Managing Up by Calibrated Context
Proactively give your boss exactly enough context to weigh in — scaled to reversibility.
- Difficulty
- Moderate
- Time to result
- ~weeks to results
- Steps
- 5
- Confidence
- 90%
Most people resent the idea of managing their boss — that's what the boss is paid for. Kao's counter is that the most senior people are the best at it, and that's precisely why they got promoted. Managing up is a proactive information discipline: understand what worries your boss, take it off their plate, keep them in the loop so they never have to pepper you with status questions, and calibrate how much context you push based on whether the decision is reversible or expensive to undo.
Origin
Wes Kao's framework (her most popular tweet). The reversible/irreversible calibration echoes Bezos's one-way vs two-way door decisions; the weekly-update pattern below is Lenny Rachitsky's 'State of Lenny' email, shared in the same conversation.
Core principles
- 01There is no seniority level at which managing up stops mattering — even managers have bosses.
- 02The most senior people are the best at managing up; that's the causal mechanism of their promotion.
- 03Proactive communication means your boss never has to ask 'how's this going?'
- 04Judgement is the constraint: telling your boss everything is as bad as telling them nothing, because it overwhelms them.
- 05Overcommunication in remote work usually lands as exactly the right amount to the recipient.
- 06Surprises are the failure mode. Avoid them except for birthday parties and snacks.
How to run it
- 1
Find out what keeps your boss up at night
Understand what is worrying them so you can take it off their plate. This is the behaviour Kao identifies as the actual promotion mechanism.
- 2
Classify the decision by reversibility
Before escalating, ask: is this reversible, or is it irreversible, difficult to reverse, or expensive to reverse? Reversible decisions need a light touch; costly-to-reverse ones need full context up front.
Pro tip This is the filter that keeps you from either surprising your boss or drowning them.
Watch out Escalating everything is overwhelming for a manager who already has a lot going on — it reads as an absence of judgement, not diligence.
- 3
Push enough context to enable a push-back
Share your thought process and rationale at the level where your boss has enough information either to push back or to approve and know it's handled.
Pro tip The done-check is: could they disagree with me intelligently from what I wrote? If not, you gave too little.
- 4
Run a standing proactive update
Send a recurring written update on a fixed cadence so alignment is continuously verified rather than assumed.
Pro tip Lenny's version, the weekly 'State of Lenny' email, had three sections: blockers he needed help with (first, so it couldn't be missed), current priorities, and what was on his mind that week.
- 5
Re-verify alignment you think you already have
Assume alignment decays. Kao reports being surprised to find that a strategy she thought everyone agreed on — after discussing it three times — was not actually agreed.
In the wild
Lenny Rachitsky sent his manager a weekly email titled 'The State of Lenny' with three sections: blockers he needed help with, his current priorities, and what was on his mind that week.
→ Priorities stayed aligned, blockers got unblocked, and surprises were eliminated — with almost no ongoing cost.
The common assumption is that once you're a director or VP you no longer need to manage up. Kao's observation is the inverse: senior people are the best at keeping their bosses in the loop and pre-empting their worries, which is how they became senior.
→ Reframes managing up from a junior-employee chore into a leadership skill worth deliberately practising at every level.
Common mistakes
Resenting the premise
Believing that because your boss is paid more and has more responsibility, they should manage you and not vice versa. Your career may be fine, but you forfeit the trust, opportunities and appreciation that managing up generates.
Escalating everything
Telling your boss every detail of everything is overwhelming and abdicates the judgement call to them. Reversibility is the filter that separates what needs their input from what doesn't.
Throwing surprises over the wall
Catching your manager off guard with news they should have seen coming is the fastest way to lose trust. The complaint is never 'why did you tell me?', it's always 'why didn't I know about this?'
Is it for you?
Best for
ICs and managers who want more trust, autonomy and opportunity from their reporting line — especially in remote or distributed teams
Not ideal for
Situations where the manager has explicitly asked for less frequent contact, or where every decision genuinely is reversible and low-stakes
From the transcript
“ironically the most senior people are best at managing up this is why they got promoted in the first place”
“they're proactive in communicating so their boss knows that certain things are taken care of”
“is this a reversible decision or is this one that um that is irreversible or or difficult to reverse or expensive to reverse”
“you think you're overc communicating but to the recipient it's actually just the right amount”
From the episode
Persuasive communication and managing up
Wes Kao (Maven, Seth Godin, Section4)