Jeremy W. Sherman, July 2018
These notes are the result of my quarterly professional development week. Many thanks to Big Nerd Ranch for giving me the time, space, and funding for this intensive self-improvement week. If you're looking for a humane and wicked-smart software engineering and training environment, we're hiring. If you'd just like to read more, we've a blog.
And more particularly, how do you "steer" what you do towards better rather than worse?
That's what I'm hoping to sort out this week.
Bonus points for:
- What's the point of a team meeting?
- What should you be looking to get out of a 1:1?
- When should you meet more or less often, and why?
- Books
- Books Read
- 2018-07-02 (Mon)
- 2018-07-03 (Tues)
- 2018-07-04 (Wed)
- 2018-07-05 (Thurs)
- 2018-07-06 (Fri)
Here are the books I started out with, grouped by rough topic:
- How to manage
- Drucker, Effective Executive
- DeMarco & Lister, Peopleware 3/e
- Lopp, Managing Humans 3/e
- Management tools
- Scott, Radical Candor
- Patterson, Crucial Conversations 2/e
- Stanier, The Coaching Habit
- Lencioni, 5 Dysfunctions of a Team
- Brooks, The Mythical Man-Month
- Growing as a leader
- Fournier, The Manager's Path
- Lau & Taylor, The Effective Engineer
- Lopp, Being Geek
- General
- Covey, 7 Habits of Highly Effective People
- Carnegie, Win Friends and Influence People in the Digital Age
Here are the five books I had focused in on by the end of the second day:
- How to manage
- Drucker, Effective Executive
- Management tools
- Scott, Radical Candor
- Stanier, The Coaching Habit
- Lencioni, 5 Dysfunctions of a Team
- Growing as a leader
- Fournier, The Manager's Path
- General
- None
Here are the books I actually wound up reading, reviewing, and digesting during this week:
- Management tools
- Stanier, The Coaching Habit
- Growing as a leader
- Fournier, The Manager's Path
- Looked through 4 of 13 books
- Survivors: 2
- Exiles: 1
- Read Later: 1
- Will continue tomorrow
Drucker's clear vision of what it means to act as an effective executive, and Fournier's diverse experience and elucidation of responsibilities and expectations along the management path, both look very promising, as well as dovetailing well together.
I spent too long skimming the entirety of a mixed-bag text today. It didn't really pay out for the time I gave it.
I'll try to move to evaluate candidates faster tomorrow, and reserve more thorough intro/outro reading for the ones that survive a first glance. I'll defer a thorough flip-through till after I've picked the strongest candidates.
I didn't get a chance to winnow down the passel of books I got ahead of time.
So I'll need to do that this morning, pick out 5 I feel will help me the most, and then dig into those.
Or I can try to plough through all 13 books with this first day, and subset after. I think I'll take that tack. That'll ensure that I've properly assessed each of them.
NANOWRIMO brain-dump of everything learned the hard way while growing a startup. Passed through all the managenment roles covered. Intended as a reference manual. Each chapter focuses on a partiticular stage and its challenges.
Addresses engineering management in particular. Recommends reading elsewhere for general management/communication skills (specifically mentions First, Break All the Rules).
Index was surprisingly useful at summarizing challenges and book recommendations.
Table of contents was surprisingly sparse and useless.
Looks to cover responsibilities and common dysfunctions. This seems like very in line with my goals. Understanding how responsibilities change from role to role will also help me understand where I am now.
Conclusion underscores that one must first excel at self-management to excel at management and points to meditation resources: podcasts at tarabrach.com, writings of Pema Chödrön. Describes master managers as masters of working through conflict.
Throughout the intro and outro there are mentions of mentors, coaches, and friends. Without these, it would be very hard to do a good job as a manager, it seems.
- First, Break All the Rules
This book focuses on how to act effectively. It focuses on self-management, not the management of others. (A surprising tie-in to the conclusion of The Manager's Path.)
