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7 Savvy Tips to Answer (or Avoid!) Questions You Hate

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Picture this: You’re at a social gathering, sipping on your favorite beverage, enjoying the company of friends and acquaintances. Suddenly, out of nowhere, someone throws a personal question your way like a curveball you never saw coming. Your mind goes blank, your palms get sweaty, and you desperately search for an escape route.

We’ve all been there. But fear not, because today we’re going to equip you with 7 savvy tips to handle those uncomfortable inquiries like a pro. Let’s dive in!

Watch our video below to learn how to answer questions you hate getting to be more charismatic:

Here are some questions that most of us hate answering:

  • “What is your biggest failure?”
  • “Why aren’t you dating anyone?”
  • “How’s the job search going?”
  • “Why are you so dressed up?”
  • “Why are you single?”
  • “When are you having kids?”
  • “What 3 words would you use to describe yourself?”
  • “Tell me about a recent failure.”
  • “Why are you doing the work that you’re doing?”
  • “What’s your story?”

How to Answer Questions You Hate

We all have those questions that make us cringe and wish we could disappear into thin air. Whether it’s about our relationship status, career choices, or even our age, these queries can throw us off balance.

Find an exit strategy

Here’s the secret sauce: You don’t have to answer them! Yes, you heard me right. You have the power to steer the conversation in a different direction. Develop a go-to response or action to smoothly transition or exit these conversations.

For example, you could say…

  • “That’s an interesting perspective. It makes me think about a book I recently read… Have you heard of it?”
  • “Speaking of that, it reminds me of a fascinating documentary I watched recently…”
  • “You know, this conversation is so stimulating. It’s like a cup of strong coffee! Speaking of which, have you tried the new coffee shop downtown?”
  • “That’s a lot to consider. On a lighter note, have you seen the latest season of [popular TV show]?”
  • “Politics can indeed be complex. By the way, did you catch the recent sports game last night?”
  • “All this talk about work really makes me think of vacation spots. Do you have any recommendations for a relaxing getaway?”
  • “There’s so much to learn from different viewpoints. Speaking of learning, have you picked up any new hobbies or skills recently?”

Action Step: Think about common topics you’d rather avoid in conversations. Draft a neutral response or a quick exit line to keep in your conversational arsenal.

Be socially prepared   

Knowing how to handle social interactions efficiently requires preparation, particularly for situations that cause discomfort or stress. Consider the questions or scenarios that might make you uneasy and devise thoughtful, confident responses.

For instance, suppose you’re an introverted software developer often asked about the latest pop culture trends. You could prepare by learning a few key points about popular shows or artists to discuss. This proactive preparation can help you navigate the conversation more confidently and reduce your social anxiety.

Action Step: Identify the types of questions or social scenarios that make you uncomfortable. Develop prepared responses or conversational redirects to use when these situations arise, thus boosting your social preparedness.

And when you’re more prepared you’ll feel much more able to master yourself and others. Check this out:

Become More Influential

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Turn the tables with positive interactions

Handling tough questions can be less daunting when you have a strong rapport with your peers. Building solid relationships can provide a cushion when navigating tricky conversations. Here’s a fun, four-step plan to transform your workplace relationships into supportive alliances:

  • Create a Safe Space for Discussions: Initiate an open forum once a week where team members can discuss various topics, including how to handle uncomfortable questions. Sharing experiences and solutions can foster empathy and camaraderie.
  • Be the Change: Be proactive in asking your colleagues questions that you’d like to be asked. This can subtly influence the kind of questions you receive and can help shift the dialogue towards more comfortable topics.
  • Learn Together: Suggest a group activity where you all explore different techniques for communication and handling difficult questions. This could be a workshop, a webinar, or reading and discussing a relevant book together.
  • Celebrate Progress: Recognize and appreciate when a colleague handles a difficult question well. This can reinforce positive behavior and encourage a supportive environment for everyone.

