Hark planned our 10-year anniversary weekend. Here’s the exact prompt I used, the other ways I’m using it, and how to set it up so nothing books without your yes.
Partnership
I partnered with Hark on this one. Every feature below comes straight from Hark’s own docs, and every prompt is one I’d actually use.
Hark Pro is the app from Hark, the company building what it calls the operating system for your life. It launched October 6 on web, iPhone and Android. You talk to it in one ongoing chat, it remembers what you tell it, and it has its own computer in the cloud, called Handoff, that opens websites, signs in for you and gets things done. Handoff can run up to six browsers at once, which is how it compares options while you do something else.
Want to see how it stacks up against the other personal agents? That’s in my October AI updates and my AI agent comparison.
I gave Tray and Hark the same dates, the same budget and the same wish list. Here’s my prompt with the blanks open. The two lines that matter most are the protected do-nothing time and the approval rule, so keep both.
01
Start a Project for the trip
In Hark, open Projects and start a new one for the trip. Projects keep one topic and its files in their own thread, so every confirmation and receipt for the weekend lands in one place.
02
Watch it work, then approve
You can watch Handoff click through sites while it works, and there’s always a button to cancel (Hark security). When the plan comes back, push back like you would with a person: "swap the hike for something shorter" or "find a spa closer to the hotel." Say yes only when the full schedule and total look right.
These are pulled from what Hark says it can do today. Each one tells Hark to show you first and wait, so you stay the one deciding.
01
Date night reservations
Hark books tables on OpenTable and Resy using your saved accounts.
02
Appointments you keep putting off
The dentist, the annual physical, the vet. It searches, compares and books, then adds it to your calendar once your email is connected.
03
Shop your insurance
Hark lists insurance quotes as one of its own examples. Give it your current coverage so the comparison is apples to apples.
04
Find the money leaks
Hark reads the bills and receipts in your email. Over time it also puts Action Buttons on your Home screen, like "Cancel" on a subscription you forgot about.
05
Inbox triage and expenses
Connect Gmail or Outlook first. Anything Hark sends goes out in your name, so keep the "don’t send until I approve" line.
06
Groceries on repeat
This one becomes a Scheduled Task. You can pause or cancel it any time.
07
A custom dashboard
Panels are tiny apps Hark builds on your Home screen from services you already use. Tap Reply on a Panel to change it or ask about the data.
08
A hiring shortlist
For business owners: Hark’s Handoff demo finds and messages candidates on LinkedIn. Read every message before it goes out.
Doing the same multi-step job every week? Ask Hark to make it a Specialty, which is a workflow it memorizes and repeats your way.
01
Download it
Sign up at hark.com with Google, Apple or your email, or get the app for iPhone (iOS 17.6 or later) or Android. You need to be 18 or older.
02
Pick a plan
Here’s the surprise: the free plan includes everything, the cloud computer and booking too. Paid plans only add usage. Pro² is $20 a month for 2x the usage, and Pro³ is $100 a month for 10x (pricing). Start free and upgrade if you hit the cap. If you turn on auto top-up, set a ceiling you’re comfortable with.
03
Connect your stuff
Connect your email and calendar (Google Workspace and Microsoft 365 connect directly). Logins and cards you save go into an encrypted vault Hark calls Secured by Hark, and it says even its own team can’t see inside.
New to giving an agent your accounts? Read my guide to safely giving an AI agent access first.
04
Know how approvals and payments work
Unless you tell it otherwise, Hark asks you to confirm before it spends money or messages anyone for you. If you give it standing permission for a type of purchase, it can buy within that without asking. Purchases go on your saved card, and the store is the seller, so refunds and cancellations go through that store or your card company (Hark terms). If something books that you didn’t mean, email support@hark.com right away.
05
Check before you say book it
Keep standing permissions small at first, like groceries under a set amount. Bigger purchases should always come back to you.