How To Ask The Right Questions At The Right Times

There is a hidden skill that helps successful people make informed decisions and forge stronger connections. This skill is the power to ask the right questions at the right times.

Questions help us break down barriers, pinpoint solutions and explore new ways of doing things. Yet, most of us assert more than we ask. We talk more than we listen. Imagine how much more effective we would be if we ask the right questions

Smart questions make you smarter . Questions —asked the right way, under the right circumstances — can help you achieve both short-term and lifelong goals. They can open doors to discovery and success, bring you closer to a loved one and even uncover answers to the universe’s most enduring mysteries.

Insightful questions help you connect with a stranger, impress a job interviewer or entertain at your next dinner party, and they can be the keys to a happier, more productive and fulfilling life. Sincere questions too often play second fiddle to certainty, ideology and outrage. But what if we asked more and asserted less? What would we discover?

Humans are built to be curious, that much is in our DNA. Our questions reflect who we are, where we go and how we connect. They help us learn, and they help us lead because effective questioning marshals support and enlists others to join. After all, asking people to solve a problem or come up with a new idea turns the responsibility over to them. It says, “You’re smart, you’re valuable, you know what you’re doing — what would you do about this problem?”

The following are the type of questions you should ask

• Diagnostic Questions
• Strategic Questions
• Empathic Questions
• Bridging Questions
• Confrontational Questions
• Creativity Questions
• Mission Questions
• Scientific Questions
• Interview Questions
• Entertaining Questions
• Legacy Questions

Diagnostic Questions

Diagnostic questioning identifies a problem then burrows down to its roots, especially when those roots are not instantly obvious. For example, your tooth is killing you. You go to the dentist. She asks where it hurts, when it hurts. When you chew? When you drink? She taps, pokes and applies cold water until you leap out of the chair. Oh sorry, did that hurt? “Yes,” you grunt, through the junkyard that litters your palate. She says the problem is this other tooth. You’re feeling “referred pain.” An X-ray confirms it. A filling fixes it.

Diagnostic questions progress systematically to describe the problem and identify it. You can learn how to ask diagnostic question by doing the following:

• Connect symptoms and specifics. Start with big, broad, what’s-the-problem questions and then narrow down, zero in. Get past the generic to identify the symptoms and describe related observations in detail.
• Ask for the bad. Don’t duck the issues or avert your eyes. Ask direct questions in search of direct answers. It may get ugly, but if you want to fix a problem, you have to acknowledge it to deal with it.
• Study history. Look back. Ask about similar experiences, events and patterns. They provide a baseline. Look for similarities to other situations.
• Ask again. The mere existence of a problem means there is something unknown or unanticipated. To be sure you’re on solid ground, ask several times and several sources. Confirm and corroborate.
• Challenge the expert. We rely on experts to diagnose our diseases. But that doesn’t mean they’re right or that they’re off the hook in explaining what’s going on. Before you accept a diagnosis, ask what it is, what it means and where it’s coming from. And reserve the right to get another opinion. 

Strategic Questions

Strategic questions ask about the bigger challenge and the long-term goal — about stakes, opportunities, costs, consequences and alternatives — as you focus on the big picture.

“Strategy, by definition, is about making complex decisions under uncertainty, with substantive, long-term consequences,” Freek Vermeulen, an associate professor of strategy and entrepreneurship at the London Business School, wrote in the Harvard Business Review.

Colin Powell was a key player in America’s two wars against Iraq. The questions he asked — and did not ask —stand as examples of how strategic questioning can shape decision-making at a time of crisis.Here are examples of strategic questions he asked:

• Have the risks and costs been fully and frankly analyzed?
• Have the consequences of our actions been fully considered?
• Do we have a clear and attainable objective?

Strategic questions are vital at any major crossroads. They are deceptively simple questions that illuminate complex decisions characterized by great risk or uncertainty. They call for answers about purpose and the big picture.

You might decide that the answers need to be unanimous and affirmative. Or you might be comfortable with a more ambiguous response. Strategic questions prompt you to examine the terrain broadly, to estimate the situation from which you can proceed with a better sense of capability and destination.

