Looking for a New Job? Here Are 5 Types of Questions To Ask To Ensure It’s the Right Fit

While inquiries about a company’s definition of success and culture can always shed light on what you might anticipate about a new job, these topics are all the more important to broach now, given rising rates of burnout, higher prevalence of remote work, and, for many, a post-lockdown realignment of workplace boundaries.

Below, career experts share the most important questions to ask a hiring manager this year in order to pinpoint whether a prospective job is likely a fit.

5 types of questions to ask a hiring manager before accepting a job offer

1. The question about a typical workday

It might seem obvious at first glance, but asking a hiring manager to describe a typical workday for the role you’re considering is a deceivingly simple way to determine if the job itself will match the written job description. “As a potential employee, it’s important for you to get the hiring manager’s viewpoint on the role to make sure there aren’t any discrepancies and that there’s cohesion between perceived and actual expectations,” says executive coach Cheryl Grace, CEO of career consultancy Powerful Penny.

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As the hiring manager speaks on the role, listen for examples of work-life balance or lack thereof, and whether they identify any personal preferences for how they expect the job to be done that might differ from the expectations of the team or company at large, says burnout expert Erayna Sargent, founder of Hooky Wellness, an anti-burnout consultancy.

2. The question about success

Figuring out how a hiring manager measures success is your key to understanding whether you could reasonably level up to that expectation and make strides within the company down the line. “It’s helpful to ask, ‘What does success look like for this role, particularly in the first 90 days?’” says Grace. Or, you could frame the question as "What kinds of people are successful in this environment, and who do you think wouldn’t be?" says mindset expert and scaling coach Julia Pimsleur, founder of Million Dollar Women.

If you can easily envision yourself embodying the qualities that they describe, there’s a better chance you’ll jibe well with the role. To practice some future-focused thinking, you could even follow up the above question with, "If I’m successful here, what kind of trajectory could I hope to have over the next 1 to 2 years?" adds Pimsleur.

3. The question about communication style

Asking how the hiring manager prefers to communicate can offer insight into whether you’ll really mesh with them on a day-to-day basis. For example, "hands-on" can sometimes be a flag for micromanaging, says Sargent. So if this comes up, you might ask for examples in order to understand if that means they’ll be available to talk you through tasks as needed, or if they’ll be overly involved in your workflow.

In this realm, it’s also helpful to ask about their after-hours email and phone-call policies, says career coach Kimberly Lucht. “The last thing you want to do is get caught up in a 24/7 work shuffle, so getting clear about communication boundaries can help you avoid that situation from the get-go,” she says.

4. The question about workplace flexibility

For many, pandemic restrictions have made remote working an everyday reality—and it’s likely that workplace flexibility (including certain fully remote workplaces) is here to stay. As such, a question about the expectations surrounding your physical workplace is essential to add to your arsenal, says Sargent: “You can ask, ‘What are the expectations regarding working from home?’ which can also help you understand how your future boss or team’s approach may differ from that of the company overall.”

If the answer includes some combination of work-from-home and office work, consider a follow-up question about how many people generally embrace one, the other, or both, suggests Lucht. “This past year has shown us that employers can be more flexible than we thought, and that employees can match that with reliability to meet objectives whether or not they’re in the office,” she adds.

And if you are considering a company that has embraced a hybrid approach, it’s also worth asking about the systems in place now to support remote workers, and how they’re generally integrated with in-office workers, says Pimsleur.

5. The question about culture

The vibe of a workplace may be every bit as integral to your success in a new role as the job itself. To get a sense of a company's culture, consider asking, "What new things has the organization done to support employee well-being over the past two years?" says Sargent. This opens the door for a conversation about how the company is handling the collective traumas folks have experienced since the onset of the pandemic; how it has (or hasn't) implemented new diversity, equity, and inclusion initiatives; and whether it’s providing adequate resources for employees to avoid burnout and even languishing.

For a more pointed approach, you might ask, "How would you describe the company culture in just a few words?" suggests Pimsleur. “Is it more family-oriented and casual, or more fast-paced and get-the-job-done, or more excellence above all, or something else entirely?” she says.

Certain cues in the hiring manager's answers may tip you off to particular elements of culture, too. “Listen for indications that it’s a competitive work environment or any discussion of ‘work-hard, play-hard’ culture,” says Pimsleur—all of which could be potential red flags. Similarly, phrases like “challenging work environment” or “rapidly changing environment” could be indicators that chaos reigns, says Grace. “‘Long hours’ typically refers to employees working frequent overtime, and may also reflect a lacking vacation policy.”

By contrast, bright forecasters of positive culture could include any indication that the hiring manager values employee feedback and that they have a history of implementing real changes when something isn’t working for their team, adds Pimsleur.

And beyond asking these questions of a hiring manager, listen to your gut during and after your conversations throughout the interview process. With some introspecting, you may find that you're more attuned to how you feel about a prospective job and company than you initially realized.

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