Be the Historian
Systematically reconstruct why past decisions were made so you inherit the lessons and see the baggage.
- Difficulty
- Easy
- Time to result
- ~weeks to results
- Steps
- 4
- Confidence
- 90%
A deliberate practice of interrogating a company's decision history — especially failures you weren't present for — to make better decisions and to anticipate organizational resistance. The goal is not to judge past decisions as good or bad but to reconstruct the reasoning, which yields both transferable lessons and a map of the emotional baggage people carry into any similar new initiative.
Origin
Anneka Gupta became the de facto historian over 11 years at LiveRamp; when she joined Rubrik three years in, she found herself without that history and deliberately reconstructed it. She then generalised the practice into an ongoing habit rather than an onboarding step.
Core principles
- 01You can learn from mistakes you didn't personally live through.
- 02Whether a past decision was good or bad is irrelevant — the reasoning behind it is the asset.
- 03Every failed past project leaves baggage that will be thrown at your new initiative.
- 04History-gathering is not an onboarding task; it's a permanent curiosity habit.
How to run it
- 1
Inventory the failures
Identify products and projects that launched and didn't succeed. Treat these as the highest-value historical objects in the company.
- 2
Reconstruct the decision, not the verdict
For each, ask what was decided, why it was decided that way, and what the perspectives of different people in the organization were. Deliberately suspend judgment about whether it was right.
Pro tip Frame questions as curiosity — 'tell me about this project, what happened with it, how did we decide to do this?' — so people share rather than defend.
Watch out If people sense you're auditing them, you get the sanitized version and lose the actual reasoning.
- 3
Extract the baggage map
Note which people carry 'we tried that before and it didn't work' about which topics. That is the resistance you will meet when you propose anything adjacent.
Pro tip Know the baggage before you pitch, and address it inside the pitch rather than being ambushed by it.
- 4
Keep doing it forever
Whenever an old project surfaces in conversation, stop and mine it. The historian role is not a 90-day onboarding artefact; it's an ongoing source of context for every forward decision.
In the wild
Coming from 11 years at LiveRamp where she was the historian, Gupta joined Rubrik into an organization full of history she didn't have. She deliberately investigated which products had launched and failed, why, how those decisions were made, and how different people perceived them.
→ She built a picture of past decision-making that let her learn from mistakes she hadn't lived through and understand which initiatives would trigger 'we've tried this before' resistance.
In any long-lived org, a product leader proposing a new initiative meets someone who says 'we've done this so many times, it didn't work, why are we thinking about this again?' Gupta treats this reaction as predictable baggage that the historian practice surfaces in advance.
→ The objection can be anticipated and addressed with the actual history of why the previous attempt failed, rather than being derailed by it in the room.
Common mistakes
Grading past decisions instead of understanding them
Arriving as a judge makes people defensive and shuts down the reasoning you need. Whether the decision was good or bad is not the point.
Treating history-gathering as an onboarding phase
Stopping after the first 90 days means the next old failure that shapes team resistance blindsides you when you pitch something adjacent to it.
Is it for you?
Best for
Leaders joining an established company, or anyone proposing an initiative in an org that has attempted something similar before.
Not ideal for
Brand-new companies or greenfield teams with no decision history to mine, where the practice yields nothing.
From the transcript
“I tried to construct this like past knowledge of what had happened and what were the decisions that were made and why were those decisions…”
“to learn from the mistakes that I didn't personally live through”
“what is the baggage that people have around trying to do something similar again”
From the episode
Becoming more strategic, navigating difficult colleagues, harnessing founder mode, and more
Anneka Gupta (Chief Product Officer at Rubrik)