20 Questions

Questions to Ask Hedge Fund Managers

Strategic questions that demonstrate your understanding of finance and help you evaluate investment opportunities and career paths in hedge funds.

1

What's your investment philosophy and how has it evolved over your career?

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Why this works

Reveals their core approach to investing and shows how they've adapted their strategy based on market experience and lessons learned.

2

How do you approach risk management in your portfolio, and what's your maximum drawdown tolerance?

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Why this works

Shows understanding of risk management principles and helps you understand their risk appetite and protection strategies.

3

What's your view on the current market environment and how are you positioning the fund accordingly?

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Why this works

Demonstrates market awareness and shows how they adapt their strategy to current conditions.

4

How do you source and evaluate investment opportunities, and what's your due diligence process?

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Why this works

Reveals their research methodology and shows you understand the importance of thorough analysis in investment decisions.

5

What's your track record over different market cycles, and how did you perform during the 2008 financial crisis?

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Why this works

Shows performance consistency and reveals how they handle extreme market stress, which is crucial for understanding their resilience.

6

How do you handle position sizing and portfolio construction to optimize risk-adjusted returns?

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Why this works

Demonstrates understanding of portfolio theory and shows you're thinking about optimization beyond just individual stock picks.

7

What's your approach to managing client relationships and communication during periods of underperformance?

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Why this works

Shows understanding of the client management aspect and reveals how they handle difficult conversations about performance.

8

How do you stay informed about market developments and what sources do you rely on for research?

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Why this works

Reveals their information gathering process and shows you understand the importance of staying current in fast-moving markets.

9

What's your view on the role of technology and quantitative strategies in modern hedge fund management?

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Why this works

Shows awareness of industry trends and demonstrates understanding of how technology is changing the investment landscape.

10

How do you approach ESG investing and what role does sustainability play in your investment decisions?

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Why this works

Demonstrates awareness of current trends in responsible investing and shows you understand the growing importance of ESG factors.

11

What's your fee structure and how do you align your interests with those of your investors?

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Why this works

Shows understanding of the business model and reveals how they structure incentives to ensure alignment with client interests.

12

How do you handle regulatory compliance and what's your approach to staying ahead of regulatory changes?

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Why this works

Demonstrates understanding of the regulatory environment and shows you're aware of the compliance challenges in the industry.

13

What's your view on the future of hedge funds and how do you see the industry evolving?

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Why this works

Shows forward-thinking perspective and reveals their thoughts on industry trends and potential disruptions.

14

How do you approach talent acquisition and what qualities do you look for in potential team members?

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Why this works

Reveals their hiring philosophy and shows you understand the importance of team building in investment management.

15

What's your approach to managing liquidity and how do you handle redemption requests during market stress?

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Why this works

Shows understanding of operational challenges and reveals how they manage the practical aspects of fund management.

16

How do you approach international investing and what's your view on global market opportunities?

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Why this works

Demonstrates global perspective and shows you understand the importance of international diversification in modern portfolios.

17

What's your approach to managing leverage and how do you determine appropriate levels of borrowing?

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Why this works

Shows understanding of leverage as a tool and reveals their approach to managing this powerful but risky strategy.

18

How do you approach alternative investments and what role do they play in your overall strategy?

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Why this works

Demonstrates understanding of the full spectrum of investment options and shows you're thinking beyond traditional asset classes.

19

What's your view on the role of macro factors in investment decisions and how do you incorporate them?

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Why this works

Shows understanding of the broader economic context and reveals how they think about systemic risks and opportunities.

20

How do you approach succession planning and what's your vision for the future of the fund?

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Why this works

Demonstrates long-term thinking and shows you understand the importance of continuity in investment management.

Best Practices for Engaging with Hedge Fund Managers

Expert tips and techniques for getting the most out of these questions.

Best Practices

Demonstrate Market Knowledge

Show you understand current market conditions, key economic indicators, and relevant financial concepts. This establishes credibility and shows you're serious about the conversation.

Ask About Risk Management

Focus on how they manage risk, not just returns. This shows you understand that risk management is often more important than return generation in professional investing.

Show Interest in Their Process

Ask about their research methodology, decision-making process, and how they stay informed. This demonstrates understanding that process is often more important than individual picks.

Question Sequences

The Investment Philosophy Sequence

1
What's your investment philosophy and how has it evolved over your career?
2
How do you approach risk management in your portfolio?
3
What's your view on the current market environment and how are you positioning accordingly?

The Performance Analysis Sequence

1
What's your track record over different market cycles?
2
How did you perform during the 2008 financial crisis?
3
How do you handle client relationships during periods of underperformance?

Common Pitfalls

Don't Focus Only on Returns

Avoid asking only about performance numbers. Focus on process, risk management, and how they achieve their results. Returns are just one part of the story.

Don't Ask for Stock Picks

Avoid asking for specific investment recommendations. Focus on their approach, methodology, and philosophy instead of trying to get free investment advice.

Don't Sound Like You're Interviewing for a Job

If you're not actually interviewing for a position, avoid questions that sound like job interviews. Focus on learning about their approach and market views.

Conversation Templates

The Market Analysis Template

1
Step 1: Start with: "What's your view on the current market environment?"
2
Step 2: Follow with: "How are you positioning the fund accordingly?"
3
Step 3: Deepen with: "What risks are you most concerned about right now?"

The Process Deep-Dive Template

1
Step 1: Start with: "What's your investment philosophy?"
2
Step 2: Follow with: "How do you source and evaluate investment opportunities?"
3
Step 3: Connect with: "What's your due diligence process?"

Further Reading

"Hedge Fund Market Wizards" by Jack Schwager
"The Big Short" by Michael Lewis
"More Money Than God" by Sebastian Mallaby

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