Empathic Questions

Empathic questions explore what makes people tick, think, fear, and feel. They focus unselfishly and spring from genuine interest. The simple act of asking, of listening without comment or judgment and letting a silence linger or a free form thought to coalesce, invites a person to reflect or think out loud. It might even prompt a revelation.

Empathetic questioning helps you connect with others. Use this line of questioning when a colleague needs to talk through an argument at home or politics at the office, or when you want to reach out to someone who comes from a different place, background or perspective.

Helen Riess is a clinical professor of psychiatry at Harvard Medical School. She studies empathy and teaches doctors how to incorporate it into their work with patients. Riess tells doctors to start with a broad question to establish an empathetic relationship. “How are you doing today?”

Riess tells her doctors that they have to do more than just ask. They have to listen closely and sincerely. They have to hear more than words. They must listen to voice tone and inflection and watch for reactions and body language. She coaches them to maintain eye contact and scan the other person’s face to see if they seem relaxed, anxious, frightened, or stressed. If they hear strong emotion, they should respond to it directly and ask compassionately. “What are you most concerned about?”

Riess believes it is the questioner’s responsibility to take in fully what the patient is communicating. This affects outcomes; patients who don’t experience empathy are less likely to trust their doctors, and they’re less likely to adhere to the treatments that are recommended. A systematic review showed that low empathy and communication in patient-doctor relationships actually lead to worse health outcomes.

You don’t need a degree to be a disciplined listener and an empathetic questioner. You just need to know who you are talking to and be able to imagine what the world looks like through their eyes.

Bridging Questions

Bridging questions are intended to encourage people to talk when they don’t want to. They coax information, glean detail and assess intent and capability.

The principles behind bridging questions support a specific and clear outcome: getting a closed person to open up. The objective is to lower a person’s defences and move his or her brain out of red-alert territory.

Start with questions the interviewee is comfortable addressing even if the questions are not relevant to the issue at hand. As you’re building rapport, ask “how” questions. “How” questions ask for explanation and background. They encourage stories. The human brain is wired for stories. It’s how we learn and how we remember.

Listen hard for “entry points” to turn the conversation to the story you want to hear. You can recognize an entry point by actively listening for an observation or a complaint that resonates with the story you’re after. A flash of anger or expression of regret can be an entry point. Use them to your advantage.

To keep people talking, use periodic “micro-affirmations.”  When you hear something relevant, signal interest by leaning forward, offering a slight nod or a barely audible “uh-huh.” These micro-affirmations reinforce without interrupting or distracting. They signal that you are engaged and sympathetic.

Use questions without question marks. Phrases like, “Tell me more,” “Explain that to me,” “Go on,” “That’s remarkable” or “Fascinating,” serve as open-ended invitations for a subject to pause, reflect and provide more detail. They convey interest and, when stated in the right tone and accompanied by open body language, offer affirmation and validation, which are important to reduce barriers and generate cognitive ease.

Questions without question marks can feel less threatening and less like an interrogation. Angry, alienated people might believe they see and understand things that others do not. By saying, “A lot of people agree with you,” you offer a measure of validation without an endorsement of the point of view. You “normalize” the conversation, creating the appearance that you understand.

Confrontational Questions

Confrontation and accountability questions put issues on the table and demand answers for the record. They air a grievance, level an accusation and reinforce the rules of acceptable behavior.

Confrontational questioning often requires assertive interruption or repetition to make it as difficult as possible for your adversary to change the subject, dodge the question or run out the clock.

When you adopt a true adversarial approach, you raise the stakes. Confrontational questioning must be approached from a position of strength. Questions can be used as weapons. If you’re going to confront someone in power, there has to be an element of aggression. You must have the courage of your convictions and realize it isn’t a popularity contest.

If you have the basics — solid information, a clear objective to your questioning and enough spine and moral indignation to stand up to authority — you can have an impact, especially if you understand your platform and know your audience.

