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Top 15 Startup Questions to Ask Yourself Before Starting a Business

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17 min. read

Updated February 18, 2025

1. “What problem am I truly solving, and how do I know it’s a real pain point?” 

Many aspiring entrepreneurs fall in love with their solution before validating the problem. They build products nobody wants or launch services that solve minor inconveniences rather than genuine pain points. 

The key is understanding the difference between a “Nice to Have” and a “Need to Have” product or service. To dig into this, you need to consider your potential customers’ priorities. Even if your solution works perfectly, is the problem you are solving important enough that your customers will invest time and money to solve it? For example, a busy restaurant owner might desperately need better inventory management but won’t prioritize a slightly better website design.

How to validate your problem:

• Talk to potential customers, but ask the right questions. Don't ask "Would you use this?" Instead, ask "How are you currently solving this problem?" If they aren't actively trying to solve it, it might not be a real pain point.
• Look for existing workarounds. Are people cobbling together complicated solutions? Are they spending significant time or money addressing this issue? These are strong indicators of a genuine problem.
• Observe behavior, not just opinions. People often say they want something but won't pay for it. Watch what they actually do, not just what they say they'll do.

Red flags that suggest you’re solving the wrong problem:

• People respond to your idea with "That's interesting" rather than "When can I get it?"
• You have to explain why people should care about the problem
• You can't find anyone currently spending money to solve this problem
• The problem only occurs rarely or affects very few people

2. “Why am I better positioned to solve this problem than existing solutions or potential competitors?” 

Standing out in today’s market isn’t just about having a good idea – it’s about having a legitimate advantage in executing that idea.

Many entrepreneurs fall into the trap of saying “Our solution will be faster/cheaper/prettier than the competition.” But that’s not always enough. You need specific, defensible advantages that make you uniquely capable of solving this problem. Think about what makes your approach fundamentally different, not just incrementally better.

Here are a few potential easy to think about competitive advantage:

Unique Insight or Experience

• Have you lived this problem personally in a way others haven't?
• Do you have insider knowledge of the industry that reveals overlooked opportunities?
• Have you accumulated specific expertise that gives you a unique perspective?

Network and Relationships

• Do you have connections to key suppliers, partners, or customers?
• Have you built trust with a specific community that's hard for others to access?
• Can you leverage existing relationships to accelerate growth?

Technical or Domain Expertise

• Do you possess specialized skills that are rare in your market?
• Have you developed proprietary technology or methods?
• Does your background combine different fields in a valuable way?

Market Timing and Positioning

• Has something changed in the market that creates a new opportunity?
• Are you positioned to take advantage of emerging trends?
• Do you have access to resources or channels others don't?

To test your advantage, you should ask yourself a few challenging questions:

• If a major player copied your idea tomorrow, what would still make you special?
• Why haven't others already solved this problem in the way you're proposing?
• What would it take for someone else to replicate your advantage?
• How sustainable is your advantage over time?

A sustainable business needs more than just a good solution – it needs a compelling reason why you’re the right person or team to deliver it. If you can’t articulate your unique advantage, keep digging until you find it or consider whether this is the right opportunity for you.

3. “What’s the minimum viable version of my product/service that I could test quickly?” 

One of the most common mistakes entrepreneurs make is fully committing to an idea and setting out to build the most perfect, feature-rich product. 

Instead, your first version of your product or service should be simple enough to launch quickly but valuable enough to generate real feedback from your potential customers.

This is called an MVP: Minimum viable product.

An MVP isn’t about launching something half-baked. It’s about finding the core value proposition that solves your customers’ primary pain point. Think of it as the “need to have” rather than the “nice to have” features. For a restaurant delivery service, the MVP might be manually taking orders via phone and handling delivery yourself, rather than building a fancy app first.

Building a simple web page and asking customers to place a pre-order can also be a form of MVP. The idea is to simplify your idea down to its core and then figure out a way to gauge customer interest.

Here are a few questions that can help you define your MVP:

• What's the one core problem your solution must solve?
• Which features are absolutely essential for solving this problem?
• What can be added later without compromising the basic value proposition?
• How quickly can you get this basic version into users' hands?

While it’s tempting to build out every aspect of your business before launching, here are a few things you can do to stay in an MVP mindset:

• Do things manually at first and automate later.
• Handle customer service personally before creating a help center
• Instead of building a product, use your time to provide the service that the product would provide and learn from your customers about what they really need.