Drucker views learning and practicing the self-discipline of effectiveness as a modest aim that anyone can accomplish that is nevertheless ennobling for the individual and essential for society in order to increase knowledge-work's economic productivity.
The introduction is surprisingly meaty and cuts straight to the point. It's got a canonical bulleted-list with sub-bullets structure. It concludes with a list of 5 types of meetings, which it should be interesting to compare with Lencioni's book on meetings.
Drucker focuses heavily on decision-making, commitment, and time usage.
The 18- to 24-month timeline recommended for an action plan surprised me in its length. I suppose I'm accustomed to planning in 6- to 12-month timelines.
- responsibility to the org
- what must be done, not what you'd like to do
- communication
- make info needs explicit - an org is its info flow
- focus on opportunities over, and before, problems
- problems can stop bleeding, but not grow your org
- opportunities are where your advantage lies
- evaluate any new or unexpected event or change in environment with an eye to the opportunities it presents for you to exploit
mindful action towards exploiting opportunities through maximizing leverage
The heart of the book is about applying the ideas of Lean and Kanban to getting your job done, and in doing so, to focus on maximizing leverage (value produced per unit time). Someone who hasn't previously read much the same things as the author did in preparing to write the book may get a lot more out of it, but it doesn't pull me in.
Plenty of war stories. Some good bits on using if-then intents to set yourself up for success when your will power is at its lowest (pre-commiting, in a way) and on on-boarding and interviewing. The "Key Takeaways" box at the end of each chapter is handy.
Skimmed the entire book; don't feel I need to delve further at this time.
- Kofman, Conscious Business - communications
- Rock, Your Brain at Work - working with reality of brains
- Halvorson, Succeed - goal-setting tactics (optimistic or pessimistic? ends- or means-focused?)
- Growth mindset
- Flow
- If-then intents to reduce the level of "activation energy" needed (contra procrastination)
- Estimate quality: Good if it enables steering project to hit its targets
- Practice failure modes
- On-boarding & hiring as high leverage in an org
- Codelabs: Walk through the why and ideas of some core code, scope out main algorithms and code in it - part of on-boarding onto internal tools
- Good bit contra rewrites
- To heck with "retros": Use intensive debriefs to grow a written body of knowledge for the future
- X triggered Y
- A fixed B
- This didn't work
- That did
- Use automation + abstraction to increase team effectiveness
- 5 min a week per person in a large org is a lot of time.
A crucial conversation is one where the stakes are high, emotions are strong, and there's disagreement. The book talks about what they are and how to safely navigate through them. Basically an operating manual for talking under stress, with lots of examples to learn from.
This is a clearly structured book with illustrations and call-outs that would be easy to skim. One of the author's afternotes point out that many have got great benefit just from being aware "hey, entering a crucial conversation here, wake up and pay attention!" without reading most of the book.
I think this would be a very useful book to read, but its application is limited (if valuable), and it is not going to shed much light on my core questions. I'd be happy to read this later, and the way it's written, it'd likely be a quick read.
- Finished reviewing all of my initial books.
- Selected five to move forward with.
- Explained how the books interact (but only at a very high level, without getting into particularities like "so what does it mean to be a manager?" - that'll be Thursday's job)
Next:
- Summarize the goals and origins of those books.
- Skim them for practical dos and don'ts in terms of actions taken
A lengthy book focused on teaching principles for building character. The 2013 foreword proposes that leadership flows from character. In this way, this may be viewed as a leadership book. But it is mostly a moral or philosophical text. It is written in the style of a workshop and frequently illustrated with short stories and fables.
It's not readily skimmable, because it preserves the conversational style of the workshops rather than adopting the structured style of a reference. It looks frankly like something of a slog to read, but it comes with high praises, so probably worth the trouble.
That said, this is a book to answer what it is to live life well, not what it is to act well as a manager, so this can be set aside for the rest of this week.
General communication focus for the most part. Last part addresses leadership some.
Looks fairly skimmable and pretty easy to read. (The cryptic chapter titles are not so helpful.)
