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Top reasons you should use note applications on iPads

By Jeffrey Schoenberger, senior consultant at Affinity Consulting Group LLC

For business development and correspondence, we know that handwritten notes and letters make the best impression. I received 18 handwritten postcards in the mail last year from my high-school best friend who was traveling across the U.S. in an RV with his family. I can’t remember the last time before then that I received a postcard, and it was a treat! When I worked around Congress, I noticed the handwritten letters from constituents were most likely to make it beyond legislative correspondent staffers to the Congressman’s desk.

We also have scientific evidence that handwritten notes beat typed notes for information retention. A recent study by Princeton University researchers compared students taking handwritten notes versus typed notes. It found students who handwrote notes performed better on exams, took shorter (but better) notes, could relay ideas better, and had better short-term retention.

For legal technologists, studies like this put us in an odd position. We spend a great deal of time convincing legal professionals that they should be less paper-dependent and more digital-native. Prior to 2015, I suggested lawyers continue handwriting their notes but make a concerted effort to date, digitize, and file those notes into a document management system. This approach remains viable and eminently affordable since the greatest expense is a scanner (if you need a new scanner, see our recommendations here). You get all of the benefits the Princeton researchers found with handwritten, and the storage and retrieval benefits of digital. The weaknesses are two-fold though: others may not be able to read your chicken scratch, and the notes you take are not text-searchable – meaning the most you can search by are file name and whatever characteristics your document management system provides.

Enter the Apple Pencil.


Apple released the iPad Pro and Apple Pencil in 2015, which was a watershed for digital handwriting. As with most first-generation implementations, there were gaps. Price was one: the first iPad Pro started at $800 and the Apple Pencil added $99. The first Pencil was prone to roll off desks (just like a regular pencil) and attached to the iPad in a way so awkward that it could double as a self-defense weapon or medieval pike.

What a difference six years makes! The second-generation Apple Pencil, priced at $130, has a flat side to prevent “roll away.” lets you change tools by tapping on the Pencil body, and it attaches and charges via magnets in the iPad. And total price came down. An iPad Air and Apple Pencil (2nd gen) start at $730 total. An iPad mini and Apple Pencil (2nd gen) start at $630 total.


Once you’ve made your purchase, here are four core note-taking programs to evaluate – two of which are free.

Notes: Every iOS device includes Apple’s Notes program that syncs between all of your Apple devices – iPads, iPhones, and Macs. If you’ve never used an Apple Pencil or other stylus in Notes, you may not know that it supports handwriting and drawing. You can even experience that with a cheap “trade show freebie” stylus to try it out, though the precision of an Apple Pencil is lightyears ahead of those giveaways – like the difference between your handwritten signature and how your signature appears on a credit card signing machine.

In Notes, you can choose your paper style – blank, lined, or dot grid. Notes performs handwriting recognition, so you can search the contents of notes and not just their names – the feature missing from our legal pad example above. iOS 15, released on Sept. 20, 2021, adds several new features:

  • Quick Notes is a “Picture in Picture” type feature that lets you make a note from wherever you are in iOS. No matter what app you have full screen, say Microsoft Word reviewing a draft brief, simply drag the Pencil from the bottom right of the screen to open a Post-It-sized window to write whatever just came to mind. That Quick Note is stored in your normal Notes app and is viewable on all your iOS devices.
  • Notes now include tagging and smart folder features. Tagging is self-explanatory. Create a tag called “Smith v Jones” and tag all of the notes for that matter with that tag. Smart Folders are a bit more complex, but fundamentally they are a way to automatically group similar notes. You could create a smart folder in Notes that looked for notes containing the “Smith v Jones” tag and the “discovery” tag that have been edited in the last month. Or you could have a smart folder that contained all notes tagged “discovery” irrespective of their matter tag.
  • Notes can be shared easily with other iOS users, irrespective of whether the user has an iPad or Apple Pencil. Any handwritten notes can also include typed words as well.

In addition to the Quick Notes, another Notes-only feature Apple offers is that if the iPad is asleep, tapping the darkened screen with the Apple Pencil will take the iPad directly to a new note in the Notes app so you can start writing immediately. This perk of Apple’s hardware-software integration eliminates the “boot up” delay that hindered prior digital note taking solutions.

Notes is not without its downsides though. Chief among them is that notes are available only within the Apple ecosystem (starting with a free iCloud account), and thus not stored natively in your firm document management system. There are ways to export individual notes as PDFs, but that’s an extra step. I think the benefits, particularly the “wake from sleep” feature, makes it worth the trouble.

OneNote: Microsoft’s OneNote application has existed since 2003 on Windows, 2011 on iOS, and 2014 on Macs. Of the handwritten note tools for the iPad, it allows the most cross-platform functionality. It’s also free, although Microsoft 365 subscribers see additional benefits. The iPad version fully supports the Apple Pencil. If you share OneNote notebooks with colleagues, they can easily see and edit notes too, also without paying extra money or venturing into a potentially unfamiliar ecosystem. In another boost for familiarity, OneNote embraces the notebook metaphor, wherein you create a notebook, divide it into sections, and add individual pages to a section. OneNote has support handwriting recognition longer than the other apps mentioned here. Finally, any Microsoft Surface users, with their accompanying pens, can join in the fun. More than Notes, or Notability and GoodNotes below, OneNote is most likely to coexist comfortably within your existing tech setup.

Notability and GoodNotes: To the extent it’s possible to have a granddaddy in a 6-year-old market, Notability and GoodNotes are it. Both existed prior to the Apple Pencil (Notability since 2009 and GoodNotes from 2012), and they really gained notoriety with the Pencil’s arrival. Feature-wise, they are evenly matched. Both allow the inclusion of images, screenshots, typed text, and just about anything else you can imagine. Prior major distinctions, like GoodNotes being able to import PDFs for editing or annotation, or Notability being able to record meeting audio that synchronizes to your handwritten notes, have greatly diminished. Today, it’s akin to a pickup truck rivalry between Ford and Chevy; a great feature one model has is quickly adopted by the other. The remaining primary difference is that Notability follows the Apple Notes model of folders and notes within them, while GoodNotes embraces the notebook metaphor like OneNote. Both Notability and GoodNotes offer Mac, but not Windows, apps and support various export options like PDFs. You can share notes, but only with other users of the respective app.

Buy and Try

Once you’ve committed to an iPad and Apple Pencil, start with the free Notes app, particularly as enhanced in iOS 15, and see if you find it lacking. If so, and you’re a Microsoft-centric firm, next try OneNote. If Notes proves insufficient and you’re not a Microsoft shop, I’d spend the $16 to get both Notability and GoodNotes, and stick with the one that works best for you.

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