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Is Hey the Future of Email?

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I have been a Gmail user since 2004. Back when the service was only accessible via a coveted invite, I plunked $20 down on eBay and got myself a golden ticket into what was supposed to be the future of email. At first, it was glorious — the power of Google search inside my email, all that “AJAX/Web 2.0 goodness,” and labels replacing folders, truly felt like email was getting the 2.0 makeover it needed.

Fast forward to 2020, and very little has changed with Gmail. Aside from some interface redesigns and pedestrian mobile apps, the core of what Gmail is has remained the same. There are some things it does very well: search (obviously) and spam blocking are still two killer features, but over the past couple of years, I’ve become disenfranchised with Gmail. I’m sick of being a product to Google, knowing that everything that goes in and out of my Gmail account is tracked to sell me more crap I don’t need or dump me into advertising targeting cohorts all around the web.

I was very intrigued when I heard that Basecamp team was looking to rebuild email from the ground up. While I personally have always hated Basecamp and found the entire suite of products a confusing, unintuitive mess, it’s obvious they know how to build things that last. After all, Basecamp was founded in 1999 and still has a rabid fanbase 21 years later. After all the hype, Hey.com is now opening its doors to the public. I’ve been testing the service and am afraid to say that we still need to wait longer for someone to fix email, assuming it’s fixable at all.

Before I dive into what I like and what I don’t about Hey, I want to make two points:

  1. I am not going to harp on what’s broken with email — this is a tale as old as time, and Brian Chen tackles a bit of this in his excellent review of Hey for the New York Times.
  2. If you aren’t aware of the drama between Apple and Hey, this is a good recap. (I’m 100% on the developers’ side and think that Apple’s App Store monopoly needs to be broken up, but that’s an article for another day.

What Hey Gets Right

From the minute you set up your Hey account, you enter into what is probably the best onboarding experience I’ve seen in years. Beautifully-designed emails from Hey appear right into your “imbox” (not a typo), and native prompts throughout the service help guide you into a new approach to email.

Their apps are equally as beautiful. I’ve tested the service via web, iOS, and Mac apps, and each feels entirely cohesive. I’m also impressed by the quality of these apps given that they are 1.0 releases; it’s obvious the decades of programming experience from the Basecamp team is shining here.

Hey has also made it easy to migrate your email into their service. Regardless of your provider, Hey has simple how-to guides on forwarding your email over to them. It’s not possible to move your old message into Hey, and they claim it is because they want you to “start fresh,” but that seems like an excuse for a feature they haven’t had time or resources to build.

The “killer feature” of Hey is what they call their screening feature. Before an email can get into our imbox, you must permit it. You’re playing the role of virtual bouncer for all new messages that are reaching your email, and you can either allow them in, block them for good, or force them into “The Feed” or “The Paper Trail.” It is satisfying to deny senders into the void and knowing they’ll never be alerted that you gave them the boot.

Hey also prides itself on privacy; they promise never to sell your information or track you, and they will show you each time an email you received has had its tracking pixel blocked. Seeing sales email show up with the big purple callout that Hey has prevented them from tracking you is also satisfying, but there have been a few reviews that point out that their tracking blocking isn’t as effective as some believe. Still, I’ll take a little over nothing at this point.

Clips is a great feature that I wish Hey would tout more. You can select an area of text and save it for easy access. This is perfect when you need to keep a confirmation number, someone’s phone number, or other bite-sized bits of information without having to search for it within an email. You can also add personal notes to any email to remind you about anything you want that is only visible by you.

Where Hey Falls Flat

While Hey does have a lot of good things going for it, I’m sad to say that I can’t see myself using this service as my Gmail replacement. There is a handful of what I call “minor annoyances” that I’ll outline below. If fixed, it would make the service much less annoying, but the fundamental way Hey approaches email that’s supposed to make me love it does the exact opposite.

The screening process is all-or-nothing. While this is great if your primary use of email is friends and family, but dealing with e-commerce is an utter nightmare. For example, I order from Starbucks and Dunkin frequently and like to get the email receipts when they’re charing my card with auto-reload. Now, if I tell Hey that emails from Starbucks or Dunkin’ should go into my “Paper Trail” box (the catch-all for receipts), in a few days, my Paper Trail is filled with marketing emails too. If I send them to “The Feed,” which is Hey’s box for marketing emails for perusing at your will in one infinite-scroll format, then I need to dig for them and move individually over to Paper Trail. Doing this is already adding 3 or 4 extra steps in managing my emails than in the “old way.” Hey says that their screening will get better over time, but I’m not willing to wait for them to improve on what is such so vitally essential for me to now.

Also, I wouldn’t say I like how anti-notifications Hey seems to be. While I’m the first to say that notifications have gone overboard for the majority of apps out there, email is one where I often welcome them, even if it’s just a badge icon for unread messages. The only way you can get notifications in Hey, at least right now, is on a per-person basis. I’d love to know how many emails I have in my imbox and my to-be-screened list without having to start up the app. Forcing me to start the app to check for mail is another thing adding more time to my email management.

Deleting messages is also a multi-tap experience. If you’re on desktop or web, merely tapping the “T” key will move a message to your trash, but in the app, you often have to go through two or three taps before you can trash a message. Hopefully, an app update will add a one-tap delete button, but for now, I dread seeing a long list of messages that I need to delete.

The Feed is also an area that Hey touts as a way to streamline your email process for all of those non-essential emails. Unfortunately, there’s currently no way that I can see to be notified when new emails have been added into the feed automatically. I need to check it all the time to make sure I haven’t missed anything that might be a bit time-sensitive (e.g., a flash sale). Also, you have to manually delete every message in there in a very awkward way, which makes me wish I just dumped it into the imbox in the first place. At the very least, adding a visual prompt when there are new messages in The Feed and auto-delete three days after reading would make this feature much more usable.

As an “inbox zero” guy, I also can’t get over my personal OCD of seeing old read messages just sitting on the bottom of my screen under the “previously seen” area. I’d much prefer these disappear into an archive and instead, put greater focus on the “reply later” and “set aside” stacks that Hey creates for emails you want to mark for follow-up or easy-access.

I also can’t live without custom snooze, which Hey doesn’t support. The aforementioned “reply later” and “set aside” features will move messages you need to follow-up on into a special box on the screen. Still, there’s no way to have them re-appear at the top of your inbox at a custom time, which has become a vital way to optimize my workflow in Gmail, Outlook and other email clients.

In Closing

Hey costs $99 a year after a two-week trial. Charing a yearly fee will alone be a dealbreaker for many people, but if you value privacy, great design, and a truly innovative process, $8.25 a month is not too much to ask for all that Hey offers. Unlike Flexibits, who has the gall to charge $5 a month for a calendar app, I could justify Hey’s yearly fee if it made me love email. Unfortunately, the only thing it’s made me realize about email is that managing it is much faster in the way we’re all accustomed to doing.

I don’t think I’m alone in saying the majority of my non-work email is transactional. It’s housing my Amazon receipts, updates from my kids’ school, and helping me track when bands I love are putting out new music or going on tour. Having to jump through hoops to move those around in the Hey model makes me hate email more than ever. Those conversations that we all used to have with family and friends over email have moved over to text messages and social media. It appears that Hey hasn’t gotten that memo yet and is trying to fix a problem that we’ve all moved on from.

I also can’t get over how much I hate the term imbox.

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