What is it really like to work at that hot startup? Three must-ask questions

Anna Starasts

March 2, 2016

There are a ton of tech community events that give you access to the work spaces and teams of startups, like Startup Open House or one of the many Meetups hosted in startup offices. Maybe you’ve imagined what its like to work there and the HR manager’s pitch about their cool brick and beam office with video games, catered meals and a friendly office dog is compelling.

But can you really learn what it’s like to work at a company in such a brief interaction? How do you know if it’s the right move for you? Foosball tables and beer fridges are fun, but they can’t tell you whether you’d enjoy the culture of a company or the technical challenges you’d be faced with.

If you’re prepared to ask the right questions, however, you can get a better picture about life at that cool startup. Here are a few questions we think you should ask.

Ask: What does it take to be successful here?

To gain… Insight into the company’s culture.

Workplace culture is something that’s both very important and very difficult to decipher from a brief interaction. While the term “culture” is used in a variety of ways, let’s define it here as what a company does to make its employees successful and happy contributors.

Ask questions like: Is being a great collaborator more valued that being an individual high-performer? How does the company handle employees making mistakes? If there’s minimal management and supervision, does that jive with how you feel you do your best work?

Looking at culture through a personality lens (asking “do I like this person I’m speaking with and can I see myself spending 8 hours a day working with them”) is a fair question but it doesn’t tell you if you’ll have successful working relationships. Equally, if you’re looking at culture as environmental factors like flex hours, free lunches, games rooms and beer fridges, you’re getting at some of the superficial perks but you won’t get a real grasp on how satisfied employees are everyday. A ping pong table does not a happy employee make.

Ask: What does your future product roadmap look like?

To understand… How technical challenges align with what you’re passionate about.

A company’s roadmap is one way to understand whether you’ll like the technical challenges of working on their product. Are they focused on maintenance and improvement of their existing platform or building out tons of new features? Have they established some serious partnerships and are anticipating their platform to scale massively because of this? Have they just landed funding that will allow them to hire more developers and put serious people-power into improving performance? Perhaps the roadmap sees the product expanding into offerings that excite you, like connected devices or a heavier mobile focus.

Ask: What does the company do to help employees learn & grow? 

To find out… Whether you’ll strategically deepen your skills and knowledge.

Especially if you’re in the first half of your career, your focus is likely on growing your technical depth and breadth, learning from as many mistakes as possible, and possibly acquiring some mentors or colleagues you can turn to when stumped. Mid-career, you might be looking to learn how to manage bigger teams and improve process (especially with the evolution of agile and the new way companies are adopting it, like Spotify’s model). Ask whether the company has a plan or budget in place to help employees reach their learning goals, or how the company discusses and learns from mistakes as a team.

What other questions have you found useful when researching companies you’re interested in working for? Add you suggestions as a comment below.

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