12 Questions to Ask if You’re a Millennial Interviewing During the Great Resignation

Danielle Roberts (she/her) gives us the data to know we’re in control of our next job search.

Headlines dub this period “The Great Resignation,” but I prefer a different phrase – one that signals a broader internal shift in people’s hearts and minds; one that resembles the clarity that came from two years at home:

The Great Awareness.

While companies cried “Black Lives Matter” across social media, employees paid attention to internal DEI initiatives and diversity percentages (or lack thereof).

While companies shouted “Here’s a Headspace subscription,” employees paid attention to managers who got promoted even though they cultivated a toxic work environment.

While companies claimed, “We can only give you a 2% raise,” employees watched company profits soar while padding the pockets of CEOs and the C-suite.

And then, employees said “Enough.” More than 24 million American employees left their jobs between April and September 2021.

What’s driving this mass exodus? According to a recent study conducted by MIT Sloan Management Review, “Toxic culture is the biggest factor pushing employees out the door during the Great Resignation.”

The study went on to identify five elements that have “by far the largest negative impact on how employees rate their corporate culture and have contributed most to employee attrition throughout the Great Resignation”:

  1. Disrespectful
  2. Non-inclusive
  3. Unethical
  4. Cut-throat
  5. Abusive

The “Toxic Five” don’t simply displace people as workers, but as human beings, as they cannot be compartmentalized and kept at work, which has only been amplified by the COVID-19 pandemic. In other words, these issues follow workers home and infiltrate every aspect of their lives, especially their mental and physical health, which can lead to further issues with finances, personal relationships, and the like.

According to the same study, “A large body of research shows that working in a toxic atmosphere is associated with elevated levels of stress, burnout, and mental health issues. Toxicity also translates into physical illness. When employees experience injustice in the workplace, their odds of suffering a major disease (including coronary disease, asthma, diabetes, and arthritis) increase by 35% to 55%.

In addition to the pain imposed on employees, a toxic culture also imposes costs that flow directly to the organization’s bottom line. When a toxic atmosphere makes workers sick, for example, their employer typically foots the bill. Among U.S. workers with health benefits, two-thirds have their health care expenses paid directly by their employer. By one estimate, toxic workplaces added an incremental $16 billion in employee health care costs.”


So what does all of this have to do with interviewing?

Millennials now make up the majority of the workforce and expect their employers to play a bigger role in the societal and environmental issues that continue to unfold outside of the workplace. And they’re willing to hold companies accountable.

Separating work and life isn’t possible, a bad work environment will effect the rest of your life, too. Photo by Tim Foster via Unsplash.

In 2021, for example, software company Basecamp banned societal and political conversations at work in one of the most charged and polarizing elections of our lifetime. The result? One-third of employees quit. 

Another study showed that most millennials would take a pay cut to work at a company who cares about climate change, and that they’ve left a job in the past because of the company’s lack of a sustainability plan.

There is a great deal of systemic career search advice that starts and ends with telling you how to strategically get your foot in the door, like how to tailor your resume, crush the interview, and negotiate salary. 

While that advice is tactically helpful, it often comes from the human resources or hiring manager’s perspective of how you can check the company’s boxes and fulfill their best interests. But it fails to consider you as a full individual trying to find the right fit for you and the world you want to create.

We are in the midst of a new era of employee activism that may well upend and challenge existing patterns of power within organizations.

Part of that activism includes you asking intentional, intelligent questions during the interview process based on your own standards and values, as well as what you are looking for in a potential employer and boss.

Here are 12 lesser-known questions to gauge their company culture and ensure you enter a healthy work environment that aligns with your values and goals:

  1. How has the company supported the health, safety, and wellbeing of employees throughout the COVID-19 pandemic?
  2. Is activism part of the company’s strategic plan? If so, how does the company create a secure space to listen to employees and communicate about broader societal and environmental issues?
  3. Why is this position available/Why did the last person in this position leave?
  4. What does your organization believe about psychological safety, and how do you nurture it on your team?
  5. Can you walk me through the last time you promoted someone on your team and what that process looked like?
  6. How do you deliver feedback? Can you walk me through the last time you approached an employee with feedback and how that feedback was received?
  7. How do you support the professional growth of the people on your team?
  8. What’s the company’s approach to supporting work-life balance?
  9. Do you have any Employee Resources Groups (ERGs) and how might they support your Diversity, Equity & Inclusion (DEI) initiatives?
  10. Can you tell me about a time when you or someone on the team made a mistake. What happened, and how was it handled?
  11. What excites you to come into work? What’s one thing you wished would change?
  12. If you were in my position, would you be excited to take this job?

Remember: you are interviewing them as much as they are interviewing you.

You don’t have to ask all of these in the same interview, but the goal is to ask intentional questions based how the interview unfolds and what’s most important to you. It’s equally important to actively listen and take notes on how they respond to refer back to late – even the words they don’t say through their body language.

Finally, take inventory of your thoughts and feelings after the interview. If you walk away feeling heard and appreciated and know you’ll flourish in that environment, that’s a wonderful sign. On the contrary, if you feel those internal red flags waving, listen to them.

As uncomfortable as asking some of these questions may feel, know that you are demanding your voice be heard while gathering enough information to make an informed decision and creating space to grow and thrive personally and professionally.

Happy Interviewing!

About Danielle:

From my humble beginnings as a broke, first-generation college student to earning six figures in my twenties as a marketer then starting multiple businesses in my thirties, I know what it takes to make bold career moves. My path led me down all of the “typical” versions of success – the job, the car, and even owning a home – only to find that I still felt empty and deeply unfulfilled. I decided to disrupt the norm, dig deep, and discover how I really could have it all based on my own definition of success.

Now, I’m a purpose-driven career coach, and it’s my mission to help millennials and dream chasers who are tired of settling for “good enough” and provide them with the tools, resources, experiences, and accountability to help them identify their self-sabotaging behaviors, uncover purpose in their careers, and find fulfillment and beauty in their lives.


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