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Portfolio & Diligence interview questions

Prepalyst has 22 portfolio & diligence interview questions with model answers, covering reference calls, technical diligence, term sheets and preference stacks. Every question is graded on technical accuracy, completeness and interview communication. Practice is free.

22
Questions
7
Easy
7
Medium
8
Hard

1.Calculate the Dilution from an Option Refresh

Easy

Portfolio associates are expected to explain simple cap-table changes clearly to founders and investment partners.

A portfolio company has 8.0m fully diluted shares before a financing and needs to create a 400,000-share option refresh immediately before the round. Calculate the dilution to existing holders from the refresh alone. Why…

Financial AnalysisCommonly asked at Sequoia, Benchmark, Greylock~8 min
Model answer & graded attempt

2.Calculating Runway and Fundraising Timing

Easy

A basic portfolio-support question used to test financial discipline.

A portfolio company has $18m of cash, burns $1.2m per month today, and expects burn to rise by $0.1m per month for the next six months. How do you assess runway and when should it start fundraising?

Financial AnalysisCommonly asked at First Round Capital, Founders Fund, General Catalyst~7 min
Model answer & graded attempt

3.Fixing Inconsistent KPI Definitions

Easy

Portfolio reviews reveal whether candidates can recognise when a clean-looking metric is misleading.

A founder reports net revenue retention of 118%, but finance calculates 104%. How do you resolve the difference before using the metric in a board meeting?

Financial AnalysisCommonly asked at Bessemer Venture Partners, Battery Ventures, Sapphire Ventures~7 min
Model answer & graded attempt

4.How Should a VC Fund Use Reserves?

Easy

Tests whether you understand that follow-ons compete for finite capital across a portfolio.

Why does a VC fund reserve capital for follow-on rounds, and how would you decide which companies receive it?

Portfolio ConstructionCommonly asked at Benchmark, USV, Spark Capital~8 min
Model answer & graded attempt

5.Running a Customer Reference Call

Easy

A foundational diligence exercise for a VC analyst or associate.

You have a 30-minute reference call with a startup's customer. How do you structure it, and which answers would concern you?

Due DiligenceCommonly asked at Index Ventures, Accel, Lightspeed Venture Partners~7 min
Model answer & graded attempt

6.Set Useful Quarterly Objectives for a Portfolio Company

Easy

A portfolio-support interview tests whether you can turn a broad company ambition into a small set of accountable operating objectives.

A seed-stage B2B software company says its quarterly goal is to "grow faster." How would you help the CEO turn that into useful objectives and key results without creating a reporting exercise?

Venture InvestingCommonly asked at First Round Capital, Initialized Capital, Founders Fund~7 min
Model answer & graded attempt

7.What Belongs in a VC Board Pack

Easy

Portfolio-team interviews test whether you can make a board meeting useful rather than merely reportable.

You are helping a Series A founder prepare the monthly board pack. What must it contain, and what should stay out?

Venture InvestingCommonly asked at Sequoia, Andreessen Horowitz, Bessemer Venture Partners~7 min
Model answer & graded attempt

8.Assessing Exit Readiness

Medium

Portfolio teams help companies prepare for strategic or financial exit processes well before a banker is hired.

A founder says the company is ready to sell. What do you assess before encouraging a formal process?

Deal AnalysisCommonly asked at Battery Ventures, Foundry, IVP~11 min
Model answer & graded attempt

9.Decide Whether to Replace a Critical Executive

Medium

A board-level portfolio case tests whether you can separate a capability gap from a difficult quarter before recommending a leadership change.

A Series B company's VP Sales has missed plan for two quarters. The CEO asks whether the board should push for a replacement before the next fundraise. How do you make the recommendation?

Venture InvestingCommonly asked at Accel, Kleiner Perkins, NEA~11 min
Model answer & graded attempt

10.Intervening at a Board Meeting

Medium

Tests board judgement: being useful to management without becoming an operator by committee.

At a board meeting, the CEO presents a plan that misses cash targets but says cutting spend would damage growth. How do you respond?

Venture InvestingCommonly asked at Greylock, Kleiner Perkins, NEA~10 min
Model answer & graded attempt

11.Reviewing a Startup Hiring Plan

Medium

Portfolio associates are often asked to pressure-test hiring plans before a board meeting.

A Series B company plans to double headcount in the next year. How do you evaluate whether that is sensible?

Due DiligenceCommonly asked at Insight Partners, a16z, GV~10 min
Model answer & graded attempt

12.Running Diligence on a Series B

Medium

The workstream a VC analyst actually owns.

You have three weeks to diligence a Series B software company. What do you do?

