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Upstart·Software Engineer·Technical Phone Screen·Intermediate

Intermediate
May 2026

Summary

Upstart software engineer interview with a string manipulation problem. Pretty focused on edge cases and the details really mattered here.

Questions Asked (1)

Q1

Given a list of keywords and a sentence string, return the sentence with all words matching the keyword list removed. Preserve the order of remaining words and handle case sensitivity, punctuation, and whole-word matching correctly.

Algorithms & Data StructuresTechnical Trade-offs
Author's notes

The base logic isn't hard but the edge cases piled up fast.

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AI HintsAI Generated

Suggested Approach

Clarify the requirements first, especially around case sensitivity, punctuation, and whole-word matching. Then outline a solution that tokenizes the sentence while preserving delimiters, filters out matching words, and reconstructs the sentence. Discuss trade-offs between different approaches (e.g., regex vs. manual parsing) and analyze time/space complexity.

Pro tip: Demonstrate attention to edge cases like punctuation attached to words (e.g., 'hello,' vs 'hello') and discuss how to handle them without breaking the original formatting. Also, mention that using a set for keywords improves lookup efficiency from O(k) to O(1) per word.

1. Clarify Requirements

Ask about case sensitivity, punctuation handling (e.g., should 'Hello,' match 'hello'?), and whether matching should be whole-word only. Confirm if the output should preserve original spacing and punctuation.

2. Choose Data Structures

Use a set for the keyword list to enable O(1) lookups. For tokenization, consider using regex to split while preserving delimiters, or manually iterate through the string.

3. Design Algorithm

Tokenize the sentence into words and non-word characters (delimiters). For each word, normalize case if needed, strip punctuation for matching, and check against the keyword set. If not a match, keep the original word (with punctuation) in the output.

4. Handle Edge Cases

Consider empty keyword list, empty sentence, multiple spaces, punctuation at start/end of words, and case variations. Ensure the output doesn't have extra spaces or missing punctuation.

5. Analyze Complexity

Time complexity: O(n + k) where n is sentence length and k is keyword list size (for set construction). Space complexity: O(n) for output. Discuss if regex might be slower due to overhead.

Key Points to Mention

  • Case sensitivity: decide whether to normalize case (e.g., lowercase both) or do exact match.
  • Punctuation handling: strip punctuation for matching but preserve it in output for non-matching words.
  • Whole-word matching: ensure that substrings (e.g., 'he' in 'hello') are not removed.
  • Tokenization strategy: use regex with word boundaries or manual parsing to separate words and delimiters.
  • Efficiency: use a set for keywords to achieve O(1) lookup per word.
  • Preservation of original formatting: maintain spaces, punctuation, and order of remaining words.

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