Making the decision to join a startup isn’t always easy. It’s regularly repeated that 90 percent of startups fail, which forces the question: Am I prepared to take the risk? After all, when you accept a startup job offer, you’re making a bet on a company that might not be around in five or 10 years.
But that risk could pay off. Billion-dollar brands like Facebook, Apple, and Amazon started small. Just 20 years ago, taking a job at Netflix would have raised eyebrows; Blockbuster was the safe alternative. Fast-forward to 2014, and all remaining Blockbuster stores shut down. Netflix, on the other hand, has surpassed more than 137 million subscribers.
Stumbling into opportunities to join the next Netflix are rare, but these examples serve as a reminder that saying “yes” to joining a startup could change the trajectory of your career. You never know if and when a company could take off. It might be worth making a bet.
Ultimately, reaching that “yes” decision comes down to answering a variety of questions. Some you need to ask yourself, while the others you should pose during the interview process.
Questions to Ask Before Joining a Startup
Before you’re seated across from the CEO, there are a few questions you need to ask yourself to ensure you’re making the right decision.
Here are four questions you should ask yourself before joining a startup:
1. Can I Afford This?
Depending on when you join the team or how well the company is performing, you need to acknowledge a hard truth: You might not always get paid on the standard schedule. Geoff Donaker, the former chief operating officer at Yelp, says you should prepare to survive a three- to six-month period with no salary and assume your equity is worth zero.
While this might not happen, having the right resources and savings in place could make the overall startup experience a little less stressful.
2. What Can I Learn?
If you are going to take the risk, you want to ensure it pays off not just financially, but professionally. In a startup environment, it’s rare to focus solely on one or two tasks. With a small team, you typically need to wear multiple hats—and that can be rewarding because it often translates into having more autonomy over what you learn.
Are there skills you can gain in this role that could advance your career and better position you for your next job? If so, now might be the right time to join the team.
3. Who Are the Founders and Do I Believe in Their Vision?
Understanding the founders and their backgrounds are crucial. Is this their first startup? Are they new to the industry? How do they approach innovation? What is their vision for the company? The answers to these questions will determine how they run the organization. For example, if this is their first startup, are you confident they can successfully and strategically guide the business through uncertainty?
You are entrusting these people with the next stage of your career, and will likely spend more time with them than you will your own friends and family. You need to trust and believe in their vision.
Founders also typically set the tone and culture of the company early, and their decisions have a trickle-down effect. If your values don’t align, consider it an early warning sign that the road ahead could be rocky. It's also important to remember that startup culture is inherently different from corporate culture, and you should evaluate whether it is right for you.
Related: 4 Questions to Ask the CEO
4. Where Is the Industry Headed?
If you’re concerned about job security, analyze the industry you’re operating in. If you work in hospitality, for example, there might be more growth opportunities at Airbnb than a regional hotel chain.
Examine what the future of your industry looks like and whether the startup you’re joining is tackling a big challenge or worthwhile opportunity. More than 2.4 million new healthcare jobs are expected to surface by 2026, in large part because startups have forced the industry to evolve and adapt. Are similar opportunities emerging in your industry? Is your prospective company poised to make a significant impact?
Questions to Ask During a Startup Job Interview
If you feel comfortable with your responses to the first four questions, you should proceed with the interviews. Next, consider which questions you should ask during the interview process to better understand the company.
Here are seven questions you can ask during an interview to determine if this is the right startup for you:
5. What Are the Company’s Values?
If the company’s values and vision can’t be clearly articulated, it’s likely there’s no roadmap in place, which poses an added risk. Some startup employees are expected to work 50 to 60 hours per week. When you commit to those hours, you want to know what you’re driving toward and believe in the guiding principles every employee should, ideally, share.
6. What Is the 30-60-90-Day Hiring Plan for this Role?
This question is particularly important when you’re in a new position. Before accepting a startup job offer, it should be clear how the company envisions your role, where the priorities are, how your responsibilities might evolve, and the ways in which you can meaningfully contribute.
What’s listed in the job description might not necessarily be the reality, and you don’t want to run the risk of accepting a job offer only to realize the scope of the role isn’t fully defined and there’s no room for growth in the company.
7. What Does Success Look Like in This Role and How Will I Be Measured?
To further clarify your role and responsibilities, follow-up with this question. It’s important to remember: You were hired for a reason. Whether to solve a particular business problem or launch a new division of the company, it should be clear what “success” means in your role. Will you be evaluated against the overall objective or smaller, predetermined milestones?
Also, who’s responsible for determining “success”—your direct manager, the founders, or the company’s board of directors? This should also be clear because you want to ensure your goals and values align with the appropriate decision-makers.
8. What Are the High-Level Team Structures? How Do Teams Collaborate?
This question can also help determine the role you’ll play in the organization and how you might partner with others outside your department. A company that operates in silos can be problematic; there’s bound to be inefficiencies and miscommunications. If you’re interested in learning more about the company culture, hearing how and if teams are encouraged to share ideas and collaborate can speak volumes.
9. What Is the Current Runway, and What Are Your Future Funding Plans?
Talking about money can often feel uncomfortable, but it’s reasonable to discuss when you’re interviewing for a startup position. Knowing the company’s runway, or the amount of time a company has until it runs out of money, says a lot about how sustainable the business is, but also the strength of the management team. Plus, the longer the runway, the greater your job security.
If the runway is less than a year, you should ask about future funding plans. Is the company trying to raise capital? If so, what types of investors are the founders looking for or working with? Some hiring managers might not want to reveal this, but them sidestepping the question could prove just as telling. You can gauge their level of transparency, as well as if they see you as a core team member.
Related: 4 Benefits of Joining a Startup
10. What Is the Company’s Exit Strategy?
Not only is it important to know what you'd be working toward, whether an IPO, merger, or acquisition, but you also want to confirm that your timeline aligns with the company’s goals. For example, if the founders say they’re aiming for an acquisition within two years, are you prepared to deal with that transition? An exit could affect your role. How would that impact your career trajectory in the long term?
11. Has Anyone Already Left the Company? If So, Why?
This question might also feel awkward to ask, but can indicate any systemic issues in the company, as well as help you gauge the company culture and the skills or traits the founders look for in employees. It might also uncover the truth about the company’s sustainability. For example, if they’ve experienced significant turnover, was it because they made financial cuts and had to eliminate several positions?
You could also zero in on your specific position. If the role existed before, consider asking why the person left. What challenges was he or she facing?
Making the Decision to Join a Startup
There won’t be one right answer to several of these questions; each person has their own list of non-negotiables. Maybe you’re willing to take a pay cut to work alongside seasoned founders, or perhaps you won’t take the job without the promise of equity. Either approach is fine, you will need to determine your walk-away point; what’s the bare minimum you’ll accept?
Ultimately, the questions you truly need to repeat are: Do I care about the mission? Do I believe in the product, service, or founders? If those answers are “yes,” you might be closer to a decision than you think.
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This post was updated on July 19, 2019. It was originally published on October 26, 2018.
