistent on getting to a solution.

An effective question is neutral. Don’t confuse “neutral” with “neutered.” A good question may be controversial. (The most interesting ones are.) But it doesn’t imply the “right” answer through biased wording.

Here’s an example of the same question, first asked in a way that implies a “yes” answer, then with a built-in “no” response, and finally phrased in a “value-neutral” manner.

Implied “yes” question: “Do you think we should improve overall quality by hiring a freelance editor?” (Who wouldn’t be in favor of improving overall quality?)


Implied “no” question: “Do you think we should add an extra step to the editorial process by hiring a freelance editor?” (Who would favor adding an extra step?)

Value-neutral question: “What do you think about hiring a freelance editor?” (Elicits more opinions than just “yes” or “no.”)

An effective question is open-ended. Ask a “yes” or “no” question, and you’ll get (at best) a “yes” or “no” answer. That’s all. So often, that’s not enough.

Consider this scenario. You’ve got a bottleneck in the production process. You’re not sure how to unsnarl things, so you do the smart thing and ask the folks on the front line.

Q: Should we hire another online supervisor?

A: No way!
End of discussion. If you want more, you’ll have to go fishing.

Q: How come?

A: It’s a bad idea.

Q: Do you think it would be a waste of money?

A: You bet.

Q: So, you don’t think there’d be any advantage to the hire?

A: Nope.

This isn’t a discussion. It’s like pulling impacted wisdom teeth. You’re no closer to an answer, or even a useful suggestion, than when you started.

If you want to know whether the folks on the line think they need another supervisor, you asked the right question—and you got a clear answer. But if you want to explore possible solutions to a production problem, ask an open-ended question: “What can we do to fix the problem on the line?”

This new question, though admirably open-ended, fails the “value-neutral” test, as it clearly emphasizes that there is a problem. Instead of useful answers, you will more likely get defensive attitudes. Rephrase your question one more time: “What can we do to speed up production on the line?”

This question doesn’t point the finger and say that production is “too slow” (a problem for which somebody must be at fault). It just says you’d like to explore ways to speed things up.


It takes a bit of thought to ask a value-neutral and open-ended question. Make sure you give each question your careful attention.

By the way, an effective manager might frame the question with a positive comment about production. If you begin, for example, with “We’ve all been very pleased with the teamwork shown on the production line and the quality of our products,” you can more easily and safely ask the question “Now, what can we do to speed up production on the line?”


To get a truly open-ended question and start a conversation that brings forth a lot of possibilities, you may need to employ verbal softeners, which are phrases and words you can use to broaden the scope of a question. When you use them, you can open up new possibilities and creativity from your employee. You take the pressure off being “right” or having a “good answer.”

For example, let’s take the question “What should we do to speed up production?” As we’ve established, this is a positive, value-neutral question that is open-ended. By using verbal softeners here, you create more opportunities for the respondent to think creatively.

Image “What can [or could] we do to speed up production?” (Note that “should” in the original question implies that a recommendation must be given, and the employee may not be comfortable with this yet. “Can” and “could” look at possibilities.)

Image “What are some of the ways we could speed up production?” (Start brainstorming before asking for a decision or recommendation.)

Image “How might we start to speed up production?” (Baby steps. No need to come up with a complete solution, although one may come forth in the conversation.)

Verbal softeners can help elicit the other person’s resourcefulness and creativity as you sort through possibilities and options together.

Seven Major Types of Questions

There are seven main categories of questions: factual, explanatory, justifying, leading, hypothetical, alternative, and summary. Let’s take a look at when to use them and when to avoid them.

1. Factual Questions. The question “How many online supervisors do we employ?” asks for a number, not an evaluation. It’s a question that seeks a factual answer.

“How many online supervisors do we need?” asks for a number, but it’s not a factual question. To answer that, you must give an opinion.

“Is it raining?” is a factual question. “How’s the weather?” isn’t factual, although it might evoke the same information: “It’s raining!” It could also involve an opinion: “It’s great!” (from a farmer) or “Lousy!” (from a landscaper who can’t work) for the same light, misty rain.

