Write Better Emails

Presented 2025-06-20

https://slides.refactoringenglish.com/

What makes an email good or bad?

Good emails: Clarity

• Subject line describes topic succinctly
• Recipients understand what you’re telling them

Good emails: Clarity

• Minimizes ambiguity / need for clarification
• Action items you expect of recipients are obvious

Good emails: Low noise

• Information is relevant to recipients
• If email has multiple audiences, each audience can find parts relevant to them
• Presents information concisely

Bad emails: Poor recipient management

• Overly broad recipients
• Everyone is bcc’ed
• People are silently added/removed
• Teams silo’ed on separate threads

Bad emails: Chatty

• Lots of quick back-and-forth
• High email volume, low progress

Bad emails: Why am I on this thread?

Process-centric emails

• Idea comes from Cal Newport
• Goal of email thread
  • Resolve the thread in fewest possible emails

Anti-pattern

• Respond ASAP to get the thread out of your inbox

Process-centric emails

Friend: Do you want to grab coffee sometime soon?

Lazy response

okay, what works for you?

Cal Newport response

Sounds great. I propose we meet at the Starbucks on campus. Below I have listed four dates and times over the next two weeks. If any of these work for you, let me know and I will consider your reply confirmation that the meeting is set. If none of these times work, then call me or text me on my cell (<number>) during one of my upcoming office hours (Tue/Thur from 12:30 to 1:30), when I’m sure to be around, and we’ll find something that works.

Process-centric emails

Friend: Do you want to grab coffee sometime soon?

My response

Sure, that sounds great!

How about Starbucks on Tuesday (June 24) at 2pm?

I’m also free at these times […] and open to other venues like Mario’s or Tabby Cafe.

Context-switching

• Costly to focus to keep returning to email thread

Diligence increases with stakes + number of recipients

• Email to entire company: Prepare and edit thoroughly
• Casual email to friends: Don’t worry too much

Tactics for high-stakes emails

• Consider a one-line tl; dr
• Break body into sections with headings
• Split out action items and questions
• Aggressively prune recipients / split threads

Subject line

• Help recipients recognize relevance
  • Similar to a blog post title or a commit message summary

Bad subject lines

Good subject lines

• Precise and descriptive
• Describe a process that the thread can resolve

• Examples
• Integrating FooLib into BarService
• Design Review: SQLite to Postgres migration plan

Subject line

• Add prefixes to indicate special attention
  • [Action required] Pick up your new ID badge
  • [Urgent] Ice cream party in microkitchen NOW

Update the subject line

• When the focus shifts, split thread and update subject

Subject: Failed deployment in us-east-1 WAS: Pushing 1.2.0 release

Subject: Choosing metrics to track WAS: Metrics tracker design review

Why am I reading this email?

Get to the point

• First few lines are most important (like in blog posts)
• Within the first three sentences:
  • Who is the audience for this email?
  • Why is it important that they read it?

Use the inverted pyramid

• Idea: Help recipients stop reading ASAP
• Add a one-line TL; DR

Trimming noise

I didn’t have time to write you a short letter, so I wrote you a long one.

-Mark Twain

Trimming noise

• The longer the email, less likely people are to read
• Techniques
  • Link to external resources
  • Split some material to separate threads / narrower audience
  • Summarize with bullet points

Tool: Markdown Here

• Browser extension
• Write emails in Markdown, convert to HTML before sending

Tool: Markdown Here

Use headings

• Break up large email
• Make it easy for readers to scan for relevant information
  • Especially if there are many recipients.

Use headings

Subject: Decomissioning DolphinSnax API

tl; dr - We’re sunsetting the DolphinSnax API on October 1, 2025. All clients must migrate before that date.

When will decomissioning begin?

The API will begin serving warnings on…

How can we migrate?

…

Recipient management

• Mention in the thread who you’re adding or dropping.

[moving moxy-dev@ to bcc]

[adding performance-stats@]

Recipient management

• Summarize thread
• Explain why you added them

[adding performance-stats@]

performace-stats@ - We’re trying to understand how the new metrics library will affect compile times. Do you have data on this?

Action items

• Create explicit action items with owners

Action items

• Gilfoyle - Investigate why FunkBot alerts keep firing.
• Dinesh - Give Jared the resource requirements for the TacoChat backend.
• Nelson - Schedule a meeting with the SRE team to get launch approval.

Action items

• Explicitly say when no action is required

billing-team@ - No action required, as we’re still waiting on the client to sign.

Questions

• For long or high-stakes emails, split out questions like action items.

Questions

• Dana - What is the ETA on the test automation for v1?
• Poppy - Which hardware architectures are we targeting for v1?

Should this be an email?

Bad discussions for email

Low-latency discussion

• Example
  • Team A wants Team B to use tool Foo
  • Team B knows nothing about Foo
  • Team A doesn’t understand Team B’s needs

Bad discussions for email

Difficult conversations

• Examples
  • Giving negative feedback
  • Cooling tensions

Bad discussions for email

Defining policy

• Email becomes canonical place for policy decision
  • Was there a later email?
  • How do I find this decision?

Preventing accidental sends

• For high-stakes emails, enter recipients last

Preventing accidental sends

• Configure your email client for undo send
  • Delayed sending, not recall emails