How to Manage Your Boss (and Beyond)


March 27, 2019



This post summarizes guidelines (or patterns) to help you manage your boss or your boss’ boss or beyond. For younger readers, I guess the tips and guidelines here could also be used to manage your parents. I hope my kids read it.

Examples & Stories

A few weeks ago Niall Larkin (@NiaLLLarkin) sent me a link to Kate Matsudaira’s article “Design Patterns for Managing Up” in ACM Queue. Niall knew I’d be interested because the guideline concept in this blog, is inspired in part by design patterns. One of our goals is to curate great knowledge. When I saw Kate’s article was already in the form of patterns, I decided to share it here and do what I can to promote it further.

In this post, I’ll summarize the guidelines in her article with a few additional maxims from my experience. I encourage you to read the full article (after you’ve read this summary of course).


In all of these situations you’re in a conversation with your manager or manager’s manager or someone even higher in your organization.

The Guidelines

These short guidelines each have three sections:

  • When: you could apply the guideline
  • What: you could do in the situation
  • Why: it is important to do this

Guideline: when you don’t know something, admit it & commit to follow-up

When: you’ve just been asked a question and you don’t know the answer. What: avoid saying a simple “I don’t know” or guessing an answer. Say something like “I don't know, but Phyllis does and I will ask her and get back to you by the end of the day”. Why: you don’t want to look stupid (now or later).

Guideline: be the bearer of bad news & give a timeline

When: something goes wrong and it’s your responsibility. What: a) let your boss know about the problem right away, b) share the next steps, c) give a timeline. If you don’t know when the problem will be solved, say when you’ll provide an update. Don’t over-analyse the problem, give your boss a head’s up straight away. A previous boss of mine had a mantra - “no big surprises”. Why: you should own the message. It’s worse if your boss hears about the problem from someone else. Don’t make her think.

Guideline: when you hear a dubious decision, don’t react, ask questions & commit

When: sometime a decision will be made that you don’t agree with. What: there’s a right way and a wrong way to disagree. First take a breath. Ask about the context and rationale. Remember, someone up there thinks this is a good idea. As Stephen Covey and Richard Carlson say “seek first to understand, then be understood”. I know it’s easier said (or written) than done but your boss is unlikely to change her mind if you freak out. If you can’t change her mind at least you’ll have a better explanation when you explain it to your direct reports (or kids). Finally if you still disagree, consider Andy Grove’s advice and “disagree and commit”. Why: you might not have all the information the decision maker had.

Guideline: when you receive negative feedback: pause, accept and commit

When: you’re going to do something wrong sometime. If your boss is any good she’ll tell you in a skillful and constructive way. What: in the article, Kate recommends you say "I hear you. I will be more mindful of that in the future." Personally I’d use slightly different words but the sentence would have that form. Like the previous guideline, I’d also “seek first to understand, then be understood”. Why: getting defensive makes your boss have to work harder to try to help you learn. Most bosses don’t like to deliver negative feedback. This guideline is also easier said than done but you’ll learn more faster if you don’t get defensive.

Bonus guideline: when you need your boss to take action, make it really clear

This guideline is not in Kate’s original article but it’s something I try to do (and I encourage my direct reports to do also). When: we all need help at times and you’ll need your boss to take action or make a decision. What: make it super clear by mentioning the action you are requesting at the start of any written communication. If email, you could put a keyword (like #ACTION or #URGENT) in the subject. Why: your boss probably gets twice as many emails and juggles three times as many issues as you do. She is not going notice a subtle, indirect request in the third last paragraph of a long email.

The bigger picture

This post is a summary of guidelines from an article. In future posts we’ll curate individual guidelines or glean collections of them from articles, books and other content. We’re planning posts on:

  • Productivity
  • Starting a business
  • Managing cash flow in a growing business

Guidelines are also known as:

  • best-practices
  • patterns
  • principles
  • tips
  • hacks
  • mental models
  • directives

If you’d like to write for LearnShareDo, please send an email to (write at learnsharedo dot com).

Thanks for reading! If you have any other examples or feedback please comment/follow/share below or on: twitter, medium or linkedin.

This post was first published on Learn Share Do.

Credits: photo by Casey Horner on Unsplash

Disclosure: some links in this post may use Amazon affiliate links.

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Welcome to Learn Share Do. Here we try to share and curate knowledge that you can use in life or business.

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