Most people suck at managing up.

They waste their boss’ time with too much (or too little) information.

Here’s how to give the right amount of context:
Star employees are exceptional at communicating and managing up.

This is even more important in a remote working environment.

They proactively communicate to show they've got it handled and prevent endless one-off questions. https://twitter.com/wes_kao/status/1451926441239719947?s=20&t=TZjCrF9HGewLbidnrH_Lsg
If you don’t share enough context, you’ll waste time on:

❌ Needless back-and-forth
❌ Avoidable follow up questions
❌ Misunderstandings and confusion

Here are 8 ways to give your boss the right amount of context:
1. Remind them where you left off.

Task switching takes a lot of energy.

Your boss is probably reading your note in between meetings (or during one!).

Assume they’re reading with partial attention. Remind them where you left off so they can task switch faster.
🚫 “Here’s the updated link.”

✅ “Here’s the updated pitch. I incorporated your feedback & included a change summary below. Let me know if you have any questions. I’ll plan on shipping tomorrow morning.”
2. Be specific & explicit about what you need.

Don’t assume your boss knows what you need from them.

Be specific about what you need and what the next step is.

Otherwise, they’ll assume you’re making progress–and will be surprised to find out you’ve been stalled for weeks.
🚫 “The new ad is updated in the Google Doc. It’s published in FB, but not running.”

✅ “Please approve the new ad copy (screenshot below). Once you approve, I’ll publish and go live on FB.”
3. Mention if it’s an FYI.

Don’t make people guess if they need to take action.

If your recipient has to follow up to ask, it slows everyone down.

Folks think they’re being helpful by forwarding a random email. But without context or next steps, these messages are useless.
🚫 [No context]

✅ “FYI. Sharing because you mentioned wanting to see examples of investor updates.”
4. Adopt an action-oriented posture.

If you’re stuck, don’t just stay stuck.

Speak up to get what you need to do your job.
🚫 “I didn’t do it because I don’t have the right permissions in Google Analytics.”

✅ “Can you add to me to Google Analytics with x permissions? I need it in order to do y.”
5. You can share LESS context when…

✔️ You’ve made this type of decision many times & you have task relevant maturity

✔️ Decision is reversible and inexpensive

✔️ This is top of mind for your boss (not one of 25 projects they’re managing)
6. Aim for MORE context when the decision is…

✔️ Irreversible and expensive

✔️ Customer-facing

✔️ You’re making this type of decision for the first time
7. Mention your criteria and assumptions.

Most bosses want to know that you did your due diligence and are thinking ahead.

Show your thought process.

Your boss can point out gaps in your logic–or update the criteria/assumptions you used.
🚫 ”I recommend this platform.”

✅ “I recommend this platform because of x, y, z criteria. My assumptions were a and b. The potential trade-off is x, but seems manageable because y. I vetted options, including [insert options] but [my recommendation] better fits our needs.”
8. Put the recommendation at the top, then context below.

Leading with a recommendation allows your recipient to read as much or as little of the context as they need.

🚫 [Actions, backstory, and context all jumbled together]

✅ 👇
It's your job to do the heavy lifting.

By providing the right amount of context, your boss won't have to guess to figure out what you’re trying to do.

Take the mental load off your boss & you’ll shine as an employee.

Win-win.
That’s it for today.

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