Venture InvestingCommonly asked at Insight Partners, Index Ventures, General Atlantic~12 min
Model answer & graded attempt

13.Underwriting a Follow-On Round

Medium

A common partner-meeting exercise for a fund deciding whether to defend ownership.

Your fund owns 12% of a company. A new investor is leading a round at twice the prior valuation. What work do you do before deciding whether to take your pro rata?

Investment ThesisCommonly asked at General Atlantic, Coatue, Thrive Capital~10 min
Model answer & graded attempt

14.Use an Investor Introduction to Test Enterprise Demand

Medium

A portfolio-platform case asks you to create value through a customer introduction without substituting a warm email for real go-to-market work.

A Series A security startup asks its VC for introductions to enterprise customers. Build the workflow for deciding whom to introduce and how you would measure whether the support was useful.

Due DiligenceCommonly asked at Andreessen Horowitz, Bessemer Venture Partners, Battery Ventures~10 min
Model answer & graded attempt

15.Deciding Whether to Lead a Down Round

Hard

A senior portfolio judgement question about price, structure and fiduciary discipline.

A portfolio company cannot raise at its last valuation. The founder asks existing investors to lead a flat round with aggressive preferences. What do you recommend?

Deal AnalysisCommonly asked at Sequoia, SoftBank, Tiger Global~13 min
Model answer & graded attempt

16.Evaluate a Founder Secondary in a New Round

Hard

A board-level portfolio case involving founder incentives, governance and an unusually large secondary request.

A Series C company is raising $60m primary capital at a $500m pre-money valuation. The founder asks to sell $15m of personal shares in the same round. Growth is strong, but the company has missed two product deadlines.…

Venture InvestingCommonly asked at Index Ventures, Benchmark, Accel~14 min
Model answer & graded attempt

17.Intervene When AI Revenue Growth Masks Margin Risk

Hard

A portfolio-support case for an AI application company scaling revenue faster than its infrastructure economics.

A portfolio company has doubled ARR to $20m, but gross margin fell from 72% to 48% as enterprise customers use more inference-heavy features. Management wants to accelerate sales hiring before the next raise. What would…

Financial AnalysisCommonly asked at Andreessen Horowitz, Bessemer Venture Partners, General Catalyst~14 min
Model answer & graded attempt

18.Liquidation Preferences and the Exit Waterfall

Hard

Tests whether you understand that headline valuation and actual economics diverge.

A company raises $100m at a $1bn post-money with a 1x non-participating preference. It later sells for $400m. What do the investors and common holders receive? Then explain how the answer changes with a 2x participating…

Venture InvestingCommonly asked at Insight Partners, Sequoia, Andreessen Horowitz~12 min
Model answer & graded attempt

19.Management Q&A: Limited-Question VC Diligence

Hard

A VC portfolio-diligence case where an associate must use scarce founder and finance-team access to decide whether a bridge round funds a financeable business.

You are diligencing a proposed $12m Series A bridge for RelayOps, a workflow-software portfolio company. The investment committee meets tomorrow, management can answer only a limited number of questions, and the company…

Due DiligenceCommonly asked at Bessemer Venture Partners, Battery Ventures, Accel~18 min
Model answer & graded attempt

20.The Terms That Matter in a Term Sheet

Hard

Tests whether you know which terms are economic and which are control.

Beyond valuation, which term sheet provisions matter most? Separate the economic terms from the control terms.

Venture InvestingCommonly asked at Sequoia, Andreessen Horowitz, Index Ventures~13 min
Model answer & graded attempt

21.Triage a Portfolio During a Funding Shock

Hard

Tests whether you can make portfolio-level decisions when financing conditions deteriorate rapidly.

Public multiples have fallen sharply and your fund's portfolio companies will struggle to raise. How do you triage the portfolio over the next 30 days?

Portfolio ConstructionCommonly asked at Initialized Capital, NEA, Craft Ventures~13 min
Model answer & graded attempt

22.When Do You Stop Funding a Portfolio Company?

Hard

The hardest recurring decision in venture, and a strong test of judgement.

A portfolio company is burning cash, growth has stalled, and the founder asks for a bridge. How do you decide?

Venture InvestingCommonly asked at Sequoia, Union Square Ventures, First Round~13 min
Model answer & graded attempt

Practise portfolio & diligence under interview conditions.

Write your answer, get it graded on technical accuracy, completeness and communication, and see exactly which mechanic you missed.

Other venture capital desks

Firm names indicate where a question type is commonly reported in interviews. They are not sourced from, endorsed by, or affiliated with the firms named.

Portfolio & Diligence Interview Questions (22 with Model Answers) · Prepalyst