Ask HN: Best book / resources on leadership, especially for tech teams?

882 points by learnaholic ↗ HN
Although I know self help books are of little value, but wondering if any author has really nailed the topic? Would be even be better if the book is specific to tech leadership.

219 comments

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Extreme Ownership is an excellent book on the topic (or so peoole tell me, I started reading it today actually).
It is. It is also filled with gratuitous disregard for human life and cruelty towards animals. But that's what war is about, and having a book about military leadership without actual examples of conflict would be kind of vacuous.
And the dichotomy of leadership.
Try "The Manager's Path" by Camille Fournier.

http://shop.oreilly.com/product/0636920056843.do

Also highly recommend this. Unlike some other books, it's highly tailored towards being a leader at a tech startup, and has great, specific advice. It's also broken down by chapter, so you can read the bits that are relevant for your role.
Having read many of the books recommended here, I found this one to be the most concretely useful of the bunch. No fluff, just solid advice from someone that went from engineer to CTO.
Agreed, I particularly like the way each chapter dealt with a rank further up. Even if you have _no intention_ of going higher, seeing what they want from you and what they should be doing was immensely helpful and clarifying.
I would also advise this one. I appreciate the section enumerating the roles that the VP of Engineering and the CTO share/split.
Seconded, this is a great book.

I think all non-managers should read it as well as it will give you some clarity on what you should expect from your manager and what their day-to-day is like.

I read both this and "The Making of a Manager", and I've got to say, "The Making of a Manager" has much better advice and is a lot easier to act on than what Manager's Path gives.

I think the primary difference is what point in their careers the book was written. Julie wrote the book early in her career while Camille has been in upper management for some time meaning that she's more distant from the challenges of becoming a first time manager.

And despite Julie's only experience being at Facebook, I still found the advice widely applicable.

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It depends on what your definition of "leadership" is - personally I found "Managing Humans" by Michael Lopp to be really insightful. It's really more a collection of anecdotes than a seminal work on the topic, but I think there's a bunch of good components in understanding team dynamics around technical / software engineering teams.
Not strictly management, but related:”The Trusted Advisor” is a book about consulting. Which is really the same soft skills you would need in leadership positions where you have a lot of domain experience and leadership is more about helping the team make their own tech decisions
"An elegant puzzle", "High output management" and "Behind Closed Doors" have all been useful to me.
It's years since I read it but Gerald Weinberg's Becoming a Technical Leader. The best general book on leadership I've read for a while is Marquet's Turn the Ship Around – great also as an audiobook. I referenced the latter in my own Right to Left: The digital leader's guide to Lean and Agile (arguably a leadership book too)
'If you are a good leader,

Who talks little,

They will say,

When your work is done,

And your aim fulfilled,

“We did it ourselves.”'

- Lao Tse, quoted in 'Becoming a Technical Leader'

I heartily second 'Becoming a Technical Leader.' The exercises there are designed to get you to think about and grow in the situation that you are currently in, so the book will be a perennial.

I'd add that Weinberg also produced a four-volume series, 'Quality Software Management', where he sums up all he learned about project management in his programming, management and consulting careers. He later republished the material in a series of smaller eBooks [0] at LeanPub.

I know of no better written resources for people who want to learn to manage software development in a way that accomplishes the technical tasks while respecting the people who do the work.

[0] https://leanpub.com/b/qualitysoftware

Upvoted. Also by Weinberg, The Secrets of Consulting.
The best management book I read this year was "The Making of a Manager" by Julie Zhou [1]. The book is concise, clearly written and actionable. It's specifically written for first time managers and the author is a design lead at Facebook.

[1]: https://www.amazon.com/Making-Manager-What-Everyone-Looks/dp...

+100 for this book. Absolutely amazing.
Thanks for sharing! Julie is amazing!
Agreed, Peopleware is great. Very good for engineering leadership specifically.
Highly recommended. 100% agree with the "emotional part" and "engineers hate wasting time... DUE TO YOU" haha. A mind changer to me.
This isn't specifically about tech, but The Culture Map by Erin Meyer is really worth reading.

