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Anthropic·Software Engineer·Technical Phone Screen·Senior

SeniorPrefer not to say
May 2026

Summary

Coding screen at Anthropic for a software engineer role. The problem was a tokenizer implementation, which sounds straightforward until you get into the follow-ups about optimization and collapsing UNKs.

Questions Asked (3)

Q1

Implement a tokenizer that splits an input string into token IDs using a vocabulary dictionary. At each position, match the longest substring found in the vocabulary. If nothing matches, emit the UNK token ID and move forward one character. Signature: def tokenize(text: str, vocab: dict) -> list

Algorithms & Data StructuresTechnical Trade-offs
Author's notes

The core logic wasn't too bad once I stopped overthinking it.

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AI HintsAI Generated

Suggested Approach

Start by clarifying requirements and edge cases (e.g., empty string, empty vocab, overlapping matches). Then describe a greedy longest-match algorithm using a trie for efficient lookup, and analyze time/space complexity. Finally, discuss trade-offs and potential improvements.

Pro tip: Mention that a naive implementation using string slicing is O(n^2) in the worst case, but a trie reduces it to O(n * L) where L is the max token length. Also, note that greedy longest-match is not always optimal for downstream tasks, but it's a common baseline.

1. Clarify requirements and edge cases

Ask about expected input size, vocabulary size, handling of unknown characters, and whether the vocabulary can contain overlapping tokens. Confirm the UNK token ID and its representation.

2. Design the algorithm

Propose a greedy longest-match approach: at each position, find the longest substring that exists in the vocabulary. If none, emit UNK and advance one character. Use a trie for efficient prefix matching.

3. Analyze complexity and trade-offs

Discuss time and space complexity. Compare naive string slicing vs. trie. Mention that greedy matching may not yield globally optimal tokenization but is fast and simple.

4. Handle edge cases and implementation details

Cover empty string, empty vocabulary, UNK handling, and potential Unicode issues. Ensure the algorithm advances correctly to avoid infinite loops.

5. Test and validate

Walk through examples, including cases with overlapping tokens and unknown characters. Suggest unit tests for correctness and performance.

Key Points to Mention

  • Greedy longest-match algorithm
  • Trie data structure for efficient prefix matching
  • Time complexity: O(n * L) with trie vs O(n^2) naive
  • Handling of UNK token and advancing one character
  • Edge cases: empty string, empty vocab, overlapping tokens
  • Trade-offs: greedy vs optimal tokenization, memory vs speed

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

Q2

Optimize the tokenizer so that at each position you only scan up to the length of the longest word in the vocabulary, rather than scanning the entire remaining string.

Algorithms & Data StructuresTechnical Trade-offs
Author's notes

Precompute max vocab word length once before the loop, then cap your inner scan at min(max_len, remaining_length).

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AI HintsAI Generated

Suggested Approach

Start by clarifying the tokenizer's goal and constraints, then propose precomputing the maximum word length from the vocabulary. Explain how to modify the scanning loop to limit the substring length to that maximum, and analyze the time complexity improvement from O(n^2) to O(n * L), where L is the max word length. Finally, discuss edge cases and potential trade-offs.

Pro tip: Mention that this optimization is especially effective when the vocabulary has many short words and the input string is long, and that it can be combined with a trie for further efficiency. Also, highlight that you would validate the change with benchmarks to ensure no regression in correctness.

1. Clarify requirements and constraints

Ask about the tokenizer's current implementation, the vocabulary size, typical input lengths, and whether the vocabulary is static or dynamic. Confirm that the goal is to reduce unnecessary scanning without changing tokenization output.

2. Precompute maximum word length

Compute the length of the longest word in the vocabulary once, either at initialization or when the vocabulary changes. Store it as a constant for the scanning loop.

3. Modify scanning loop

At each position, only consider substrings up to the precomputed maximum length (or until the end of the string, whichever is shorter). This avoids checking substrings that cannot match any vocabulary word.

4. Analyze complexity and trade-offs

Explain the improvement: from O(n^2) to O(n * L) where n is input length and L is max word length. Discuss memory overhead (negligible) and the assumption that vocabulary is fixed; if dynamic, update max length accordingly.

5. Test and validate

Propose unit tests with edge cases (empty string, max length word at end, etc.) and benchmark against the original implementation to ensure correctness and performance gains.

Key Points to Mention

  • Time complexity improvement from O(n^2) to O(n * L)
  • Precomputing the maximum word length from the vocabulary
  • Handling edge cases: empty string, no match, word longer than remaining string
  • Trade-offs: memory for storing max length is negligible; dynamic vocabulary requires updating max length
  • Alternative approaches: trie or Aho-Corasick for further optimization
  • Importance of benchmarking and correctness testing

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

Q3

Further optimize the tokenizer to collapse consecutive UNK tokens in the output into a single UNK token.

Algorithms & Data Structures
Author's notes

Honestly the simplest of the three parts.

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AI HintsAI Generated

Suggested Approach

First, clarify the tokenizer's current behavior and the definition of consecutive UNK tokens (e.g., adjacent in the output sequence). Then propose a linear-time algorithm that scans the token list and collapses runs of UNK tokens into a single UNK, discussing edge cases and potential impacts on downstream tasks.

Pro tip: Mention that collapsing UNK tokens can lose information about the number of unknown tokens, which might be important for some applications; suggest making it configurable or documenting the trade-off.

1. Clarify requirements and assumptions

Confirm what 'consecutive UNK tokens' means (e.g., adjacent in the output list) and whether the optimization should be applied during tokenization or as a post-processing step. Ask about any constraints on preserving token count or indices.

2. Design the algorithm

Propose a single-pass algorithm that iterates through the token list, keeping track of whether the previous token was UNK. When an UNK is encountered and the previous was also UNK, skip it; otherwise, append it to the result.

3. Analyze complexity and edge cases

State that the algorithm runs in O(n) time and O(n) space (or O(1) extra space if modifying in place). Discuss edge cases: all UNK tokens, no UNK tokens, UNK at start/end, and interaction with special tokens.

4. Discuss integration and testing

Explain how to integrate the change into the tokenizer pipeline, ensuring it doesn't break existing functionality. Suggest unit tests for various scenarios and possibly a flag to enable/disable the behavior.

5. Consider downstream impact

Mention potential effects on model training or inference, such as reduced sequence length and loss of information about the number of unknown tokens. Recommend evaluating the change's impact on metrics.

Key Points to Mention

  • Linear time complexity O(n) and space complexity O(n) or O(1) extra space.
  • Edge cases: all UNK, no UNK, UNK at boundaries, and special tokens like CLS/SEP.
  • Configurability: allow enabling/disabling the collapse via a parameter.
  • Downstream impact: sequence length reduction, information loss, and potential need for retraining.
  • Testing: unit tests for various input sequences and integration tests.
  • Alternative approaches: regex-based or using itertools.groupby for readability.

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