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Lessons Learned Becoming a Manager of Managers - Engineering Leadership Utah - July 2019

Lessons Learned Becoming a Manager of Managers - Engineering Leadership Utah - July 2019

When I was promoted to become the director of multiple teams, I was excited. I had my years of experience and toolbox of well-practiced skills. "It's simple," I thought, "I'll do what I did for one team with multiple teams. Easy enough. I'm totally ready!"

Narrator: he totally was not ready.

Everyone talks about the transition from an individual contributor to a manager is difficult, but fewer people talk about the transition of managing a single team to multiple teams. For me, this transition was the more difficult of the two. One moment, I felt everything was going just fine, only to realize a week later, each team had its own fire going on. What's worse, you can't just grab every issue by the horns and wrangle it down, but instead coach your teams through solving their own problems.

We'll talk about the hard-learned lessons on becoming a manager of managers. We'll talk about leading leads, growing team members, and keeping a pulse on your teams with far fewer data points than when you're in the trenches with them.

About the presenter:

Justin Carmony is the Senior Director of Engineering at Deseret Digital Media, overseeing multiple teams supporting KSL.com and it's analytics platforms. He is an international speaker having given over 50+ presentations over the last decade at user groups and conferences. He is a Utah native who currently lives in Layton with his wife and two kids.

Justin Carmony

July 09, 2019
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Transcript

  1. Lessons Learned
    Becoming a Manager of Managers
    Justin Carmony - Engineering Leadership Utah - July 2019

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  2. About Carmony
    Sr. Director of Engineering
    Deseret Digital Media
    Engineer 15+ Years
    Manager 7+ Years
    @JustinCarmony
    [email protected]

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  3. A few things...

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  4. Will post slides
    online on Twitter

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  5. Based off of my own experiences…
    …your mileage may vary.

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  6. Dive deep for a few things...
    …shallow for other things

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  7. Lessons applicable to everyone...
    …not just managers of managers

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  8. Feel free to ask questions

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  9. Terminology

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  10. Terminology
    Individual Contributor (IC) - A team member whose primary
    contribution is their individual work on a project
    Manager (Front-line Manager) - A team member whose primary
    responsibility is the collective contributions of their single team. Only ICs
    report to them.
    Manager of Managers (Director) - A person whose primary
    responsibility is the collective contributions of multiple teams, each with
    their own manager.

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  11. Manager of Managers
    Manager
    ICs
    Manager
    ICs
    Manager
    ICs

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  12. Poll

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  13. Let’s Start
    With A Story

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  14. Note for people reading the
    slides after the presentation:
    The next 77 slides are a lightning-talk style portion of the
    presentation, where each slide is 3-5 seconds. If you’re just
    reading the slides, feel free to jump ahead, it’s just an attention
    grabbing device for in-person presentations. In other words…
    TL;DR: This is a awkward “you had to be there” kinda thing.
    Feel free to skip ahead to “END OF STORY".

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  15. We’ll borrow from the LEGO movie...

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  16. You’re a manager

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  17. You work for a great company

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  18. You have a great team

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  19. Your team works hard

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  20. And builds awesome stuff!

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  21. You’re happy, your team is happy, your clients are
    happy, everyone is happy!

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  22. Your boss is so happy, he gets this great idea

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  23. “Promotion” to
    Manager of Managers
    BOSS: “Let’s promote you to become a director!”

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  24. You head up to corporate

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  25. And your boss pitches the promotion...

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  26. … directly to the President of the Company.

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  27. Boss: “This Manager is so great, let’s promote him!”

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  28. Director
    Manager
    Engineers






    “Here is the plan”

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  29. President Business: “I love it! LET'S DO IT!”

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  30. You get the promotion!

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  31. You head on home

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  32. Read some books...

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  33. Watch some TED Talks...

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  34. Follow some thought leaders...

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  35. You Feel Ready!

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  36. You head into work...

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  37. Meet your new teams...

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  38. … have some meetings ...

