1. You can not not communicate. Not discussing the elephant in the room is communicating. Few things are as important to study, practice, and perfect as clear communication.
2. Real-time sometimes, asynchronous most of the time.
3. Internal communication based on long-form writing, rather than a verbal tradition of meetings, speaking, and chatting, leads to a welcomed reduction in meetings, video conferences, calls, or other real-time opportunities to interrupt and be interrupted.
4. Give meaningful discussions a meaningful amount of time to develop and unfold. Rushing to judgement, or demanding immediate responses, only serves to increase the odds of poor decision making.
5. Meetings are the last resort, not the first option.
6. Writing solidifies, chat dissolves. Substantial decisions start and end with an exchange of complete thoughts, not one-line-at-a-time jousts. If it’s important, critical, or fundamental, write it up, don’t chat it down.
7. Speaking only helps who’s in the room, writing helps everyone. This includes people who couldn’t make it, or future employees who join years from now.
8. If your words can be perceived in different ways, they’ll be understood in the way which does the most harm.
9. Never expect or require someone to get back to you immediately unless it’s a true emergency. The expectation of immediate response is toxic.
10. If you have to repeat yourself, you weren’t clear enough the first time. However, if you’re talking about something brand new, you may have to repeat yourself for years before you’re heard. Pick your repeats wisely.
11. Poor communication creates more work.
12. Companies don’t have communication problems, they have miscommunication problems. The smaller the company, group, or team, the fewer opportunities for miscommunication.
13. Five people in a room for an hour isn’t a one hour meeting, it’s a five hour meeting. Be mindful of the tradeoffs.
14. Be proactive about “wait, what?” questions by providing factual context and spacial context. Factual are the things people also need to know. Spacial is where the communication happens (for example, if it’s about a specific to-do, discuss it right under the to-do, not somewhere else).
15. Communication shouldn’t require schedule synchronization. Calendars have nothing to do with communication. Writing, rather than speaking or meeting, is independent of schedule and far more direct.
16. “Now” is often the wrong time to say what just popped into your head. It’s better to let it filter it through the sieve of time. What’s left is the part worth saying.
17. Ask yourself if others will feel compelled to rush their response if you rush your approach.
18. The end of the day has a way of convincing you what you’ve done is good, but the next morning has a way of telling you the truth. If you aren’t sure, sleep on it before saying it.
19. If you want an answer, you have to ask a question. People typically have a lot to say, but they’ll volunteer little. Automatic questions on a regular schedule help people practice sharing, writing, and communicating.
20. Occasionally pick random words, sentences, or paragraphs and hit delete. Did it matter?
21. Urgency is overrated, ASAP is poison.
22. If something’s going to be difficult to hear or share, invite questions at the end. Ending without the invitation will lead to public silence but private conjecture. This is where rumors breed.
23. Where you put something, and what you call it, matters. When titling something, lead with the most important information. Keep in mind that many technical systems truncate long text or titles.
24. Write at the right time. Sharing something at 5pm may keep someone at work longer. You may have some spare time on a Sunday afternoon to write something, but putting it out there on Sunday may pull people back into work on the weekends. Early Monday morning communication may be buried by other things. There may not be a perfect time, but there’s certainly a wrong time. Keep that in mind when you hit send.
25. Great news delivered on the heels of bad news makes both bits worse. The bad news feels like it’s being buried, the good news feels like it’s being injected to change the mood. Be honest with each by giving them adequate space.
26. Time is on your side, rushing makes conversations worse.
27. Communication is lossy, especially verbal communication. Every hearsay hop adds static and chips at fidelity. Whenever possible, communicate directly with those you’re addressing rather than passing the message through intermediaries.
28. Ask if things are clear. Ask what you left out. Ask if there was anything someone was expecting that you didn’t cover. Address the gaps before they widen with time.
29. Consider where you put things. The right communication in the wrong place might as well not exist at all. When someone relies on search to find something it’s often because it wasn’t where they expected something to be.
30. Communication often interrupts, so good communication is often about saying the right thing at the right time in the right way with the fewest side effects.

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