17 Powerful Interview Questions from Top Tech Leaders

Introduction

Interviewing is a critical skill for both hiring managers and job seekers in the tech industry. The right questions can reveal a candidate's true potential, while thoughtful answers can set you apart from other applicants. This article compiles 17 powerful interview questions shared by top tech leaders, offering valuable insights for both sides of the interview table.

1. AKA Demano: Reflecting on Success

AKA Demano, former head of product at Ro and PM at Stripe, asks:

"To what do you attribute your success? And you can't say luck."

This question aims to assess:

• Self-awareness
• Ability to reflect on personal growth
• Understanding of factors contributing to success

A strong answer demonstrates:

• Thoughtful analysis of one's career journey
• Recognition of key skills, experiences, or decisions that led to success
• Humility balanced with confidence in one's abilities

2. Jeff Charles: Overcoming Challenges

Jeff Charles, head of product at Ramp, poses this question:

"What's the hardest thing you've ever done?"

This question evaluates:

• Resilience in the face of difficulty
• Problem-solving skills
• Ability to work with others under pressure

A compelling response includes:

• A specific, challenging situation
• Clear explanation of why it was difficult
• Steps taken to overcome the challenge
• Lessons learned from the experience

3. Shashir Reddy: The Teleportation Device

Shashir Reddy, CEO and co-founder of Commsor, presents a unique scenario:

"A group of scientists have invented a teleportation device. They've hired you to be their business counterpart to bring this to market. What do you do?"

This question assesses:

• Ability to think critically about complex problems
• Skill in identifying key information needed for decision-making
• Creativity in developing business strategies

A strong approach involves:

1. Asking clarifying questions (limited to two in this scenario)
2. Identifying the most critical information needed
3. Developing a strategic plan based on the available information

Example of effective questions:

1. "Is it safe enough for humans?"
2. "Is it more expensive in terms of capital expenditure or operating expenses?"

These questions allow the candidate to create different scenarios and develop appropriate strategies based on the answers.

4. Yuki Yamashita: Navigating Controversial Decisions

Yuki Yamashita, Chief Product Officer at Figma, asks:

"Describe a time when you were part of a controversial product decision. What did you do?"

This question evaluates:

• Ability to handle conflicts and differing opinions
• Communication skills in presenting multiple perspectives
• Decision-making process in complex situations

A good answer should:

• Clearly explain the context and nature of the controversy
• Present different viewpoints objectively
• Describe the decision-making process and rationale
• Reflect on the outcomes and lessons learned

5. Katie Dill, Karri Saarinen, and Camille Hearst: Proudest Achievements

These leaders from Stripe, Linear, and Spotify respectively ask:

"Tell me what work you are most proud of."

This question reveals:

• Personal values and motivations
• Quality standards and work ethic
• Areas of expertise and passion

An impressive response includes:

• A specific example of a significant achievement
• Clear explanation of why it's a source of pride
• Insights into the process and challenges overcome
• Reflection on personal growth or impact made

6. Jackie Bavaro: Navigating Ambiguity

Jackie Bavaro, head of product at Webflow, focuses on handling uncertainty:

"How do you navigate ambiguity?"

This question assesses:

• Ability to work in unclear or evolving situations
• Problem-solving skills in complex environments
• Proactivity in seeking information and guidance

A strong answer demonstrates:

• Structured approach to breaking down ambiguous situations
• Strategies for gathering information and input from others
• Flexibility in adjusting plans based on new insights
• Examples of successfully managing ambiguous projects

7. Noah Weiss: Unfair Secrets for Product Success

Noah Weiss, Chief Product Officer at Slack, asks:

"What unfair secrets have you learned to improve the velocity and energy level of a product team?"

This question looks for:

• Unique insights gained from experience
• Innovative approaches to product management
• Ability to drive team performance and motivation

An impressive response might include:

• Specific techniques or strategies not commonly known
• Examples of how these "secrets" were applied successfully
• Measurable improvements in team performance or product outcomes

8. Ben Williams: Personal Growth and Values

Ben Williams, former VP of Product at Snap, poses two questions:

"Fast forward three years, what's different about you?"

"Tell me about the diversity, equity, inclusion, and belonging initiatives you've recently been personally involved with."

