in: Featured, How To, Skills

• Last updated: September 25, 2021

Thinking On Your Feet: How to Answer Difficult Questions

Vintage men being interviewed at conference table.

“Why didn’t Acme Co. accept our offer?”

“Why should I hire you over somebody else?”

“Where do you see this relationship going?”

“Where do babies come from?”

Questions. Sometimes they’re as innocuous as “What’s up?” and other times they get our hearts pumping and our mouths stuttering.

Part of being a man is knowing how to improvise, and part of improvisation is being able to think on your feet. It’s a skill that includes the ability to give impromptu remarks, as well as to answer unexpected and difficult questions.

People ask pointed questions to obtain information, but there are often other reasons behind their queries as well. What they really want, in many cases, is to get a feel for your attitude towards a certain subject, and how calm, confident, and trustworthy you seem.

So the ability to answer difficult questions is built on two tenets: 1) possessing ample knowledge and giving the right information, and 2) delivering that information in a poised manner.

The number of potential questions you might be asked is so infinite and context-specific that it’s not possible to learn a scripted response for each. But it is possible to hone your improvisation skills by learning methods that will allow you to give a smooth answer, no matter what you’re asked.

These methods come from the surprisingly handy Thinking on Your Feet by Marian K. Woodall and we’ll be sharing them with you today.

The Overarching Plan: Always Buy Yourself More Time

When someone aims a question our way, we’re tempted to jump on it as if it’s a live grenade. We fear that even a bit of silence will be read as hesitation, and perhaps even shiftiness. So we rush in…only to be forced to stick our feet in our mouths.

The answer you blurt out on impulse is unlikely to be the best response, and you’ll kick yourself later while mulling over the things you wished you had said.

So the biggest thing you can do to improve your responses to difficult questions is to buy yourself more time to come up with answers. Even a few extra nanoseconds gives your brain a chance to do a little more processing and pull out the pertinent information and needed words.

Allowing yourself a tiny pause to collect your thoughts is completely fine. Just don’t fill that gap with an “Uhhh…” or “Ummm…” which makes you sound halting and unsure. A moment of silence, on the other hand, will lend you a thoughtful air.

You can also repeat the question before launching into your answer. Speaking the question and then the answer offers a fuller response; it also helps others in a large audience who may not have heard the question when it was first asked.

In addition to embracing the silent pause or repeating the question, there are other techniques that will not only buy yourself extra processing time, but have other benefits as well. Let’s take a look at how they work.

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

Questions come in many forms, and you’re not always lucky enough to get the short, clear, focused variety; sometimes, you’re presented with a vague, complex, rambling, and downright impenetrable query.

Don’t guess at what information the inquirer is looking for; misinterpreting their question may end up causing offense, or at least invoking an irritable response: “That’s not what I asked you.”

The much more effective approach is to clarify the question — to essentially get yourself a better one — before giving your response. This will not only make the question easier to answer, but will create a delay that gives your brain more time to think.

Woodall recommends several ways to nudge the inquirer into giving you a better, easier-to-handle question:

1. Ask them to repeat the question.

Just as you often wish you could take back an answer, people frequently wish they could reword their question because they aren’t happy with how it came out. Here you give them the chance for a do-over. Their second take is likely to be shorter, clearer, and more focused than the first.

Asking to have a question repeated has something of a formal air; I suppose we associate it with job interviews or courtrooms or something. So keep in mind that this is a tactic which is more natural in professional settings than casual conversation.

  • “Would you mind repeating the question? I want to make sure I got all of it.”

2. Ask for clarification.

If a question is vague and/or all over the place, respond with a question of your own that seeks to clarify and specify what the seeker is trying to get at. Which product is he referring to? What timeframe does she have in mind? Which aspect of something are they thinking about?

  • “There are several different insurance packages available. Which one were you interested in specifically?”
  • “Motivation is a broad subject. Is there something in particular you’re looking for advice on?”
  • “The subject of tax reform is quite complex. Is there an area that you’d particularly like me to address?

An especially effective way to focus the question is by asking the inquirer to select between choices:

  • “Are you concerned about the sales numbers for 2013 or 2014?”
  • “Was it what I said to you before the party or in the car afterwards that made you upset?”

3. Ask for a definition.

Even when everyone is using the same words, they can mean different things to different people. To avoid talking past each other, ask the questioner how they define key words in their inquiry.

  • “Before I answer that, can you tell me what you mean by ‘negligent?’”
  • “I’m totally open to this discussion, but before we have it, tell me what it means to you for us to be ‘officially dating.’”

