5 Questions That Will Tell You Everything About A Company’s Culture

5 Questions That Will Tell You Everything About A Company’s Culture

Earlier this year, 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 prioritise culture not because I like to have a cappuccino machine in the office. I prioritise 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 holidays, 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:

Too often, companies have a “jobs” or “career” link that are a list of open positions or, even worse, only a contact email. A company may have the most enjoyable workplace in the world, but if it’s not clearly communicated on the “about” page, job seekers are incentivised to take their talents elsewhere.

On culture: The 5 questions you need to ask your next employer [Sean Blanda]

Sean Blanda is a journalist/entrepreneur living in Brooklyn. He currently works at Behance. Read more on his about page.


  • “Does the company give a damn?”, I would actually change to be “Product or profit? Which does the company value highest?”

    I’m fortunate to work for one of the rare few in the former. It’s very VERY rare these days.

  • As someone who has been to a few interviews…. How would one ask these questions before working there?
    It seems a lot of these are evident in hindsight, but might not be that obvious when you are trying to decide on taking a new job or not…

    • 2 Ways that I have tried.
      1) At the start of the interview ask them about the culture of the place – you may not get an honest answer though
      2) Ring the place/department before the interview and have a chat with the secretary. I found they give great information on the place and often tell you what you want to know long before they ask exactly who you are and why are you asking. You can try ringing another department within the same organisation and asking them what they think of the department.

  • My biggest bugbear are good companies ruined by penny pinching accountants who don’t realise that cost cutting doesn’t lead to growth. Too often I have seen good employees leave through frustration over small directives issued by penny pinching accountants.

    • +1 to you Who knew…

      Posting under a pseudonym of course, just in case….

      The company I currently work for was a great place to work when I joined 6 years ago. We were given freedom, treated like adults to manage our own time, was able to work from home on a whim, and we delivered great results for our clients.

      Since then, several management changes have resulted in an accountant becoming a middle manager. All of a sudden targets increased to unrealistic levels, thus eliminating the possibility of meeting them, and also of us getting our bonus. The technical resources are being pushed to sell stuff, which is not something a lot of us want to do.

      Travel for things like courses has all but dried up, and expenses elsewhere are being scrutinised, or removed.

      All while we are working longer and harder, and getting nothing in return for it.

      Basically, the culture and vibe of the place has gone downhill, and so has morale with it.

      Sad state of affairs really.

      Accounts, good for 1.354 million times zero.

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