This may be useful when managing, but it won't help answer my questions. Next!
A series of essays in answer to, "Why is managing programming so hard?" (vs hardware).
Big software projects are qualitatively different from smaller and encounter different issues (mostly coherency).
20th anniversary edition includes No Silver Bullet, a follow-up essay to that, a listing of all the propositions of the book itself, an update to the book's contents (looks very useful - one section is, "Parnas was right, I was wrong about info-hiding"), and a retrospective.
This looks like a very interesting book, but it deals primarily with project management rather than people management. Since I do a fair chunk of project leadership, I want to read this very soon, but it's not going to help answer the questions I'm focusing on this week.
Section two touches on management and being managed, and the index shows a good bit addressing boht meetings and managers, but this is more like 7 Habits meets career counseling for geeks.
Chapter 40 does touch on scripts, calls out geeks as oriented towards learning rules to beat the system and the drive to predictability that comes with that, and how disruption and challenge and trouble are key for learning and career growth.
Overall, this does not have enough relevant content to continue looking at this week.
This book directly addresses a key management skill, that of building and managing successful teams.
The first 3/4 of the book are a fable; the last 1/4 lays bare the model at play and provides tools, assessments, and steps for putting it into practice.
The book is a refocusing and adjustment of The 5 Temptations of a CEO. The author was surprised to see that those lessons could be applied to teams with success, and ran with it.
Presents coaching as a key skill of management and leadership. Provides 7 questions that can be used to drive coaching. Aims for daily, informal, brief (less than 10 minutes), and habitual coaching.
Solid collection of annotated book recommendations at the end, as well as a section listing the research behind each of the questions (sans helpful annotations, alas).
- Flawless Consulting
- Scaling Up Excellence
- Switch
This is a beautiful, focused, well-written book that aims to teach a core skill for managing.
This makes an interesting contrast with The Coaching Habit and with 5 Dysfunctions. It should be fun and instructive to play those off each other.
Defines what it means to be a boss, illustrates that in detail in part one, and then provides tools to do that well in part two, with a final "how to roll this out" chapter wrapping it all up and sequencing it temporally.
A thoughtful book written based on significant personal experience. In that, it resembles Fournier's Manager's Path.
Would be interesting to see the course content for "Managing at Apple."
Working title for a couple years was Cruel Empathy.
- Competing on the Edge (Shona Brown)
Updated in 2013 to address recent trends and to incorporate new insights.
Pretty much everything else I've been looking at builds on and was enabled by the central insight of this book, that people problems dwarf technical problems in shipping software.
That said, this book's focus in very much on the organization and its environment itself. While parts are more directly addressed towards management and leadership, and it's certainly more on-topic than The Mythical Man-Month, it doesn't look like it's mostly material that will help answer my core questions.
As such, this stays in the "to-read" pile, but doesn't get further attention during this week.
This is a long list of essays with minimal visible structure and no supports for applying them to your work or even identifying the ones relevant for your current challenge.
Lopp's vision of managing as accumulating a dossier on each person in order to support, deploy, and defuse them is a clear and people-focused one. In this, it does dovetail with Radical Candor and The Coaching Habit.
But its structure does not make it amenable to processing during this week. It looks to have a lot of relevant content, but it'll be a lot of work and time to transform that content into something directly applicable.
This is better as a "read a chapter a day" book than as a "devour the whole thing and put it to work" book. I suspect it will also be more meaningful read in light of the other books I've identified.
My goal here is to pick out books that'll best help me understand what I should be doing as a manager in order to be the best I can be at it. Because of the contrastive reading I'm expecting to do, I'm also looking for ones that touch on much the same topics. Luckily, these goals line up pretty well - if you're answering my core question, then you're pretty much guaranteed to be speaking to the same topics.
So here's my final list of five books:
- The Manager's Path provides a clear vision of responsibilities across roles.
