Become a Historian

Study past decisions and their context to make better decisions going forward

Anneka Gupta
Becoming more strategic, navigating difficult colleagues, founder mode, more

Become a Historian

"One of the things that I decided to do when I joined the company was to really understand what happened in the past. What were the products that we launched that weren't successful? Why weren't they successful? What was the perspective on the history of how we've decided to develop the things that we did and why?" - Anneka Gupta

What It Is

Becoming a Historian is a deliberate practice of understanding an organization's past decisions—both successful and unsuccessful—to make better decisions in the present. Rather than starting fresh or assuming you know better, you actively seek out the institutional memory that explains why things are the way they are.

This is especially valuable when joining a new company, but can be practiced continuously. The goal isn't to be bound by the past, but to understand its lessons and navigate the "baggage" that shapes how others will respond to new proposals.

How It Works

The Core Practice:

  1. Seek out stories of past initiatives—especially failed ones
  2. Understand not just what happened, but why decisions were made
  3. Learn about the context and constraints that existed at the time
  4. Identify patterns of what works and what doesn't in this specific organization
  5. Map the "baggage" people carry from past experiences

What You're Learning:

  • What products/initiatives were launched but didn't succeed?
  • Why weren't they successful?
  • How were decisions made?
  • What was the perception of different stakeholders?
  • What organizational patterns keep repeating?

How to Apply It

When Joining a New Company

  1. Schedule history conversations: In your first weeks, ask colleagues: "Tell me about projects from years ago—what happened with them?"

  2. Ask about failures: "What are some initiatives that didn't work out? Why did they fail?"

  3. Understand decision-making patterns: "How did we decide to build this? What alternatives were considered?"

  4. Map the baggage: Note when people say "we've tried that before"—understand what they tried and why it didn't work.

Ongoing Practice

  1. Stay curious: When you hear about past projects, ask follow-up questions even if they seem irrelevant to your current work.

  2. Document learnings: Build your own institutional memory that others can learn from.

  3. Use history strategically: When proposing something similar to a past failed initiative, proactively address what's different this time.

When to Use It

  • During your first 90 days at a new company
  • When proposing initiatives that feel like they should have been done before
  • When encountering resistance with "we've tried that before"
  • When you need to understand organizational dynamics
  • When making strategic decisions that have long-term implications

Benefits

  • Better decisions: Learn from mistakes you didn't personally live through
  • Navigate resistance: Understand why people push back on certain ideas
  • Build credibility: Colleagues respect leaders who understand context
  • Avoid reinventing failures: Don't waste time on approaches that have already failed
  • Find hidden assets: Discover past work that can be leveraged or revived

Source

  • Guest: Anneka Gupta
  • Episode: "Becoming more strategic, navigating difficult colleagues, founder mode, more"
  • Key Discussion: (00:28:07) - Anneka explains her approach to learning organizational history
  • YouTube: Watch on YouTube

Related Frameworks

No directly related frameworks in current library

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