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Managing Up & Difficult Bosses

A working relationship with your manager that you steer: their goals and style understood, priorities agreed in writing, a weekly rhythm, tactics for each kind of difficult boss, and a clear stay or leave call.

Free · Mac (Apple silicon) and Windows · v1.0.0 · Other platforms

Then open the Marketplace in the app, search for Managing Up & Difficult Bosses, and click Install. It goes into your own files, and works offline from then on.

What it installs.

1

Pillar

1

Area

50

Projects

202

Starter tasks

🧭 Career Growth

Managing Up & Difficult Bosses

Working effectively with a manager, aligning on priorities and handling a difficult boss before deciding to stay or leave.

  1. What your manager is measured on
  2. A working-style profile of your boss
  3. Top three priorities agreed in writing
  4. Expectations reset conversation with your manager
  5. Success measures for your role agreed
  6. Decision rights map with your manager
  7. A personal working guide shared with your boss
  8. Private log of interactions with your manager
  9. Diagnosing what kind of difficult your boss is
  10. Honest audit of your own part in the friction
  11. Weekly one-to-one agenda you own
  12. Friday status note to your manager
  13. Monthly priorities check against your boss's asks
  14. Running list of asks awaiting your manager
  15. Quarterly feedback request on working together
  16. Light-touch relationship with your boss's boss
  17. Early warning routine for bad news
  18. Your boss's key dates in your own calendar
  19. Quarterly relationship health check
  20. Monthly stay or leave temperature reading
  21. Bringing problems with options and a recommendation
  22. Disagreeing with your boss and then committing
  23. Saying no by renegotiating priorities
  24. Giving upward feedback that lands
  25. Writing for a busy manager
  26. Getting clarity on vague instructions
  27. Staying steady with a volatile boss
  28. Earning autonomy from a micromanager
  29. Working with an absent or unreachable boss
  30. Handling a boss who takes credit for your work
  31. Working with a boss who keeps changing direction
  32. Reporting to a boss with less expertise than you
  33. Repair conversation after a blow-up
  34. Deciding whether to escalate beyond your boss
  35. Stay, transfer or leave decision about your boss
  36. First meeting with a new manager
  37. Mid-year alignment meeting with your manager
  38. Briefing your boss before a high-stakes meeting
  39. Requesting a change of reporting line
  40. Handling a change of boss in a reorganisation
  41. Managing up in your first job after education
  42. Managing up from a different location
  43. Reporting to a boss much younger than you
  44. When your boss is the business owner
  45. Managing up as a parent or carer with fixed hours
  46. Reporting to two bosses in a matrix
  47. Managing up while managing a team
  48. Anticipating your boss's next quarter
  49. Working directly for an executive or founder
  50. Your principles for working with any boss

Where it starts.

Each project arrives with its purpose, milestones and first tasks written out. Here is how the first three read.

What your manager is measured on

Most friction with a boss comes from pulling against goals you cannot see. Finding out the three or four things your manager will be judged on this year, and what their own boss keeps asking them about, tells you which of your work they will value and which they will barely notice.

First tasks

  • Find your team's published goals or plan for this year
  • Ask your manager what a great year looks like for them
  • Mark each of your projects against your manager's targets
  • Recheck your manager's targets after each planning round @recurring(quarterly)

A working-style profile of your boss

Some managers want a two-line message, others want the full document; some decide in conversation, others need a night to think. Writing a short profile of how your boss takes in information, makes decisions and reacts under pressure lets you package everything you send in the form they actually use.

First tasks

  • Create a private page for your manager from the Person template
  • Note which of your recent messages got quick answers and which were ignored
  • Ask a longer-serving colleague how the boss likes to receive updates
  • Write down two communication changes and try them this week

Top three priorities agreed in writing

When everything is urgent, a boss can be disappointed with you for working hard on the wrong thing. A short written list of your three priorities, confirmed by your manager, settles arguments before they start and gives you something to point to when the next request lands.

First tasks

  • Draft your three priorities with a definition of done for each
  • Put the list on the agenda for your next one-to-one
  • Send a short message confirming the agreed list after the meeting
  • Redo the priorities list with your manager each quarter @recurring(quarterly)

Make it yours.

Install Managing Up & Difficult Bosses, then tell Aurum the date you're aiming for. It checks whether the plan fits the weeks you actually have.

Free · Mac (Apple silicon) and Windows · v1.0.0 · Other platforms

Blueprints are general information to help you organise your own work. They are not medical, financial, legal or other professional advice. See the Terms.