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  39. and put together some plans.

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  40. After a Few Weeks...

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  41. Director
    Manager
    Engineers






    Status

    Everything is looking sweet!

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  42. You celebrate your successful promotion!

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  43. and spend some time on your hobbies

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  44. Everything
    is
    awesome!

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  45. A Few Weeks Later….

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  46. You’re getting ready one morning

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  47. and your phone rings

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  48. It’s one of your managers with a big problem

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  49. Manager: “Remember how I talked with you about
    Bob last week?”

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  50. Manager: “And how he can have a attitude with our
    team?”

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  51. Manager: “Well, he reviewed some of our PR’s…”

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  52. Manager: “And got into a massive fight with Wayne.”

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  53. You: “WHAT?? Are you serious??”

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  54. Manager: “Oh, it gets worse!”

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  55. Manager: “Remember that startup who was going
    after Wayne?”

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  56. Manager: “Wayne just accepted their offer since he is
    tired of Bob.”

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  57. Not only is your manager sad...

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  58. THEY ARE LIVID WITH YOU!!!

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  59. Manager: “I WARNED YOU ABOUT THIS!”

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  60. You start to think about what to do...

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  61. When another one of your managers call you...

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  62. Manager #2: “Hey, we’re stuck, and have been waiting
    on Benny for weeks to help out!”

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  63. What the heck has Benny been doing??

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  64. Turns out, Benny hasn’t been
    working on that critical project...

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  65. but on his own secret project codenamed Spaceship!

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  66. You: “Benny, why the FLIP are you working
    on this and not helping your team??”

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  67. Benny looks genuinely dumbfounded...

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  68. Benny: “I thought you told me
    I could work on Spaceship…”

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  69. You’re super confused how on EARTH
    he thought you approved that crazy project...

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  70. When Manager #3 storms into your office...

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  71. Manager #3: “Hey, um, my
    crew is so awesome and fast…”

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  72. Manager #3: “That our last
    release took down EVERYTHING.”

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  73. Manager #3: “And now all of our customers…”

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  74. Manager #3: “Are, like, SUPER PISSED!!”

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  75. Manager #3: “And we don’t know how to fix it…”

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  76. You’re freaking out...
    what the heck is going on??

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  77. Director
    Manager
    Engineers






    Status

    Last week, everything was looking awesome...

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  78. Director
    Manager
    Engineers






    Status


    And now everything IS ON FIRE!

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  79. And now Mr. President’s
    new product launch is in jeopardy...

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  80. Mr. President: “WHAT DO YOU MEAN
    WE’RE MISSING OUR DEADLINES?!?!?”

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  81. You: “We’ll fix it, I promise…”

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  82. A Couple of Days
    Later….

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  83. Your teams are still in shock,
    trying to put out all of the fires...

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  84. When your boss asks you...

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  85. Boss: “What the hell is Project Spaceship?
    And why is Benny still working on it?”

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  86. And you lose it...

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  87. Why is this so hard?
    This promotion wasn’t supposed to be like this...

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  88. No only are individual team members sad...

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  89. But entire teams are sad….

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  90. Your entire department is devastated...

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  91. You: “I thought I was ready…”

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  92. You: “I thought this was
    going turn out differently...”

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  93. END OF STORY

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  94. Now, that was
    a little dramatic...

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  95. For me...
    The transition from Manager to
    Manager of Managers was
    MORE DIFFICULT
    than the move from Individual
    Contributor to Manager

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  96. Why?

