Strategy question
You own Core Experience across search, discovery, curation, and sharing. How would you build a 12-month strategy that delivers near-term wins for existing enterprise customers while moving Glean toward an intelligent work assistant? Walk through your segmentation, strategic bets, and how you would sequence investments across user-facing experience versus underlying platform capabilities.
- Glean
- Strategy
- Hard
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What this question tests
Tests long range strategic thinking: balancing near term enterprise wins against a multi year platform shift toward an intelligent assistant.
How to approach it
- Segment the current customer base by maturity, some want better search today, others are ready to adopt agent style assistance.
- Identify near term bets that deliver visible wins within two quarters, such as improved search relevance or better curation tools for power users.
- Identify the underlying platform capabilities, like a unified context layer across connectors, that both near term wins and the assistant vision depend on.
- Sequence investment so near term feature work also builds toward the platform capability, rather than treating them as separate tracks.
- Set explicit checkpoints at 3, 6, and 12 months to confirm near term wins are landing before committing further to the assistant vision.
- Communicate the roadmap in two horizons to stakeholders, so near term customers see continuity even as the long term bet takes shape.
What a strong answer includes
- Finds overlap between near term feature work and the long term platform bet instead of treating them as competing tracks.
- Segments customers by readiness for an assistant, since some enterprise buyers value reliable search far more than a still maturing agent.
- Uses staged checkpoints to de risk the 12 month bet instead of committing fully upfront.
Common mistakes
- Chasing every near term feature request without connecting it to the longer term platform vision.
- Jumping straight to the ambitious assistant vision without securing near term wins that keep current customers happy.
Likely follow-up questions
- What would you cut from the near term roadmap if the assistant investment needed more resourcing?
- How would you know at the 6 month checkpoint whether the platform bet is on track?
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More questions from Glean
Learn the skill behind it
Chapters of the AI PM course that teach what this question tests.
- Chapter 4: Discovery and strategy for AI products
- Chapter 9: Prove it paid off: outcomes, economics, and pricing
- Chapter 14: Get the job: the AI PM interview loop