Jenny Silva
3 min readAug 16, 2020

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Hey.com — A cool reimagination of email that needs work.

Have you been interested in trying Hey.com, but haven’t gotten around to it yet? Maybe I can save you some time. Hey.com has received a lot of attention for having a new approach to email created by the makers of Basecamp. I have a lot of respect for the Basecamp team, so I tried it out. I like the new approach, but, reluctantly, I won’t be buying a subscription. Right now, there’s too much I would lose in making the switch. There are a lot of already documented issues with hey.com (archived email, custom domains), so I’m focusing on issues I haven’t seen addressed elsewhere.

Reasons I will not switch to Hey.com

  • No advanced search for email. I cannot move to hey.com with the current email search. There is one master search box, and no advanced search. I am constantly wanting to narrow my search to specific time periods, or from specific senders or email that I sent.
  • Replying to an email is always “reply all”. If you do not want to reply all, you have to manually remove every other person on the email. If you do a fair amount of collaboration, and so have many threads with multiple people, this is very cumbersome.
  • Contacts only include email address (and some hey specific features). I’m a little shocked that I can’t add the company name or title to a contact, nor the phone or other details. If I can’t remember who I spoke to at a company, I can’t search my contacts for the company. Given this, I will have to maintain a contact database outside of hey. I don’t want to do this.
  • There is no way to create a contact group. I have a number of groups that I am a part of, and using a contact group, I never have to worry about forgetting someone, accidentally emailing someone outside of a group, or of using the wrong email.

Things I might tolerate but I’d like changed.

  • The layout of the inbox — The Google in box is very easy to scan, with one line per email, and the alignment of the “from” and subject line. The Hey inbox is surprisingly harder to scan, covering two lines and no differentiation between the “from” and the email snippet. The subject line is given prominence over the “from”. For me, the “from” is almost always more important.
  • Read together — I like the read together feature. I wish that it marked emails as read when you use it. Right now it feels redundant, as any email you read this way needs to be manually marked as seen.
  • Files — any file that comes in automatically gets saved, including every logo and calendar invite attached to an email. Within days, I have dozens of files and no way to delete any of them. I’d love to get rid of unimportant files. Over time, it’s clearly going to be very difficult to find files — you can only search by type and who it is from. No title search or name search.
  • No canned responses — I could live without signatures, although that seems dumb to not allow. But there are often times that I need to send out similar, but personalized emails to people (soliciting donations for a school auction, for example). It’s really annoying to not have canned responses.

Things I really like — Even with all of the above, there’s much to applaud. If the features above were added, the email experience would be a massive upgrade for me, and I’m happily pay more than $99/year. Some users might not need the features I list above, and will be very happy with what it has. I appreciate the new outlook and thinking on how to manage email. Just add a bit more, and I’ll be a convert.

  1. The feed feature — I really like being able to split off newsletters and non-urgent things, and to read at my lesiure.
  2. Files — If they improve this, it’d be really great.
  3. Clips — The ability to save pieces of emails that I want to follow up on.
  4. Ability to add notes to emails
  5. Ability to rename threads
  6. The built-in workflow, and the ability to easily move emails between flows.

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Jenny Silva

pro-Yimby. school bus & school funding advocate. houseboat dweller. mask wearer. Co-founder, Racial Equity Playbook by the GSB Class of 94 @EquityPlaybook