- The Effective Executive provides a focused vision of the work of an executive, as constrained by limited time. Its vision of the organization as flows of information gets wheels turning for me, its focus on effectiveness speaks to my personal interests, and it gives concrete advice for what the heck an executive ought to be doing, without wasting a ton of pages.
- The Five Dysfunctions of a Team is here in part to answer "what am I supposed to be doing with a team" and in part as a stand-in for The Five Temptations of a CEO. It also seems to cover much the same ground as Radical Candor, but with a different focus, so this should be good.
- Radical Candor may turn out to be something of a slog. It's a lotta pages. And choosing to sequence the tools section based on the order in part one rather than the order you need to apply those tools in sounds like a recipe for frustration for me as a reader. But the book also speaks directly to my questions, and it provides a framework and tools, and it also comes highly recommended by my colleagues, so it stays.
- The Coaching Habit has a very strong vision of what a manager ought to be doing in interactions with their team members. It's also well-written and strongly structured, and it has some beautiful layout to boot. I'm excited to read it just to enjoy the design of the text; it's just great that the content also appears equally wonderful.
The last three seem to overlap strongly; the first one provides a bird's eye view; and the second one provides a different perspective on what a manager's job is, one that's less relationship-focused and more principle-driven.
Now let's see what all these books have to say to each other.
- Enumerated the origins and goals of each of my chosen books
- Began mining books for practices
- Manager's Path: Rough going for this purpose - often rather abstract
- Coaching Habit: A lot easier, but still required pretty much reading the whole thing.
Mining for practices proved harder than expected. All too frequently, advice is abstract and general ("try to, you know, like, do your best for your team") rather than concrete and situated ("when someone says this to you, don't say this back, do this instead").
- Origins:
- Distills advice from personal experience of four years at a fast-growing startup
- Goals:
- Help you focus on each level individually
- Address challenges of engineering management in particular, not general management
- Serve as a career-long reference manual for engineering managers
- Origins:
- Not revealed in text
- Goals:
- Teach you to be an effective executive, for your and society's own good
- Drucker sees most knowledge workers as (personal) executives, so increasing executive effectiveness is crucial for society to flourish in the Information Age.
- Teach you to be an effective executive, for your and society's own good
- Origins:
- Grew from observing people effectively applying the lessons of 5 Temptations of the CEO to their teams
- Goals:
- Help your team achieve more together than apart
- (Honestly, the goals are mostly implicit. The author assumes you're on the same page and doesn't really state much about them explicitly.)
- Help your team achieve more together than apart
- Origins:
- 5+ years of training managers in coaching
- training company founded: 2008
- started writing the book: 2012
- book published after two rewrites: 2016
- 5+ years of training managers in coaching
- Goals:
- Instill the coaching habit so you can have more impact with less hard work
- Make coaching a viable leadership style by providing tools to make it rapidly effective and by countering misconceptions about how time-consuming it is
- Origins:
- Over a decade of management experience, primarily at Google
- Management training experience at Apple University
- Goals:
- Reassure you that management is hard and you aren't alone (part 1)
- Give you the tools to manage better (part 2)
- Save the world from bad bosses
Today:
- Finished an initial read-through of The Coaching Habit
- Finished an initial read-through of The Manager's Path
- Wrote up thoughts on goals and practices derived from those two books
OK, this took a different turn than I expected. Concrete practices are actually rather thin on the ground.
Rather than looking to try to mine other books, I'm going to focus on squeezing the most I can from these two books, and as time allows, have a good think on the questions that led me to spend this week.
In the unlikely event I've still got time left, I'll then maybe look into Radical Candor. Why Radical Candor? Because comments in The Manager's Path tell me that the other two books I singled out are less relevant for my current situation.
Aims to provide concrete micro-habits that enable you to coach in short exchanges.
Coaching is helping someone else help themselves - guiding them to learn something new and solve their own problems.
Implicit in this is:
- This is a good thing to do
- You should probably be doing more of it than you already are
Embracing the practices in this book will likely substantially change your interactions with others. Misapplication likely causes similar frustrations as being subject to the Socratic method.
