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Headway Interview Questions

The questions to prepare for Headway interviews, across all roles. Questions from real interview reports rank first. Updated weekly.

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1
CodingStart here. 6 questions · ~60 min
Find Most Efficient Available SlotMedium
Practice

Merge booked intervals and use a greedy scan to find the earliest available Headway scheduling slot of a required duration.

intervalsSchedulingHeadway
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2
Metrics6 questions · ~60 min
Investigate User Engagement DeclineMedium

Investigate a 15% engagement decline by decomposing the metric, isolating root causes, and proposing actions.

RetentionDiagnosisEngagement MetricsHeadway
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3
Execution6 questions · ~60 min
Quality Under Tight DeadlineMedium

Explain how you protect quality on a fixed-deadline engineering project by managing scope, risks, and release criteria.

Launch PlanningTrade-offsScope ManagementHeadway
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4
Strategy6 questions · ~60 min
Staying Current on Industry TrendsEasy

A practical approach for tracking industry trends, competitor moves, and market changes in a way that informs strategy decisions.

EstimationCompetitive AnalysisGrowth StrategyHeadway
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5
A/B Testing & Experimentation4 questions · ~40 min
Common Pitfalls in Experiment ResultsHard

Identify the main pitfalls that can distort A/B test interpretation and explain how to guard against them.

PeekingNovelty EffectSample Ratio MismatchHeadway
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6
Product Sense5 questions · ~50 min
Build an Engagement FeatureMedium

Approach for identifying, prioritizing, and launching a new feature that increases user engagement.

Feature PrioritizationUser NeedsUse CasesHeadway
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7
More topics17 questions · ~171 min
Ingest and Reconcile Billing ClaimsHard

Tests your ability to build robust data pipelines for reconciliation, idempotency, and correctness across payers.

ReconciliationingestionHeadway
Running Total with Window FunctionsMedium

Tests window function knowledge for partitioning and cumulative metrics per patient.

Window FunctionsRunning TotalsHeadway
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Hands-on SQL practiceWrite and run real queries in the editor. 3 drills · ~30 min
Identify Funnel Bottlenecks in OnboardingHard
Practice
Practice drill

Use joins, CTEs, and aggregations to find the weakest step in an onboarding funnel and estimate lost conversions.

Funnel AnalysissqlDiagnosisAtlassianRevolut
Analyze Decision Impact by RegionEasy
Practice
Practice drill

Use joins, CASE WHEN, and date filtering to compare outcome rates before and after a decision.

Data WranglingDiagnosisAggregationsHarbourVest Partners
7-Day Rider Retention in NYCHard
Practice
Practice drill

Compute 7-day NYC rider retention by signup cohort using joins, CTEs, date filters, and distinct retained-user aggregation.

Window FunctionsRetentionRunning TotalsUberAsana
The finish line: interview-readyComplete all 50 questions plus 3 hands-on drills to finish this plan.