What to ask about benefits when starting a new job


The excitement of starting a new job is often accompanied by the anxiety of stepping into a new working environment. Yes, you’ve gotten past the salary negotiation and a high-level review of benefits, but now that you’re officially on the team, how do you know – and take advantage of – all the employee benefits available to you?

Larger organizations are likely to have official – even mandatory – benefits orientations, which painstakingly outline everything from how you accrue vacation time to the different flavors of health insurance. But can a seminar or online training session detail all that’s available? And how could it possibly cover the unexpected?

Smaller companies that offer fewer employee benefits present an additional challenge. How do you get ownership to consider a benefit that some employees would enjoy were it available?

Below are descriptions some of the most popular employee benefits. You’ll want to ask if your new employer offers these perks and, if so, how generous the benefit is.

Health insurance

Unless your new employer is very small, it must offer health insurance. The federal Many states impose additional mandates for medical coverage.

Most large employers, and many smaller ones, offer a range of health plans that meet or exceed the government mandates. But regardless of the available health insurance options, a critical consideration is this: When do the benefits kick in? Do you have insurance to cover you and your family until your employee coverage starts?

You’ll also want to know to what degree your health coverage is subsidized, and how often can you change your health benefits. Is it annually, or more frequently?

The commute

If your job lies in an urban hub or a sprawling suburban business park, your benefits likely include some type of commuting subsidy. This may come in the form of van pools, a free bus pass, a monthly stipend you can apply to public transportation, or subsidized parking. You’ll want to fully understand what’s available and how to take advantage of it. You’ll also need to be aware that under the Tax Cut and Jobs Act, as of January 1, 2018 companies can no longer take a tax deduction for qualified transportation benefits, so such perks might be on the chopping block.

What if you’re a cyclist? Is there a secure place to store your bike? Is there a changing room, and does it have showers?  Do you get discounted bike tune-ups or discounts for safety equipment, such as helmets, lights, and reflective gear? The new federal tax law allows employers to deduct qualified bicycle commuting expenses through December 31, 2025. After that, they will join the other commuting subsidies as being non-deductible.


Ask if your company offers incentives for keeping fit , such as subsidized health club memberships. If you’re a smoker, are there incentives to help you kick the habit? Are you required to get a flu shot each year to minimize the risk of everyone getting sick during flu season – and if so, does the company offer it free of charge?

If “sitting is the new smoking,” does your employer provide ergonomic benefits, such as a standing desk? What about a standing mat to go with it, to ease pressure on your legs when you’re standing? If you inherited a used office chair, can it still be properly adjusted?

Professional development

Does your organization encourage personal professional development, either through a mentorship program or external study? Can you attend workshops and conferences related to your field? Would you be able to attend workshops during working hours? Are there tuition reimbursements for advanced degrees or certificate programs, and are they limited to what would be directly applicable to your line of work?

Large organizations may offer internal training programs, or regular meetups with others in similar roles, to share best practices and develop related skills, so be sure to ask about these.


Is working remotely an option during an emergency? Employers in Seattle and San Francisco are acutely aware of how even a minor earthquake could shut down critical infrastructure for days, turning already lengthy commutes into multiple hours of gridlock.  Tornadoes can wreak similar havoc in places like Tulsa and St. Louis, while hurricanes threaten Miami, Houston, and other coastal cities.  Does your new employer have provisions that allow you to work from home during such natural disasters?

And what’s the policy if, during extreme weather events like snowstorms, government officials recommend people stay home? Would you lose pay if you were unable to work on site?

Unwritten rules

Be sure to inquire about the existence of unwritten benefits. Many employers permit flex time, even if there’s no explicit policy statement in the employee handbook. So, it’s worth asking. Maybe your manager wouldn’t mind if you worked at home one day a week, or altered your commute to avoid traffic, starting your day working from home then going to the office after rush hour.

Is the office animal friendly? Many people are allergic to animals, but some companies, like Avvo, promote their dog-friendly policy.

Broken benefit promises

Employers often boast of their great benefits because it helps them attract and keep talent. In addition to reducing turnover, which can be costly regardless of a company’s size, benefits can help foster team building, collaboration, and productivity. If the benefits you’re getting are not what were promised, or if you feel your employer isn’t offering benefits to which you’re entitled, talk to your human resources representative. After that, if you still feel that you’re being shortchanged, it’s best to seek legal advice.