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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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  1. Lessons Learned Becoming a Manager of Managers Justin Carmony -

    Engineering Leadership Utah - July 2019
  2. About Carmony Sr. Director of Engineering Deseret Digital Media Engineer

    15+ Years Manager 7+ Years @JustinCarmony justin@justincarmony.com
  3. A few things...

  4. Will post slides online on Twitter

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

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

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

  8. Feel free to ask questions

  9. Terminology

  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.
  11. Manager of Managers Manager ICs Manager ICs Manager ICs

  12. Poll

  13. Let’s Start With A Story

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

  16. You’re a manager

  17. You work for a great company

  18. You have a great team

  19. Your team works hard

  20. And builds awesome stuff!

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

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

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

    become a director!”
  24. You head up to corporate

  25. And your boss pitches the promotion...

  26. … directly to the President of the Company.

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

  28. Director Manager Engineers “Here is the plan”

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

  30. You get the promotion!

  31. You head on home

  32. Read some books...

  33. Watch some TED Talks...

  34. Follow some thought leaders...

  35. You Feel Ready!

  36. You head into work...

  37. Meet your new teams...

  38. … have some meetings ...

  39. and put together some plans.

  40. After a Few Weeks...

  41. Director Manager Engineers Status ✅ Everything is looking sweet!

  42. You celebrate your successful promotion!

  43. and spend some time on your hobbies

  44. Everything is awesome!

  45. A Few Weeks Later….

  46. You’re getting ready one morning

  47. and your phone rings

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

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

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

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

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

  53. You: “WHAT?? Are you serious??”

  54. Manager: “Oh, it gets worse!”

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

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

    of Bob.”
  57. Not only is your manager sad...


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

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

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

  62. Manager #2: “Hey, we’re stuck, and have been waiting on

    Benny for weeks to help out!”
  63. What the heck has Benny been doing??

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

  65. but on his own secret project codenamed Spaceship!

  66. You: “Benny, why the FLIP are you working on this

    and not helping your team??”
  67. Benny looks genuinely dumbfounded...

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

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

    that crazy project...
  70. When Manager #3 storms into your office...

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

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

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

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

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

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

  77. Director Manager Engineers Status ✅ Last week, everything was looking

  78. Director Manager Engineers Status ‼ And now everything IS ON

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


  81. You: “We’ll fix it, I promise…”

  82. A Couple of Days Later….

  83. Your teams are still in shock, trying to put out

    all of the fires...
  84. When your boss asks you...

  85. Boss: “What the hell is Project Spaceship? And why is

    Benny still working on it?”
  86. And you lose it...

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

    be like this...
  88. No only are individual team members sad...

  89. But entire teams are sad….

  90. Your entire department is devastated...

  91. You: “I thought I was ready…”

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


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

  95. For me... The transition from Manager to Manager of Managers

    was MORE DIFFICULT than the move from Individual Contributor to Manager
  96. Why?

  97. Let’s talk about logs

  98. None
  99. To know what’s going on… Engineers use logs

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

  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
  102. Observations Standup Codebase Slack Email Coworkers Sprint Meetings Tasks /

    Stories Observation Sources Senior Individual Contributor
  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
  104. Manager

  105. Standup Codebase Project Tracker Other Meetings Coworkers Sprint Meetings Tasks

    / Stories Observation Sources One on Ones Slack Email Stakeholders Peers Complaints Manager Observations
  106. Observation Sources Manager Observations

  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
  108. I got this, bring on the promotion!

  109. Manager of Managers

  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...
  111. Manager of Managers

  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
  113. … reality check

  114. You are Receiving Sampled Input

  115. Examples

  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.
  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?
  118. Proximity of Data Sources Influences Sampling Rate

  119. It Will Not Feel Like Sampled Input

  120. Data Points Manager Manager of Managers What you know What

    you don’t…… What you know What you don’t
  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!
  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
  123. None
  124. None
  125. I needed to learn to walk manage again...

  126. Lessons Learned (the hard way)

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

  128. Manager of Managers

  129. Awesome blog post

  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/
  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/
  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/
  133. Your Signal Network Critically Fresh • Informational sweet spot •

    Critical to you • You have time to act https://randsinrepose.com/archives/the-signal-network/
  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/
  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
  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
  137. Anti-Patterns to Avoid

  138. Micromanaging

  139. Becoming a Speed Bump

  140. Desired Outcomes, Not Details Lesson #2:

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

  142. None
  143. “My Expectation Is….”

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

  145. Getting Stuck In The Weeds

  146. Not Getting The Result I Wanted

  147. Who Fault Was This? Mine.

  148. A + B = C

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

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

  151. Advantages • Communicated how you will measure success • It

    is empowers your managers and teams • Facilitates productive questions & conversations
  152. Spectrum of Outcomes Outcomes To Avoid... Outcomes you Want...

  153. The Ideal When your team comes up with a better

    solution than you would have thought of!
  154. Question: Can I ever go into the weeds?

  155. Absolutely! … but by invitation only

  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
  157. The Observer Effect Lesson #3:

  158. Quantum Physics

  159. The Observer Effect - the theory that the mere observation

    of a phenomenon inevitably changes that phenomenon.
  160. Schrödinger's cat

  161. Schrödinger's team

  162. DO NOT OPEN THE BOX! (at least not frequently or

    w/o intention)
  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/ “
  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
  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.
  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
  167. Repeat Yourself All. The. Time. Lesson #4:

  168. Over-communicate (typically know as…)

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

  170. I felt like a robot

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

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

  174. Variety with delivery

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

  176. No Emergency Button Lesson #5:

  177. Manage Your Time & Commitments Lesson #6:

  178. Monitor & Manager You Energy Lesson #7:

  179. Self- Reflection Lesson #8:

  180. Assemble Your Voltron Lesson #9:

  181. None
  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/ “
  183. Learn Your Blindspots Lesson #10:

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

  185. Find other who can see, empower them to tell you,

    and LISTEN. ;<=>
  186. The final lesson for today…. Lesson #11:

  187. Curiosity

  188. Open Ended Questions

  189. Coaching, Mentoring, & Sponsoring

  190. whew...

  191. It’s okay...

  192. I’m still figuring it out

  193. Take it one step at a time

  194. Rely on your “Voltron”

  195. Always Remember

  196. It’s about humans.

  197. Thank you

  198. Any Question?

  199. None