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  97. Let’s talk about logs

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  98. View Slide

  99. To know what’s going on…
    Engineers use logs

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  100. To know what’s going on…
    Managers use
    observations

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  101. Examples of Observations
    ● John fixed bug #668 and hotfixed it this afternoon
    ● Paul and Susan had a heated disagreement over a pull request
    ● The Skunkworks team is two weeks ahead of schedule
    ● Pablo called in sick with the stomach flu
    ● Mary just posted a funny cat video in #watercooler
    ● Nagios alerted that Mongo Replica #4 has a full disk
    ● Victoria, Jake, and Chris vented to me about their frustrations at
    lunch

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  102. Observations
    Standup
    Codebase
    Slack
    Email
    Coworkers Sprint
    Meetings
    Tasks / Stories
    Observation Sources
    Senior Individual
    Contributor

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  103. Awareness is good as Senior IC
    Primary Sources of Information:
    ● First-hand observations
    ● Shared context w/ team
    ● Common team meetings (sprint review, planning, retro, etc)
    ● Codebase
    Results:
    ● High degree of awareness
    ● Low variance between perception and reality

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  104. Manager

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  105. Standup
    Codebase
    Project Tracker Other
    Meetings
    Coworkers Sprint
    Meetings
    Tasks / Stories
    Observation Sources
    One on Ones
    Slack
    Email
    Stakeholders
    Peers
    Complaints
    Manager
    Observations

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  106. Observation Sources
    Manager
    Observations

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  107. Awareness Increased as a Manager
    Primary Sources of Information:
    ● One-on-ones
    ● Some Meetings
    ● First-hand observations
    ● Shared context w/ team
    ● Common team meetings (sprint review, planning, retro, etc)
    ● Codebase
    Results:
    ● Very high degree of awareness
    ● Lower variance between perception and reality

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  108. I got this, bring on
    the promotion!

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  109. Manager of Managers

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  110. Standup
    Codebase
    Project
    Tracker Meetings
    Coworkers Sprint
    Review
    Tasks /
    Stories
    One on
    Ones
    Slack
    Email
    Clients
    Peers
    Complaints
    Manager of
    Managers
    TEAM #1
    Standup
    Codebase
    Project
    Tracker Meetings
    Coworkers Sprint
    Review
    Tasks /
    Stories
    One on
    Ones
    Slack
    Email
    Clients
    Peers
    Complaints
    TEAM #2
    Standup
    Codebase
    Project
    Tracker Meetings
    Coworkers Sprint
    Review
    Tasks /
    Stories
    One on
    Ones
    Slack
    Email
    Clients
    TEAM #3
    New Responsibilities
    New Meetings
    New Emails
    New Slack
    Channels
    New Reports
    New
    Dashboards
    New HR Tools
    New Peers
    New...
    New...
    New...

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  111. Manager of
    Managers

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  112. Awareness Decreased as a Director
    Primary Sources of Information:
    ● One-on-ones
    ● Some Many Meetings
    ● First Second- & third-hand observations
    ● Shared context w/ team Slack / Email
    ● Common some team meetings (sprint review, planning, retro, etc)
    ● Codebase
    Results:
    ● Lower degree of awareness of everything going on
    ● Higher chance of variance between perception and reality

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  113. … reality check

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  114. You are
    Receiving
    Sampled Input

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  115. Examples

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  116. As a manager, things I relied on:
    ● Body language
    ● Tone
    ● Attitude / Demeanor
    ● Quality of their work
    ● Conversations
    ● So many other little things...
    First-hand Observations
    As a Manager of Managers, your
    first-hand observations decrease significantly.

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  117. 1:1’s with Managers
    ● Your manager cannot perfectly
    transfer what is in their brain to yours
    ● They filter, prioritize information
    ● Criteria on what they share with you:
    ○ How will you react?
    ○ Will you take action on it?
    ○ What action will you take?
    ○ Is this something safe to share with you?
    ○ Do they remember everything they need to
    share with you?

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  118. Proximity of Data Sources
    Influences Sampling Rate

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  119. It Will Not
    Feel Like
    Sampled Input

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  120. Data Points
    Manager Manager of Managers
    What you know What you don’t……
    What you know What you don’t

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  121. Problems Caused Sampled Input
    ● Misconceptions
    ○ Sampled Data Point: Jerry complained a lot about the last Python project he
    worked on.
    ○ Perception: Jerry doesn’t enjoy working on Python-based projects
    ○ Reality: Jerry doesn’t like working on projects with extremely outdated
    dependencies.
    ● Outlier vs Pattern Detection
    ○ Sampled Data Point: Amy seems a little frustrated today
    ○ Perception: Amy is just having an off day
    ○ Reality: Amy is regularly frustrated and is on the verge of quitting
    ○ You can have the inverse of this scenario!