You can verify the answer to a factual question by checking a second or third source. For the first question, count the number of online supervisors on the payroll (assuming they all actually carry the same job title, of course). For the second question, stick your head outside and see if you get wet. You can’t “verify” an opinion question.

If you want facts, ask factual questions. You may find it useful to begin coaching sessions with factual questions to establish common understanding and background.


2. Explanatory Questions. Most kids go through a “why?” stage. Parents of kids in this stage often find themselves running out of answers and patience: “Why do I have to take a nap now?” “Why do I have to eat my green beans?” “Why does Mommy wear red stuff on her lips?” “Why is it raining?”

“Why?” is a basic explanatory question. It can make a fine follow-up question.

“What can we do to speed things up on line?”

“Get rid of that new supervisor!”

“Why?”

Be careful how you ask “Why?” Your tone of voice can make all the difference between a “Why?” that means “What makes you think so?” and a “Why?” that means “You stupid idiot.” Inject some genuine curiosity into asking “why?”

Ask without conveying any other meaning with tone of voice, gestures, or facial expression (which can often turn your “why?” into “why not?”). If you can, asking “why?” will serve you well.

3. Justifying Questions. That versatile little word why can also signal a justifying question.

You may have heard this key question on almost any reality TV show that involves a competition (Top Chef, Project Runway, or Hell’s Kitchen, for example). At some point, the judges ask a contestant who might be up for elimination: “Why should you stay in this competition?” The response usually is a pouring forth of justifications and promises to succeed.

Asking “Why?” in response to the suggestion to get rid of the online supervisor can mean “Why should we get rid of the online supervisor?” (explanatory) or “Why do you think so?” (justifying). If you intended to ask the first question but got an answer to the second, everybody walks away confused. Ask for what you want.

Most often, you will want explanation rather than justification. It’s difficult to ask for justification without putting someone on the defensive. Too often, justifying questions sound like “Says who?” For that reason, it’s best to avoid this category.

A simple phrase change might help you get a more informative response and avoid justification. Instead of asking “why?,” try to ask “how?” In the example of asking about the new online supervisor, instead of asking why you should get rid of him, ask “How would that help?”

4. Leading Questions. As the name suggests, this type of question leads the responder toward a desired answer. Phone solicitors use this tactic all the time.

At its worst (and phone solicitation is surely an example of the worst), the leading probe serves as a rhetorical question, which is asked to make a point or elicit a set response rather than to gather information. At its best, this type of question is still pretty annoying. Avoid asking leading questions.

Common examples of leading questions include ones that start with “Don’t you think …?” or “Don’t you want to do XYZ?” In the case of whether to dismiss the line supervisor, a leading question might be “Don’t you think that would hurt productivity?” You can obviously see how the speaker’s own opinion is worded in this phrasing. The employee immediately gets the picture that you think firing the supervisor is a bad idea, and that you aren’t necessarily open to suggestion. He will hush up and agree with you rather than make waves.


5. Hypothetical Questions. These are your basic “what if?” questions. At their best and most useful, they call for creative thinking based on knowledge, an estimate, or educated guess. At their worst, they call for speculation, a “wild guess.” If you follow up this wild speculation with a little dose of reality, you can elicit some truly creative responses to issues at hand.


In either case, a hypothetical question asks someone to comment on circumstances that haven’t happened (and might never happen).

Suppose you ask a shift supervisor, “How much of a drop-off in production do you think we would experience if we eliminated two workers from each shift?” The shift supervisor should be in a position to give you at least an educated guess, based on past productivity and his or her knowledge of work flow. The same question, asked of one of the shift workers, probably calls for some broader speculation.

When you ask this question of a supervisor who has already stated strong opposition to reducing the workforce, it becomes manipulative, more of a weapon than a sincere attempt to gather information.

“Okay,” you say, “I understand that you don’t want to lay anybody off. Neither do I. But just suppose we did reduce the force by two workers per shift. How do you think that would affect productivity?”

