Email Tips from the HackMIT Team

At HackCon, I presented a talk on inbox management. I decided to transcribe the presentation here for reference.

On the HackMIT team, we receive around 200 emails a day during peak organizing weeks. Mistakes happen. And often, these mistakes can be a bit embarrassing:

After visiting a potential alternative venue suggested by a sponsor, a team member accidentally replied all while insulting the venue.

A team member accidentally sent a snarky remark to a recruiter, who then humorously feigned innocence.

These mistakes are often realized about ten seconds after hitting send. The CC field is often overlooked until it’s too late: you glance over the sent email, realize the mistake, and feel your stomach drop in embarrassment.

Fortunately, Gmail provides an easy fix:

Do this. Activate the Undo Send Gmail Lab by looking in the “Labs” tag in the Settings menu; solve one of the first world’s paramount problems.

On a different note, an ineffective ping is as bad as adverse reply all. A “ping” is when the point person for an email leaves it unanswered, and another member of the team has to remind them to take care of it. Below you see an email thread in which I ping a team member six times in a row, all without reply. You also see an example of an effective ping.

Here, I ping a member of the HackMIT team six times in a row with no success.

Here, the team member who is the point person for travel reimbursement only needs one ping to remember to respond to the email.

The HackMIT team heavily relies on pinging to make sure no email or task falls through the cracks. Yet, who takes on the task of pinging the point person until an email is taken care of? Any two or three people can be assigned to the task; to avoid email clutter, these people should snooze messages rather than leaving them in their inboxes.

What is a snooze? Inbox, Mailbox, and Boomerang all advertise the feature; snoozing allows you to remove an email from your inbox and to have it return at some specified later date. So, you can imagine a hackathon sponsorship-specific use case as follows:

1. A sponsor emails your team, interested in sponsoring your hackathon.
2. The two people designated as “ping” point people snooze the email.
3. If the sponsorship point person responds to the interested sponsor, then no ping is needed and the “ping” point people can archive that email.
4. However, if the sponsorship point person forgets to respond, then this email will return to the inboxes of the “ping” point people after the designated snooze time. These “ping” point people then remind the sponsorship point person to respond.

In an ideal world, no pings would be necessary. On the HackMIT team, we try to follow these guidelines on email promptness:

1. Reply to sponsor emails in less than 1 day. Leaving a sponsor hanging for days is unprofessional and decreases their confidence in the competence of your organization.
2. Reply to attendee emails in less than 12 hours. Attendees are impatient, and will begin to complain on social media if their concerns are not addressed immediately.
3. Reply to urgent emails within the hour. Urgent emails include time-sensitive logistical emails or emails about decisions that need to happen by the end of the day.

Some members of the HackMIT team started competitively timing their shortest email response times. I think the record was about seven seconds—shoutout to Kate Yu, HackMIT 2014 director of sponsorship. With practice, you too can be Kate Yu; she received universally positive remarks from sponsors about her fast email turnaround.

Alternatively, the flip side of email neglect is the double reply. An interested sponsor emails the team, and two members respond. Confusion ensues. Luckily, this problem is far easier to fix than forgotten emails. If an email is sent to a mailing list, BCC that mailing list in your reply to the sender. Then, all parties involved will be aware of your reply, but that mailing list will not continue to be included on the email thread.

My next email tip is a personal favorite: the strongly worded email.

What is a strongly worded email? Think short paragraphs containing no more than four sentences. Each sentence should be short, to the point, and state facts rather than opinions. Strongly worded emails never use filler phrases such as “I think,” “maybe,” or “potentially.” You can see an example of a strongly worded email below.

On the left is an email sent from me to a sponsor of HackMIT ‘13. We ended up resolving past issues and they attended HackMIT ‘14, but this email attracted the immediate attention of the recruiting lead of the company, as illustrated by the response I received on the right.

In short, strongly worded emails are emails that prompt action. If a vendor has failed to deliver, if an administrator has delayed progress significantly, or if a participant is acting aggressively presumptuous, you should speak strongly. Yet, speaking firmly and clearly is not limited to dealing with disaster scenarios. Even when sending an ordinary email to sponsors or attendees, make sure to keep paragraphs and sentences short and to the point.

Email formality also affects your recipients’ likelihood of responding. Imagine receiving an email that starts with “Dear Mrs./Mr. <insert name>.” If you are in your twenties, would you even read further? Maybe, but only to add humor to your day. Yet, if the email started with a “Hey <first name>,” you would at least scan the email body.

Remember: recruiters are normal people. People you could be friends with, people often only a few years older than you are. So, address recruiters how you would address a new friend—be casual within reason, and don’t embellish sentences with unnecessary formalities.

To the left is a standard email that HackMIT uses to recruit sponsors. It’s reasonably short and casual, but still uses proper capitalization and full sentences.

Furthermore, even if a sponsor were to just skim the first two lines of the email, that person would be able to gather exactly why the sender was emailing. In general, your first one or two sentences should be a TL;DR for the entire email. In the example to the left, Jessica first introduces herself, then inserts the buzzwords “HackMIT” and “sponsor.” So, after reading the first sentence, Rob will know exactly what the email was about.

What about emails that must necessarily be lengthy, such as a thoughtful response to a university administration’s concerns and demands? Usually, assigning one person the burden of composing the entire email is inefficient. On the HackMIT team, we compose these emails as a group, decreasing the risk of forgetting a key point. When the team receives an email that warrants a lengthy response, one team member will reply all to the team mailing list with a link to a google doc. Whoever is online at the time then hops on the google doc and helps compose the email. After the email is completed to the satisfaction of the team, the point person will send the reply to its intended recipient.

The technique is even more pertinent with time deadlines—say, if your university newspaper gives you one hour to compose a 500-word response to an opinion piece condemning your hackathon for straining students’ mental health. Of course, most news sources have professional standards that would prevent such a situation from happening, but the group compose technique is a lifesaver in similarly adverse situations.

My final tip is better phrased as a question: when is it appropriate to introduce two people over Facebook, rather than over email? When you do a Facebook intro, you are essentially saying that two people should be friends. So, definitely use it to meet fellow hackathon organizers. And, except for rare cases, never do sponsor intros over Facebook chat.

Regardless, the process for introducing two people over Facebook or email is about the same. Say person A wants an introduction to person B. The process is as follows.

1. First, make sure to ask person B whether he/she would be open to an introduction to person A.
2. Then send an email to person B, ccing person A and making the introduction. Succinctly explain why you are introducing person A to person B.
3. Finally, person A should reply to the email, thanking you for the introduction and moving you to the BCC field.

Intros are powerful—they can make the difference between a sponsor responding and ignoring your email. Intros can help you recruit a high profile speaker for your event, or simply connect you with other event organizers.

Overall, just remember these eight tips:

1. Enable undo send.
2. Use pings effectively.
3. Word emails concisely; avoid filler phrases.
4. Address recruiters as you would address a new friend.
5. Use a TL;DR opening sentence.
6. Respond to emails promptly.
7. Use group compose for lengthy emails.
8. Wield Facebook and email introductions effectively.

~ Written with ❤ from the HackMIT team.