brad dickason
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How to manage your manager

Early in my career, I loved going on pitches with my CEO. We would meet with powerful media companies like the New York Times and I always kept a new mockup or screenshot in my back pocket. I LOVED wow'ing everyone with the latest designs or features. Everyone always ooh'd and aah'd.

I loved surprising people with new ideas. Especially my CEO.

One day he pulled me aside and said, "Brad, I'd appreciate it if you would share new mockups with me before presenting them to the clients."

I thought he was being ridiculous. Why not show the best things we have to offer?! Why do I need to share anything?!

In hindsight, it probably wasn't a great idea to surprise our CEO every time we met with a client. By focusing on impressing our clients, I was leaving my manager in the dark. He felt caught off guard. Uncertain of what to expect. I cared more about making a good impression with our clients than working together with my manager. I was selfish.

Since then, I've learned alot about working with managers. I used to do my job and wait for my manager to ask me questions. I now take charge and make sure that my manager and I are tightly aligned at all times. I'll call this 'managing your manager.'

On my best days, I'm providing the right information at the right time. I'm sharing decisions and rationale. I'm asking them for concrete, actionable help.

On my worst days, I leave them completely in the dark and go into a cave, emerging from hibernation after days or weeks without any updates.

Building Trust

A great relationship between a manager and their direct report is based on trust.

Trust enables your manager to

Most people build trust via sporadic conversations spread across 1:1's, meetings, and product reviews. They hope that by talking about the right topics and doing good work, their manager will trust them.

Instead of leaving trust up to chance, you can engineer it by building a repeatable system. You'll rely on processes and tools to deliver important information at the right time, rather than sporadic conversations.

Creating a system of trust

First, you need to identify what it means to build trust. Trust comes from repeatedly aligning over time to ensure that you're both on the same page in any given moment.

When you have trust, your manager

  1. is never surprised
  2. understands what you're doing
  3. understands why you're doing it
  4. understands what you're trading off as a result
  5. understands what you expect of them

Notice that I didn't say that your manager agrees with everything you are doing. This is important. The amount of times you disagree with your manager increases the more senior you get.

Here are four tools (stack ranked in order of importance) that you can implement as part of your system of trust:

Weekly Update

Format: Document Cadence: Weekly

A good weekly update helps you stay in sync on priorities and rationale. It serves as the heartbeat of your communication and forms the basis for subsequent conversations. Your weekly update should be posted at the start of the week so that your manager has visibility into what you're doing and time to ask questions, disagree, or flag issues to discuss in your 1:1.

Your weekly update should contain the following items:

  1. Blockers - Where are you stuck?
  2. Priorities - What you are doing this week (stack ranked)
  3. Rationale - Why you are working on each of these things
  4. Asks - What can your manager do to help?

The most important section is the rationale or the 'why.' It's hard for people to react to a statement like "My top priority is to move the boulder." If you don't understand why, it's hard to disagree that it should or shouldn't be your top priority. On the other hand, "My top priority is to move the boulder because it's about to fall on a small town" starts to get at why you are prioritizing this issue and your manager can decide if they agree that the small town should be saved :)

Each item should be 1-2 lines long so it can be quickly written and quickly read. If you can't communicate each item in 1-2 lines, this is a good sign that your thinking on these areas also isn't clear.

If you do this well, you'll be 70% of the way to a great relationship with your manager! :)

Note: I also recommend including some personal information, especially during the pandemic. This is another opportunity to form a human connection with your manager which will help during challenging situations.

Pre-flight for Reviews

Format: Document or Deck Cadence: Before an important decision is made

Reviews are important meetings where decisions are made. Your company may call these something different, but the principles are the same.

Decisions are the highest leverage opportunity for your manager. They aren't as close to the work as you are, so decisions are the moment where they can definitively change your trajectory or give you and the team feedback. We pre-align to make it more likely that the decision lands in the direction you want.

Pre-flighting allows you to discuss the decision in a safe space without the pressure of group dynamics during the actual review.

Before an important meeting, make sure you've sent any documents or decks you plan to review to your manager. I'll call these pre-reads (See also: How to write great pre-reads) In addition, highlight any areas you disagree with and any specific asks you have of your manager during the review.

For example, you might give them a heads up that you're going to be pushy with a specific team member who is underperforming. Maybe you're proposing to kill a project that they care about and you want to know their stance. Maybe you want them to ask a certain question or help you convince a stubborn teammate of something.

Pre-flighting helps you align in advance of the meeting and surface any tension before you're in the room.

Chat during reviews

Format: Chat Cadence: As needed during reviews

If pre-flighting can ensure that you're aligned with your manager before the review, chatting during the review (sometimes called backchanneling) can ensure that you don't drift out of alignment throughout the review. You can keep your chat open and discretely send messages throughout.

Here are some suggested messages you can send:

Be careful not to chat all the time (you should have discussion in the room) but don't be afraid to use this when there's a touchy subject being discussed or you need a hard read on what your manager is thinking.

1:1

Format: Meeting Cadence: Weekly

Your 1:1 should be your primary synchronous discussion with your manager. It's the one time in the week where you have dedicated face to face time with no distractions. Your 1:1 is your time. Use it to get what you need from your manager.

You should set the agenda for your 1:1 (Remember, this is your time). If you can't think of anything to talk about, look at your Weekly Update post and pick an item that looks remotely contentious. I recommend sending the agenda in advance so your manager can prepare and add topics.

Your 1:1 should be used to resolve any remaining issues between you and your manager and to help reinforce your human connection by sharing smalltalk (e.g. 'what did you do this weekend').

Don't discount the 'get to know each other' part of the 1:1. Especially with most people working remote, having even a simple discussion about your personal lives will make you feel more human and help relieve the pressure during any tense moments. At the end of the day, we're all just people.

Progress Report

Format: Document Cadence: Bi-weekly

A good progress report gives a sense of what your team accomplished each week. It also shows how you're tracking against your goal(s) for the half.

A great format is:

Your progress report should be less than one page and should take less than 15 minutes to assemble each week. I like to ask my tech lead and designer to help me fill it out so my role is more of editor (vs writer).

I recommend a bi-weekly cadence because your progress doesn't change dramatically from week to week. Every other week should be frequent enough to give an update but infrequent enough to not require a ton of work from the team.

Note: Not all projects need progress reports. For example, projects that don't ship publicly like a vision or strategy don't need a progress report unless you need feedback on revisions. The more complex the deliverable is, the more likely you need a progress report.

Was this helpful? Are there other tools or processes you use when working with your manager? I'd love to hear more: @bdickason

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Soundtrack: Electric Youth - We Are The Youth

See all songs I’ve used on my website.

Post last updated: Feb 19, 2021

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