10 tough questions you must ask in your next job interview

By Brie Weiler Reynolds

December 05, 2021

You’ve lined up a coveted job interview. You spend time preparing to make a great first impression, researching the company, anticipating questions, practicing your answers, and thinking of your own questions about growth opportunities and what a typical day on the job is like. But there’s something else you may not think to prepare: Difficult questions you might need to ask the employer during the interview.

Deciding to change jobs and work for another company isn’t just about getting the best salary and benefits package possible, or jumping at the chance to work on an exciting project, or growing your skills in new ways. It’s also about how you’ll spend your time every day, the culture of your new company, and whether you’ll ultimately be happy you made the decision to take the job, weeks, months, and maybe years into the future.

As the career development manager at the remote job search website FlexJobs, my team of career coaches and I strongly encourage our jobseeking clients to consider asking tough-but-fair questions that help them make the right decision for their careers.

We’ve outlined 10 hard questions to ask an interviewer, along with why you might want to be brave and ask that in your next job interview.

1. Why is this position available?

Why ask it: The answer from this question can tell you a few helpful things including whether this is a new position (which comes with its own challenges), or whether someone left the position because they were promoted, moved laterally at the company, quit, or were fired. Whatever the answer, you will learn something valuable about the job and team you might join.

2. What makes it a great day and what makes it a challenging day at work?

Why ask it: Rather than a vague question about what a typical day may look like, this subtle, yet hard-hitting question will allow you to get a much clearer picture of the highs and lows of the job.

3. When was the last time you promoted someone within your team, and why?

Why ask it: This question can provide insight into what the hiring manager considers to be the most important traits, skill sets, and achievements to progress within the company. Plus, it also gives intel on career progression within the organization and how often employees are able to move up through the ranks.

 

4. What are some of the challenges you expect the person in this position to face?

Why ask it: Every job will have its challenges, but asking about them specifically can help you learn what they may be ahead of time and whether they’re the types of challenges you’d feel comfortable tackling.

5. How are criticism and feedback handled within the team?

Why ask it: Some managers and teams do a great job of handling feedback and critical discussions in a way that helps everyone grow and evolve, and some just don’t. The answer you receive from this question will help you know what to expect and whether it’s an environment you’d be well-served in.

6. What is the main reason employees stay at or leave this company?

Why ask it: Not only will this question provide a better sense of a company’s existing culture, it will also offer insight as to how aware the company is about employee experience and if they take employee feedback, such as exit interviews, to heart.

7. Do you have any Employee Resource Groups (ERG) and how might they support your DEI work?

Why ask it: By asking directly about ERGs, you’ll be able to determine if the company is vested and committed to their DEI strategic plans and if they’re creating programs and policies to support their employees. This question is also an excellent way to determine if your values align with the company’s values and mission statement and if the company provides opportunities for its employees to grow while being valued as a contributor.

8. What’s the company’s approach to supporting work-life balance, and what are some recent initiatives you’ve put in place related to the pandemic?

Why ask it: The answers received from this question will help you determine if the company really does support work-life balance and in what ways. Asking about any new things they’ve done as a result of the pandemic will tell you if the company is responsive to the ever-changing needs of its workforce.

9. How does the company determine salary levels or ranges for remote workers and is it at all different for in-office workers or hybrid workers?

Why ask it: Companies with remote workers have several different ways they might determine salary levels. Typically, it’s based on either the company’s location, the worker’s location, or another metric like the national average. Knowing how they calculate their pay rates gives you solid information to make informed decisions if/when you’re negotiating salary requirements.

10. Do you have any hesitancy in hiring me?

Why ask it: This offers a chance to immediately address anything they might say, and hopefully help the interview move past whatever is making them hesitant about hiring you for the role. Plus, it can provide solid information for how to improve for future interviews.

Will you need a bit of nerve to ask some of these questions? Absolutely. But when you approach them with a positive mindset and see them as a chance to gain a much deeper understanding of a team before you’re a part of it, they’re worth it.

Not all of these questions will be helpful for every interview you have, but consider asking some of these to glean more nuanced and helpful information to better inform your next professional move.


Brie Weiler Reynolds is the career development manager and a career coach at FlexJobs and Remote.co.


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