I'm not 100% sold on it being correct, but it does give you a framework to think within when you're working with other people, no matter which culture you're from.

Forbes have a decent write-up:

https://www.forbes.com/sites/rawnshah/2014/10/06/the-culture...

Be Slightly Evil: A Playbook for Sociopaths

is pretty good on this topic.

Saved
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Everything by Simon Sinek, but most important for me is "Leaders Eat Last" [0]. I haven't read the last one (The Infinite Game), but I've heard it's pretty good as well.

Also Extreme Ownership [1] and Dichotomy of Leadership [2] by Jocko Willink and Leif Babin.

All of these books had tremendous impact on me as a leader and I highly recommend them.

[0]: https://www.amazon.com/Leaders-Eat-Last-Together-Others/dp/B...

[1]: https://www.amazon.com/Extreme-Ownership-U-S-Navy-SEALs-eboo...

[2]: https://www.amazon.com/Dichotomy-Leadership-Balancing-Challe...

Leaders Eat Last was one of the best books I read this year. Extreme Ownership was also quite good but Simon really explains the “Why” of leadership that most books are missing. High-Output Management is another classic.
I understand the “why” of leadership very well, but as a high-functioning autistic person, I struggle very much with the “how”, especially around communication.

Like - for all possible values of X, if X is what I want someone to do, how do I communicate that so people (a) understand that I want X from them and (b) aren’t offended and understand that it is meant kindly/charitably (which it really is, I often just don’t know how to say so without sounding weird or changing the value of X).

Here’s a small example scenario from home life: my son was crying in his room. I was in the middle of something but wanted to take care of him and let my wife rest. She got up and started down the hall. I said “I was going to get it” expecting her to say “OK” and come back. Instead she sighed and did it anyway, and later said she felt frustrated that I made an excuse instead of either taking action or not. I explained to her what I wanted and asked what I should have said instead, and she said to say “Please stop. I’ve got this.” Next time I said that instead, and was amazed how different her response was - she was happy/grateful to let me take cars of it.

I guess I need a book full of “scripts” that would help me communicate both text and subtext accurately. Any resource suggestions?

- High-Ouput Management - Five Disfunctions of a Team - The Goal - Principles by Ray Dalio - Good Profit by Charles Koch

All of the books above cover some aspect of what you want but don’t seem to cover the whole picture. Further, a lot of it comes down to shared mental models. If you are coming from the perspective of action taking then the other person also assumes that you will take the action. I think Leader Eat Last explains this brilliantly and actually significantly changed the way I am trying to approach leadership as well as how I work with other people in general.

This is not a book full of "scripts," but will hopefully help inform future actions:

The "Please stop. I've got this." is an action-oriented message that is conveyed before the action. It says "I would like for you to do X because of Y." It is conveyed in an imperative structure, which is used for a command or a request. "Please stop." <- request. "I've got this." <- followed by a rationale for your request. The request is conveyed first, followed by the rationale for why you are making it. "Do this. Here is why." The "I've got this" also carries succinct subtext of "I agree with you that our son crying is a problem that someone should take care of, I just think it should be me instead of you."

Conversely, when you say "I was going to get it," it is a declarative message rather than an imperative message. It does not tell your wife what you would like for her to do. It is merely additional data that does not help her make better decisions, which means it is mostly useless for her. An extreme comparative example is looking at a person who has just burned their hand at the stove and then saying "that stove appears hot."

Humans don't like to receive an array of "reasons" data before they've received the "request." We don't like statements in the form of "because of Y, Z, A, B, C... please do X." Our subconscious can typically detect that we are receiving a stream of "reasons" and we are starting to brace for the "request" (because the request might be unpleasant).

