5 Questions To Ask When Interviewing Millennials

Millennials — often described as the next major workforce generation — are typically those born between 1980 and 1999.

They’re selective about where they work and are known to change roles in pursuit of their personal goals and career growth.

To attract them, your hiring process needs to align with what they value. Beyond career progression, many are looking for work that feels meaningful and contributes to something bigger.

Your goal is to make choosing your company an easy decision.

When you meet their expectations and provide opportunities for growth, you’re more likely to retain them and reduce job-hopping.

It’s also important to recognize that Millennials often prioritize different things than older generations. While previous generations may have focused primarily on job security and salary, Millennials tend to evaluate what a role offers them overall—especially in terms of growth and development.

To help you navigate this, we’ll cover five key questions to ask when interviewing Millennials in 2026.

1: Dig Into Their Previous Job Experience

You want to know how the Millennial candidate fared at their last job. You can ask a question like, “What is one thing you’d change about your previous job and why?”

This can also give you insight into their long-range goals. You can then assess whether these align with your company’s goals.

This open-ended question might also give you a peek into your candidate’s salary requirements, desired hours, working conditions, benefits expectations and more.

2: Ask Questions to Gauge Personality Fit

There are a few questions to choose from in this category:

1. Describe your perfect work week. The answer to this question opens the door to their expectations of flex time and working hours.
2. Describe your perfect work environment. Would you rather work in a traditional office, office with an open floor plan or at home? This helps ensure your Millennial will be happy in your chosen work environment.
3. What kind of relationship would you like with your boss? Many Millennials will expect a friendly relationship with their boss. This may be their first experience with someone in authority who may not want to pal around.
4. Throw in a question that catches your Millennial off-guard and offers him a chance to shine. Ask your Millennial candidate what television character best describes him and his work ethic. This helps you decide if he’ll fit in with your company culture.

3: Ask About Failures

Millennials have grown up in a generation where they’ve been accustomed to multiple rewards. Consider the many sporting activities that hand out trophies all the way to 12th place.

For many Millennials, they’ve received constant positive feedback whether they’ve deserved it or not. They are used to getting their way.

You want to know if they think they have ever failed. You want to go one step further and find out what they learned from it if they did know they had failed. It’s important for you to know how they’ll respond to failure and criticism.

Consider a question like this, “Did you ever get a test score or evaluation that wasn’t what you expected? Or, did you have to follow instructions that you didn’t agree with? Explain the situation.”

In addition to these questions, you can pose a query about how they’d like to receive feedback. This is your gentle way of letting them know there will be reviews, and they won’t always be perfect.

Another version of this question is to ask them if they’ve ever been passed over for an award or promotion they thought they were going to get and how they reacted.

You can also ask them about their expectations when it comes to feedback and let them know how you conduct staff assessments.

4: Ask About Job Expectations

Because Millennials want a job that meets their needs and feels fulfilling to them, you want to know why they applied for the job and what they expect to get out of it.

Bottom line – you want to know if they see the job as a stepping stone, or if they are in it for a longer period of time.

If you have a long-range plan in mind for the candidate, let him know. Detail a three-year road map so the Millennial knows how long it will take. Make sure that your job expectations and his are a match. Be doubly sure that he’ll stick around.

5: Ask About Volunteer Work

Millennials are often very concerned about giving back to society. Ask them what kind of volunteer or charity work they do.

People who offer their services are giving, often selfless employees who make great leaders and team members.

If you want to find out the same information, but ask the question less personally, you can ask them what they would do if you gave them time off to be involved in the community.

You do two things here – you let them know philanthropy is important to you, and you gauge their enthusiasm for it.

Final Thoughts:

When interviewing Millennials, give them the space to share their goals, interests, and experiences. Let them tell their story.

They often bring strong energy, curiosity, and a collaborative mindset. Most are looking for roles that feel meaningful and help them move closer to their long-term goals.

With more than 80 million Millennials in the United States, using the right interview questions can help you build a more effective hiring strategy.

**Have you hired Millennials? What strategies have worked for you? Please comment below to share your tips with others.**

JD Spinoza

JD enjoys teaching people how to use ZoomShift to save time spent on scheduling. He’s curious, likes learning new things everyday and playing the guitar (although it’s a work in progress).