Woodall points out that when someone has asked a question with the purpose of cornering you, asking them to define their terms can turn the tables and stump the stumper. For example, someone may ask, “Why do you think hunting is manly?” To which you reply, “Well, first of all, how do you define manliness?” Oftentimes, the person isn’t actually sure what they’re asking, in which case they may either withdraw the question, or, tangle themselves up in such knots that the original question is forgotten. If they do come up with a definition, well, now you’re both on the same page, and you gained extra time to think about your response.

4. Clarify or define a point yourself.

One way to take greater control of an interaction is to define the question as you see it within your response:

  • “Why was your pitch to Acme Co. a failure?”
    • “If by failure, you mean that nothing good came out of it, then I don’t think it was. We didn’t connect on this deal, but we established a good relationship and they’re open to future projects.”
  • “Why are you going out with her if we’re dating?”
    • “Dating simply means that we see each other regularly, not that we’re in an exclusive relationship.”

The downside of asserting your own definition of things is that the other party may not see it that way, and may become frustrated by your response.

Dealing With Inappropriate Questions: The Art of the Hedge

Sometimes questions are relatively clear, but they’re inappropriate, and you don’t wish, for various reasons, to answer them in full. Your response must then be hedged. Hedging has a somewhat unsavory reputation, as it’s associated with dishonesty and manipulation. But it need not be used for nefarious purposes. Sometimes you really can’t give someone the answer they seek, whether it’s because that information is classified, private, sensitive, or isn’t appropriate for a particular audience. You’re not obligated to talk about private things you don’t want to talk about.

Furthermore, sometimes people ask questions that have a hidden agenda or are simply off-topic, and will sidetrack you from your own agenda in a meeting or class. It’s important to know how to keep your remarks on track with what you want to accomplish.

Yet, you also typically don’t desire to offend or make the inquirer feel embarrassed. So, while a straight “That’s none of your business,” is all that’s needed in some scenarios, it’s oftentimes in your best interest to deliver your “noneya” in much more diplomatic terms. An artful hedge will at the least spare the inquirer from feeling like a toad, and at best, leave the seeker feeling that their question was in fact answered.

Here are techniques Woodall recommends for pulling off a successful indirect response:

1. Respond to one aspect of the question/line of questioning.

If a question is multi-faceted, and there are some aspects you don’t want to address, but at least one you’re comfortable speaking to, focus your response on that part:

  • “I’ve heard that there may be a new round of layoffs coming up. I also heard that a pay cut is being considered. I’ve even noticed that the free soda has disappeared from the break room; is that connected to the company’s declining profits?”
    • “I can assure you that there are not going to be any layoffs in the next six months. And contrary to what you heard, the company is quite strong and our earnings were higher than expected this quarter.”
  • “How’s your new gig going? How much are they paying you over there?”
    • “It’s going really well. It’s amazing how much different the office culture is. Every Friday we end work early and drink beer and play softball. Have you been playing much this spring?” (Ending with a question will help move the conversation away from the question you’d rather not answer.)

While you might think failing to answer each of a seeker’s questions will leave them unappeased, you’d be surprised how often they’ll let it go at your single answer. Sometimes an inappropriate question slips out, and the inquirer is actually relieved when you ignore it. And oftentimes folks who ask a particularly long-winded, multi-faceted question aren’t exactly sure what they want to know; they’re just feeling generally concerned. A simple answer that demonstrates positivity and confidence will leave them satisfied.

If the seeker is not satisfied, however, and wants to circle back to the unanswered parts of their question, that’s fine; by forwarding the initial exchange, you gave your brain a couple more minutes of subconscious processing time to figure out how to respond to the more difficult bits.

2. Refocus the question.

If there’s a part of a question you can’t, or don’t think it’s a good idea to speak to, focus on an aspect that you are able to discuss. You do that, Woodall writes, by taking “one word from the question (usually not the main topic word) which you are willing to talk about, and [building] a strong, supported response around it.”

  • “Have you heard anything about whether they’re considering me for the position? I really felt like I showed a lot of confidence during my interviews and was able to knock all their questions out of the park.”
    • “For sure. Frank said everyone was really impressed with your confidence and how prepared you seemed.” (You’re focusing on the confidence aspect, while choosing not to answer about the position specifically.)
  • “Why do you think I’m not getting ahead? I feel really stuck in life, and I feel like in every job I have the boss doesn’t appreciate me. I don’t want to sound prideful, but I’m really smart. Yet I don’t seem to be getting anywhere.”
    • “You are really smart, man. And when you’ve been intentional about applying your mind, you do really well. What do you think are some ways you could be more consistent about following through on the ideas you’ve started on?” (Instead of listing off his flaws, you’re focusing on the fact that he is indeed smart, and positioning your response in a positive direction.)
  • “Why are you breaking up with me? You can’t deny the passion we feel for each other.”
    • “The passion is definitely real. But sometimes it takes more than passion to make a relationship work.” (Focusing on the inadequacy of passion, while not necessarily going into other reasons.)

