Finding Employees: 5 Interview Questions for Millennials & Gen Z

As older baby boomers retire in droves, younger generations are beginning to fill today’s workforce. But these new generations have vastly different values than older generations did – which makes sense given rapid technological advances and inevitable cultural shifts. For those who may not know, the two newer generations are Generation Y (aka millennials) and Generation Z. According to the Pew Research Center, millennials are born between the years 1981 and 1996; Gen Z is anyone born after that.

Read, ‘How to Reject Job Candidates Without Burning Bridges’ for more helpful tips on running your business.

Characteristics of Millennials & Gen Zers

Before getting into some key interview questions to ask this generation, it’s important to understand some of their defining characteristics and therefore their values. Of course, there are always exceptions to these, but generations tend to reflect ever-changing societal norms through their values and priorities.

Millennial Characteristics:

  • Tech-savvy: Millennials grew up with technology and they tend to integrate it into their lives as often as possible, making them both adept and knowledgeable.
  • Family/community-oriented: On the whole, millennials tend to value family, friends and community over their careers. This means they are often willing to trade high pay for flexible schedules and better work/life balance.
  • Authentic: Millennials don’t tolerate sugar-coating. They value candor, authenticity and transparency, refusing to pretend to be something they’re not. They see how older generations played “the game” and do not want to partake. They tend to value individuality and equality over hierarchy.
  • Emphasize self-preservation: Some see it as narcissism or entitlement, but millennials value self-preservation. They’ve seen their parents experience frightening shifts in corporate culture: devaluation of seniority, worker exploitation, etc. and will not hesitate to take their skills elsewhere if they do not feel secure and empowered in their workplace.

Gen Z Characteristics:

  • Technologically advanced: Unlike Gen Yers & Xers before them, Gen Zers were born once cell phones and the internet were established. This means these technologies are really second nature to them almost from the get-go.
  • Independent: The entrepreneurial spirit tends to flow strongly in Gen Z, since they strive toward self-autonomy and independence.
  • Low Attention Span: With access to nearly infinite knowledge at their fingertips, Gen Zers tend to have short attention spans – 8 seconds, to be exact. Despite this, if you do manage to capture their attention, they tend to remain loyal.

5 Interview Questions for Millennials & Gen Z

1: Do You Work Better Alone or With Others?

Millennials pride themselves on being an inclusive generation that values community. Asking this question gives you some insights on how well they work collaboratively with others. Be sure to ask them how they handle situations in which they’ve had to work with diverse opinions and always ask them to give a real-life example.

2: What Type of Office Do You Prefer?

Because millennials tend to value company culture that aligns with their personality, spend time in the interview asking about these types of specificities. Many companies offer alternative styles of office. Some companies have flexible schedules, some have liberal work-from-home policies, and some still have rigid 9-5 office structures. If their preferences don’t vibe with your established culture or work environment, they probably won’t last long in their role.

3: When Was the Last Time You Were in Over Your Head?

The one interview question everyone dreads: what is your greatest weakness? It almost always feels like a trap; and the whole philosophy of spinning it into a positive often feels contrived. However, asking when was the last time you were in over your head?, or alternatively, when was the last time you failed? asks a similar question but with more room for interpretation – and it can be more rewarding in the end. A negative stereotype of millennials and Gen Zers is that they’re narcissistic, so put it to the test. This question will make them challenge their own abilities and show you if they are capable of objectivity and introspection, while teasing out some real-world learning experiences.

4: What Type of Boss-Employee Work Relationship Do You Expect to Have?

Ask the candidate if they expect a hands-on approach from their bosses or if they prefer more autonomy. Oftentimes, millennials and Gen Zers like to get frequent positive feedback, so setting expectations and ensuring you have those types of reporting structures available is key to their overall productivity. Additionally, since younger people tend to prefer meaningful personal connections over hierarchy, a boss that is more friendly, socially active and in tune with them (eg. someone they can go to happy hour with) will make for a better work environment for them.

5: What Position Do You Want to Have in 5 Years?

Younger generations tend to have an exceptional work ethic, with higher drive and a lot of ambition to boot. Finding out just how much ambition they have will help you determine not only where they see themselves in the future but will also allow you to set expectations. Most candidates don’t expect or want to remain in the position for which they are interviewing, so asking this not only gives them an outlet to express their professional desires, it shows that you are willing to facilitate their achievements and provide upward mobility to meet their goals.

For more tips on interviewing, small business advice and more, check out the Society Insurance HR blog series. At Society, our people make the biggest difference; learn more about our career opportunities.


We strive to ensure each new hire will make a contribution to help keep Society moving forward. Beyond the necessary skills required for the job, we look to hire those with additional attributes to create a cohesive environment within our company. Join us and maximize your potential here at Society Insurance by applying at

Latest Articles

Resolving Conflict in the Workplace Amicably

On average, 85% of employees will experience conflict in the workplace (Essential Workplace...

The Benefits of Active Listening in the Workplace

When people on a team struggle to listen to each other,...

Can You Use FMLA for Mental Health?

The Family and Medical Leave Act (FMLA) guarantees qualified workers the right to unpaid leave for...

Why Remote Teams Need Inclusive Workplace Practices

For most businesses, remote work is now a way of life in some capacity. Advances in technology and...

How to Motivate Employees as a Manager During Uncertain Times

As a manager in the restaurant industry, it can be challenging to motivate your employees during...

3 Reasons Why Authenticity in the Workplace Matters

Regardless of industry, a business is only as strong as its employees. Even the best products,...

Top Advice For Graduates Trying to Start a Career

As of 2020, there is an average of over 4 million students who have graduated from colleges in the...


Originally published January 29, 2019, updated January 18, 2023. Many parts of the country are no...

A Guide to Safe Keg Handling

At one time or another, almost everyone who works in the restaurant and bar industry has been...

2022 Year in Review

Society Insurance is committed to providing blog posts to help business owners optimize daily...

Stay up to date with industry updates by subscribing to the Society Insurance blog!