The goal of an MVP isn’t perfection – it’s learning. Every day you spend adding features before launch is a day you’re not getting real feedback from actual customers. Start small, learn fast, and iterate based on evidence rather than assumptions.

4. “What’s my pricing strategy, and have I tested these price points with potential customers?” 

Setting prices isn’t just about covering costs and adding a markup. It’s about understanding value perception, market positioning, and customer psychology. 

Most entrepreneurs make the mistake of starting with their costs and adding a margin. Instead, start with the value your solution provides:

• How much money does your product/service save customers?
• How much time does it free up for them?
• What expensive problems does it help them avoid?
• What opportunities does it create for them?

Before setting prices in stone, use these strategies to gauge what customers will actually pay:

• Create different landing pages with various price points
• Offer pre-sales at different tiers
• Have direct conversations about pricing with potential customers
• Test different pricing models (subscription vs. one-time, tiered vs. flat rate)

Many new entrepreneurs stumble by starting their prices too low out of fear or insecurity. Others make the mistake of simply copying competitors without understanding the underlying business model that makes those prices work. Another common error is failing to account for all costs, especially customer acquisition costs, which can significantly impact profitability.

Remember that your price is a powerful signal about your brand and offering. Premium pricing can signal quality and excellence, but it also sets high expectations for service and results. Lower prices might attract more customers initially, but these price-sensitive customers often cost more to serve and may be less loyal over time. Mid-market positioning requires careful differentiation from both high-end and budget options.

Your pricing strategy affects everything from your marketing message to your target customer to your operational costs. It’s worth spending time getting it right and being willing to adjust based on market feedback.

5. “How will I know when to pivot versus when to persist?” 

One of the most challenging decisions entrepreneurs face is knowing when to stay the course versus when to change direction. While persistence is crucial for success, knowing when to pivot can be the difference between building a thriving business and exhausting your resources on a failing strategy.

The key to making this decision lies in understanding the difference between normal startup challenges and fundamental business model problems. Every business faces obstacles, but not every obstacle requires a pivot. When customers aren’t buying, is it because your marketing isn’t reaching them effectively (a tactical problem), or because your solution doesn’t actually solve their problem (a strategic issue)?

Your market is telling you something important when you see consistently low customer engagement despite having tried multiple approaches to reach them, when you’re hearing the same objections repeatedly from potential customers, or when your early adopters aren’t becoming repeat customers. These patterns suggest fundamental issues with your business model or core assumptions.

On the other hand, steady progress, even if slower than expected, usually signals you should stay the course. This is especially true if you’re seeing positive customer feedback, increasing repeat business, or growing word-of-mouth referrals, even if the numbers are small. Early wins with a small group of passionate customers often indicate you’re on the right track and need to optimize rather than overhaul.

6. “What are three ways my initial business plan could fail, and what’s my contingency for each?”

Smart entrepreneurs don’t just plan for success – they actively imagine and prepare for potential failures. This exercise isn’t about being negative; it’s about being prepared and building resilience into your business model from day one.

Your most dangerous assumption might be about market demand. Many entrepreneurs overestimate how many customers will buy their product or service. Your contingency plan should include a lean operating model that can sustain the business with 50% fewer customers than projected. This might mean starting with contractors instead of full-time employees or choosing a flexible workspace over a long-term lease.

Even profitable businesses can fail due to cash flow problems. Your customers might pay more slowly than expected, or your startup costs might exceed projections. Plan for this by maintaining relationships with multiple funding sources, keeping a low-overhead model initially, and having clear strategies for accelerating customer payments or delaying vendor payments if necessary.

The market might shift faster than you expect, with new competitors entering or existing players copying your innovation. Your contingency should include ways to differentiate beyond your initial unique selling proposition. This might mean developing secondary revenue streams, building strong customer relationships that transcend product features, or maintaining flexibility in your business model to pivot if needed.

The key is not just identifying these potential failures but having specific, actionable plans for each scenario. Write these contingencies down and revisit them regularly – they’re as important as your primary business plan.

7. “Who are three people in my network who could be key to my success, and have I talked to them yet?” 

Success in business rarely happens in isolation. The right connections can provide crucial advice, open doors to opportunities, or become your first customers. Yet many entrepreneurs overlook valuable relationships already within their reach.

