Technical Strategy and Roadmapping Questions

Covers defining, communicating, and operationalizing multi quarter to multi year technical and engineering strategy that aligns engineering investments with product and business objectives. Candidates should be able to describe planning horizons, trade offs between near term delivery and long term investment, and how strategic direction maps to architecture and platform decisions. Topic coverage includes migration and modernization planning, assessing current state and technical debt, sequencing initiatives and milestones, prioritization frameworks and cost of delay thinking, capacity and resource planning including hiring and team structure, vendor evaluation and integration, compliance and data considerations, governance and operating model, and execution planning with timelines and review cadences. It also includes balancing feature delivery, reliability, platform evolution, developer experience, and maintenance; making the business case for infrastructure and platform investments; defining success metrics and objectives and key results and measuring outcomes; risk identification, mitigation and contingency planning; and communicating roadmaps and trade offs to engineers, product leaders, business stakeholders, and executives. Domain specific concerns such as cloud adoption, business intelligence roadmaps, and marketing technology integration are included as examples of how technical strategy varies by context.

MediumTechnical

0 practiced

Scenario: You must make a business case to invest in an observability and monitoring platform for BI pipelines to reduce downtime. Outline the structure of your pitch to product and finance stakeholders, what KPIs you would include, and how you would estimate the ROI over 12 months.

HardTechnical

0 practiced

Design an advanced prioritization framework for a BI roadmap that blends RICE scoring, OKR alignment, and cost-of-delay. Describe inputs required for each axis, how you would normalize scores, and an algorithm to produce a ranked roadmap for quarterly planning.

HardTechnical

0 practiced

You are the BI lead and need to restructure teams to move from project-based reporting to a platform-first model. Propose an organization structure (roles, squads, platform team vs. embedded analytics), hiring priorities for the next 18 months, and metrics to show success of the new org design.

EasyTechnical

0 practiced

You join as a BI analyst and inherit a chaotic reporting environment with many duplicated dashboards, unclear ownership, and frequent data issues. Outline your first 30/60/90 day plan: what will you audit, who will you talk to, what short-term fixes you would prioritize, and what long-term roadmap items you would propose.

MediumTechnical

0 practiced

Write a SQL query (standard SQL) to compute a 7-day retention cohort table based on the schema below. Explain how you handle users with multiple signups and late-arriving events.

users(user_id bigint, signup_at timestamp)
events(user_id bigint, event_at timestamp, event_type varchar)

Output should show cohort_week, day_0_count, day_1_retention_pct, ..., day_7_retention_pct.

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