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  122. Problems Caused Sampled Input
    ● Delay of Information
    ○ A major issue affecting revenue happened three weeks ago…
    ○ You just found out today.
    ○ It’s too late to act

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  123. View Slide

  124. View Slide

  125. I needed to learn
    to walk manage
    again...

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  126. Lessons Learned
    (the hard way)

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  127. Embrace & Fine-tune
    Your Sampling Data
    Lesson #1:

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  128. Manager of
    Managers

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  129. Awesome
    blog post

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  130. Your Signal Network
    Criticality - the individualized
    importance of a given piece of
    information.
    Freshness - how long a given piece
    of information takes to get to the
    human who gets the most value
    from its arrival.
    https://randsinrepose.com/archives/the-signal-network/

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  131. Your Signal Network
    Stale & Slow
    ● The data is outdated
    ● Most boring
    ● No need to act
    ● Just ignore
    https://randsinrepose.com/archives/the-signal-network/

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  132. Your Signal Network
    Voluminous Spam
    ● Data is fresh, new
    ● But not useful
    ● At an extreme, it’s spam.
    ● You’re wading through lots of
    unnecessary info
    ● How much time are you
    wasting? Your team?
    ● Warning signs of efficiency
    https://randsinrepose.com/archives/the-signal-network/

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  133. Your Signal Network
    Critically Fresh
    ● Informational sweet spot
    ● Critical to you
    ● You have time to act
    https://randsinrepose.com/archives/the-signal-network/

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  134. Your Signal Network
    Important, but Slow
    ● The “Danger Zone”
    ● Discovering unexpected
    developments long after they
    happen
    ● You’re unable to react
    ● The conclusion is already history
    https://randsinrepose.com/archives/the-signal-network/

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  135. Getting Critically Fresh: Invest in your Team
    ● Goal: High Signal Humans
    ● Ask yourself daily:
    ○ How much critical information did I discover?
    ○ How fresh is it?
    ● Fanatic discipline with holding your 1:1’s
    ○ Regularly make clear what critical information you care about
    ○ Consistently share the critical information your team needs
    ● You & your reports will incorrectly flag essential information as spam
    ● With practice, you will calibrate over time

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  136. “Your ability to effectively lead is a function of the
    collective quality of the decisions you make on a
    daily basis. You can take your time on many
    decisions. [...] Other decisions must be made
    right now. At that moment, […] the amount of
    critical information that has arrived in a timely
    fashion makes the difference between an
    informed decision and the flipping of a coin.
    Michael Lopp, VP of Engineering, Slack

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  137. Anti-Patterns
    to Avoid

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  138. Micromanaging

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  139. Becoming a
    Speed Bump

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  140. Desired Outcomes,
    Not Details
    Lesson #2:

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  141. When I was a manager, I focused
    on expectations

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  142. View Slide

  143. “My Expectation Is….”

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  144. When I became a Director, that
    started become a problem

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  145. Getting Stuck In The Weeds

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  146. Not Getting The Result I Wanted

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  147. Who Fault
    Was This?
    Mine.

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  148. A + B = C

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  149. A + B = C
    Wrongly Talk
    About The Pieces

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  150. A + B = C
    State what you
    want!

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  151. Advantages
    ● Communicated how you will measure success
    ● It is empowers your managers and teams
    ● Facilitates productive questions & conversations

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  152. Spectrum of Outcomes
    Outcomes To
    Avoid...
    Outcomes you
    Want...

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  153. The Ideal
    When your team comes up with a
    better solution than you would have
    thought of!

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  154. Question: Can I ever go into
    the weeds?