Start by mapping out your network across different spheres: professional contacts, former colleagues, industry peers, friends, and family. Look specifically for three types of connections:

The Industry Insider – Someone who deeply understands your target market. This person might be a former boss, colleague, or even a competitor. They can provide invaluable insights about market dynamics, potential pitfalls, and opportunities others might miss.

The Potential Customer Champion – Someone who fits your target customer profile or has strong connections to your target market. This person can become not just a customer but an advocate, providing feedback and referring others. Their real-world perspective is invaluable for product development and marketing.

The Business Mentor – Someone who has built or scaled a business before, even in a different industry. They’ve faced similar challenges and can help you navigate common pitfalls. This might be a former entrepreneur, a business advisor, or an experienced executive.

Don’t just identify these people – reach out to them. Most people are willing to help if approached authentically and with respect for their time. Prepare specific questions and be clear about how they can help you succeed.

8. “Am I prepared to make personal financial sacrifices for my business?” 

Starting a business isn’t just a professional commitment – it’s a deeply personal financial decision that affects every aspect of your life. Before taking the leap, you need to honestly assess your willingness to adjust your lifestyle and financial habits.

Common sacrifices most entrepreneurs face:

• Reducing or eliminating discretionary spending like dining out, travel, and entertainment
• Potentially going without a salary for 6-12 months or longer
• Using personal savings or taking on debt to fund the business
• Postponing major life purchases like homes or vehicles

The impact often extends beyond just spending habits. You might need to:

• Move to a less expensive living situation
• Take on side gigs to maintain some income
• Sell valuable assets or tap into a retirement fund to generate startup capital
• Ask family members for financial support

Before proceeding, create a detailed personal budget that reflects these potential sacrifices. Calculate your minimum monthly living expenses and multiply that by 12-18 months. This is your personal runway – the time you can survive while building your business.

Remember, being prepared for financial sacrifice doesn’t mean being reckless. Set clear boundaries about what you won’t risk, like your retirement savings or your children’s education fund.

9. “How much money is it really going to take to get up and running?”

Many entrepreneurs underestimate their startup costs by focusing only on the obvious expenses. A realistic financial assessment needs to consider both direct costs and hidden expenses that can drain your resources before revenue starts flowing.

Essential Startup Expenses:

• Legal and administrative fees (business registration, licenses, permits)
• Insurance and compliance costs
• Initial inventory or materials
• Essential equipment and software
• Website and branding expenses

Often-Overlooked Costs:

• Working capital for at least 3-6 months of operations as your business grows
• Credit card processing fees and bank charges
• Professional services (accounting, legal counsel)
• Marketing and customer acquisition costs
• Buffer for unexpected expenses (typically 20% of projected costs)

Calculate your costs in three tiers: bare minimum to open doors, comfortable operating budget, and optimal scenario. This gives you a range to work with and helps identify which expenses are truly essential versus nice-to-have.

Most businesses require about 30% more capital than initially estimated. Build this buffer into your calculations from the start, and consider both one-time startup costs and recurring monthly expenses. Your goal isn’t just to launch – it’s to stay operational long enough to reach profitability.

10. “How long can I sustain operations if my revenue is 50% lower than projected?” 

Every business plan includes revenue projections, but smart entrepreneurs plan for scenarios where these projections fall short. This isn’t pessimism – it’s prudent planning that can mean the difference between survival and failure during tough times.

To figure out what it will take to sustain your business if sales drop or don’t materialize as quickly as you’d like, it’s important to know your monthly fixed costs (rent, salaries, utilities, loans) as well as your variable costs that scale with revenue.

Start by creating a “bare bones” budget that outlines the absolute minimum needed to keep your business functioning. Then calculate your runway – how long your resources will last – when less revenue than projected is coming in.

Key Survival Strategies to Consider:

• Identify costs that can be quickly reduced
• Explore potential revenue sources outside your core business
• Plan trigger points for making tough decisions
• Document which expenses can be deferred

The 50% question isn’t just about financial planning. It’s about understanding which parts of your business are essential versus optional, and having clear decision points for when to cut costs or seek additional funding. Most successful businesses faced lean times before finding their footing – the key is surviving long enough to get there.

11. “How will my relationships with family and friends change, and am I prepared for that?” 

Starting a business doesn’t just transform your professional life – it fundamentally shifts your personal relationships in ways many entrepreneurs don’t anticipate. Understanding and preparing for these changes is crucial for both your business success and personal well-being.

