250+ Investor Questions You’d Better Have Answers For

Stop guessing. This is the definitive list pulled from real term-sheet meetings, demo-day grills, and partner pitches—plus blunt guidance on how to answer without sounding like a rookie.

Traction & KPIs

Investors don’t buy projections; they buy proof. If you can’t put numbers on the table, be ready to discuss experiments and leading indicators.

Growth Metrics

• What is your month-over-month revenue growth for the last six months?
• What is your current run rate (ARR or GMV)?
• How does retention look after 3, 6, and 12 months?
• What’s the split between organic and paid acquisition?
• Where did last month’s growth actually come from—channel, geography, or product line?

Market & Competition

Market Sizing

• Credible, bottom-up TAM over three years—no fantasy CAGR multipliers?
• Serviceable slice at your current GTM speed?
• Which segments will you ignore (and why)?

Competitive Landscape

• Top three competitors your customers name (not Gartner)?
• How you win vs. each competitor today?
• Where you lose—and why?
• What moat makes copying you expensive?

Business Model

Revenue Drivers

• Which revenue streams exist today vs. planned?
• Average contract value, contract length, payment terms?
• Gross margin by product line?
• Upsell / cross-sell penetration?

Unit Economics

• Fully-loaded CAC?
• Payback period on new customers?
• LTV : CAC ratio across cohorts?
• Sensitivity of margins if AWS spikes 20 %?

Team & Culture

Founders & Leadership

• Why is this team uniquely qualified to solve the problem?
• Hard evidence of founder-market fit—not just passion?
• Critical hire that keeps you up at night?
• Equity split & vesting schedules?

Culture & Execution

• Your written decision-making process?
• Biggest failure in the last 12 months & what changed?
• Attrition rate and honest reasons people leave?

Product & Tech

Product Roadmap

• What shipped last quarter vs. original plan?
• How do you prioritise features—data, customer pull, or gut?
• Which upcoming feature unlocks the next pricing tier?

Technical Stack & IP

• Key third-party dependencies and risk profile?
• Security certifications achieved or in progress?
• Data advantage: proprietary dataset size + refresh rate?

Financials

Historical Performance

• P&L for the last 24 months?
• Cash burn vs. budget each quarter?
• Runway at current burn vs. post-round burn?

Forecasting

• Top-line trigger for Series A?
• Key growth assumptions (ACV, churn, hiring ramp)?
• Sensitivity if sales slip 25 %?

Fundraise Mechanics

Round Details

• Target raise, pre-money valuation—evidence it’s market-priced?
• Use of funds buckets—headcount, GTM, R&D, cushion?
• Milestones this round must hit to unlock the next?

Existing Investors

• Cap-table breakdown (commons, SAFEs, notes, options)?
• Pro-rata intentions from current investors?
• Any liquidation prefs or structure we should know?

Risk & Downside

Market & Execution Risk

• Single point of failure that could kill the business tomorrow?
• Regulatory overhang that might bite?
• Plan B if growth stalls for two quarters?

Tech & Security Risk

• Last penetration-test result & remediation timeline?
• Data-loss incident history?
• Disaster-recovery RTO/RPO targets—actual vs. target?

Legal & Compliance

Regulatory

• Licences or approvals required by geography?
• GDPR / HIPAA / SOC-2 status?
• Pending litigation or IP disputes?

Corporate Governance

• Board composition today vs. post-round?
• Founder vesting cliffs and acceleration triggers?
• Outstanding employee option grants not issued?