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13 Entrepreneurs Share Their Favorite Job Interview Question

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Professional success doesn’t come easy. If you want the best jobs, you have to answer the toughest interview questions. And can find them in the following guide from online CV builder resume.io. It includes 13 of the most challenging interview questions from highly successful business founders. More importantly, it shows you how to answer them.

Let’s start with an ‘easy’ one!

You need to be pretty smart to design electric cars or reusable space rockets. And that’s why Elon Musk tests potential employees with this post-grad level question:

“You’re standing on the surface of the Earth. You walk one mile south, one mile west, and one mile north. You end up exactly where you started. Where are you?”

If you’ve got some serious cerebral processing skills, it won’t take long to figure out the answer. 

(It’s The North Pole!)

But what do you do if your talents are in other areas, like people management? 

According to resume.io, the trick to dealing with complex questions is honesty. Admit you don’t know, then ask follow-up questions to help you understand the problem. This demonstrates humility, a willingness to learn, and an inquisitive mind. The best employers know these qualities are just as important as raw brain power.

Get comfortable with feeling uncomfortable

Self-reflection is hard. However, it’s something that many of the world’s most successful business people look for when hiring new staff.

Chad Dickerson, former Etsy CEO, slips this uncomfortable question into every interview:

“Tell me about a time you really screwed something up. How did you handle it? How did you address the mistake? 

Luis Von Ahn’s favorite interview question demands even greater levels of soul searching. The Duolingo CEO  challenges applicants by asking, “What would someone who doesn’t like you tell us about you?”

Both questions are meant to make you feel uncomfortable. They’re designed to test your self-awareness and ability to take responsibility for your development. 

Again, honesty is the best policy, But this is an interview, so make sure you reframe your ‘faults’ into positives. Explain how you identified them and what you’re doing to overcome them.

Don’t be afraid of a little boasting!

Roli Saxena prefers to give candidates a chance to shine.

“What are you better at than most other people? What’s your superpower, and how will it impact this company?” asks the Adroll President.

There’s a fine line when it comes to the art of self-promotion. Resume.io advises focusing on your strengths that relate to the role. And use real-world examples to back up your claims. Otherwise, you’ll just sound like a big head. And nobody likes those!

You can find more tips below. Use them on your next job finding mission. They’ll help you turn your current dream into that next big win.


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The Entrepreneur’s Reading List That Transforms Ideas Into Empires

These must-read titles and writing insights reveal how entrepreneurs turn bold ideas into empire-level success.

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top entrepreneurship books for business growth
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Entrepreneurship is powered by stories—of accomplishment, failure, and decision moments that define businesses. Books are maps, providing insight from individuals who’ve traversed the road ahead. (more…)

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Entrepreneurs

The Leadership Shift Every Company Needs in 2025

Struggling to keep your team engaged? Here’s how leaders can turn frustrated employees into loyal advocates.

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Bridging the gap between employees and employers
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In workplaces around the world, there’s a growing gap between employers and employees and between superiors and their teams. It’s a common refrain: “People don’t leave companies, they leave bad bosses.”

While there are, of course, cases where management could do better, this isn’t just a “bad boss” problem. The relationship between leaders and employees is complex. Instead of assigning blame, we should explore practical solutions to build stronger, healthier workplaces where everyone thrives.

Why This Gap Exists

Every workplace needs someone to guide, supervise, and provide feedback. That’s essential for productivity and performance. But because there are usually far more employees than managers, dissatisfaction, fair or not, spreads quickly.

What if, instead of focusing on blame, we focused on building trust, empathy, and communication? This is where modern leadership and human-centered management can make a difference.

Tools and Techniques to Bridge the Gap

Here are proven strategies leaders and employees can use to foster stronger relationships and create a workplace where people actually want to stay.

1. Practice Mutual Empathy

Both managers and employees need to recognize they are ultimately on the same team. Leaders have to balance people and performance, and often face intense pressure to hit targets. Employees who understand this reality are more likely to cooperate and problem-solve collaboratively.

