Questions to Ask Before Joining a Startup
Critical questions to ask before joining a startup to assess the opportunity, understand the risks, and make informed decisions about your career move.
1What is the company's current financial situation, and how long is the runway?
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What is the company's current financial situation, and how long is the runway?
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Why this works
Understanding their financial health helps you assess the stability of the opportunity and your job security.
2What is the company's business model, and how do you plan to achieve profitability?
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What is the company's business model, and how do you plan to achieve profitability?
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Why this works
Learning about their business strategy helps you understand if the company has a viable path to success.
3Who are your investors, and what is their involvement in the company?
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Who are your investors, and what is their involvement in the company?
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Why this works
Understanding the investor base helps you assess the company's credibility and support system.
4What is the equity compensation structure, and how does vesting work?
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What is the equity compensation structure, and how does vesting work?
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Why this works
Learning about equity helps you understand the potential upside and long-term value of joining the startup.
5What stage is the startup in, and what are the key milestones for the next 12-18 months?
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What stage is the startup in, and what are the key milestones for the next 12-18 months?
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Why this works
Understanding their stage and goals helps you assess the opportunity and what your role would entail.
6What is the company culture like, and how would you describe the work environment?
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What is the company culture like, and how would you describe the work environment?
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Why this works
Learning about culture helps you determine if the environment would be a good fit for your work style and values.
7What would my role be, and how might it evolve as the company grows?
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What would my role be, and how might it evolve as the company grows?
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Why this works
Understanding role expectations and growth potential helps you assess if the position aligns with your career goals.
8How does the founding team work together, and what is their track record?
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How does the founding team work together, and what is their track record?
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Why this works
Learning about the leadership helps you assess if they have the skills and dynamics to lead the company to success.
9What are the biggest risks facing the company, and how are you addressing them?
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What are the biggest risks facing the company, and how are you addressing them?
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Why this works
Understanding risks helps you make an informed decision about whether the opportunity is worth the potential downsides.
10What is the work-life balance like, and what are the expectations for hours and availability?
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What is the work-life balance like, and what are the expectations for hours and availability?
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Why this works
Learning about work expectations helps you understand if the role fits with your lifestyle and personal priorities.
11How do you approach product development and decision-making?
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How do you approach product development and decision-making?
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Why this works
Understanding their processes helps you assess if you'd enjoy working in their environment and have input.
12What is the competitive landscape, and how are you differentiated from competitors?
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What is the competitive landscape, and how are you differentiated from competitors?
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Why this works
Learning about competition helps you understand if the company has a defensible position in the market.
13What benefits and perks are offered, and how do they compare to larger companies?
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What benefits and perks are offered, and how do they compare to larger companies?
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Why this works
Understanding compensation beyond salary helps you assess the total value of the opportunity.
14What happens to my equity if the company is acquired or goes through another funding round?
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What happens to my equity if the company is acquired or goes through another funding round?
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Why this works
Understanding equity implications helps you protect your interests and know what to expect in different scenarios.
15What is the exit strategy, and what is the realistic timeline for liquidity?
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What is the exit strategy, and what is the realistic timeline for liquidity?
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Why this works
Learning about their exit plans helps you understand when and how you might realize value from your equity.
Evaluating Startup Opportunities
Expert tips and techniques for getting the most out of these questions.
Smart Startup Assessment
Do Your Due Diligence
Research the company, founders, and market thoroughly before making your decision.
Get Everything in Writing
Request written offer letters and equity agreements to ensure you have clear documentation of the terms.
Talk to Current and Former Employees
Seek out employees to understand the real culture and working conditions at the startup.