People like to know what others expect of them. Your comment says you would like to know what your wife expects of you. When you follow the <command> <rationale for command> order of operations you are giving people what they want (what you expect of them) followed by your reason for wanting that. When you go in the opposite order, you are conveying the converse: "I want something of you but I haven't told you what it is yet."

This is probably some of the most helpful advice I've ever received. I think it will be challenging (and scary) to learn to use imperative requests instead of declarative statements. Thank you so much for helping me understand and speaking my language!
Thank you. I'm sorry I can only upvote this once.
Hi Tim, this had happened to me a lot before I finally realized that effective communication comes after good emotion. Try listening and talking about her emotions and feelings, and then communicate the subjects. I believe there may be "full of script book", but I doubt that gonna help you. Cheers,

Robert

"I was going to get it" is past tense. Using past tense for something can imply that it's something that was true in the past, but not now.

This can irritate people because it comes off as trying to claim credit for intent to do the task without actually doing it.

While "Please stop. I've got this" is the best phrasing because its what your wife has requested as well as what the other commenter stated, I imagine you would have still got a fine result if you used present or future tense. "I"m getting it" or "I'll get it".

Tenses, and other grammar on their level, is definitely something you will be able to find scripts for.

Extreme ownership is awesome.
Already been said a few times, but just feel like I had to add again for added emphasis. Extreme Ownership is the best book on Leadership I have ever read. Changed my thinking forever.
I must have missed something, seeing extreme ownership praised so much but I stopped reading it after a chapter or so. The whole macho thing didn’t jive and I’m struggling to find parallels to ordinary life. Lives aren’t at stake for 99.9999% of work out there. The whole military hierarchy and all the idealization doesn’t exist in normal contexts. Leaders aren’t trusted implicitly always or “lives are at stake”. So how does it translate??

Perhaps my view is tainted having been through mandatory military service, and hated every minute of it. But I guess I simply “don’t get it”

Veteran here as well and Sinek annoys the hell out of me. If it’s the first and only book you’ve read on leadership then maybe some of the points are helpful, but I find it to be mostly self-absorbed superficial garbage that business majors flock to five minutes after graduating.

It’s the leadership equivalent of that Not Giving a Fuck book.

I agree /lives/ aren’t directly at stake, but depending on what your business is, /livelihoods/ are.

When you’re an entrepreneur and have a small team, each of them may have a family. As the leader you are responsible for running a profitable company that can pay its employees so their families can eat.

At the large company I work for my team’s product is B2B. When we go down, other businesses go down. The number of people affected is very high. Treating every incident like someone’s business is dependent on you and they have put their trust in you to support them is very sobering.

Corporate business leaders here in America tend to be obsessed with trying to apply military-style terminology and doctrines to their business. In their minds, business is war, and "lives are at stake" gets translated to either "jobs are at stake" or "revenue is at stake," depending on the person. There are so many war-isms in business it's impossible to list them all. "In the trenches," "boots on the ground," framing sales territories as battlegrounds...

In short, these things sell because American business leaders fetishize these sort of ex-SEAL types.

It's all a little much for me. Not to mention unfortunate, because the sort of leadership that works best in the military is decidedly not the sort of leadership that works best in business. The military demands that soldiers immediately and unquestioningly follow commands given by their superiors (particularly during combat). Lives are literally at stake, so any hesitation for even a moment could spell doom.

Meanwhile, in business, I strongly believe leaders need to be in more of a team-servant role -- yes, motivating, providing vision, etc., but also cultivating a sense of "your voice matters," if that makes sense. Being a 'force multiplier' in business requires a different mentality than in war zones.

> In their minds, business is war

Relevant David Brent quote:

"Does a struggling salesman start turning up on a bicycle? No, he turns up in a newer car - perception, yeah? They got to trust me - I’m taking these guys into battle, yeah? And I’m doing my own stapling."

> The military demands that soldiers immediately and unquestioningly follow commands given by their superiors (particularly during combat).

This doesn't jive with my understanding of US military (or human nature). Out of combat, a top-down command and control hierarchy leads to poor decision making by troops on the ground. A general can't and shouldn't make decisions on day-to-day operations at the platoon-level.