2. Maintain Professional Boundaries

Superiors should separate personal issues from professional decision-making. Consistency, fairness, and integrity build trust, and trust is the foundation of a motivated team.

3. Follow the Golden Rule

Treat people how you would like to be treated. This simple principle encourages compassion and respect, two qualities every effective leader must demonstrate.

4. Avoid Micromanagement

Micromanaging stifles creativity and damages morale. Great leaders see themselves as partners, not just bosses, and treat their teams as collaborators working toward a shared goal.

5. Empower Employees to Grow

Empowerment means giving employees responsibility that matches their capacity, and then trusting them to deliver. Encourage them to take calculated risks, learn from mistakes, and problem-solve independently. If something goes wrong, turn it into a learning opportunity, not a reprimand.

6. Communicate in All Directions

Communication shouldn’t just be top-down. Invite feedback, create open channels for suggestions, and genuinely listen to what your people have to say. Healthy upward communication closes gaps before they become conflicts.

7. Overcome Insecurities

Many leaders secretly fear being outshone by younger, more tech-savvy employees. Instead of resisting, embrace the chance to learn from them. Humility earns respect and helps the team innovate faster.

8. Invest in Coaching and Mentorship

True leaders grow other leaders. Provide mentorship, career guidance, and stretch opportunities so employees can develop new skills. Leadership is learned through experience, but guided experience is even more powerful.

9. Eliminate Favoritism

Avoid cliques and office politics. Decisions should be based on facts and fairness, not gossip. Objective, transparent decision-making builds credibility.

10. Recognize Efforts Promptly

Recognition often matters more than rewards. Publicly appreciate employees’ contributions and do so consistently and fairly. A timely “thank you” can be more motivating than a quarterly bonus.

11. Conduct Thoughtful Exit Interviews

When employees leave, treat it as an opportunity to learn. Keep interviews confidential and use the insights to improve management practices and culture.

12. Provide Leadership Development

Train managers to lead, not just supervise. Leadership development programs help shift mindsets from “command and control” to “coach and empower.” This transformation has a direct impact on morale and retention.

13. Adopt Soft Leadership Principles

Today’s workforce, largely millennials and Gen Z, value collaboration over hierarchy. Soft leadership focuses on partnership, mutual respect, and shared purpose, rather than rigid top-down control.

The Bigger Picture: HR’s Role

Mercer’s global research highlights five key priorities for organizations:

  • Build diverse talent pipelines

  • Embrace flexible work models

  • Design compelling career paths

  • Simplify HR processes

  • Redefine the value HR brings

The challenge? Employers and employees often view these priorities differently. Bridging that perception gap is just as important as bridging the relational gap between leaders and staff.

Treat Employees Like Associates, Not Just Staff

When you treat employees like partners, they bring their best selves to work. HR leaders must develop strategies to keep talent engaged, empowered, and prepared for the future.

Organizational success starts with people, always. Build the relationship with your team first, and the results will follow.

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Entrepreneurs

What Makes an Entrepreneurial Leader? Traits of the World’s Best Innovators

Inside the mindset of entrepreneurial leaders who transform risk, passion, and vision into world-changing results.

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When you think of Richard Branson (Virgin Group), Bill Gates (Microsoft), Steve Jobs (Apple), Rupert Murdoch (News Corporation), and Ted Turner (CNN), one thing becomes clear: they are not just entrepreneurs, they are entrepreneurial leaders. (more…)

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Entrepreneurs

Building a Business Empire: Lessons from the World’s Boldest Entrepreneurs

Learn essential lessons, success strategies, and mindset shifts every aspiring entrepreneur needs to overcome challenges and build a thriving business.

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Back in July 2017, I attended a business seminar on entrepreneurship in India. With my appetite for learning and meeting new people, I wanted to explore the latest developments in the entrepreneurial world. (more…)

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