The 3 Best Questions to Ask Millennials

Guest Post by Dan Negroni

The only way to get powerful answers is by asking powerful questions. And powerful questions are the key to creating authentic relationships and connecting with anyone—especially millennials. As a manager, finding a way to relate with your millennial workers is critical…and not just because generation Y is way different than boomers and gen Xers, but because they will soon be the most dominant group in the workforce. Don’t know what to ask? Here are some great questions that will help you get to know your millennials in no time.

1.  What do you need from me to help you learn, grow and provide value?

Understanding the needs of your millennial workers is key to creating powerful relationships. Expressing you care enough about them to teach them is what they (and all of us) are seeking. This question will allow you to discover what your workers honestly need and in turn find challenging. And since you made it about them, you can trust the answer. Another surprising benefit is that your millennials may reveal potential flaws and inefficiencies within your company or your direct relationship with them. These 20 something’s’ are smarter than we give credit. This simple question may lead to discovering the strengths and weaknesses of your millennials and connection. As a manager, this will give you insight into what areas you need to focus on to deliver value to your team while also understanding what your workers excel in and where they would perform best. We call it bridging the gap on their terms, not yours.

2.  What do you care most about?

Everyone loves this question because it is directly about them.  It’s well known that millennials skew more toward seeking purpose in the workplace. This question will allow you to get to know your millennial workers on a deeper level—it will reveal your employee’s “why.” Once you understand what inspires and drives your millennials, you can figure out how to align individual, team and company’s goals. Understanding what motivates millennials is key to your success. This crossover is where the magic happens.

Bonus, you may find that your millennials have similar values and ambitions, which opens the way up for an authentic relationship to form. Millennials want you to be a trusted resource, a mentor, not just their boss. This question shows you are making an effort to get to know them personally and show up for them. It designates respect for them. Make an effort, show you care and be authentic. This question will help you accomplish all three!

3.  How can you be most helpful to the company?

At LaunchBox, we teach millennials to identify their strengths so they can communicate what they are best at. We operate best when we lead from our strengths and can articulate and communicate our value. Personal interests usually correlates with skill, so if this question doesn’t get the answer you want, go deeper, ask them about what they enjoy doing (an activity where they lose track of time, forget to eat, etc.)  

Don’t judge a fish by its ability to climb a tree. This question will help you place your millennials in the optimal position for the company, which is likely the most optimal position for them personally.

Bottom lining you …. Ask, ask, ask! Unless you make an effort to reach out and ask your millennials questions, you won’t bridge the generational gap. Use the power of questions and create awesome, authentic relationships today!



Dan Negroni, Author, Speaker, Attorney, Business Consultant, Coach, and proud Dad of a few Millennials delivers actionable solutions.  Different from all other millennial experts, Dan’s empowering business approach at LaunchBox, creates quick value and seamless connections with millennials and management each on their own terms. Using unique content and delivery methods that audiences respond to immediately he leverages results from the inside out. To start click here to grab your copy of Chasing Relevance: 6 Steps to Understand, Engage and Maximize Next Generation Leaders in the Workplace or call them at 858.314.9687 for a free Coaching Assessment.


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2 thoughts on “The 3 Best Questions to Ask Millennials

  1. I like these 3 questions not only for Millennials but for ALL employees.

    From Baby Boomers on down the world is shifting into a time when MEANING and PURPOSE really matter!

    What really matters to you and how does it tie into your career?

    1. Bob Tiede says:

      Gail you are 100% correct! Thanks for sharing your insights!

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