Reference: 

https://firstround.com/review/a-tactical-guide-to-managing-up-30-tips-from-the-smartest-people-we-know/

Summary

Leave your assumptions at the door

Alignment

• Always align on the following two questions with your manager:
  • What is success for me personally?
  • What is success for my manager’s team?
• Intersection between your success and your manager’s success is where your opportunities for fulfilling impact lies
• Keep this conversation ongoing as success criteria changes over time

Show your work with what matters most

• Create an empathy towards your manager and understand what he/she needs to know to develop the trust
• Once you find that out, repeatedly show the work in relation to the aspects that your manager values the most (eg. metrics, progress reports, transparency, etc.)

Hone your communication

Open up about your “work love language”

• Share with your manager about what motivates you and what drives you to do great work
• Some tools to aid in doing just that:
  • Myers-Brigg assessment of personalities
  • Creating a User Guide – anything that is valuable to know right off the bat

Observe how your manager listens

• Understand how the manager listens and accordingly craft the message 

Calibrate to match manager’s involvement

• For micro-managers:
  • Provide concise but comprehensive updates on all topics being worked upon
• For those that you cannot get hold off:
  • Share team’s wins and challenges
  • Focus specifically on challenges and areas where you need their support
  • 15% time on wins, 85% time on challenges

Communicate early and often 

• Proactive communication leads to less surprises
• Communicating often helps push the ball in manager’s court to either take action, make note or ignore
• Communication help as data points to serve better decision making
• Whenever something is not going according to the plan, communicate that early enough

Boosting your chances of hearing “Yes” to your ask 

Start leaving breadcrumb trail

• Anything complex or abstract takes time to internalise, so start talking about these from the beginning
• Do not wait for collecting all the information and then present it to the manager. Anything that is complex will take time 
• Rule of seven dippings
  • Multiple exposures on the same topic to understand and internalise
  • The rule of thumb is to have it done 7 times

Feedback

• Always hear your positive feedback loud and clear, your manager has no intention of providing you with false praise. Do not let the imposter syndrome diminish the positive feedback you receive
• Do not try to please your boss. Always try to push back when you believe something is not correct or is not in the interest of the company goals
• Helping directs with their prioritisation is almost definitely in the manager’s job description
• When the managers push their own ideas over yours, try to ask probing questions to them to invalidate or falsify your ideas instead of challenging your manager’s idea
• Train your manager on how to treat you by your actions instead of mentioning them explicitly

Regular 1:1s 

• Maintain a document of topics or agenda to be discussed during 1:1s
  • FYIs that do not need action
  • Updates from reports
  • Updates from managers
  • Follow-ups from previous week action items
  • Discussion agenda
• Ask: “Who is someone that you had a great relationship with that reported to you and why did it work so well?”
• “FYI, no action needed” emails. Provide TLDRs with the just enough context
• Do consistent grading on alignment: compare your notes with the top discussion points and if they are consistently different then you should talk to your manager about alignments
• The whole your manager sees yourself (work and private life), the better would be the relation

Sharing information

• A weekly “State of me” email report with:
  • The blockers that I need help with
  • My current priorities
  • On my mind
• “If you want to be interesting, then first be interested”