The One Question You Should Always Ask in Job Interviews

Share

We all know the stock interview questions that are almost guaranteed to come up in any job interview. Questions like “Where do you see yourself in five years?” “What do you think we can improve on as an organization?” and “Why do you believe you are the right fit for this role?” However, there is one question that hiring managers could easily avoid, as it can be seen as a waste of valuable time: “What’s your biggest weakness?”

While the intention behind this question is to be helpful, it more often than not leads to canned answers. As Simon explains, people tend to respond with the usual clichés like, “I’m a perfectionist.”

If you truly want to uncover a candidate’s weaknesses, there is a much more effective approach. Simon recently shared his go-to question during interviews on his podcast, A Bit of Optimism. He asks, “I hate surprises. Can you tell me something that might go wrong now so that I’m not surprised when it happens?” According to Simon, this question elicits incredible answers.

The beauty of this question is that it doesn’t put the candidate on the defensive. Instead, it focuses on the interviewer’s need for information and assistance. “I’m not making it about them,” explains Simon. “I’m making it about me. I’m asking them to help me.”

Start Your Learning Journey Today

At the Optimism Company, we teach the human skills you need to unlock your potential and inspire a brighter future. Click below to read about The Optimism Library— our extensive collection of class offerings.

Feedback from our fellow employees at The Optimism Company, who have been interviewed by Simon, confirms that the question works. One employee admitted to getting stressed and frustrated when having to give big presentations on short notice, while another revealed that she can be overly sensitive to critical feedback. “Simon asked me so many questions, but that’s the one that stuck with me the most vividly,” said one employee.

Simon explains that when we position the question as a way to seek help and support rather than evaluate and critique, candidates tend to be more authentic. Being aware of potential challenges upfront allows both the employer and the employee to navigate them more efficiently, fostering a smoother and more productive working relationship.

Ultimately, leadership is about understanding, guiding, and supporting. Are you ready to lead with more authenticity and clarity? Explore our vast collection of classes in The Optimism Library, all designed to mold you into a more adept leader.

Popular Reads

Inspiration for Your Inbox

By entering your email, you agree to receive exclusive offers, promotions, and a treasure trove of uplifting content. But no pressure—unsubscribe whenever you wish!

The Optimism Library

Certified WHY Coach Program Framework

Learn the exact process Simon Sinek uses to help people discover their WHY and guide them to inspire others.

What You’ll Learn

By the end of the program, you’ll be able to:

  • Explain The Golden Circle and its components — WHY, HOWs, and WHATs
  • Guide someone through a WHY Discovery process that leads to a resonant WHY statement and actionable HOWs
  • Help people use their Golden Circle to make better decisions and create positive change in their careers and lives

You’ll also develop essential human skills you can use every day:

  • Building trust
  • Listening to understand
  • Asking better questions
  • Handling emotional conversations with care

How You’ll Learn

The program includes four structured units combining independent learning, live training, and practice:

Day 1 – The Foundation

  • Get to know The Golden Circle 
  • Find out what it means to bring a Golden Circle to life
  • Learn what a WHY Discovery is, how it works, and what the benefits are

Day 2 – The Human Skills

  • Hone the human skills to guide someone through a WHY Discovery:
    • Creating psychological safety
    • Asking effective questions
    • Engaging in active listening

Day 3 – The Process in Practice

  • Learn notetaking strategies that will help you facilitate a WHY Discovery session
  • Develop the analytic and collaborative skills you need to help someone identify and articulate their WHY and HOWs

Day 4 – The Golden Circle in Action

  • Apply everything you’ve learned to facilitate a full WHY Discovery
  • Learn how to wrap up a session
  • Prepare for your next steps to becoming a Certified WHY Coach

Program Details

Format: 4 live classes + independent learning + group practice

Duration: ~ 8-10  hours per unit (including independent learning and live classes) plus ~5 hours to complete the final exam

Certification Requirements:

  • Complete independent work
  • Attend and participate in all live sessions 
  • Pass a final exam and performance assessment

Your Support Team

  • Regular updates and reminders
  • Opportunities to ask questions
  • Personalized feedback from master trainers
  • Ongoing support through your final evaluation

Program and Participation Terms and Conditions

Our mission is to create a supportive learning environment where we grow together to help others. By joining, you agree to show up in service to one another.

Professional Expectations

  • Attend and participate in ALL live classes in their entirety.
  • Complete ALL assigned online coursework.
  • Must be fluent in English.
  • Show up to live classes, community spaces, and group work with respect, kindness, and gratitude.
  • Support your fellow participants with a service mindset.
  • Keep all personal stories shared during the WHY Discovery process confidential.
  • Approach the WHY Discovery journey with empathy, integrity, and care for those you serve.

Participant Cancellation and Transfer Policy

  • Cancel up to 10 days before your cohort start date: Full refund.
  • Cancel less than 10 days before: We’re unable to offer a refund at this stage.
  • Transfer up to 7 days before: You may transfer your spot to another participant for a $200 (USD) fee.

Recording and Photography

  • Participants may not record or screenshot sessions.
  • The Company will record sessions and make them available internally for 30 days.
  • By joining, you understand you may appear on screen and agree that recordings and photos may be used by the Company for program or marketing purposes.

If you prefer not to be included, please contact the team before the first session at [email protected].

Unleash Your Infinite Mindset

Quantity: 1 quantity = 1 team of up to 20 participants

Teams 20+

Contact Sales

For teams of 20+ contact us

Teams of up to 20

Purchase: $999

Unleash Your Infinite Mindset

Bundle & Save: $1,198 SAVE $800

Buy Unleash Your Infinite Mindset and The Art of Building Fiercely Loyal Customers together for only $1,198.

The Art of Creating Fiercely Loyal Customers

Quantity: 1 quantity = 1 team of up to 20 participants

Teams 20+

Contact Sales

For teams of 20+ contact us

Teams of up to 20

Purchase: $999

The Art of Creating Fiercely Loyal Customers

Bundle & Save: $1,198 SAVE $800

Buy Unleash Your Infinite Mindset and The Art of Building Fiercely Loyal Customers together for only $1,198.

Curiosity is essential
                for progress.
SimonSignature

We fully agree, so we like to reward curiosity.
Use code GETCURIOUS for 20% off your next purchase.

A spark is something quite small and, by itself, not very powerful. But a spark has the ability to ignite. An idea is like a spark; alone it is just a set of words, but it too can ignite. A great idea can inspire others to dream bigger. Let us all work together to ignite something greater than ourselves.

Let us all be a Spark of Optimism.