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Daniel Doubrovkine

aka dB., @awscloud, former CTO @artsy, +@vestris, NYC

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In his 2001 memoir “How to Lose Friends & Alienate People” Toby Young proposed a universal theorem.

Some people are lucky enough to stumble across the right path straight away; most of us only discover what the right one is by going down the wrong one first.

He may have been talking about one of my former colleagues who made a career limiting move by hitting Reply All to a team re-org announcement and saying out loud what everybody already thought: “I cannot believe you have promoted that idiot.”

The corollary of Toby Young’s theorem is that you should never write anything you don’t want to be read.

That said, such incidents can be avoided with a bit of discipline from the e-mail senders, described below.

Always Bcc and Announce Lists

Only put individual e-mail addresses on the to: or cc: lines and bcc: mailing lists. Maybe even address the e-mail to yourself to keep a copy. This prevents the knee jerk Reply All reaction to a wide distribution list when one only meant to reply to the sender.

Furthermore, a recipient doesn’t know who is being bcc-ed or whether they were e-mailed directly or were part of a list, therefore the polite thing to do is to tell them.

From: me
To: me
Bcc: team, hr
-------------

Team (team@ and hr@ on the bcc),

Today I am happy to announce that Alice was promoted.

-Me

Forward Instead of Bcc

If you are trying to bcc someone as an FYI, don’t. Forward that e-mail with a personal note.

A bcc is not an FYI, and you are hiding the fact that another person is being bcc-ed, creating an opportunity for an unpleasant surprise when that person hits Reply All to visible recipients.

From: me
To: Bob
--------

Bob, FYI, here's the team announcement from this morning.

_________________________________________________________

From: me
To: me
Bcc: team, hr
-------------

Team (team@ and hr@ on the bcc),

Today I am happy to announce that Alice was promoted.

-Me

Move People to Bcc

If someone made an introduction, thank them and move them to the bcc. Spare their inbox from conversations they dont’t care about.

From: me
To: Bob
Bcc: Alice
----------

Thanks Alice, moving to bcc. Nice to virtually meet you, Bob.

______________________________________________________________

From: Alice
To: me, Bob
-----------

Daniel meet Bob!

-Alice

Did someone not follow the rules above? Move everyone to bcc when replying all. You might save someone’s professional relationship.

Say Congrats on the To Line

When replying to a piece of good news, don’t Reply All. Make it count by sending them something personal and sparing everyone else.

From: me
To: Alice
---------

Congrats Alice, you've done a tremendous job. This is well deserved!

-Daniel
_______________________________________________________________________

From: Bob
Cc: Alice
Bcc:
---------

Team (on the bcc),

Today I am happy to announce that Alice was promoted.

-Bob