I finally tackled my genealogy paper pile—here’s how I used AI

After years of avoiding it, I finally sorted through the papers I’d collected. Here’s how I organized everything, scanned the documents, and used AI to help me understand what I had.

Welcome back to Chronicle Makers, where we turn genealogy facts into engaging stories. In this post, I show you how I organized my piles of genealogy research and used AI to better understand the records I found.

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Do you have a pile of genealogy research in your house? It’s what happens when you’ve done a lot of digging but haven’t dealt with the aftermath. I had one of those piles too. And I finally tackled it. Not just to clear my desk, but to actually use what I found in my family history writing.

Here’s exactly how I did it and how I used AI to help me understand the parts that confused me.

Step 1: Facing the pile

My pile was one entire family line’s worth of research: maps, printouts from RootsWeb, census records, newspaper clippings, deeds, and my own scribbled index cards and post-its.

To begin, I sorted everything into three rough piles:

• Useful for writing: things like maps, personal letters, and documents that helped tell the story

• Helpful for research: materials I’d need to double-check or revisit later

• Dead ends or duplicates: clippings that no longer applied or were already saved digitally

This first pass took less than 20 minutes. It felt like it would take hours, but the key was not stopping to do research. This took an immense amount of self-control.

Here’s a video of what organizing looked like:

Step 2: Scanning essential records

Next came scanning. I pulled out my all-in-one printer and set it up to scan at 600 dpi with OCR (optical character recognition) so the documents could be read and searched later.

Here’s what I learned through trial and error:

• Black & white is better than color for photocopies—it’s sharper and the file size is smaller

• PDF is more flexible than TIFF, especially for combining files

• Naming matters: I used “LastName_FirstName_DocumentType” as my file format

I also had to remove staples, unfold pages, and test my scanner’s feeder with long documents. It was slow and tedious to get started. But I kept going because of the hope that AI could help me get a deeper understanding of these records.

Step 3: Using AI to analyze an estate file

The first big document I scanned was the 1929 estate (probate) file of my ancestor John Wilmer. I wanted to know what actually caused a family rift that I remembered as a child. I’d read the documents before but never fully understood them. This time, I used AI to help.

I tried three tools:

• ChatGPT-4o for a conversational analysis

• Google’s Gemini 2.5 for a legal and historical analysis

• Google’s Notebook LM for structured reading and interactive Q&A

Here’s what worked:

• AI gave me summaries, timelines, and even a plain-English rewrite of legal language

• I could double-check AI interpretations against the original, side-by-side

• Notebook LM even generated an audio overview as if two historians were talking through the file—wild, but surprisingly useful

And what didn’t work:

• AI got people’s names wrong because it tried to fill in gaps based on past conversations in the AI’s memory

• It made date mistakes that I had to cross-check manually

• I had to keep reminding it to keep going—it doesn’t always know what “done” means

Even with all the errors, I still got something I never had before: a way to engage with the documents instead of letting them sit in piles.

What I learned in the process

The hardest part wasn’t the sorting or the scanning. It was confronting the overwhelm.

Once I blocked the time, I could take that first step to deal with the mess. Knowing that I had the possibility of having AI help me understand the records was a good motivator for me. Even when it failed in truly helping, I still found pieces of the conversation that were useful. And at least I no longer had the pile!

If genealogy research piles are an issue for you, let me know in the comments. We could form an accountability group to tackle them together.

Happy pile sorting!

—Denyse