This question is probably the most blatantly selfish question in the entire section. Finding good questions becomes an obsession for leaders who learn the value and power of asking questions. What better way to find questions than to ask for them?

Asking for questions within your organization works for a while. Every leader, even those who don’t make questioning a priority, will have a few questions they routinely ask. But you’ll often find that within an organization, questions seem to cluster around certain themes. Asking for new questions from people who come from different organizational backgrounds will provide you with a whole new set of possible questions.

But there is another, less selfish reason for asking this question of a new hire. Their reaction will provide you with insights into their comfort with a leader who asks questions. Some people will eagerly share questions, some will haltingly respond with a question, and others will stare blankly as if you’ve asked the most bizarre question ever uttered.

The eager sharer is telling you either that they’ve joined your team from a question-rich culture or that they understand the power of questions and are happy to share. Work with this new employee to strengthen their commitment to questioning and to encourage them to share new questions as they find them.

The slow responder is letting you know that they haven’t had a lot of experience with leaders who ask questions but are willing to participate. Make sure you thank them for their contribution and encourage them to make others in the future. Keep them in mind for some gentle questioning in the near future so you can help them understand this part of your leadership style.

The blank looker is harder to read. They may be confused by a leader who asks questions, frightened by this level of interaction with their new leader, or genuinely surprised by the action of a leader asking them for their opinion. No matter which interpretation might be accurate, don’t jump to a conclusion. It’s now your job to find out which of these (or any of many other explanations) is the right one.

No matter which situation you encounter with this question, like asking any good question of the right person at the right time, you’ll get valuable information that you’ll be able to use in the future.

More words adding up to longer answers do not necessarily provide more insight. Sometimes questions that force brevity can provide interesting answers that are easy to compare. This question falls into that category. Imagine asking this question of all new hires for six months. Depending on the size of your organization and your rates of turnover and expansion, you could develop and keep track of the one-word answers pretty easily. What would be the value of that? I can think of three.

1. As your list of descriptive words grows, you can compare them and look for consistency of expectations from those who join your organization or department. What do you think it means if half the people respond with words like “fun,” “energetic,” and “creative,” and the other half of the people you’ve asked respond with words like “stable,” “traditional,” and “respectable”? My analysis of those responses would be that half of the people who responded were going to be disappointed. It’s up to you to decide which half. A split response like this tells you that you haven’t established a consistent image in your marketplace. A consistent response that you like tells you your image is intact. A consistent response you don’t like means you have some actions to take.

2. As your list of words grows, you’ll gain insight into the way people feel about your organization or department. Leaders have responsibilities for feelings as well as facts, and you might as well find out how people are feeling as they join your team. Waiting until later isn’t exactly stellar leadership behavior.

3. Keep track of whom you’ve asked, how they answered, and when you asked them. Use a milestone—four-to six-month anniversaries would work—and ask the question again: Now that you’ve been with us for a while, what one word would you use to describe our organization? Asking and comparing these answers will give you insight into the consistency of experience your people have as they become part of your team.

Don’t let the fact that my imagination was limited to three possibilities stunt your thought processes. What are other ways you could use this information? Think about it.

Some people live their lives as though joy were a very limited resource. As if they were allocated an amount at birth, squandered much of their share during childhood and must now, as responsible adults, hoard their remaining supply for some unspecified time in the future. Given these parameters, why would anyone in their right mind waste joy on work?

Let me think. Artists often do. Teachers do, I hope. The waiter at my favorite Wausau restaurant, The Back When Café, does. The vendors I do repeat business with do. The most successful leaders I’ve known do. The organizations that thrive, year in and year out, do. If you agree with the conventional wisdom that joy is an endangered species, then these people are fools. The day will come when they’ll simply run out of their allotment of joy—and won’t you have the last laugh then. However, what if they’re wrong? What if you run out of life with your allotment of joy untouched?

Work is a great place to express joy. If you look, you’ll see that there are so many little opportunities for happiness when you work with people you respect, do tasks that make a difference, and use the talents you’ve been given. If you read that and don’t agree that your job affords those possibilities, then you’re either in the wrong job or not paying attention. No matter which is true, you can and should make some changes.

Remember these thoughts as you listen to the answers to this question. Do people find joy in their work at your organization? What are the implications for you if they don’t? You can help people find joy in their work by showing them how what they do matters. Many people in today’s workplace have no idea how the things they do on a daily basis affect the success or failure of their organization. A receptionist needs to understand that the way he answers a phone could make or break the biggest deal your organization may ever have. A filing clerk needs to know that her daily efforts make it possible for the customer service team to respond quickly to a customer request. A pipe fitter deserves to look at the architect’s drawing and know that, because of her efforts, the building she’s working on will shelter the children at a daycare center. It is your job to help all team members understand the importance of their work. Do that and watch the joy spread.

