Answering the Dreaded Difficult Question

by Carla Howard


Questions can be tricky—on the surface; a question is a simple part of conversation.

Here’s how Merriam Webster’s Dictionary defines a question:

“an interrogative expression often used to test knowledge”

Sounds pretty straightforward. Yet, there are times when our friend the question is ohhh sooo much more. 

People use questions to:

  • Seek understanding
  • Find solutions
  • Resolve an argument
  • Demonstrate compassion


  • Make others uncomfortable
  • Embarrass the listener or audience
  • Derail a conversation
  • Sway a decision
  • Establish control
  • Challenge a person or group
  • Gain political ground

Whew! Figuring out the motive behind a question can be a daunting task.

As our minds begin to swirl with our own questions about the reason for the inquiry, we start talking—and then back tracking—and then talking some more.

And that’s when we get into trouble.

Answering questions is a skill, and one that we can improve upon with practice. Here are a few tips that will help improve the quality of your responses:

  • Answer the question
    • I know… that’s an obvious one. Yet, how many times have you been in a meeting when someone is asked a question that they never answer? Even if the answer is going to be one that others won’t like, drum up the courage to provide a direct and truthful response.
  • Be concise
  • Avoid long and rambling explanations 
    • These types of responses often frustrate the person using the question and others in the room. It is also possible that you’ll give away more information than you intended. After answering the question, ask:
      • “Would you like more detail?”
      • “Do you have questions about my response?”
    • This will let the listener know that you have more to share, and that you understand they may not need the additional context.
  • “Yes or No” questions
    • Pick one. Even when it’s hard. Most of the time, it’s possible. Give a single short sentence (two max) about the reason for your answer (only when absolutely necessary). When someone is trying to back you into a corner, try one of these options:
      • “I believe we have another option, may I explain?”
      • “As long as we <fill in the blank>”, my answer would be <yes or no>.”
    • “Either / Or” questions
      • Pick one. When possible, choose one of the options presented. When neither option feels right, change the conversation:
        • “I’m not comfortable with either option. Can we brainstorm other solutions?”
        • “I have an idea that would give us a third option. What if we …?”
      • Ask for clarification, additional details, or time to research
        • Be specific about the details you’re missing, or what you need to know more about before making a decision.
        • When asking for time to research, give a date that you’ll provide a response.
      • Request time to think about your response
        • Many times, an immediate answer isn’t necessary. It may feellike you must answer the question the second it’s asked, but you are always in control of your response. That includes answering when you’re ready. This is an especially helpful tactic when you’re feeling emotional about a topic, or when a little more time will help you to form a more thoughtful response.

We often respond to questions without much planning or thought. This works great for simple inquiries and casual conversations. For the more challenging questions, we need a few tools to rely on.

Having a few tips and key phrases in your back pocket will help you answer tough questions with confidence!

IAAP works with the best trainers in the industry to ensure you have relevant, engaging, practical content at your fingertips. This blog is written by a speaker with a program in the IAAP Approved Programs database. Search by name or keyword to find their contact information and book them for your Branch or Region event. 

If you’d like to attend one of these events, you can find one in your area here.

Carla Howard is a professional speaker and mentor. Her passion is helping professional women become more influential and promotable so they can rise with confidence and grace. You can learn more about her and the services she offers by visiting her website at Carla would love to answer your questions in future articles, so please email them to

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