Joining a Startup? 12 Things to Consider First

June 12, 2016 By Brian Shoicket

Joining a startup is not for everyone. Really, it isn’t.

Here are some questions to ask yourself—without the bright light, one-way mirror, and good cop/bad cop—to figure out not only if a startup is right for you, but also what to look for when joining a startup:

The Fish:Pond Ratio
Do I prefer working on a large team where everyone has a specialized, more focused role? Or a smaller team where projects require the agility of a bullfighter, flexibility of an Olympic gymnast, and high tolerance for (potential) chaos?

The Atlas Workout
Does the idea that my work at a smaller company will account for a larger part of its livelihood excite or intimidate me?

Living the Dream
Am I truly, genuinely, 100% passionate about the companies to which I’m applying and the products or services they offer? This tends to hold more gravity in hiring decisions at startups.

Check Mates
If necessary, would I take a smaller salary to work at a startup that seems like a perfect fit for me than I could potentially make in a similar role at a larger company that I’m less passionate about?

Interior Design
Do I prefer the productivity and isolation that come with cubicles and offices, or the collaboration and distractions that come with a bustling, no-wall open office (which startups are notorious for)? Do I dream of one day calling the corner office with floor-to-ceiling windows “home,” or sharing a workspace with coworkers regardless of seniority, and oftentimes role?

Clock Work
Is “9-to-5” a personal requirement, suggested schedule, or cruel joke? Startup hours can be unpredictable – though often more flexible and with later starts, which sometimes can mean later nights…

Clothes Call
Does “business attire” mean tailored suits, blouses, and button-downs? Or simply “whatever is clean”? Startups seldom require formal garb, but dressing to impress can be an important factor for some job seekers.

Where the Wild Things Are
Am I comfortable around – or allergic to – animals? Startups are more likely to have the occasional roaming pet!

Your New Best Friends
Do I like the people with whom I’d be working? I mean, do I really like them? At a startup, you tend to bond more closely with your coworkers. And even if your role changes, chances are that you’ll still be working with the same folks. At a larger company, however, changing roles or departments could mean less or even no communication with certain colleagues.

Security Guard
Is “job security” a deciding factor, or am I open to a company that’s high-risk/high-reward? Most startups don’t make it, and the end can come quickly. On the other hand, success can be on an unimaginable scale: Facebook acquired WhatsApp for $19 billion when they had 55 employees, Yahoo! acquired Tumblr for $1.1 billion when they had 178 employees, and even powerhouses like Microsoft, Google, and Apple were once startups.

How Do You Take Your Coffers?
Do I prefer a company that is well-funded, has received some funding, or is bootstrapped? Do I understand how this affects not only my compensation (salary + equity) in the short- and long-term, but also how this can affect business decisions and founder/team autonomy?

Game Changers
Am I looking for a company that’s taking chances and moving quickly to disrupt industries and transform the world (realizing that they might not succeed in doing so)? Or do I prefer a company that’s been in the same line of business for decades and shows no sign of deviating (realizing that they could be overthrown by a new product or service)?

Feeling more and more like joining a startup is right for you?

Take the next step by getting to know the people behind them and the problems they are solving. You can learn new skills, strategies, and tips from today’s most innovative startups right here on Uncubed.

If startup life doesn’t feel quite right for you, fear not! There are, of course, plenty of other options at larger, more traditional companies. But if you find yourself longing for the best of both worlds, it might surprise you to learn that many larger companies have divisions that operate very similarly to startups including IBM Watson, @WalmartLabs, GE Open Innovation, and Capital One Labs, just to name a few.


Recent Uncubed Posts
  • 33 Companies define their promise to employees + Spotify’s remote work plan + Employee wellbeing + Being an ally + Improve your employer brand

  • Check out our new look + Office of the future + Clubhouse + Top HR questions to ask yourself for 2021 + Difference between recruiting & TA

  • Be better at diversity recruiting + Pipeline D&I fails + Unifying your employer & customer brand + Creating remote work boundaries