How to Answer Difficult Questions

Some questions we get asked frequently. Let’s explore the how, when and why of these difficult topics.

The “how to answer difficult questions in an interview” is a question that many people find difficult. In order to answer this question, it’s important to know what the interviewer is looking for and be able to demonstrate your skills.

Vintage men being interviewed at conference table.

“What went wrong with Acme Co.’s decision to reject our offer?”

“How why I should employ you instead of someone else?”

“What do you think the future holds for this relationship?”

“Where do infants originate from?” says the narrator.

Questions. They might be as simple as “What’s up?” at times. Sometimes they have our hearts racing and our lips stuttering, and sometimes they don’t.

Knowing how to improvise is a part of being a man, and being able to think on your feet is a component of improvisation. It’s a talent that involves the capacity to make spontaneous comments as well as the ability to respond to unexpected and challenging queries.

People ask direct questions to gather knowledge, but their inquiries are often motivated by other factors. In many situations, what they truly want is to gain a sense of your attitude about a certain issue, as well as how calm, confident, and trustworthy you seem.

As a result, the ability to answer tough questions is based on two tenets: 1) having a wealth of knowledge and providing accurate information, and 2) conveying that information in a calm way.

It’s impossible to memorize a rehearsed answer for every question you could be asked since the number of possible inquiries is endless and context-specific. However, you may improve your improvisation abilities by mastering techniques that will enable you to offer a fluid response to any question.

These techniques are from Marian K. Woodall’s unexpectedly useful Thinking on Your Feet, which we’ll be sharing with you today.

The Overarching Strategy: Always Buy More Time for Yourself

When someone asks us a question, we often feel compelled to answer it as if it were a live grenade. We’re afraid that even a brief pause may be seen as hesitancy, if not outright shiftiness. So we rush in…only to find ourselves with our feet stuck in our mouths.

The answer you give on the spur of the moment is unlikely to be the greatest, and you’ll blame yourself afterwards when you reflect on what you should have said.

To enhance your replies to tough questions, the most important thing you can do is give yourself extra time to think about answers. Even a few more nanoseconds allows your brain to conduct a bit more processing and extract the necessary information and words.

Allowing yourself a little pause to gather your thoughts is quite acceptable. Fill in the blanks with “Uhhh…” or “Ummm…” to avoid seeming hesitant and uncertain. On the other hand, a minute of stillness will give you a contemplative air.

You may also ask the question again before giving your response. Speaking the question and then the answer allows for a more complete response, as well as assisting those in a big crowd who may have missed the question when it was initially asked.

Other strategies, in addition to embracing the quiet pause or repeating the question, will not only buy you more processing time, but will also have other advantages. Let’s take a closer look at how they function.


The Art of Getting a Better Question When Dealing With Vague, Complex Questions

You’re not always fortunate enough to obtain the short, clear, focused sort of question; occasionally, you’re greeted with a vague, convoluted, meandering, and downright opaque enquiry.

Don’t imagine what information the inquirer is searching for; misinterpreting their query might result in offence or, at the very least, an irritated response: “That’s not what I asked you.”

Clarifying the question — effectively getting yourself a better one — before responding is a far more productive strategy. This will not only make it simpler to answer the question, but it will also cause a delay, giving your brain extra time to ponder.

Woodall suggests various approaches for persuading the inquirer to ask you a better, more manageable question:

1. Request that they rephrase the question.

People often wish they could redo their inquiry because they are unhappy with how it came out, just as you wish you could take back an answer. You’re giving them a second opportunity here. Their second take will most likely be shorter, more focused, and clearer than the first.

Requesting that a question be repeated has a formal ring to it; I think we identify it with job interviews or courtrooms. So bear in mind that in a professional situation, this is a more natural strategy than informal talk.

  • “Could you please restate the question?” I want to double-check that I got everything.”

2. Make a clarification request.

If a query is ambiguous and/or all over the place, ask a follow-up question to clarify and describe what the seeker is attempting to achieve. To what product is he alluding? What is the time period that she has in mind? What part of anything are they considering?

  • “There are a variety of insurance packages to choose from. Which one piqued your curiosity the most?”
  • “Motivation is a big topic. Is there anything in particular on which you’d want advice?”
  • “Tax reform is a difficult topic to grasp. Is there anything in particular you’d want me to cover?

Asking the inquirer to choose between options is a very effective technique to concentrate the question:

  • “Are you worried about the 2013 or 2014 sales figures?”
  • “Did you become offended because of anything I said to you before the party or in the vehicle afterward?”

3. Inquire about a definition.

Even though everyone uses the same words, they might have distinct meanings for different individuals. Ask the questioner how they define important terms in their inquiry to prevent talking over each other.

  • “Can you explain what you mean by ‘negligent’ before I respond?”
  • “I’m very open to having this conversation, but first, explain me what it means to you to be ‘formally dating.’”