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  155. Absolutely!
    … but by invitation only

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  156. If you’re struggling
    ● Identify when you’re talking implementation, not outcomes
    ○ Are you getting too far into the weeds?
    ● Think “why do I care about these details? What outcome am I going
    for? What am I trying to avoid?”
    ● Communicate those outcomes, both desired and ones to avoid

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  157. The
    Observer
    Effect
    Lesson #3:

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  158. Quantum Physics

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  159. The Observer Effect - the theory that
    the mere observation of a
    phenomenon inevitably changes
    that phenomenon.

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  160. Schrödinger's cat

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  161. Schrödinger's team

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  162. DO NOT OPEN
    THE BOX!
    (at least not frequently or w/o intention)

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  163. Every team’s project is a cat, and
    every manager has to constantly
    decide whether to look in the box
    at the risk of killing it.
    James Everingham
    Head of Engineering
    Instagram
    Source: The Principles of Quantum Team Management
    https://firstround.com/review/the-principles-of-quantum-team-management/

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  164. Be Aware of Your Observer Effect
    ● When you’re in a meeting, you change the outcome
    ● When you’re at lunch with your team, you change the outcome
    ● When you give your team suggestions & starting points, you reduce
    the number of possible outcomes
    You MUST be aware of this
    impact that you have

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  165. Why You Don’t Want to Open the Box
    ● Anchoring & limiting your team’s
    problem solving abilities
    ● By reducing the possibilities for failure,
    you also reduce the possibilities for
    success.

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  166. Sometimes, You Have to Open the Box
    ● Sometimes you need to debug serious
    issues going on
    ● Sometimes you need to help a team get
    back on track

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  167. Repeat Yourself
    All. The. Time.
    Lesson #4:

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  168. Over-communicate
    (typically know as…)

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  169. why
    “Repeat Yourself”
    Is better than
    “Over-communicate”

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  170. I
    felt
    like a
    robot

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  171. I felt frustrated….
    “This isn’t efficient!”

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  172. A friend of mine once paraphrased David
    Gergen, saying on the subject of repetition, “If
    you want to get your point across, especially to
    a broader audience, you need to repeat yourself
    so often, you get sick of hearing yourself say it.
    And only then will people begin to internalize
    what you’re saying.
    Jeff Weiner, CEO of Linkedin
    Source: The Power of Repetition: the Secret of Successful Leaders
    https://getlighthouse.com/blog/power-of-repetition-successful-leaders/

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  173. The goal is not knowledge transfer...
    The goal is:
    Internalization

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  174. Variety with delivery

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  175. Other Lessons
    (but we don’t have time to go deep on)

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  176. No
    Emergency
    Button
    Lesson #5:

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  177. Manage
    Your Time
    & Commitments
    Lesson #6:

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  178. Monitor &
    Manager
    You Energy
    Lesson #7:

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  179. Self-
    Reflection
    Lesson #8:

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  180. Assemble
    Your
    Voltron
    Lesson #9:

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  182. Here’s the bad news: no one person will ever be
    able to manage you the way you want or need.
    But here’s the good news: there are a plethora of
    people out there whom you can lean on to find
    the variety of support you need.
    Lara Hogan, Co-founder of Wherewithall
    When your manager isn't supporting you, build a Voltron
    https://larahogan.me/blog/manager-voltron/

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  183. Learn Your
    Blindspots
    Lesson #10:

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  184. You will have ALWAYS blindspots
    that you will struggle to see

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  185. Find other who can see,
    empower them to tell you,
    and LISTEN.
    ;<=>

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  186. The final
    lesson for
    today….
    Lesson #11:

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  187. Curiosity

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  188. Open Ended
    Questions

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  189. Coaching,
    Mentoring,
    & Sponsoring

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  190. whew...

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  191. It’s okay...

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  192. I’m still figuring it out

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  193. Take it one step at a time

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  194. Rely on your “Voltron”

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  195. Always Remember

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  196. It’s about humans.

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  197. Thank you

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  198. Any Question?

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