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Preparing for Tough Questions

You got the interview – now it’s time to nail it. This playbook gives you the tools and strategies to respond confidently, even when you’re not feeling your most confident. Learn how to turn challenging moments into opportunities to showcase your skills and stand out as a candidate.
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Let’s face it: interviews can be nerve-wracking, especially when the interviewer throws in those tough, unexpected questions designed to see how you think on your feet. But here’s the thing: most of these questions follow common themes, and with the right preparation, you can turn them into opportunities to stand out. This playbook is here to help you anticipate and craft thoughtful responses that highlight your strengths, keep your cool, and showcase the best version of yourself, even when the pressure’s on. Whether it’s addressing gaps in your experience or handling those “what’s your biggest weakness” moments, we’ve got strategies to help you stay ahead of the game.

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Exercise

Interview Prep Worksheet

Review the Job Description: Highlight 3-5 key skills or competencies that seem most important for the role. Consider these clues to help you anticipate what the interviewer may focus on.

Research Common Questions: A simple Google search can go a long way. Look up common interview questions related to those skills or competencies. This will give you a sense of what might come up.

Apply the STAR Method: For each skill or competency, prepare responses using the STAR (Situation, Task, Action, Result) framework.

Practice: Rehearse your answers in front of a mirror or with a friend to build confidence and refine your delivery. We get it – this can be a little uncomfortable, but repetition will help your delivery feel more natural come interview day.

Work Smarter Not Harder
Rate each of the following statements.

Starter Scripts

Being nervous for an interview is practically universal, but having the right mindset can make all the difference. Use these affirmations to get your mind right pre-interview.

When you’re feeling unsure, say to yourself:

  • "I’ve prepared, and I am ready for this conversation."
  • "These interviewers already see potential in me. I’ve caught their interest, and they want to know more.”
  • "I’m interviewing them just as much as they’re interviewing me. This is my chance to see if the role and the company are the right fit for my goals and values."
  • "There’s power in the process. Every interview is a chance to grow, learn, and refine my skills. Regardless of the outcome, I’m gaining valuable experience that gets me closer to where I want to be."
  • "It’s normal to feel anxious—this just means I care about the opportunity. I’ll take a deep breath, acknowledge my nerves, and use that energy to stay focused and present."

Sample responses to tough questions…

Think of these examples as thought starters rather than scripts. They’re here to help you approach common tricky questions, but it’s important to make them your own. As you review, ask yourself how you can add your personality, insights, and unique experiences to craft a response that feels genuine and authentic.

  • Tell me about yourself…

"Well, professionally, I’ve been working in [industry X] for the past [Y years], starting my career as [initial role] where I learned a ton and developed skills in [key area]. Since then, I’ve moved into [current role] where I focus on [specific tasks or responsibilities that ideally tie into the role you’re interviewing for]. I’m now excited to bring my experience in [relevant skills] to a new challenge, which is why I’m interested in this role.

Personally, I love [mention a few personal interests]. For instance, I’m a big [gamer/foodie/pet lover], and in my free time, I [describe a specific hobby or passion].

Tip: Let the interviewer see a real glimpse of who YOU are. Are you a bookworm? AWESOME. Love home brewing? – great. Avid surfer? – far out.  Letting them know what excites you outside of work can help build a connection and show that you’re a well-rounded and unique individual.

  • Walk me through your resume…

"Sure! I started my career at [company] as [role], where I [briefly describe responsibilities]. After [X] years, I transitioned to [next role] at [company], where I focused on [highlight a major responsibility or project]. And most recently, I’ve been in [position Z] at [current/most recent company], where I’ve managed [describe key tasks]. That about sums it up! I really think each role has helped me build skills in [specific skills], and I’m excited to leverage these experiences in a new role that allows me to [connect to the job you’re applying for]."

  • Tell me about a time when you disagreed with your manager…

At my previous job, my manager and I had different approaches on how to prioritize a client project. I believed that focusing on the client’s immediate needs would yield better results, while my manager preferred sticking to our existing timeline. Instead of arguing, I presented my perspective using data and explained how adjusting the approach could enhance client satisfaction and long-term loyalty. Ultimately, we reached a compromise that incorporated elements of both strategies, and the client was very satisfied with the outcome.