These questions evaluate:

• Self-awareness and commitment to personal growth
• Alignment with company values and culture
• Active involvement in creating inclusive work environments

Strong answers should:

• Demonstrate humility and recognition of areas for improvement
• Show a clear vision for personal and professional development
• Provide specific examples of DEI initiatives and their impact

9. Merci Grace: Sibling Perspective

Merci Grace, head of growth at Dbt Labs, asks:

"What would your siblings say about you?"

This question reveals:

• Self-awareness and ability to see oneself from others' perspectives
• Honesty and humility in self-assessment
• Personal relationships and character traits

An authentic response:

• Balances positive attributes with areas for improvement
• Provides specific examples or anecdotes
• Demonstrates self-awareness and a sense of humor

10. Paige Costello: Handling Failure

Paige Costello, co-head of product management at Asana, inquires:

"Tell me about a time something went wrong. What was it, and what did you do about it?"

This question assesses:

• Ability to handle and learn from failures
• Problem-solving skills in challenging situations
• Accountability and proactivity

A compelling answer includes:

• A specific example of a significant failure or setback
• Clear explanation of the context and impact
• Steps taken to address the issue and mitigate consequences
• Lessons learned and how they've been applied since

11. Naomi Pilosof Ionita: Challenging Conventional Wisdom

Naomi Pilosof Ionita, VP of Product at Evernote, asks:

"What's something that everyone takes for granted that you think is essentially hogwash or inaccurate?"

This question evaluates:

• Critical thinking and willingness to challenge assumptions
• Ability to form and articulate independent opinions
• Innovative thinking and potential for driving change

A strong response:

• Presents a well-reasoned argument against a common belief
• Provides evidence or examples to support the contrarian view
• Demonstrates thoughtful analysis and original thinking

12. Ayo Omojola: Unexpected Outcomes

Ayo Omojola, Chief Product Officer at Carbon Health, poses:

"Tell me something you did that worked out but not for the reason you thought it would, or tell me something you did that was a good decision that didn't work."

This question reveals:

• Ability to reflect on and learn from experiences
• Adaptability and openness to unexpected outcomes
• Honesty in admitting when initial assumptions were wrong

An insightful answer includes:

• A specific example of an unexpected outcome or failure
• Analysis of why the original reasoning was flawed
• Lessons learned and how they've influenced subsequent decisions

13. Scott Belsky: Self-Reflection and Luck

Scott Belsky, Chief Strategy Officer at Adobe, asks two questions:

"What have you learned about yourself that reveals a limitation in how you work?"

"Do you consider yourself lucky?"

These questions assess:

• Self-awareness and willingness to acknowledge weaknesses
• Ability to learn and grow from limitations
• Humility and recognition of external factors in success

Strong responses demonstrate:

• Honest reflection on personal limitations and efforts to overcome them
• Recognition of the role of luck and privilege in one's career
• Balanced perspective on personal achievements and external factors

14. Lauren Isford: Defining and Delivering Impact

Lauren Isford, head of growth at Notion, asks:

"Tell me about a time that you delivered something that was impactful."

This question evaluates:

• Understanding of what constitutes meaningful impact
• Ability to execute and deliver results
• Alignment of personal motivations with business objectives

An impressive answer includes:

• A specific example of a high-impact project or initiative
• Clear metrics or evidence of the impact achieved
• Explanation of the process and challenges overcome
• Reflection on personal growth and lessons learned

15. Paul Adams: Reference Call Insights

Paul Adams, Chief Product Officer at Intercom, suggests asking references:

"What feedback will I be giving this person in their first performance review?"

This approach:

• Encourages honest feedback about areas for improvement
• Provides insights into the candidate's potential growth areas
• Helps set expectations for onboarding and early performance

When preparing references, candidates should:

• Choose references who can provide balanced, honest feedback
• Discuss potential areas for improvement with references in advance
• Be prepared to address growth areas proactively in interviews

Conclusion

These 17 interview questions from top tech leaders offer a wealth of insights for both interviewers and candidates. For hiring managers, these questions can help uncover a candidate's true potential, assessing not just skills and experience but also cultural fit, values, and growth mindset. For job seekers, understanding these questions and the reasoning behind them can help you prepare more effectively for interviews, showcasing your strengths and demonstrating your ability to reflect, learn, and grow.

Remember, the best interviews are conversations, not interrogations. Whether you're asking or answering these questions, approach them with curiosity, honesty, and a genuine desire to learn and improve. By doing so, you'll be well on your way to finding the right fit – whether that's the perfect candidate for your team or your ideal next role in the tech industry.

Article created from: https://www.youtube.com/watch?v=UhASMW6X4AY