5 Questions To Ask Yourself Before Taking A Startup Job

As yourself these important questions to help decide if your startup option will be rewarding–or if the entire office will be packing its boxes before the end of summer.

5 Questions To Ask Yourself Before Taking A Startup Job


A few weeks ago, I wrote an article for Fast Company on why those searching for jobs should consider working at a startup over a bigger, more established corporation. While many Fast Company readers agreed with the sentiment, a few did point out the inherent risks of working at a startup. Jobs at a startup are naturally sketchy, with less job security, lower pay, and more turnover than a bigger corporation. But just because something is risky, doesn’t mean you shouldn’t do it. It does mean that you need to weigh the risks against the many positives I outlined in my previous article.

To do so, ask yourself these important questions to help you decide if your startup option will be rewarding or if the entire office will be packing their boxes before the end of summer.

Question 1: Would you use the product?

This may seem like a very simple question, but it’s one that is often overlooked. When deciding whether you think a startup will live or die, and therefore can provide you with an income for the foreseeable future, whether you would use the product or not is a pretty good measurement of your confidence in the product.

If your answer is yes, you would definitely use the product, than you’ve passed the most rudimentary test of judging a startup’s success. However, this doesn’t mean an answer of “no” completely writes off the validity of the startup. The follow-up question “Why wouldn’t you use the product?” is definitely necessary. If your answer is: “Because it sucks,” then you need to move on, my friend.

But if your answer is more logical and thought-out (geez, put in some effort, at least), and the result is that the product or site is targeted for a different type of user than you, then you can still believe in a product without using it. I may not be the target audience for a site that caters to travelers who want to tour through Europe, stay in 5-star hotels, and participate in wine tastings every night, but I can definitely understand the appeal. So, if anyone starts that company and needs a writer, photographer, or videographer, call me.


Question 2: Do the founders have a positive track record?

One of the best ways to predict future behavior is to study past behavior. This is true for founders of startups as well. Do the founders of the startup in question have a track record of success or failure? If this isn’t their first startup or business venture (and it’s not your current college roommate), then you’ll be able to ask about or look up how they have fared in the past. Before you even go into an interview with a startup, you should know the history and track record of the founders. Where did they go to school? What did they study? Where did they work right out of school? Have they started their own company before? Once you’ve done your research, you should be able to answer all of these questions and come to at least a preliminary judgment about the type of people who run your potential employer. With LinkedIn, Facebook, and more startup and tech blogs than ever, finding this information shouldn’t be difficult. But please don’t friend them on Facebook (creep).

Question 3: Does working at a startup mesh with your career goals?

I noted in my previous article, “8 Reasons To Choose a Startup Over a Corporate Job,” that there are a lot of good reasons to take a job at a startup. One that I believe is most beneficial is the ability a startup has to give you more responsibility and give you the chance to have a larger impact on a company’s success. In turn, this gives you the opportunity to enhance your skills in different areas as well as focus specifically on the skills you want to improve. Depending on your career goals, whether it’s to become a better writer, move to freelance developing, or retire at the age of 29, match it with the benefits of working at a startup.

Along the same vein, another question is: do you hope to start your own company some day? This answer doesn’t have to be “yes,” but it sure does help. If your answer is “no,” then there are still plenty of reasons to take a job at a startup–including becoming more self-sufficient and having the opportunity to try out a lot of different types of positions and tasks. But if your goal in life is to start your own company, then taking a job at a startup is a great way to learn the ropes of everything involved. As an employee at a small company, you should have plenty of opportunities to study the founders, the CEO, and the top guns in the company as they deal with fundraising, company pivots, monetization strategies, personnel additions, management styles, and everything that it takes to run a startup. Being in the startup world will also give you an inside look into dozens of companies and how they function (there’s always the CEO who screams at his team on the other end of the co-working space. Don’t be that guy).

Question 4: Are the founders willing to mentor you?


One of the best parts about larger companies that many small startups can’t give you is a mentorship program that helps you in your career goals. You continually hear great things about larger companies’ mentorship and training programs, giving employees the chance to continue their education in their desired field long after they have left school. As someone who loves to learn, I’m definitely jealous of some of these programs.

However, even in a small company, you still may have a chance to do just that. At the beginning of my time at Wanderfly, my boss Christy and I set up a time every few weeks to meet and talk about my goals and what else I would like to work on. This allowed us to talk through my position, what goals I have for the coming month, and how I can meet my own growth objectives while thinking of new and creative ways to help the company. While it’s difficult to keep a regular schedule for these meetings, even sporadic chats are helpful. Don’t be afraid to ask for help and guidance. The more you improve and the more you are satisfied with your job, the better off the company will be.

Question 5: What are the growth projections?

This is a question that’s answer can be broken into two parts.

The first is personal: Is there room for your own growth in the company, both financially and in responsibility? Many take a job at a startup exactly for the former reason. They hope that their startup hits it big, gets bought by Google or Facebook, and they walk away with a cool million or two in the bank. If you’re one of the first employees and get a healthy amount of stock options upon signing, this is a possibility. But beware that not every startup (see: very, very few) will end up being bought for a boatload of money. The second option is to grow with the company, move into new positions with more responsibility, and continue your career-growth in that way.

This brings us to the second type of growth: company growth. Does the company have a coherent plan to grow and monetize its product? The problem a lot of startups fall into is creating a product and having no way to monetize it or grow its user-base. You can create the coolest, most revolutionary product in the world, but if no one uses it or there is no way to monetize it, than it’s going to be real hard to grow with the company. When deciding whether to take a job at a startup, you are definitely allowed (and hopefully encouraged) to inquire about the company’s monetization and growth strategy. If there isn’t one in place, and you have a hard time figuring out what it could be, then tread lightly. A company without the ability to make money and no plan to do so isn’t a company. It’s just an investor parasite (or a government organization).


Bonus Question: Are you drowning in student loans and/or debt?

If yes, and you have another chance to work in a corporate position, you probably shouldn’t take a job at a startup. Really–get a more secure, probably higher-paying job, get out of debt, and then re-read questions 1-5.

Kerrin Sheldon is a writer, photographer, and cofounder of a new travel documentary series launching soon. He was the writer and content manager for Wanderfly and is currently at Everest’s doorstep. Follow him around the globe @kerrinsheldon.

[Image: Flickr user Cody Kapcsos]


About the author

Kerrin is the co-founder of Humanity.TV, a new online series focused on authentic travel. A filmmaker, photographer, and writer, Kerrin is currently shooting documentary shorts in Southeast Asia