When someone asks a question with the intent of cornering you, Woodall points out that asking them to explain their terminology may turn the tables and stump the stumper. “Why do you believe hunting is manly?” someone could inquire. “Well, first and foremost, how do you define manliness?” you respond. Often, the individual asking the question isn’t sure what they’re asking, in which case they’ll either withdraw the inquiry or wrap themselves up in knots to the point where the original query is forgotten. If they do come up with a definition, you’ll both be on the same page, and you’ll have more time to consider your answer.


4. Defining or clarifying a point on your own.

Defining the question as you perceive it inside your answer is one method to have more control over an interaction:

  • “What went wrong with your proposal to Acme Company?”
    • “I don’t believe it was a failure if by failure you mean nothing positive came out of it.” We didn’t work out on this contract, but we built a strong rapport, and they’re interested in future initiatives.”
  • “If we’re dating, why are you going out with her?”
    • “We’re dating because we see one other on a regular basis, not because we’re in an exclusive relationship.”

The disadvantage of stating your own definition of things is that the other person may not agree, and your reaction may irritate them.

The Art of the Hedge: Dealing with Inappropriate Questions

Sometimes inquiries are straightforward, but they’re improper, and you don’t want to answer them completely for a variety of reasons. Then you’ll have to be cautious in your reaction. Hedging has a shady image due to its associations with deception and manipulation. It does not, however, have to be utilized for bad means. You can’t always give someone the response they want, whether it’s because the material is confidential, private, sensitive, or inappropriate for a certain audience. You are not bound to discuss private matters that you do not choose to discuss.

Furthermore, at a meeting or class, individuals may ask questions with a hidden agenda or that are just off-topic, detracting from your own agenda. It’s critical to understand how to keep your comments on track with your objectives.

You don’t want to offend or humiliate the inquirer, but you also don’t want to offend or embarrass the inquirer. While a simple “That’s none of your business” may suffice in certain situations, it’s typically in your best benefit to express your “noneya” in a more polite manner. At the very least, a well-placed hedge will keep the inquirer from feeling like a toad, and at the very best, it will give the impression that their inquiry has been addressed.

Here are some tips from Woodall on how to pull off a great indirect response:

1. Address one component of the question/line of inquiry.

If a topic has several elements to it, and you don’t want to cover some of them, but at least one of them is something you’re comfortable talking about, center your answer on that part:

  • “I’ve heard that a fresh wave of layoffs is on the way. A wage decrease is also being contemplated, according to what I’ve heard. I’ve even observed that the complimentary Coke in the break room has vanished; is this related to the company’s diminishing profits?”
    • “I can tell you that no layoffs will take place in the next six months.” And, contrary to what you may have heard, the firm is doing well, and our profits this quarter were greater than planned.”
  • “How’s it doing with your new job?” “How much do they pay you over there?” says the narrator.
    • “Everything is going swimmingly. It’s incredible how different the workplace culture is. Every Friday, we finish work early and play softball while drinking beer. “Have you had a lot of time to play this spring?” (Ending with a question can assist shift the subject away from the question you don’t want to answer.)

While you would assume that neglecting to answer all of a seeker’s inquiries will annoy them, you’d be surprised how frequently they’ll accept your single response. Sometimes an incorrect inquiry is asked, and the asker is glad when you disregard it. And, in many cases, people who ask a really long-winded, multi-faceted inquiry aren’t sure what they want to know; they’re simply worried. They will be happy with a short response that exhibits enthusiasm and confidence.


If the seeker isn’t happy and wants to return to the portions of their query that haven’t been addressed, that’s great; by forwarding the first discussion, you provided your brain a few more minutes of subconscious processing time to figure out how to react to the more challenging sections.

2. Shift the emphasis of the inquiry.

Focus on one element of the issue that you can talk about if you can’t or don’t believe it’s a good idea to talk about another portion of the subject. Take “one word from the question (typically not the major theme word) that you are eager to speak about, and [create] a solid, supported answer around it,” adds Woodall.

  • “Have you heard anything about whether they’re thinking about hiring me?” During my interviews, I felt that I exuded a lot of confidence and was able to answer all of their questions with ease.”
    • “Without a doubt.” Everyone was blown away by your confidence and preparedness, according to Frank.” (You’ve chosen not to respond about the job in particular, concentrating on the confidence component.)
  • “How come you don’t believe I’m moving ahead?” I’m terribly trapped in life, and I feel that my bosses don’t respect me in every job I’ve had. I don’t want to come out as arrogant, but I’m really intelligent. Despite this, I don’t appear to be making any progress.”
    • “You’re a genius, dude.” And when you’ve been deliberate about using your thinking, you’ll perform really well. What are some ways you believe you might be more consistent at completing the projects you’ve started?” (Instead of concentrating on his weaknesses, you’re emphasizing his intelligence and directing your reaction in a good way.)
  • “Can you tell me why you’re ending your relationship with me?” You can’t deny our feelings for one other.”
    • “It’s clear that the enthusiasm is genuine. However, making a relationship succeed often needs more than just passion.” (Focusing on the insufficiency of passion rather than addressing other factors.)

