The 5 Questions That Will Tell You Everything About a Company's Culture

This summer, I was fortunate enough to be able to relax and thoughtfully enter the next phase of my working life. For the first time in my life, I could take the next step in my career on my terms. After enjoying the spoils of working for myself, I was ready to join a company again. This led to me spending a handful of weeks looking for the perfect fit. As I talked to friends and browsed company websites I found myself caring about one question above all others: "What's it like to work there?"

In other words: "What's the company's culture?"

Cynical members of older generations like to point to some sort of entitlement as the primary motivation here, but that's a lazy assessment. As a job seeker, I prioritize culture not because I like to have a cappuccino machine in the office. I prioritize culture because I want to be dedicated without any reluctance or regret. I want to believe that if I hustle I'll be moving some cosmic needle (and my own career) in the right direction while having a good time.

And I'm not the only one. There are startups like Culture Sketch in the works to help solve this problem. Indy Hall cofounder Alex Hillman talks about this often: better work starts with better coworkers. Which really means people that share our values and priorities while challenging us to be better.

From a business owner's perspective, clearly communicating an enjoyable culture is an easy win to attracting the best talent. From a job seeker's perspective, asking the right questions is an easy way to assure a good fit and avoid wasting months, even years. Here are some of the questions that I was asking as I looked at each company or sat in job interviews:

Does this company work to live or live to work?

Most startups fall squarely in the "live to work" category. Startups expect some degree of personal sacrifice from their employees in exchange for the promise of the sort of sudden shared prosperity that can only come from a rapidly scaling startup. Alternatively there are established companies like 37 Signals that have four-day workweeks in the Summer. Or Red Frog Events which pays employees to take long sabbaticals. Neither approach is "wrong," but should be clearly communicated.

Meritocracy vs. Seniority

When employees ask for more vacation, higher salary or a promotion how does the company decide to allocate its resources? Can a second-year employee leap-frog a long time worker based on exceptional work? Or does the company prefer to reward loyalty?

Does this company give a damn?

To paraphrase Reddit founder Alexis Ohanian: Does the company give a damn? Whether the company makes clothes or builds links, it should care about what it does and strive to be a leader in the industry. An offshoot of this question is: Is the leadership invested? Is the founder or CEO likely to leave for another opportunity?

What do the company's offices look like?

Offices don't have to be huge open floor plans with movable pods and slides, but it needs to at least be a pleasing space, a space that is clearly designed with employees in mind instead of overhead.

Do smart people work here?

One of the primary advantages of being an employee instead of an entrepreneur is mentorship. As a entrepreneur the unknown is exhilarating, and often lonely. When you work for smart people you have a chance to learn new tricks to eventually stake out on your own again or make the company you work for better.

The best companies made sure to clearly communicate their culture on their website. Below are a few "culture" pages that are worth emulating: