Tales of Abundance

Redefine Your Hiring Process with These 13 Powerful Questions

By Randy Lorensen · Entrepreneurship · Leadership & Culture

Have you ever felt like the questions you ask during interviews are a waste of time? You’re not alone. I spent years asking the standard questions, only to find people just gave me the answers they thought I wanted to hear. They yielded little useful information, wasting my time and theirs.

The Problem with Common Interview Questions:

In my early 20s, I interviewed thousands of people a year. Like many, I asked the typical questions:

  • Tell me about yourself.
  • What are your strengths?
  • What are your weaknesses? (Do you think they actually told me?)
  • How do you deal with pressure or stressful situations?
  • Do you prefer working independently or on a team?
  • How do you keep yourself organized when balancing multiple projects?
  • Are you good with people? (Of course, everyone was a people person.)
  • Why should I hire you? (After hearing the same answers over and over, all I heard was blah, blah, blah.)

These questions often led to repetitive, uninspiring answers that provided little insight into the candidates. It became clear that we were asking the wrong questions.

The Revelation:

Through experience and learning from various sources, I discovered that one of the keys to effective interviewing is asking questions that reveal a candidate’s true values and characteristics indirectly. Direct questions like "Are you reliable?" often lead to uninformative responses. Instead, consider these transformative questions:

Transformative Questions to Ask:

  1. What are you entitled to? — The only good answer is "nothing." Unless you want a company full of entitled workers.
  2. Why is your best friend your best friend? — This reveals what they value, particularly in relationships.
  3. What's the best lesson your father, mother, or a mentor ever taught you? — Like the best-friend question, this gives you a clear window into what they value, who shaped them, and what they find important.
  4. Share a memory of your dad, mother, or grandmother. — This highlights who and what they cherish and appreciate most.
  5. What's the thing you've been most excited about? — I want to gauge if they still have excitement and enthusiasm. I look for their body language, the gleam in their eye, and their tone more than the words.
  6. What's the longest you've worked on something without sleep? — While not always applicable, it shows their dedication and limits.
  7. Where did your drive come from? — I want to see what their drive is built on—whether it comes from a chip on their shoulder, family example, or internal standards.
  8. What failure changed you the most? — I'm watching as much as anything how they respond to this question. Are they comfortable? I'm trying to see if they are willing to learn. People unwilling to fail are likely also unwilling to grow very much. BTW, that may be OK for some jobs.
  9. What's the most successful organization you've been part of? Why? — I'm trying to determine if they know how to win. It's a skill. But, asking the follow-up questions is the most important part. They will tell you what they value and appreciate.
  10. What's your favorite organization you've been part of—and what made them successful? — You can ask both follow-up questions—"Why did you consider them successful?" and "What made them successful?"—to see what kind of culture they like, where they thrive, and their preferred work environment.
  11. What is your favorite movie or book? — Once they name it, ask follow-up questions about decision-making, leadership, and management inside that story. For example, if they say Game of Thrones, I’ll ask: "Who was the best leader? Who was the best spotter of talent? Who would you most want to hire or work with—and why?" The specific character they pick matters far less than their thought process. Again, you will see what they value and how they think.
  12. Tell me something true that almost nobody agrees with you on. — The answer is more about their beliefs and how they think. Are they willing to think outside the box?
  13. How successful are you going to be? — This explores their self-belief, confidence, and ambition.

Improving Standard Questions:

To improve the effectiveness of standard questions, make them situational. For example, instead of asking how they handle pressure, describe a specific stressful scenario they might encounter in the job and ask how they would respond. This approach provides deeper insights into their problem-solving and coping mechanisms.

For example, instead of asking, "How do you deal with pressure?" ask: "Imagine you are overwhelmed, there are supposed to be three people there, but it’s only you. You have an irate customer demanding a refund for a product in front of you. You also have a high volume of calls, and you are trying to get a few warranty fixes out in the mail—all happening at once. What do you do?" This will tell you much more about how they handle pressure. The answer is more about seeing how they respond, think, and process the information.

Practical Questions to Cover Essential Details:

In addition to the transformative questions, you still need to cover some basics:

  • Availability: Ensure their schedule aligns with your needs.
  • Salary expectations: Instead of asking for their expected salary, ask, "What is the most you’ve ever made?" or "What did you make last year?" (where permitted, or ask what range they're targeting to feel well-compensated).
  • Employment gaps: If they have gaps in their employment, ask, "Why did you take a gap year?" or "Why did you switch jobs so often?" For job switches, you could also ask, "Tell me about your job at ____."

Questions to Ask Yourself:

Maybe the most important questions you ask are those you ask yourself:

  1. Is this someone you'd like to interact with?
  2. Does this person represent our values, ideals, and goals?
  3. How will this person succeed here? — Can they do the job? — Desire? — Belief system? — Ability/talent? — Skills? — Do we have the support they need? — Do we have a plan for their success?
  4. Will they be happy here?
  5. Would I regret not hiring this person?

Conclusion:

Since I started asking questions like these, I've become much better at interviewing and finding people who fit my company. While I still make bad hires—we all do—these questions have significantly helped me identify not only red flags but also the attitudes and beliefs that signal the right candidates for the job. By using these questions, you can uncover the true potential of your candidates, ensuring they align with your values and can thrive in your organization. These transformative questions will help you not only fill positions but also cultivate a team that embodies the abundance mindset, driving personal and professional growth.

Related Tales of Abundance Tools & Episodes

Put the ideas in this article into practice today with our free fillable worksheets and companion podcast conversations:

Frequently Asked Questions

Why do traditional job interview questions fail to predict performance?

Most candidates rehearse polished answers to standard questions like 'What are your weaknesses?' or 'Are you good with people?' Indirect, character-focused questions cut past the script to reveal what a candidate truly values, how they think, and whether they take ownership.

What is the best answer to 'What are you entitled to?' in an interview?

As Randy notes, the only good answer is 'nothing'—unless you want a company full of entitled workers. Pair this with 'What failure changed you the most?' to see whether a candidate is comfortable owning mistakes and learning from them.

Why should you define your company's core values before interviewing?

Skills can be trained, but character and core values rarely change on the job. When you clarify your non-negotiable standards first—using Tool #01: Core Values & Personal Standards, our companion guide Rules of the Road to Abundance: Starting a Business, and Episode 11: Core Values and Culture—every interview question becomes a clear filter.

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Written by Randy Lorensen for Tales of Abundance. Every week, Dr. John Oberg, Randy Lorensen, and Anthony Marino explore practical frameworks across the 5 Fs: Finance, Fitness, Family, Friends, and Fun.

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