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.

HardTechnical

63 practiced

You need to build the business case including cost-benefit and cost-of-delay for migrating dashboards from hourly to near-real-time (5 minute) analytics. List required assumptions, how you would quantify benefits and costs, and produce a simple formula to compute ROI over a 12-month horizon. Explain sensitivity to latency and cost per compute hour.

EasyTechnical

61 practiced

SQL task (write in standard SQL): Given a transactions table:

transactions(transaction_id bigint, user_id bigint, amount decimal, occurred_at timestamp)

Write a query that returns monthly active users (MAU) per month for the last 12 months and the percent change vs previous month. Include handling for months with zero users and explain assumptions about timezones and late-arriving events.

HardSystem Design

91 practiced

Create a multi-year BI platform roadmap for a medium enterprise that is planning an acquisition in year two. Include high-level milestones for years 0-3, how you would allocate budget across feature delivery and platform investments, and how acquisition integration work influences sequencing and risk buffers.

EasyTechnical

123 practiced

Define technical debt in the context of a BI stack (dashboards, ETL pipelines, semantic layers, data models). Propose a lightweight assessment approach you could run in two weeks to score and prioritize technical debt across the stack, including 4 measurable signals you would collect and how you'd convert them into prioritization.

EasyTechnical

74 practiced

Describe three prioritization frameworks (e.g., RICE, WSJF, impact-feasibility) and give a concrete example of how each could be applied to prioritize BI work such as new dashboards, refactoring ETL, or investing in a semantic layer. Explain strengths and weaknesses for BI contexts.

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