Invoking community is one of the surest ways to give more heft to your case and more edge to your questions.Whether at a town hall or a staff meeting, confronting a powerful person is not easy. But having a community on your side creates an alliance. Your questions become

the group’s questions, which are harder to dismiss as the ranting of a malcontent and easier to amplify because of the implied voices ready to join you. If you’ve done your homework, are prepared to stand up to the pressure of the encounter and have crafted your questions so that you succinctly express the problem and the challenge, you can take the high ground and demand answers.

You should prepare for an evasive or confrontational response. Effective confrontational questioners have to be fast and uncompromising listeners. It’s what good lawyers do in a courtroom and good interviewers do in front of a camera. They pick up on a voice tone and swoop in on hesitation. They shut down attempts to filibuster or self-aggrandize. They keep the laser aimed at the core issue they’re after.

With accountability questioning, you want precision. You want to pin someone down. Often, questions that elicit one-word answers can be the most effective crowbars to the truth. Examples of Yes-no questions include :

• You were late yesterday. Is that correct?
• Did you call when you knew you were going to be late?
• Did you think about the consequences of being late?

Lawyers like yes-no questions because they establish the record and draw precise boundaries. They put on the record a definitive response to a specific action or moment and give the questioner almost complete control over the witness and the testimony.

Confrontational questions entail risk because they put relationships and reputations on the line. If you’re wrong, or if you sound ill-informed or like a bully, the questions will boomerang and hit you and not the person you are trying to hold to account.

Creativity Questions

Creative questioning asks people to close their eyes and imagine. It welcomes crazy ideas, shrugs off the obvious and seeks alternatives.

The president of Middlebury College was in the early stages of crafting a 10-year strategic plan. At the fall retreat, a facilitator started with a question that invited participants to think creatively about the college’s future by going there. “It is 10 years from now,” he said, “and the latest college rankings have just come out. This school is at the top of the list. What are we doing?”

He put the future in present tense. His question was a time machine. Once inside the machine, the obstacles that often interfere with big ideas — practical considerations like cost, resources, staffing and economics — fell away.

Participants listed qualities that earned them the top spot. There was a new science center, a new library, more students who brought more diversity, more faculty and more funding. The future was clear!

Then, they worked backward to determine how to make it happen, from program design to funding. Today, the college has accomplished many of the goals set out in that exercise. The school is in the top ranks of liberal arts colleges. Imagined reality became actual reality.

A publisher convened an off-site retreat with his top editors. He began with an exercise. Crunch time had arrived, and each magazine had to cut its budget by 50 percent. He asked:

• What do you cut?
• What do you do?
• Where do you start?

The teams went to work prioritizing and calculating, cutting staff and expenses. Though this was just an exercise, everyone played along and took it seriously. Then came the twist. In a surprise move, the publisher gave his editors their money back. Every penny. But, he told them to use the budget they’d cut just a few minutes earlier as their new baseline. They could invest the money they had “saved” in any way they wanted.

• What will you build?
• How will you invest?

Their answers helped transform the company’s five newsstand magazines and led to more National Magazine Awards than any of their rivals. The net profit for the company doubled in two years

Mission Questions

Mission questions help you draw people into a genuine conversation about shared goals and what everyone can bring to the task. They help you convey your priorities. Mission questions require you to talk less and listen more.

Karen Osborne, founder of the Osborne Group, a fundraising consultancy, developed a set of questions to help her identify what people care about and where and why they give. Osborne’s discovery questions generate a conversation. They ask what people care about and the motivations behind their passions. If they are now in a position to do something more about a problem they’re passionate about, what will they do?Examples of  those questions includes:

• What are the guiding principles that have helped you in life?
• What do you hope to accomplish with your philanthropy?
• What values do you consistently support?

Osborne asks her questions to get answers, but she also asks to be sure the other person is doing the talking. As research shows: People forget what they heard, but they remember almost everything they say.

Your questions prompt people to answer and to engage. That’s a critical step, Osborne says, if people are going to embrace a cause for which they’re going to provide significant financial support. Osborne insists that engagement is the key to philanthropy. The more that people are involved in an initiative, the more they give to it.

