You speak about 150 words per minute. You type about 40. AI dictation closes that gap: tools like Wispr Flow ($12-15/month) put accurate speech-to-text anywhere your cursor is, in any app, with no voice training. Dictate the rough version, let Claude structure it, and a 20-minute email becomes a 4-minute one. For privileged content, on-device options like Superwhisper’s local mode keep the audio on your machine.
The math nobody runs
A lawyer is a word factory. Emails, case notes, letters, memos, instructions to staff. If you bill or manage by output, your words-per-minute is a production number, and most lawyers cap theirs at typing speed.
Average conversational speech runs about 150 words per minute. Average typing is around 40, maybe 60 if you’re fast. That’s a 3x difference on the single activity that fills most of a lawyer’s day. A 400-word client email is 10 minutes of typing or under 3 minutes of talking. Do that five times a day and you’ve bought back a half hour, every day, forever.
I dictate most of my first drafts now. Not because my typing is slow, but because talking doesn’t interrupt thinking the way typing does.
This is not Dragon
If you tried legal dictation in the 2010s, you remember the ritual: reading training passages to Dragon for hours, building custom vocabularies, correcting “tortious interference” for the tenth time, and eventually going back to typing.
Whisper-class AI models killed that ritual. They were trained on enormous amounts of real human speech, so they understand natural talking out of the box: fast talkers, accents, mumbled half-sentences. They punctuate on their own. And legal vocabulary is already in there. Say “res ipsa loquitur” or “subrogation” and it just types it. No training file, no correction sessions, no weekend lost to setup.
The newer tools go one step further and clean as they write. Say “um, so, tell the client we, uh, we got the offer” and Wispr Flow types “Tell the client we got the offer.” That’s the part that makes dictation usable for real work instead of demos.
The tools
| Tool | Price | Where it runs | Best for |
|---|---|---|---|
| Wispr Flow | ~$12-15/month | Mac, Windows, iPhone | Most lawyers. System-wide, works in any app, auto-formats and removes filler |
| Superwhisper | One-time or subscription | Mac, iPhone | Privacy-focused lawyers. Local processing mode keeps audio on-device |
| MacWhisper | One-time (~$30-60) | Mac | Fully local transcription, pay once, no account |
| Apple dictation | Free | Mac, iPhone | Trying dictation today. On-device, improved a lot, weaker punctuation |
| Dragon Legal | $500+ | Windows | Heavy dictators who want hands-free control and legal templates |
Start with Apple’s built-in dictation if you want proof of concept for free. Upgrade to Wispr Flow when you’re convinced, which usually takes a day.
The workflow that makes dictation click
Here’s what most lawyers get wrong: they try to dictate finished prose. Full sentences, correct order, like reading a letter aloud. That’s exhausting and it misses the point.
The workflow that works is a two-step split. Dictation gets the words out. AI does the formatting.
Dictate your actual thoughts, messy and out of order: “Client called, transmission failed again, third repair attempt, dealer had it 22 days total, we’re past the presumption threshold, need repair orders before I send the demand.” Then hand it to Claude with one instruction: “Turn this rambling into a client email” or “Structure this as a case note.” Thirty seconds later you have clean output built from your own thinking.
My prompt library guide has prompts built for exactly this handoff, and the AI email guide covers the email half in detail. Once you have both pieces, the bottleneck in your writing stops being your hands.
Where dictation pays off
Case notes right after the client call. This is the highest-value use. Details decay fast, and a 90-second spoken brain dump while everything is fresh beats a typed summary an hour later. Every time.
Email. Your five most common email situations are all faster spoken. Dictate the substance, let AI handle the structure.
Brief outlines on the commute. Phone dictation into your notes app turns dead driving time into a working outline. Some of my best delegation instructions started as rambles at a red light.
Instructions for staff. Spoken delegation is naturally more complete than typed delegation, because talking is cheap and typing makes you compress. Dictate the full context, send it, and watch the follow-up questions drop.
Confidentiality: where the audio goes
One distinction decides everything here: on-device or cloud.
On-device tools (Superwhisper in local mode, MacWhisper, Apple dictation) transcribe on your own hardware. The audio never leaves your machine, so dictating privileged content is no different from typing it.
Cloud tools like Wispr Flow send audio to the vendor’s servers for processing. That’s a vendor relationship, the same category as your practice management software or cloud email. Read the data retention policy, check whether audio is stored or used for training, and apply your state bar’s normal vendor diligence.
A reasonable split: cloud dictation for general drafting and internal notes, on-device for anything you’d mark privileged. And note this is dictation, not transcription of recordings, which has its own tools and its own consent rules.
The 10-minute setup
- Test the free option first. On Mac, press the dictation key (or F5) in any text field and talk for 30 seconds. On iPhone, tap the mic on the keyboard. This is your baseline.
- Download Wispr Flow and set its hotkey. Pick something you’ll actually hit, like holding the fn key.
- Dictate one real email. Not a test sentence. An actual email you owe someone, spoken the way you’d explain it to a colleague.
- Run the Claude handoff. Paste your messy dictation into Claude with “turn this into a client-ready email” and compare it to what you would have typed.
- Pick your privilege rule. Decide now which tool handles privileged content (on-device) and which handles everything else, so you never decide under deadline.
That’s the whole setup. The habit takes about a week: your hands will reach for the keyboard out of muscle memory, and then one day they won’t.
Today’s action: dictate the next email you owe someone instead of typing it. Time both. The math will make the argument for me.