Dennis Yu

The key to your email inbox

Want to know the secret to never missing a thing? For years that answer was Boomerang for Gmail — archive the thread, and bring it back if nobody replied. That timer still works. It is just no longer the hall monitor.

Today Tanner (my Grok Bot Executive Assistant) is the sole Gmail inbox router. 24×7 every 30 minutes, he does Do, Delegate, Delete on the cafeteria: archive noise, farm real work, and only page me for Dennis Attention, money, domain, or security. When a thread needs a chase, the agent labels it Awaiting Reply, archives it, and follows up after two business days by default. That is the same job Boomerang used to do for me — only the hands changed.

The downside of any chase system is the same: if the other person continually does not reply, you get a chain of follow-ups. That is useful signal. Too many returns means the farm-out failed, not that you need a louder timer. The full method is on how I manage 1,000 emails a day.

This still works most of the time — a lifesaver if you are a business owner who is the last line of defense. But it also means you have to be willing to deal with stuff like in the screenshot below.

Some people will say that you should fire people who can’t get organized or to ignore clients that can’t reliably respond. Yet some of the most loyal people I’ve known over the years were in this state of disorganization and are now solidly on top of their communication game.

I believe communication skills are more important than any sort of digital wizardry– that a reliable team beats the super genius.

Amen?

Scroll to Top