# From Spreadsheets to AI: The Evolution of Program Management Tools

*By [Gianfranco Mileo](https://gianfranco-mileo.com/) · Published December 10, 2025 · updated September 6, 2026 · 2 min read · Category: AI & Technology · Tags: Program Management, AI Agents, Productivity · Canonical: https://gianfranco-mileo.com/blog/from-spreadsheets-to-ai-the-evolution-of-program-management-tools*

> I've managed programs using everything from sticky notes to enterprise software. Here's where AI fits in the evolution — and where it's still falling short.

## A Brief History of "How We Track Things"

When I started GFM Corp in 2010, my project management stack was literally a whiteboard, a Google Sheet, and weekly email updates. When I joined Google, I graduated to an enterprise suite of internal tools. Now, in 2025, AI is adding another layer — and it's worth stepping back to understand what's actually changed and what hasn't.

## The Eras of Program Management

### Era 1: The Spreadsheet Era (2005-2015)

Everything lived in spreadsheets. Color-coded cells. Manual status updates. Pivot tables for executive reviews. It worked because teams were smaller and programs were more contained. The tool matched the complexity.

### Era 2: The SaaS Era (2015-2023)

Jira, Asana, Monday, Linear — tools that promised to automate the tedious parts of tracking. They delivered on some of that promise, but they also introduced new problems: tool fatigue, context switching, and the illusion of progress through ticket management.

### Era 3: The AI-Augmented Era (2023-Present)

Now we have AI that can read across these tools, synthesize patterns, and suggest actions. The promise is enormous. The reality is still catching up.

## Where AI Actually Helps Right Now

- **Pattern detection across large programs** — AI can spot when velocity is dropping before humans notice
- **Natural language queries** — "Show me all blockers that have been open for more than a week" beats clicking through 12 dashboard filters
- **Draft communications** — first drafts of status updates, escalation emails, and post-mortems
- **Meeting summarization** — turning 60-minute meetings into structured action items

Related: see [How TPMs Can Build an MCP Server That Connects to Google Workspace — And Automate Everything](https://gianfranco-mileo.com/blog/tpms-build-mcp-server-gsuite-automation) and [How I Use AI to Run Cross-Functional Programs at Google](https://gianfranco-mileo.com/blog/how-i-use-ai-to-run-cross-functional-programs-at-google).

## Where AI Still Falls Short

- **Judgment calls** — AI can flag a risk but can't decide whether to escalate it now or wait a week
- **Relationship context** — it doesn't know that the SRE lead is going through a tough quarter and needs extra support
- **Organizational politics** — navigating conflicting priorities between VPs requires emotional intelligence AI doesn't have

The best tools in every era didn't try to replace the TPM — they made the TPM more effective. AI tools that understand this will win.

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