Strategy question
Glean already supports 100+ connectors, but engineering capacity is limited. How would you choose the next connector to build when the inputs conflict: a few large prospects want niche systems, many existing customers want deeper support for common tools, and some sources are strategically important for improving enterprise search coverage? Walk through the framework, data, and tradeoffs you would use.
- Glean
- Strategy
- Hard
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What this question tests
Tests prioritizing the next connector build across conflicting demands, large-prospect asks, existing-customer depth requests, and strategic coverage, with limited engineering capacity.
How to approach it
- Quantify each option: revenue at risk or won for the prospect-driven niche system, number of existing customers requesting deeper support for common tools, and expected search coverage lift from strategically important sources.
- Convert each into comparable units, for example expected revenue impact and reusability, prospects' niche system likely helps one deal, common-tool depth likely helps many accounts, strategic sources help platform positioning broadly.
- Weigh implementation effort and connector reliability risk for each, since a shallow or unreliable connector can hurt trust more than no connector at all.
- Use a weighted framework, revenue impact, customer reach, effort, and strategic value, to rank the three options rather than picking by whoever asked most recently.
- Likely prioritize deeper support for a common existing tool if it has the broadest customer reach and lowest incremental risk, while flagging the niche system as a targeted deal-specific build if the deal size justifies it.
- Communicate the decision and reasoning to sales and the affected prospects so expectations are set, including a timeline for the deprioritized options.
What a strong answer includes
- Converts three very different asks into comparable units, revenue impact, customer reach, and strategic value, instead of comparing them qualitatively.
- Weighs connector reliability risk explicitly, recognizing a shallow or broken connector can damage trust more than not building it.
- Chooses breadth of customer reach as a tie-breaker when revenue impact is comparable, since it compounds across future deals too.
- Proposes clear communication back to sales and prospects, not just an internal prioritization decision.
Common mistakes
- Prioritizing purely by deal size for the single largest prospect without weighing broader customer reach.
- Building a connector without validating reliability requirements, creating a support burden later.
- Making the decision without communicating reasoning back to sales, causing repeated escalation of the same request.
Likely follow-up questions
- How would you handle it if the large prospect's deal falls through after you built for them?
- What would you do if strategic coverage and customer demand point to different connectors?
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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