In combat, certainly the stakes are higher, and lives are on the line. If anything, that means trust plays MORE of a role than hierarchy. If a leader I don't trust tells me to do something that seems wrong and reckless enough to get me killed, I'm not going to do it. I'd rather get court martialed back home than die in the dirt. It's all about trust. If the leader has earned trust, I'll know that they have the bigger picture, and what seems wrong to me now makes sense in some way I can't see from where I am. And of course, it's not all black and white, these are matters of degree, including measuring the desperation and force in the tone of an order.

See for example Team of Teams by General Chrystal--which is also a good book about organization/business generally.
+1. Team of Teams is a great intro to leadership for tech. General Chrystal identifies the distinction between complicated and complex areas and shows best practices for dealing with complexity (it's not just a semantic argument but actually something substantial, where tech leaders generally deal with complex problems and not complicated problems).
> The military demands that soldiers immediately and unquestioningly follow commands given by their superiors (particularly during combat).

I don't think the way you've phrased this is quite accurate, although I understand what you're getting at.

In the book the author discusses how it is the responsibility of leaders to plan missions and to ensure that all voices and concerns are heard during planning. It's also the leader's responsibility to ensure that a decision about how to proceed is reached. Once a decision is reached though the expectation is that it will be carried out without question (I don't have any quotes handy unfortunately).

This sounds awfully similar to Amazon's principle of disagree and commit. I think this principle is congruent with the way the way the book suggests that leaders should operate.

From my own personal experience I think this is actually a really important principle. I find nothing more frustrating in a team environment than when one member of the team disagrees with a decision and decides to take it upon themselves to head off in their own chosen direction. It's very frustrating to have team members not following a plan.

Extreme ownership is not about the pressure of having to deal with "lives on the line".

It is primarily about owning responsibility yourself, and not externalizing blame. Even CEO and CTOs are prone to deflecting blame when there's politics and external parties involved.

All of the case studies show how managers suffer from defense mechanisms and logical fallacies that are harmful rather than helpful.

It also talks about the dangers of operating in a high complexity environment and the need to develop an understandable and legible method of communication.

* He says that leaders aren’t trusted implicitly in the Seal teams either, btw, and it's part of the job of the leader to build rapport with their teams, sell them on the plan, and make sure everyone understands the higher intent, if the team is really to be effective rather than dysfunctional. (this comes later in the book).

The war stories are what folks seem to focus on here, but I feel those are there mostly for entertainment, in addition to an example of the underlying value it's trying to demonstrate.

That said, the book really boils down to continual repetition of a few core points over and over. That may be necessary to drive the relatively few points home, with even fewer actually changing their behavior.

This is deliberately not an academic-level treatise on leadership. It is a challenge to accept the most fundamental challenges of responsibility - how many managers have you met which fail to do that?

The Infinite Game is also great. The focus is on building companies that last hundreds of years, so you need leadership, culture and investors that are all about long term stability over keeping sort term investors happy. There are some rants, but nothing I disagree with!
Simon Sinek has never actually led anything and is basically someone who is an expert at marketing himself. His advice doesn’t say anything new and is usually extremely banal.

He’s the classic example of fake it till you make it in modern America. A guy who makes flashy viral videos, has zero actual experience of leading organizations or teams, yet someone has acquired some guru like reputation at a genius leader.

Ok, where's your book so I can read and compare?
I've never directed a movie but I'm not allowed to say that Dumb and Dumber 2 is a terrible movie? Your logic makes no sense.

I've read well and deeply across a broad spectrum of classic philosophy and psychology and I think Simon Sinek is a dilettante and basic thinker. I'm allowed to have that opinion regardless of whether I have written books or not.

I wholeheartedly agree. A great example of marketing fluff content.

Still, a great example of marketing and proof that fluff sells and is probably useful for many.

> Simon Sinek has never actually led anything and is basically someone who is an expert at marketing himself.