Watching people as they enter the workplace at the beginning of the workweek gives you one view of organizational morale. Watching them as they leave at the end of the week gives you a different perspective. That’s why both questions are included as significant questions to ask.

What you’re really asking with this question is What does our work environment do to your spirit? This is a question asked by brave leaders. The answer you’re looking for goes something like this.

“Let me think. At the end of the week I’m exhausted and exhilarated. Some weeks it’s more one than the other, but it’s always a combination of both.” Exhaustion means that a person has given their all when they do their work. Exhilaration means that they believe that their work has meaning and that they have derived satisfaction from doing it.

The answers you’re apt to get when you ask this question might be very different from the one I outlined. In fact, the answer you get to this question might be an uneasy giggle followed by silence, a confused look with a mumbled “Why do you care,” or a blunt “It’s none of your business.” Those answers tell you a lot, too. Leaders ignore the spirit in their workplace at their own peril. Don’t ask this question unless you intend to take action to change the status quo. Before you turn the page, allow me to ask you a quick question: How do you feel at the end of your workweek? Do the words “exhausted” and “exhilarated” play a part in your answer?

This question marks a change in the focus of our inquiries. Until now the questions have asked people to share the facts and information they know. Fact and information answers are important—in fact, business runs on them. But they don’t tell the whole story. Organizations are filled with people, and people are filled with feelings. Leaders who believe that they can focus their work on the tasks at hand and leave the “soft stuff” to the human resources department shouldn’t really call themselves leaders! If you choose to continue to accept my challenge and focus your attention on the way people feel about working in your organization, the next several questions are the perfect place to start. Remember, the process is simple—ask, listen, and say thanks. Take the risk. I know you can do it.

Remember those questions on intelligence tests that give you a list of words and then ask which word doesn’t belong? Try this one: Enthusiasm, Passion, Excitement, Fun, Work. What is your answer? Hopefully, you came to the conclusion that this was an example of a poorly constructed or trick question. They all go together, don’t they? Or, maybe you’re wearing your Dilbert hat and wonder why anyone would bother to ask such an obvious question. Work has nothing to do with those other words. If that’s your response, shame on you! Think of the energy an organization would have if everyone in it agreed that enthusiasm, passion, excitement, fun, and work were synonyms. What could your organization accomplish if just half your employees believed that? Has it occurred to you that even 15 percent would be an improvement? Are you clueless about how people feel when they enter your doors? Believe me, how your employees feel as they start their workweek provides great insight about how they’ll interact with each other and with your customers. When you decide to start talking about the feelings that fill your workplace, make a commitment to find, support, and showcase the positive ones. Don’t read that to mean you should ignore or dismiss the negative emotions; just don’t make them the center of your action. Look for ways to increase enthusiasm for solving problems, ignite passion for learning, encourage excitement around success, foster fun as a stress reliever, and discourage seeing work as a four-letter word. You’ll be doing your job.

For years we have all joked and/or raged about the “it’s not my job” attitudes we’ve encountered in organizations, big and small. Have you ever stopped to ask yourself if there is a customer somewhere who thought that way about your organization? Or have you honestly wondered if you’ve got employees that are looking for jobs elsewhere because they believe that no one in your organization cares enough to fix internal systems? Dr. W. Edward Deming,the man whose name is forever linked with quality, believed that 85 percent of quality problems in the workplace are caused by systems, not by an individual’s inefficiencies. Our organizations are filled with policies and procedures that prohibit people from doing their best to satisfy our customers, and you need to know where it’s happening in yours.

This is the first risky-to-answer question we’ve encountered in our list. The answer to this particular question can often be a department or a person’s name. Please remember that an answerer may need some time to decide whether or not it is actually safe to tell you the truth. Describing an outdated policy or explaining an easy to streamline procedure is a fairly safe answer. Identifying a bottleneck department or an obstructionist co-worker is another decision process entirely. You will have to consider time and place when you venture forth with this question. A comfortable pause after asking a high-risk question will facilitate your receiving a thoughtful and productive answer.