Once you have established the mission and concluded that your goals coincide, you can start thinking about the next step: actually doing something.

Rick Leach, founder of the World Food Program USA, rallies support, raises money, and finds partners in business and government to support efforts to get desperately

needed food to victims of drought, poverty, war and natural disaster. To attract people to social movements, he believes, you must engage their curiosity and connect passion with mission. He focuses on turning commitment into concrete action. “It’s earnestly asking questions and learning to more fully hone the need in search of the opportunity to address the need,” he said. His template for partnerships is built on four questions.

• How do we define the problem?
• What are the strategies to solving the problem?
• What’s the goal?
• How can we all play a role in achieving the goal?

When the 2015 Ebola crisis hit, food and nutrition quickly became a big problem, as whole areas of some countries shut down. Business stopped. Leach turned to his longtime sponsor, United Parcel Service, Inc. (UPS), knowing its capacity in logistics. Leach asked if UPS would help distribute food, medical supplies, generators, and equipment. UPS agreed. The company provided invaluable logistical support to assemble material, equipment and relief supplies and fly them into West Africa. World Food Program distributed food to more than 3 million people in the year and a half after the Ebola outbreak.

This approach to mobilizing people and defining roles can be applied at virtually any level — whether you are trying to change the world or the town where you live. Get good people together and use Leach’s questions to define the challenge, consider strategies and set roles.

Scientific Questions

Scientific questioning drives a process that revolves around data, experimentation and observable fact. The discipline this line of questioning imposes makes for better inquiry and better decisions across the board.

There’s a line of inquiry characterized by the slow question, the one that doesn’t yield an immediate answer and dares you to embrace uncertainty. The slow question is expressed through the inquisitive lens of science. The method builds logically from the ground up. Consider the following when looking at scientific questions

• Observe a problem, frame a question. Take what you see or know to be objectively and measurably true from the real world and ask a question. What’s going on here? What’s causing this?
• Offer an explanation. Based on your observations, your experiences, and the facts and data that exist, put together a clear hypothesis that could explain the situation.
• Put your hypothesis to the test. Experiment and measure over time. Try to prove yourself wrong. What else could explain this situation? What did you miss? What could be wrong with your approach and your data? If your hypothesis holds up, you are making progress.
• Share. If you think you’re onto something, shop it around and show it to other knowledgeable people. Let them review it. Do they see something that you didn’t Do they have a problem with your data or your methods. If not, you might just have a theory you can act on.

The methodical, logical approach to scientific investigation provides a blueprint for inquiry that rewards reality, not emotion, one step at a time.  

The discipline of scientific questioning moves us toward a more methodical form of inquiry that invites more data and better measurement into the questions we ask and the answers we get. As data becomes more accessible, we can expect more science and more metrics in the decision and questioning process.

Interview Questions

The first rule of the job interview: Don’t wing it. Preparation pays. Know what you’re talking about and to whom. Know as much as possible about the job. Have a

list of questions on a pad and in your head. You are not sitting down for a random chat. You are trying to learn as much about the other person as you can to establish whether this position is a good fit for both of you.

If you’re the applicant, you can anticipate that most every interview will ask you touchstone questions.

• Why are you interested in this position?
• What do you think you can do for us?
• What makes you qualified and unique?
• Why should we hire you?

Prepare a series of responses for each question. Organize your thoughts in bullet points, two or three distinct characteristics for each response, so you can talk about several traits without getting lost or long-winded. Practice your answers. You want to be clear, concise and prepared to address the question — or a variation of it — directly and confidently. Think of some examples or short stories that highlight relevant experience or set you apart.

Keep in mind that your tone will convey as much about you as the words you use, so strike a balance in how you present yourself. Talk about your successes without bragging, express confidence without sounding cocky and acknowledge your shortcomings without sounding insecure. Be prepared to speak about your character and personality by citing a tough decision or a dilemma you faced and how you worked your way through it.

Know what questions you want to ask. The questions that you, the candidate, will ask are nearly as important as your answers to the interviewer’s questions. You need to project informed curiosity about the position, the enterprise, the competitive landscape, and the measures of success.