3. “Discuss” the question.

Sometimes it seems like people are looking for a specific answer to a question, when really they just want to have their question discussed. There really isn’t a singular answer to give. They want to hear both sides of an idea, or they just want to know that you’ve been thinking about it too, or they simply want acknowledgement that their question is something it’s okay to wonder about. In many cases, these inquiries are answered with a question that tries to probe deeper into the topic at hand.

  • “Why isn’t the school board reaching out more to get feedback from parents about this issue?”
    • “We are reaching out more than you might think. We just sent out a survey to 500 households. But the situation is complicated; parents of older kids want different things than parents of younger students. We’re carefully considering all opinions and options, and looking for a way we can compromise.”
  • “Where do babies come from?”
    • “What do you think?” or “What do you already know about where babies come from?”
  • “Why aren’t you happy in our relationship?”
    • “What’s given you the impression that I’m unhappy?”

4. Build a bridge.

With this technique you build a bridge from what the question asked to what you really want to talk about. This technique is similar to the refocusing strategy, but the break between the content of the question and that of your answer is sharper.

If you’ve ever watched politicians on TV news shows and candidates in debates, you’ll be very familiar with the bridging technique. A politician will be asked about their stance on the war, and they’ll answer, “The war is an important issue that needs to be addressed. But I really want to talk about the tax hike my opponent is proposing.”

The bridge response can be infuriating, and I certainly don’t recommend dodging important questions with it. But it can also be essential in sticking to your agenda when you’re presented with off-topic queries in a meeting you’re leading, a Q&A you’re facilitating, or a lecture you’re giving.

The trick is to bridge to your talking points as smoothly as possible so the transition isn’t very awkward or noticeable. To do this, first acknowledge the significance of the question’s subject, and then look for a logical pivot point towards what you think is the more important issue:

  • “What about Area 51? Didn’t the government take possession of UFOs there during the 50s?”
    • “UFO sightings were certainly one of the consequences of the overall paranoia that prevailed during the Cold War period. What most Americans feared was a nuclear bomb though. As I was saying, the Soviets tested their H-bomb in 1953…”
  • “Why would I sign on with you, when your competitor’s services are significantly cheaper?”
    • “Price is certainly an important factor to consider. But quality is crucial too. We can deliver a much faster and more secure experience….”

5. Use a funnel.

With the bridge technique, you pivot entirely away from the question’s main subject. But sometimes you just want to narrow the field of discussion, while also encouraging follow-up questions and continued conversation on one certain aspect. With the funnel approach, you can accomplish this by acknowledging the larger issue and then using narrowing words to direct your audience’s attention to the area you most want to spotlight:

  • “What work experience do you have that makes you a good candidate for this job?”
    • “I have experience in the hospitality business and as a customer service representative, but the experience that most aligns with what you’re looking for is the five years I spent managing social media for one of your competitors.”
  • “Do you have a plan for how you will execute this project?”
    • “We do, and the most crucial step will be securing funding for it. As you can see from this chart, we’ve already raised half the money we need.”

The key with all these hedging strategies is delivery. Hesitating and acting sheepish will render them wholly ineffective. Demonstrating confidence and strength will lend you the air of a captain directing a tour boat; people will enjoy coming along for the ride. Remember, when people ask questions, they’re not just looking for answers; they want to get a sense for what you’re like and how you handle pressure.

Sometimes Straightforward Is Best: The Art of Shooting from the Hip

Sometimes the best way to answer a difficult question is to give a totally straightforward answer. This forthrightness can be refreshing and disarming.

Now, I know some of you are thinking (in a cowboy drawl voice): “You should always shoot from the hip! A real man doesn’t hedge.”

That certainly sounds nice, but as with most bumper-sticker-esque maxims, it’s basically complete poppycock.

We all hedge our answers to questions every single day. Else, when someone asks, “How’s it going?” you answer with, “Well, I had a big fight with my wife last night, and my truck needs new brakes…” We all refocus and only partially answer the questions that are regularly put to us.

The art of improvisation simply requires knowing how and how much to respond in widely varying circumstances; when to pull the accordion out, and when to contract it. Learning this skill, and buying yourself extra time to deploy it, assures that you won’t blurt out answers you’ll spend the next month wishing you could take back, and that your confident, smooth responses will help you navigate your relationships and career like a sir.



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

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