3. Respond to the question by “discussing” it.

When individuals seem to be seeking for a precise response to a topic, what they actually want is to have their question debated. There isn’t a single response that can be given. They want to hear all sides of an argument, or they just want to know that you’ve been thinking about it as well, or they just want confirmation that their query is valid. In many circumstances, these queries are addressed with a query that attempts to elicit further information about the subject at hand.

  • “Why isn’t the school board reaching out to parents for further comment on this issue?”
    • “We’re reaching out a lot more than you believe.” We just sent a survey to 500 families. However, the issue is complex since parents of older children have different expectations than parents of younger children. We’re carefully evaluating all viewpoints and ideas and trying to find a middle ground.”
  • “Where do infants originate from?” says the narrator.
    • “How do you feel?” or “How much do you already know about the origins of babies?”
  • “What is it about our relationship that makes you unhappy?”
    • “Can you tell me what’s making you think I’m unhappy?”

4. Construct a bridge.


You may use this strategy to create a link between the question and what you truly want to speak about. This method is similar to focussing, but the difference between the substance of the question and your response is more pronounced.

You’re probably acquainted with the bridge approach if you’ve ever seen politicians on TV news broadcasts or candidates in debates. When questioned about their position on the conflict, a politician would say, “The war is an important subject that has to be handled.” But I actually want to speak about my opponent’s proposed tax rise.”

The bridge answer may be aggravating, and I don’t encourage using it to avoid essential questions. It may also help you stay on track whether you’re leading a meeting, mediating a Q&A session, or presenting a lecture when you’re confronted with off-topic questions.

The key is to move as easily as possible to your talking points so that the shift isn’t too uncomfortable or obvious. To do so, recognize the importance of the question’s topic first, and then search for a logical pivot point toward the problem you believe is more important:

  • “How about Area 51?” says the narrator. “Didn’t the government take control of UFOs in the 1950s?”
    • “One of the effects of the general paranoia that existed throughout the Cold War period was UFO sightings.” The majority of Americans, however, were concerned about a nuclear attack. As I already said, the Soviet Union tested its H-bomb in 1953…”
  • “What makes you think I’d join up with you when your competitor’s services are much less expensive?”
    • “Price is definitely a major consideration. However, quality is also important. We’ll be able to provide a considerably quicker and more secure experience……”

5. Make use of a funnel.

With the bridge approach, you pivot completely away from the primary topic of the query. However, there are occasions when you just want to reduce the scope of the conversation while still encouraging follow-up questions and more debate on a certain topic. You may do this utilizing the funnel strategy by identifying the bigger problem and then using narrowing terms to focus your audience’s attention to the specific region you want to highlight:

  • “What work experience do you have that qualifies you for this position?”
    • “I’ve worked in the hotel industry and as a customer service representative, but the five years I spent managing social media for one of your rivals is the experience that most closely matches what you’re looking for.”
  • “Do you have a strategy for completing this project?”
    • “We do, and the most important step will be to get finance.” We’ve already collected half of the money we need, as you can see from this graph.”

The most important aspect of all of these hedging techniques is delivery. They will be rendered completely ineffectual if they hesitate and seem bashful. Demonstrating confidence and strength will give you the aura of a tour boat captain, and others will like going along for the journey. People aren’t just seeking for answers when they ask questions; they’re trying to get a feel of who you are and how you manage pressure.


When it comes to shooting from the hip, sometimes it’s best to keep it simple.

Giving a completely direct response to a challenging topic is sometimes the best way to respond. This candor may be both invigorating and disconcerting.

“You should always shoot from the hip!” some of you are thinking (in a cowboy drawl voice). Hedging isn’t something a true guy does.”

That sounds good, but it’s really total nonsense, as are most bumper-sticker-style maxims.

Every day, we all obfuscate our responses to queries. If not, you’ll reply, “Well, I had a terrible quarrel with my wife last night, and my vehicle needs new brakes…” when someone asks, “How’s it going?” We all refocus and only half respond to the questions that are posed to us on a daily basis.

Improvisation is just understanding how and how much to react in a variety of situations; when to pull out the accordion and when to contract it. Learning this ability and giving yourself additional time to practice it ensures that you won’t make rash decisions that you’ll regret for the following month, and that your confident, smooth replies will help you navigate your relationships and profession like a gentleman.

Improvisation is just understanding how and how much to react in a variety of situations; when to pull out the accordion and when to contract it. Learning this ability and giving yourself additional time to practice it ensures that you won’t make rash decisions that you’ll regret for the following month, and that your confident, smooth replies will help you navigate your relationships and profession like a gentleman.


Marian K. Woodall’s Thinking on Your Feet: How to Communicate Under Pressure



The “responding to questions examples” is a blog post that gives an overview of how to answer difficult questions. The article will also give some example responses and will go over the different types of questions.

Frequently Asked Questions

How do you respond to difficult questions?

A: I read the question and then give a brief answer.

How do you respond when you cant answer a question?

A: I will ask you if you want me to go away. If the answer is anything other than yes, then my response will be Ill try harder.

How do you answer difficult questions in a presentation?

A: This is a difficult question.

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