Engineering managers operate at the intersection of numerous information streams, leading to significant context-switching overhead and potential loss of critical information. This post outlines the design for a context-aware AI assistant, orchestrated by the Gemini CLI, to solve this problem. We will explore two solutions: a short-term workaround using a command-line bridge and the recommended long-term solution involving a dedicated local server.

The life of an engineering manager is a constant exercise in context switching. Between processing a flood of emails, keeping up with Slack channels, managing Jira tickets, reading Confluence pages, and preparing for one-on-one meetings with notes in OneNote, the mental overhead can be staggering. The core challenge isn’t just managing tasks; it’s about maintaining and retrieving context across a dozen different platforms, often in parallel.

This Week’s Challenges:

• Promotion nominations (Management)

This Week’s Challenges:

• Setting individual goals for FY26 (Management)

This Week’s Challenges:

• Engineering strategy for FY26 (Management)

This Week’s Challenges:

• Annual Performance Review (Management)

This Week’s Challenges:

• FY25Q4 retrospective (Management)

This Week’s Challenges:

• FY26Q1 planning - Q1 Game Plan (Management)
• Engineering excellence metrics (Engineering)

This Week’s Challenges:

• Finalize FY26Q1 planning (Management)
• Engineering excellence metrics (Engineering)

Engineering Team Planning Process - LOE Estimations

This document outlines the process followed by the engineering team for planning and estimating work for the next quarter of the fiscal year.

This Week’s Challenges:

• Planning FY26Q1 - Level-of-Effort (LOE) estimations

Quaterly Planning Process

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1. PRD reviews
2. Capacity Planning
3. Level-of-Effort Estimations
4. Prioritization and commitment (see Week 4 of the year 2025)
5. Build a game plan (see Week 5 of the year 2025)
6. Present next quarter to the team

See also:

1. Quarterly retrospective meeting in Week 6 of the year 2025

Quaterly Team Capacity Planning

This formal process provides a structured approach to team capacity planning, enabling more accurate resource allocation, improved project predictability, and enhanced team performance.

This Week’s Challenges:

• Navigating Team Capacity Planning (Management)