Tip: Honesty, authenticity and tact are critical here. Avoid exaggerations, negative comments about your boss, or attempts to shift blame. Focus on your actions, your behavior, and how you constructively contributed to a resolution of that worked for everyone.

  • How many basketballs can you fit on a school bus?

Ooh – tricky question.  Let me think… Ok, so I think this depends on a lot of factors. What size bus are we talking about? Do the basketballs have to be inflated? Are their kids on the school bus?  My ideal situation would be to magically shrink the basketballs down to the size of tennis balls…if we did this, we could probably fit a couple thousand on the bus, effectively turning it into a giant, bouncy ball pit – which sounds pretty awesome to me.

Tip: remember – the interview likely isn’t looking for one “right answer”. Rather, they’re trying to get a sense of how you think on your feet, your creativity, and how you react under pressure. So while you should definitely answer the questions, it’s ok to have a little fun with it and showcase your creativity.

  • How do you handle stress?

For me, communication makes a big difference in stressful situations, if even over-communicating to ensure everyone is on the same page. For example, I was working on a project with another team and we found there was a lot of duplicate work being done which, as you can imagine, was pretty stressful and frustrating for everyone.

So I started a weekly standup and to help open up lines of communication with our teams and managers, we were able to push the project forward and ended up moving the needle on a company goal in a big way.  

I also do my best to get ahead of stressful situations by planning ahead and staying organized. But when stressful situations do arise, I tend to notice I can produce some of my best work under a bit of healthy pressure.

  • What piece of critical feedback do you most often receive?

One thing I’ve been told in the past is that I can sometimes get a little too caught up in the details, which can slow down my decision-making process. While I take pride in my attention to detail, I’m super aware that analysis paralysis is a real thing – and there are times when a quick decision is more valuable than a perfect one. So I’ve really taken this feedback to heart and have worked on it by time-boxing myself, especially when making lower-stakes decisions and reminding myself to trust my instincts. It’s been helping me find a better balance between thoroughness and efficiency.

When you don’t know the answer or are having trouble coming up with a response:

"Oooh, that’s a good question! Let me take a moment to organize my thoughts."
(This shows enthusiasm and buys you a little time to think.)

"I appreciate you asking that. Just to make sure I’m understanding correctly, are you asking about [paraphrase the question]?"
(This lets you test your understanding and gives you a chance to process your response.)

"I love that question and have so many thoughts. Let me take a moment to think about the best way to answer it."
(This demonstrates thoughtfulness and creates a natural pause to give you time to organize your response.)

When you don’t have experience in a particular area they’re asking about:

"I actually haven’t had that experience myself, but from what I know, it often involves [insert general insight]. How has it played out for you?"

"I haven’t faced that particular situation before, but I’ve read/heard about [related example]. What’s your perspective on it?"

When you have a gap in your resume:

If you were laid off

Unfortunately, like many folks in [industry X] my last company went through a major reorg, and as a result, my position was eliminated. I won’t lie – it was a really hard experience, but it also gave me a chance to reflect on the skills I gained and strong relationships I built there. I’m now ready to apply those experiences in a new role where I can make a meaningful impact."

If you were fired

"My previous role and I weren’t the best fit in terms of values. Looking back, I’ve learned a lot from that experience and have taken time to grow professionally and focus on where I want to take my career. I’m excited to bring the lessons I’ve learned and my refreshed perspective to a new opportunity where I’m more aligned with the values and can thrive and contribute fully."

If you took time off for personal reasons

"I took some time off to focus on personal growth and think about  what I really want in life and work. It was an important period for me, and I’m glad I had the opportunity to take this time as it prepared me to take on new challenges with renewed energy and focus. Now I’m excited to tackle this new role with my fresh perspective.

If you left the workforce to be a caretaker

"I took time away from my last role to focus on taking care of my family, which was an important and fulfilling experience for me. During that time, I remained committed to my professional growth and always planned to return to the workforce when the time was right. I’m super grateful to have had that time, but now I’m ready to re-engage my skills and contribute to a new team."

Important Reminder: These scripts are here to guide you, but the most important thing is to show up as your authentic self. Answer questions honestly and confidently—interviewers can tell when responses are too rehearsed or canned. And remember… no one is looking for perfection; they want to see the real you—your personality, your thought process, and what makes you tick. Use these scripts as a foundation, but let your own voice and experiences shine through.

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