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Anthropic·Software Engineer·Technical Phone Screen·Intermediate

IntermediatePending
May 2026

Summary

Phone screen for a Software Engineer role at Anthropic. The coding portion was a duplicate file finder problem, which sounds manageable until you realize there's no helper code and you're manually reimplementing filesystem methods from scratch. Follow-up questions pushed into distributed systems territory. Still waiting to hear back.

Questions Asked (3)

Q1

Implement a solution to find duplicate files across a filesystem, without any provided helper code or libraries for filesystem operations.

Algorithms & Data Structures
Author's notes

The problem itself is pretty classic but not having any scaffolding meant I spent a chunk of time just rebuilding basic filesystem traversal stuff.

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AI HintsAI Generated

Suggested Approach

Start by clarifying requirements and constraints, then propose a two-phase algorithm: first traverse the filesystem to collect file paths and sizes, then group files by size and compare content hashes only for files with matching sizes. Discuss trade-offs between hashing entire files versus using partial hashes, and consider edge cases like symlinks, permissions, and large files.

Pro tip: Mention that you would use a streaming hash (e.g., SHA-256) and compare files byte-by-byte only when hashes match, to avoid false positives and minimize I/O. Also, discuss how to handle hard links and avoid infinite loops with symlinks.

1. Clarify requirements and constraints

Ask about the filesystem size, file types, performance requirements, and whether symlinks/hard links should be considered. Confirm if the solution should be recursive and if it needs to handle permission errors.

2. Design the traversal strategy

Choose between recursive DFS or iterative BFS to walk the directory tree. Discuss using a stack/queue and handling symbolic links to avoid cycles.

3. Group files by size

Collect all file paths and their sizes, then group files by size. Only files with identical sizes are candidates for duplicates, reducing the number of content comparisons.

4. Compare file contents

For each group of same-sized files, compute a cryptographic hash (e.g., SHA-256) of each file's content. Group files by hash; any group with more than one file contains duplicates. Optionally, verify byte-by-byte to handle hash collisions.

5. Handle edge cases and optimize

Address symlinks, hard links, permission errors, and large files. Discuss using partial hashing (e.g., first and last few KB) for quick elimination, and consider memory usage for large numbers of files.

Key Points to Mention

  • Two-phase approach: first group by size, then compare content hashes to minimize expensive I/O.
  • Use streaming hashing (e.g., SHA-256) to handle large files without loading them entirely into memory.
  • Handle symbolic links to avoid infinite loops and decide whether to follow them.
  • Consider hard links: files with different paths but same inode are not duplicates in terms of storage.
  • Discuss trade-offs: full hash vs. partial hash vs. byte-by-byte comparison.
  • Mention error handling for permission denied, non-existent files, and special files (e.g., sockets, devices).

AI-generated suggestions, not part of the candidate's original notes. May be inaccurate — verify before relying on them.

Q2

Where could your duplicate file detection solution break down or produce incorrect results?

Technical Trade-offsRoot Cause Analysis
Author's notes

They pushed on edge cases pretty quickly.

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AI HintsAI Generated

Suggested Approach

Acknowledge that duplicate detection is inherently probabilistic and context-dependent, then systematically walk through failure modes across data ingestion, hashing, comparison, and output stages. Emphasize that understanding these limitations is crucial for building robust systems and for setting correct user expectations.

Pro tip: Frame limitations as design trade-offs rather than flaws—this shows you understand that every solution involves balancing accuracy, performance, and complexity. Mention that you would instrument the system to detect and log these failure cases for continuous improvement.

1. Identify Assumptions

List the core assumptions your solution makes, such as files being immutable, hash functions being collision-resistant, or metadata being reliable. Explain how violating these assumptions leads to incorrect results.

2. Analyze Edge Cases

Discuss specific edge cases like empty files, very large files, files with identical content but different metadata, or files that change during scanning. Describe how each could cause false positives or negatives.

3. Evaluate Scalability and Performance

Explain how scaling to massive datasets or high-throughput environments can introduce errors, such as hash collisions becoming more likely or sampling techniques missing duplicates.

4. Consider Environmental Factors

Mention external factors like file system inconsistencies, network partitions, or concurrent modifications that can lead to incomplete or stale comparisons.

5. Propose Mitigations and Monitoring

Suggest ways to detect and mitigate these breakdowns, such as using multiple hash algorithms, verifying with byte-by-byte comparison, or implementing logging and alerting for anomalies.

Key Points to Mention

  • Hash collisions (e.g., MD5, SHA-1) and the need for cryptographic hashes like SHA-256
  • False positives from metadata-only comparison (e.g., same size and timestamp but different content)
  • False negatives due to partial content hashing or sampling strategies
  • Race conditions and file mutations during scanning
  • Scalability issues: memory constraints, distributed systems, and eventual consistency
  • Handling of special file types (symlinks, sparse files, compressed archives)

AI-generated suggestions, not part of the candidate's original notes. May be inaccurate — verify before relying on them.

Q3

How would you scale or improve the efficiency of your solution, for example in a distributed environment?

System DesignTechnical Trade-offs
Author's notes

Talked through sharding the file index and doing parallel hash comparisons across nodes.

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AI HintsAI Generated

Suggested Approach

Start by clarifying the current solution's bottlenecks and constraints, then propose a scaling strategy that addresses those bottlenecks using distributed systems principles. Discuss trade-offs between consistency, availability, and partition tolerance, and how you would measure success. Emphasize iterative improvement and monitoring.

Pro tip: Show awareness of Anthropic's focus on safety and reliability by mentioning how you'd handle failures gracefully and ensure data consistency in a distributed setting. Also, quantify improvements with metrics like latency, throughput, and cost.

1. Identify Bottlenecks

Analyze the current solution to find performance bottlenecks, such as CPU, memory, I/O, or network limits. Use profiling and monitoring data to pinpoint the most critical constraints.

2. Propose Scaling Strategies

Suggest horizontal scaling (e.g., adding more machines) or vertical scaling (e.g., upgrading hardware) based on the bottleneck. Consider partitioning data, sharding, or using load balancers to distribute traffic.

3. Address Distributed Challenges

Discuss how to handle consistency, availability, and partition tolerance (CAP theorem). Mention techniques like replication, consensus algorithms (e.g., Raft), and eventual consistency where appropriate.

4. Optimize Efficiency

Propose algorithmic improvements, caching, batching, or asynchronous processing to reduce latency and increase throughput. Consider using message queues or stream processing for decoupling.

5. Measure and Iterate

Define metrics (e.g., p99 latency, QPS, error rates) to evaluate the scaled solution. Plan for monitoring, alerting, and continuous improvement based on real-world feedback.

Key Points to Mention

  • Horizontal vs. vertical scaling and when to use each
  • CAP theorem and trade-offs between consistency and availability
  • Data partitioning and sharding strategies
  • Caching, load balancing, and CDNs
  • Asynchronous processing and message queues
  • Monitoring, metrics, and observability in distributed systems

AI-generated suggestions, not part of the candidate's original notes. May be inaccurate — verify before relying on them.