A word of caution: One of the ground rules of good questioning is that when a question is asked and an answer is given, the questioner does not (and often should not) respond. Given an answer, you should simply acknowledge the information, clarify any ambiguities, and assure the answerer that their opinion is valuable and will be considered. If you express an opinion or make a promise based on a single response to your question, you might find yourself in the middle of something more complex than that one answer indicated. This is especially problematic when a response to your question points a finger at an individual. An emotional reaction from you may satisfy the answerer but cause great difficulty for the other person mentioned. Your best response to this situation is “Thank you for bringing this to my attention. As I understand it, your situation is [restate the problem]. You have my word that I will look into this matter and will get back to you with a resolution. Please know that I appreciate your efforts to make our organization better.” Now your job becomes one of detective. By asking more questions and listening to the additional answers carefully, you’ll be able to fulfill your promise to deliver a resolution to the original answerer. It may not be exactly what they wanted or envisioned, but they will appreciate the fact that you kept your word and followed through.

The nature of my work requires that I spend a great deal of time away from home. Time alone in hotel rooms provides fertile ground for unusual questions to surface. One evening I got to wondering how a hotel concierge learns about the places they recommend. So I asked. I was amazed to discover that, for the most part, they are expected to learn about shops, restaurants, and local attractions on their own time with their own dollars. That got me thinking about how organizations learn about their competition.

(If this apparent leap in subject is uncomfortable for you, get used to it. Not because it is a fault of mine, but because it is a common occurrence when you get serious about asking questions all the time. One interesting question seems to fire brain activity that may appear to be random but with close scrutiny is connected. My experience has been that the effort to find the connection brings little insight, so I’ve learned to ignore the leap and focus on the seemingly new topic. I suggest you do the same.)

I can remember only one time in my corporate career when my employer asked what I knew about our competition. As it happened, I knew quite a lot about a new product that was being introduced by one of our hottest competitors because one of my customers had just gotten a bid from them and had given me a copy. I had read and filed the information. I’m ashamed to admit that it had never occurred to me that this might be important information for the whole organization, and if I hadn’t been asked, it would have remained buried in my file.

Employees are consumers before they are employees, and many of them choose to do business with the organizations that vie for the attention and the dollars of your customers. Or they know people who regularly interact with your competition. How are you mining the information they have?

Even more interesting, there is the possibility that your employees may have some insight that you don’t into who the competition really is. I remember attending an American Booksellers Association BookExpo in 1995 without hearing one bookstore owner mention Amazon.com. I have to believe that many of them had heard about the new company, but most seemed to dismiss it as a fad for the few. They were focusing on the growth of the large bookstore chains, a serious threat to be sure, but nothing compared to the impact of Internet book buying.

I’m pretty confident that out there somewhere is an Amazon.com like competitor for at least part of your business. Asking this question might just give you the heads-up you need.

I don’t believe I’ve ever been asked this question. The closest I ever got was on a performance review form that had Where do you see yourself in five years? as the last question on the bottom of the last page. Silly me, I took it seriously. I thought about the work I was doing, the work I’d like to be doing, the problems and concerns expressed by our customers and developed a mini job description and envisioned myself in it. When my boss read it he said to me, “You can’t want to want to do that.” I could have handled a “You can’t do that,” answer, but I walked away from that performance review muttering, “You can’t tell me what I want to do!”

What a different experience that would have been if he had only said, “This is an interesting proposal. What made you think of it?” I would have gladly shared the frustration—mine and my customers’—that made my job difficult. There were things he could have helped me do, right away, to become more effective and to make our clients happier, without creating a new job description. Questions are powerful, and this is a great one. Issues that appear small from a leader’s vantage point can be enormous barriers from the employee’s. The people on your team may know what needs to happen to make their jobs more effective, but they may not know how to make the change. Helping someone think through those ideas and then, when appropriate, breaking down the barriers that hinder implementation, is a leader’s job. But how can you break a barrier if you don’t know it’s there?

Ask this question more than once and you’ll begin to see the quality of the thinking and the depth of caring about outcomes your people have. Working with them to eliminate the organizational barriers to trying these ideas will benefit you both.

Back to the money stuff. Well, one could argue that most of business is about the money stuff, but asking about the money often gets you to something more valuable. This question does that. Leaders ask this question to investigate, challenge, and assign responsibility. They use it to investigate the forgotten areas within their control but not in their view, to challenge people to think for themselves, and to let people know that they are expected to engage their brains on the job. Look at it this way. Pretend you don’t do the grocery shopping in your household. In fact, you very seldom even go into a grocery store. The balance in your checking account is running lower than usual, and you notice that the checks made out to the grocery store represent a significant percentage of your monthly expenditures. So you sit down and develop a strategy to lower your grocery cost and present your plan to the family shopper for implementation. If you had to guess, how’s that going to work for you?