The supervisor grudgingly dredges up a number—which you then use to justify the layoffs. The supervisor probably feels manipulated—and will be wary of answering another question from you.


6. Alternative Questions. When asking these kinds of questions, you provide the alternative responses, essentially like a multiple-choice test. Evaluation forms provide a classic example: “Write the number that best corresponds with your reaction: 5, agree strongly; 4, agree; 3, neither agree nor disagree; 2, disagree; 1, disagree strongly.” These kinds of questions can be helpful when quantifying a qualitative response, but can also be limiting because people don’t always fit neatly in boxes.

Preference and personality tests pose an either/or choice:

Image “Would you rather be (a) a sanitation engineer or (b) a forest ranger?”

Image “Would you rather be (a) a professional athlete or (b) a college professor?”

Image “Would you rather be (a) Dr. Oz or (b) Dr. Phil?”

By suggesting choices, you make it easier to respond. But you also limit that response. Your respondent might not want to be either a sanitation engineer or a forest ranger, but you’ve forced a choice.

A forced choice may also be manipulative. Instead of asking for a general assessment of potential layoffs on productivity, suppose you ask, “Should we lay off one, two, or three operators per shift?” The answer “None” isn’t an option.

7. Summary Questions. As governor of California and then as president, Ronald Reagan required staffers to prepare mini-memos on important issues. From air pollution to the Strategic Defense Initiative, Reagan wanted their best judgment rendered in one crisp paragraph.

Supporters called him the Great Communicator. Detractors dubbed him the Great Simplifier. Either way, he required that his advisers be great synthesizers.

When you ask a summary question, you’re saying, “I don’t have time to do the math; I just want the bottom line. I have no patience for closeups; I want the big picture.” You put blinders on to context, reasoning, and other information that might be very important.

Summary questions often begin with phrases like “In general” and “Overall” and can be a productive category of questions for you as a manager. Keep in mind, though, that summary questions are often hard to answer and may come across as threatening. Having to come up with an overall assessment can take time, thought, and even in-depth research.

Three Techniques for Asking Questions

Here are three techniques on how to ask appropriate questions and ensure better responses.

1. Give employees time to think. Silence is an acceptable answer and a valuable tool. So is the statement “I don’t know.” If the question requires thought, provide time and opportunity for thought to take place. Avoid handing out new material at a meeting, for example, and then asking for an immediate response. You might get a gut-reaction response (which can be useful, if that’s what you are looking for), but if you want a well-thought-out answer, wait a bit.

2. Tell employees what’s at stake. Most of us learn to associate questions with tests and grades. The teacher knows the answers; she wants to see if you know them. You can be right or wrong; when you’re wrong, if you’re lucky, you might get partial credit.

What do employees win or lose when they answer your question? Will they be punished for a “wrong” answer, an answer you don’t want to hear? If so, you’ll probably never get an honest answer.

How binding are their answers? Can they change their minds later? Will their answers factor into your decision? Or are you just asking to be asking and tend to ignore their input?

Be honest about your motives for asking and what you intend to do with the responses. In most cases, you’re asking for advice, not taking a vote. You aren’t bound to act according to the advice you receive. But the input should make a difference or else you shouldn’t ask.

If your actions contradict the information you get, explain why.

If you ask the question simply to give the impression of wanting an answer (without any real intention to do so), you’ll do more damage to your working relationships than if you never asked at all.

3. When you’re done asking, shut up and listen. We look at ways to become a more effective listener in the next chapter.

The Coach’s Checklist for Chapter 5

Image Effective questions help you get useful information from the people who work with you. They also help people get at what they might not realize they know, and they help everyone become aware of what they need to do to improve.

Image Good coaching questions that will help people learn and improve are brief, clear, focused, relevant, constructive, neutral, and open-ended.

Image There are seven main categories of questions: factual, explanatory, justifying, leading, hypothetical, alternative, and summary.

Image Here are three ways for getting better responses to your questions: (1) give employees time to think about their responses; (2) tell them what’s at stake, why you need this information; and (3) when you’re done asking, be quiet and listen.

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