Action Step: Begin with the first step of creating an open forum for discussions—whether it be through email or even a virtual communication tool. Gradually introduce the other elements to build an environment where dealing with uncomfortable questions becomes less intimidating for everyone.

Deal with challenging coworkers

Engaging in tough conversations with challenging co-workers can feel like taming a dragon. However, with a clear strategy in place, you can find your way through and establish more effective communication. Here’s how:

  • Map the Terrain: Understanding is the first step to resolution. Make it a point to observe and note the specific behaviors that pose a challenge. This insight will provide a clear picture of the issue at hand and guide your strategy.
  • Extend the Olive Branch: Engage your coworker in a calm, non-confrontational conversation. Express your concerns clearly and constructively. Offering a solution or compromise can also demonstrate your willingness to work through the issue.
  • Engage Reinforcements: If one-on-one discussions don’t yield results, it’s time to involve a third party. This could be your supervisor or HR. They can offer impartial advice and intervene if necessary.

With these steps, you’ll not only be taming the office dragon but also nurturing a more peaceful and productive work environment.

The power of pause

When you’re asked a challenging question, sometimes the best immediate response is to not respond at all. Allow yourself a few seconds to process the question, gather your thoughts, and plan your answer. Take, for example, Steve Jobs. When asked an insulting question, he didn’t immediately respond. Jobs took his time and answered after more than a 10-second pause (pause starts around 33 seconds in):

In fact, one study1 found that longer pauses equaled more fluency in speech! Use your pause to think about your response.

Harness the Spotlight Effect

It’s human nature to feel like we’re center stage when we’re asked a challenging question. Our mind plays a trick on us known as the “Spotlight Effect,” where we overestimate how much attention others are paying to us. It can feel like all eyes are scrutinizing our every word and gesture, waiting for our response. However, the truth is often far from this.

In reality, people are absorbed in their own thoughts and concerns, just like you. 

Action Step: The next time you’re asked a question, take a moment to gauge your physical and emotional response. Recognize these symptoms as signs of the Spotlight Effect in action. Take a deep breath, and practice one of several mindfulness techniques to calm down.

Master the Boomerang Effect

Imagine yourself in a scenario where you are caught off guard by a challenging question. Instead of panicking, you use the “Boomerang Effect”—a technique where you respond to a question with another question, particularly when the original one is opinion-based.

The goal of the Boomerang Effect is not to avoid answering the question, but to create an opportunity for dialogue, gathering other perspectives, and buying yourself some time to craft a thoughtful response.

Here’s how:

  • Identify Boomerang Opportunities: Not every question is suitable for the Boomerang Effect. Look for open-ended, opinion-based questions. These provide an excellent opportunity for bouncing back the query to the asker.
  • Craft Your Boomerang Response: Your response should include acknowledgment of the question, a brief mention that you have thoughts on the matter, and an invitation for the asker to share their viewpoint. For example, “That’s an insightful question. I have some thoughts on it, but first, could you tell me more about your views on this?”

Take Control of Your Response

Remember, you are in control of the conversations you engage in. You have the power to establish boundaries, choose what you want to share, and redirect the discussion to more comfortable ground. Don’t be afraid to assert yourself gracefully and embrace the inner captain of your conversations. And remember these key strategies:

  • Exit Strategy: Devise ways to redirect or transition out of uncomfortable conversations.
  • Social Preparedness: Plan responses ahead for potentially awkward scenarios or questions.
  • Positive Peer Interactions: Build strong relationships to create a supportive environment for tricky conversations.
  • Manage Difficult Coworkers: Understand challenging behaviors, communicate effectively, and involve a third party if needed.
  • Master Communication Techniques: Use the Power of Pause, Spotlight Effect, and Boomerang Effect to navigate tough questions effectively.

Tired of bad questions? Read on for the best ones: 450 Fun Questions to Ask People in ANY Situation (That Work!)

How to Deal with Difficult People at Work

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