The Manual
Vol. I · No. 1 · September 2026
The Gentleman's Guide
Part III · Work & CareerNo. 105 · Page 5 of 20

Managing up

Understand what your manager is measured on and frame your updates in terms that connect to it. A manager who has to chase you for status updates trusts you less than one who gets them proactively.

Managing up

Learn how your manager works

Managing up is not flattery but the ordinary work of making yourself easy to manage, and it starts with observation. Notice whether your manager prefers a written summary or a conversation, detail or headlines, mornings or late afternoons, a warning well ahead or a finished proposal. Ask outright in an early one-on-one how they like to receive updates and how often. Then find out what they are being pressed on from above, because the two or three numbers on their own review are the ones your work will be judged against.

The weekly update

A short written update, sent at the same time each week, removes most of the reasons a manager has to check on you. Four lines are enough.

  • You list what you finished this week.
  • You list what you will work on next week.
  • You name anything that is blocked and what would unblock it.
  • You flag any decision you need from them, with a date.

It takes ten minutes to write, and it doubles as the record you will want at review time.

No surprises

The rule that matters most is that your manager never learns bad news about your work from someone else. Report a slipping deadline, an unhappy client or your own mistake as soon as you are sure of it, together with what you have done so far and what you propose next. Early bad news is a problem to be managed. Late bad news is a judgment on you. Bring options where you can: two or three ways forward, the cost of each, and the one you recommend.

Own the one-on-one

Treat the regular meeting as yours. Arrive with a written agenda of three or four items, put the decisions you need first, and leave status for the written update. When you are given more work than fits, do not refuse and do not silently absorb it. Lay out the current list and ask which item should move.

Disagreeing well

Disagree in private, with evidence, and once. State your concern, propose an alternative and listen to the reasoning, which may include facts you did not have. If the decision stands, carry it out properly and without commentary to colleagues. A manager will keep asking the opinion of someone who argues candidly behind the door and supports the decision outside it.

Tip Ask your manager once or twice a year what their biggest worry is right now. The answer tells you where help would be most valued.