Alongside these conversational habits are:
- Guidance on how to develop new habits in the first place (this leads the book)
- Shifts in mindset, including helpful framing devices
- Justifications for changing your approach and even for the specific wording at play in the questions
The practices together suggest these goals for management:
- To challenge your reports to learn and grow through active thinking and enquiry
- To resist the urge to step in and do someone else's work for them
Those are kind of two ways of saying the same things, but one tells you what to do, and one, what not to do. Both can be challenging.
There is more to management, but mastering this book would provide a solid tool that will help in balancing your work, in successfully delegating, in having difficult conversations, and in communicating during your 1:1s.
Enumerating the actual details of these things strikes me as better-suited for a mindmap than for a flat text, so I'll defer that step till later.
This book is both what I hoped it would be and very much not what I expected.
I hoped it would lay out clear responsibilities for each level and help me sort out the heart of what my job is and what doing it exceedingly well would mean. And it kind of did that - though perhaps not so well in the context of a consultancy rather than a product organization, but that's expected.
I also hoped I'd be able to just read the first few chapters relevant to my role. The introduction even suggested as much. But I feel you really need to read all around that role in order to understand your responsibilities to those above you in the org and their expectations for those below them.
Further, I hoped it would be easy to pick out concrete practices. I based this on mention in the intro of "Bad Manager, Good Manager" contrasts. But those are hard to find: they're not in call-out boxes, but rather are in-line sections - and there's no detailed table of contents that includes them. And they also tend to focus more on tendencies or approaches than concrete mis/steps. They're at a higher level than I anticipated.
All that means that I didn't get a ton of clear practices out of this. The best section for that was probably the one about how to hire managers, since that did get down to specific things they should be able to do and you can watch them do, like running a few 1:1s. The section on the diversity of approaches in 1:1s was also freeing and eye-opening. (Unfortunately, there was nothing helpful here about running team meetings. I suspect standing team meetings are more an artifact of a team of consultants not otherwise having a lot of exposure to each other; that exposure happens in the context of the project for a project-team.)
The breadth of content here, running from "hey I'm a new hire as an engineer" up to "OK, so, uh, I'm a CTO, or maybe a VP Eng, what does that even MEAN?!" has led to a lot of the details not sticking in my mind. So I'll have to make another tour here to mop up and distill the relevant bits.
Off the top of my head though are these responsibilities:
- Identifying problems before they happen
- Dealing with problems before your manager has to deal with them
- Making your team productive and happy
- Retain people
- Deliver product
- Identify broken processes and get them fixed
- Identify broken teams and get them fixed ("team debugging")
- Preparing your team members for promotion
- Helping them learn the skills they need at the next level
- Identifying and preparing potential managers
- Represent your team's interests to the rest of the org
- Avoid just being the execution arm for others' needs
- Address roadmap instability
- Make the impact of changes of direction obvious
- Proactively communicate timeline and estimates
- Request those estimates as needed
- Modeling behavior you want to see reflected in your team's subculture
- Set clear expectations and communicate measures used as part of accountability
I think there are some good concrete practices in this book to go with these more general guiding lights, but I'll have to pull them out, write them down in one place, and make sure they're ones appropriate for the level I'm thinking about.
Today:
- Mapped out the information in The Coaching Habit
- Looked for practices buried in The Manager's Path
- Turned out there weren't really many.
- Listed out pitfalls from both of those books
- Mostly failures of judgment or character flaws run amok
- "Managing well is acting judiciously"?
- Weekly 1:1s
- Can titrate back to bi-weekly in rare cases
- Performance review
- Share your notes the night before, so you can all discuss in light of that.
- Promotion
- Cultivate a network
- Help build your reports' networks
- Recognize one praiseworthy act of your team each week
- Delegate
- Pre-mortems (project lead)
- Control focus and schedule intentionally
- Avoid surprise meetings
- Also avoid bowing out of useless meetings - they should probably just be stopped, rather than you just stopping your own attendance