Potential impacts on your daily life might include:

• Less time for social events and family gatherings
• Missing important moments due to work commitments
• Changed dynamics when friends become customers
• Strain on relationships due to financial stress

Relationships can be impacted, too. 

• Family members may not understand your dedication to the business
• Friends might feel neglected or distance themselves
• Partner/spouse relationships often face new pressures
• Children may struggle with your reduced availability

Start by having honest conversations with your closest relationships about what to expect. Set clear boundaries and expectations about your availability, and create specific plans for maintaining important connections despite your new commitments.

Success means little if you lose your most important relationships along the way. Build regular family time into your schedule, just like any other business commitment. Consider this part of your business planning – because maintaining strong personal relationships isn’t just good for your well-being, it provides crucial emotional support during the entrepreneurial journey.

12. “What skills do I lack that are crucial for success, and how will I acquire or access them?” 

One of the most important skills an entrepreneur can have is the ability to identify and acknowledge their weaknesses. When you know where you need support, you’re able to fill those gaps with education or the right partners, so that you can improve your chances of building a sustainable and successful business.

Essential Business Skills to Assess:

• Financial management and accounting basics
• Sales and negotiation abilities
• Marketing and customer acquisition
• Technical knowledge specific to your industry
• People management and leadership

Strategies for Skill Development:

• Take online courses or attend workshops
• Find a mentor in your weak areas
• Hire professionals to fill crucial gaps
• Partner with someone who complements your skills
• Join industry associations and networking groups

Start by creating a skills inventory: list what you’re good at, what you need to learn, and what you should delegate. Be realistic about which skills you can develop versus those better handled by others. Remember that trying to do everything yourself can actually hold your business back.

You don’t need to master every skill – you need to understand enough to make informed decisions and know when to seek help. Focus on developing the most crucial skills for your specific business model while building a network of experts you can rely on for other areas.

13. “What metrics will I use to define success beyond revenue?”

While revenue is important, defining success solely by financial metrics can lead to shortsighted decisions and missed opportunities for meaningful growth. A more holistic view of success ensures you’re building not just a profitable business, but one that aligns with your broader values and goals.

Key Performance Indicators to Consider:

• Customer satisfaction and retention rates
• Employee happiness and turnover
• Work-life balance metrics
• Community impact and social responsibility
• Personal growth and learning
• Innovation and product development goals

Start by writing down your definition of success across multiple dimensions. Create specific, measurable goals for each area, just as you would for financial targets. Review these metrics regularly to ensure your business growth isn’t coming at the expense of other important aspects of success.

True business success should enhance your life, not consume it. The most sustainable businesses find ways to generate profit while also creating value for customers, employees, communities, and the entrepreneur’s personal growth.

14. “Am I prepared to make mistakes?” 

Every entrepreneur makes mistakes – it’s not a question of if, but when and how many. The real question is whether you’re mentally prepared for the inevitable missteps and have the resilience to learn from them rather than be defeated by them.

Common Early Mistakes:

• Pricing services too low
• Trusting the wrong partners
• Spending money on the wrong priorities
• Taking on the wrong clients out of desperation
• Waiting too long to adapt or pivot

Start by examining your relationship with failure. Are you someone who dwells on mistakes, or can you analyze them objectively and move forward? Consider how you’ve handled past failures and what you learned from them.

The goal isn’t to avoid all mistakes – that’s impossible. The goal is to make survivable mistakes that you can learn from quickly. Successful entrepreneurs aren’t those who never fail; they’re those who fail forward, learning and adapting with each misstep. Make sure you have both the emotional and financial capacity to weather these learning experiences.

15. “What’s my exit strategy?” 

While it might seem premature to think about leaving your business before you’ve even started it, having an exit strategy shapes crucial decisions from day one. Your intended destination influences the path you take to get there.

Common Exit Options:

• Selling to a larger company
• Passing the business to family members
• Going public through an IPO
• Selling to employees or management
• Walking away and closing down
• Maintaining ownership but hiring management

Start by asking yourself what “success” looks like in the long term. Are you building a lifestyle business to run indefinitely, or do you want to grow and sell quickly? Do you want complete control of the company over time or do you imagine selling off ownership as you go? Your answers affect everything from your business structure to your growth strategy.

It’s OK if your exit strategy changes as your business evolves, but having a vision helps guide important decisions about investment, growth, and operations. It also ensures you’re building something with value beyond your personal involvement – a crucial factor for most exit options.

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