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]

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  • Rob K.

    I've worked for two startups.  The first I worked part time as they were
    just not large enough to justify the head count.  Then when they were
    large enough they offered me a position.  I had to think hard about it
    because I was already working for a company that (at the time) was
    stable.  I was treated well but I had no further growth path.

    As aforementioned, I worked for the first startup as a part time worker so I had the advantage of seeing what it was like.  

    Even though I had worked for them on a part time basis for over a year I still had to interview for the position.

    The interviews went well and was perhaps the most relaxed interview I
    had ever had.  Everyone one I met with already knew me and knew what I
    was capable of. 

    It wasn't until I interviewed with the CFO.  Although he too knew me and
    my abilities his first question was "How do you feel working for a
    company that has no product, yet, and could fold at any moment?"

    I thought this was a very pessimistic question but then I really thought
    about what he was asking me.  He was making me aware that the company
    (at that time) was still relying on investor money and that if we could
    not deliver and become cash flow positive we would fold. He was asking
    that if I wasn't ready or willing to take that risk there was no real
    point in continuing with the interview.

    Because of what I knew of the company, the people, the business plan and
    overall vision, I was confident in my decision.  In fact my answer was
    more-or-less that. 

    I also knew I had a lot more growth potential with this company and they
    needed people who were willing to do whatever was necessary for the
    company to succeed.  We had people doing three or more different jobs,
    often times jobs that were not in our job description but we knew it had
    to be done and we knew that it wouldn't be forever - if we succeeded we
    would be able to hire people to do those jobs.

    So I got to learn a lot of different things in the company and proud to
    say I was with them for 15 years before moving to the next company.

    The next company was in the same industry but doing something different 
    I really had to think if I wanted to get back into a startup.  With my
    previous company it was fun and I was also younger.  :)  I knew the
    physical and mental toll it took.  But I was also looking for a
    challenge and wanted to learn something new.

    I was with them for about 6 years before they had to downsize due to the
    economy.  I will say that we did weather the economy storm a lot better
    than many of our competitors. 

    When we were looking at a possible layoff in 2009 the management
    (including myself) agreed to not take a pay raise and forfeited our year
    end bonus in order to save jobs.  This told me a lot about the company
    the people I was working with and was proud that we did that.  It bonded
    the company.  We did have to let some people go but not as many as we
    had thought. 

    Though I was let go in 2012, I did learn a lot from my second company and have no regrets.

    Because of the skills and experience I got from both companies, the
    ability to truly work dynamically (you have to when working in a
    startup) made finding a position with another company easier.  In fact
    within a month of being let go in 2012 I was hired at my current
    employer.  My past experience is what attracted the attention with my
    current employer.

    All of that said - my advice is that you have to be patient and be able
    to go with the flow.  Things may seem chaotic at first, frustrating at
    times, but in the end it will be well worth it. Often times you will
    have to do many jobs at once.  Take advantage of this.  It's something
    that you can put on your resume.  Remember, it won't always be like

    I learned early on that there's no guarantee or job security in either.  You can be let go just as easy in a stable company.


  • Alex

    Hi Rob, 
    Thanks for sharing your story. Could you give the name of the first startup that you worked for?