Try practicing by recording your answers on your smartphone. Practice will allow you to fine tune your answers so you project confidence and fluency.

If you’re the interviewer, you have to ask precisely and persistently to get beyond the resume and practiced responses. If you’re filling a management position, ask

about how your applicant deals with people, motivates success and handles setbacks. You are asking questions that call for tangible answers that shed light on your applicant’s talent, experience and personality. You want to get a sense of what will motivate her and keep her productive. You ask about situations or experiences that illuminate intangible characteristics, such as how the person deals with adversity or thinks creatively. You want insight into the other person’s work ethic and professional expectations, goals and ambitions. As an interviewer you can ask the following questions

• What’s the most successful project you’ve run?
• What is it about this job that interests you most?
• How does this job connect with your larger professional aspirations?

If red flags have come up through reference checks, askabout those, too: “What would your detractors say about you?” You want honesty and realism. Self-awareness is essential to being a successful leader.

Entertaining Questions

Entertaining questions allow you to engage your audience and keep the conversation interesting and lively so everyone plays. You can be commanding or charming, funny or unpredictable, but the objective always revolves around creating an experience that your guests will enjoy and remember. Use questions the same way a chef uses spices: subtly but deliberately to bring out the flavors of the meal. So what are the basic ingredients of entertaining questions?

• Know your audience. Who are you talking to? What have they done? Where have they been, and what do they care about? Pick questions that intrigue and interest everyone.
• Think creatively and choose deliberately. Draw from a menu of topics and questions to create a flow and distinctive moments. You want a combination of topics that will engage different people on different levels.
• Set a mood, and set a rhythm. Funny or serious? Provocative or reflective? Set the mood through signals, prompts words, and timing.
• Engage emotion. You trigger emotions through the subjects you pick and the questions you ask. Serious or snide? Funny or flippant? It’s your call.

Start with an exchange that is spontaneous and a little unexpected. You can often break the ice, get a smile and set a tone that is more relaxed and will lead to a more genuine experience.

Good hosts are always on, always listening and always interested in their guests and the conversation around them. If you’re the host, prepare accordingly. Adopt a strategy that creates the event you want. If you want a fun, free-flowing evening, roll out some questions that tap into the easy currents of daily life. Make them open-ended and friendly questions. Ask about the new restaurant, the local football team or the newest Leonardo DiCaprio movie.

By applying a little “conversation leadership” to get people interacting, you can create an environment that is inclusive, interesting and dynamic. A few well-placed questions will jump-start a conversation. The more you ask, the more you get.

Legacy Questions

Legacy questions ask what we’ve accomplished or changed and inquire about the lives we’ve touched. They are questions about meaning, spirituality, lessons learned, gratitude, regrets, people and purpose.

Legacy questions open the door for reflection and resolution. They seek context. They can be existential or spiritual. Legacy questions ask about meaning and gratitude, mistakes and adversity.

A properly told life story can capture life’s impact and its meaning. But not all stories have happy endings, and not all lives end with clarity or resolution. A question can prompt a reply brimming with guilt or sadness. Anger and sorrow are not uncommon emotions at the end of life.

Some burdens may seem insurmountable: feelings of acute failure, a sense of a wasted life. End-of-life expert Ken Doka believes every life has meaning, though sometimes it takes hard work and persistent questioning to find it. He asks:

• How do you put your mistakes in context?
• What lessons would you share?
• What high points in life would you point to?

We do not need to wait for the deathbed moment to ask about the meaning in our lives. Legacy questions travel with us. If we have the courage to ask them, they help us get our bearings and write our story. If we listen closely to our answers, we gain perspective.

Questions are our way to connect with other human beings. Inquiry, not imitation, is the sincerest form of flattery. Ask a good question, and you convey interest.

Slow down, listen closely and ask more and you engage at a deeper level. You show that you care. You generate trust. You empathize, and you bridge differences. You become a better friend, colleague, innovator, citizen, leader or family member. You shape the future.