Okay, try this approach. You catch the shopper as you walk through the kitchen and say, “You’re spending way too much at the grocery store. I expect to see smaller checks in the future.” And as you walk out of the room you add, “By the way don’t let the quality of our meals suffer.” Is that better?

Please tell me you didn’t think that either of these approaches would work well. Please tell me that, as you read the last two paragraphs, you were shaking your head and grinning. Unfortunately, we act that way at home way too often. This behavior (as expressed about grocery shopping, punishment for children, and other areas too numerous to mention) has far-reaching implications—ask any-one you know who’s gone through a divorce. Don’t kid yourself. If you do it at home, you do it at work.

The problem with this behavior (in case you’re not certain) is presuming that you know better than the person closest to the issue does. When you ask about saving the company money, you send a message that you expect and value your employees’ expertise because they’re the ones who do the work, day in and day out. Of course, the reasoning goes, they have ideas and I want—no, need—to hear them. The more you ask this question, the better the answers you get will be.

Tip 68: Answer One Question at a Time; Avoid Multiples.

When someone asks you multiple questions in one large chunk, you have several choices: (1) Answer all of them. (2) Pick one or two to answer. (3) Lump them all together and give a general answer. Examples: “You’ve asked three good questions. For the sake of time, let me deal with only the last one….” “Whoa–I don’t know if I can remember all those. Let me pick out a couple to respond to….” “Your questions really all point to one concern, I think: Do we know how to Y? I can answer in a word–yes.”

Tip 69: Stop Your Own Monologue Answers.

Long-winded answers irritate as much as long-winded questions. If you intend to wax on about an issue, seek a group platform where the audience knows you intend to give a speech and grants you the privilege. If your answer runs longer than 30 to 45 seconds, you’re no longer in a dialogue; it’s a monologue. If you feel you’re going on too long and haven’t finished what you intended to say, pace yourself by stopping to ask the other person for some reaction to what you’ve just said–do they agree, disagree, not care, have different information? Then, after you listen to their comments, deliver your next point on the earlier answer.

Tip 70: Turn a Negative Question into a Benefit Statement.

A customer asks, “Why do you have so much red tape associated with these service agreements?” “Benefit” answer: “Why does having a list of all the company liaisons benefit you: Well, let’s say Kathy in your word processing department calls for service. Within seconds, we can check the file, verify her as an authorized contact, and answer her question while she’s on the line–without waiting for a callback. You’re doing the paperwork up front in providing us names of liaisons saves you time when you have a problem and need service immediately.”

Tip 71: Bridge from the Questioner’s Agenda to Yours.

If you don’t want to answer the question you’re asked, bridge to your own points with one of the following: “I appreciate your question, but more to the point in our organization, I think, is the issue of X. The X issue involves…” or “A more fundamental issue than that in your question is…” or “The larger question than the one you raise is…” Chase your own rabbits.

Tip 72: Know When Flippant Answers Are Out of Line.

Having a sense of humor is an advantage in any situation, but flippant answers about serious issues or during a time crunch frustrate people. Some people find themselves tossing out humor when they can’t face issues squarely. Try to identify those times when you’re using humor as an avoidance technique. Recognize that even humor, however generally welcome and refreshing, has a time and a place.

Tip 73: Forget Feedback if You Want to Show Confidence in Your Answer.

In situations with your superiors, to end a question with “Did I answer your question?” or “Did I cover what you wanted to know?” makes you appear insecure, lacking confidence in your ability to answer. Give the best answer you can and wait for your superior to assume his or her question was unclear or inadequate. If the question is rephrased, make another attempt to answer it.

Tip 74: Use Verbal Stalls with Care.

As a lecturer or instructor, you may have learned to reinforce questioners or give yourself thinking time with comments such as “That’s a good question” or “I’m glad you brought up that point.” But when talking one on one, these comments may sound patronizing. And comments such as “As I mentioned earlier today in the staff meeting…” can sound like a verbal slap on the hand and a reprimand for not listening. They destroy rapport with your listener. Be silent with a reflective gaze rather than stall with judgmental phrases that sound as though you’re about to hedge, make something up, or respond with great reluctance.

Tip 75: Remember That the Whole Performance Counts.

When it comes to questions, style is equal to substance. Your competence can be communicated in the clarity, resourcefulness, and conciseness of the content; in your delivery of the answer—with courtesy, confidence, composure, concern; and finally, in the results you achieve with your answer. Substance plus style equals success.