Taking him at his word on several of his talks, he leads a team right now. Presumably one focused on advancing your second point: his marketing of himself.

> His advice doesn’t say anything new and is usually extremely banal.

The corollary being they’re banal to you, cue tangential XKCD: https://www.xkcd.com/1053/

Note I’m not necessarily disagreeing with you. He also seems to me like someone who teaches what he learned by theory, not practice. However, I do believe his intentions are genuine, that he wants to make the workplace better for everyone, and that his points are actionable and positive. Contrast that to someone like Tony Robbins, which I view as little more than a scammer that wants to trick you into thinking anyone can be successful at anything if they just believe in themselves and pay him hefty sums to attend his seminars.

simon sinek is a motivator, and had no experience in leadership
I'm typically a Simon Sinek fan but (The Infinite Game) left a poor taste in my mouth.

I had just finished (Finite and Infinite Games) by James P. Carse. He normally does a great job distilling information from mulitple sources, but in this case it seemed like he added nothing, condensed nothing, and in my opinion came really close to just rewriting the first 1/2 of someone else's book and calling it a new thing.

I'm not calling it plagiarism, he's obviously too smart to cross that line. But if you read the books you will see what I mean.

I can’t handle the level of repetition. You read one chapter and you’ve read the entire book. It could literally just be a bumper sticker - ‘real leaders eat last’ - ok got your thesis
That is unfortunately most Simon Sinek material for me. I think he is a super sharp thinker, but I always come away feeling like his books could have been a blog post and his blog posts could have probably been a tweet.
Simon Sinek is a charismatic speaker with good points and interesting stories, but I find his books full of fluff: a central thesis padded to the length of a book so it’s publishable.

You get the same information by watching videos of his talks, with the advantage they are free, more direct, and take less of your time. Plus, they’re released sparingly and have quite a bit of repetition with slow changes between them, so the points get to sink in over time.

Creativity, Inc. [1] It's not a textbook but a really fun read for the inside stories that pushed Pixar to its success. Maybe it's just me personally but I found it hard to follow some syllabus to learn management --- instead, I enjoy being inspired by other great managers through their concrete stories.

[1] https://www.amazon.com/dp/B00FUZQYBO/

This was an amazing read. Ed Catmull explains many nuanced aspects of leadership, management, creative organizations, and related. All of these lessons are wrapped into the personal history and narrative surrounding Pixar, which is fascinating in its own right.
I run Developer to Manager (https://devtomanager.com), where we interview tech leaders and ask them for advice they have for someone new to this field.

I'm of course biased, but I do feel it's turning out to be a good resource. Feedback is always welcome!

The Hard Thing About Hard Things by Ben Horowitz and The First 90 Days by Michael Watkins.
"Manager tools" and "career tools" podcasts have been eye-openers for me about corporate relationships and management politics.
My boss gave me a copy of _Talking with Teach Leads_ by Patrick Kua. I enjoy it. It's an anthology of testimonials by tech leads. It helped give me some perspective on what I need to focus.

edit: grammar

Satya Nadella’s ‘Hit Refresh: The Quest to Rediscover Microsoft's Soul and Imagine a Better Future for Everyone’
When managing people in tech, I think it is equally as important to know how to organize as it is to know how to lead. I would recommend "The Phoenix Project" and "The Unicorn Project" and "The Goal" to all tech managers.

No matter how good your communication/leadership skills are, your team will be severely handicapped if they are working in an inefficient/limiting environment.

Coming at the same lessons from a different perspective, I have also found "Turn The Ship Around!" to be a very good resource.

"Turn the Ship Around!" has been awesome resource for our team, most definitely recommend
> I would recommend "The Phoenix Project" and "The Unicorn Project" and "The Goal" to all tech managers.

Goldratt's "The Goal" and its sequels are interesting reading, but please, please internalize the principles he was arguing from for the theory of constraints before trying to apply it to software. Otherwise you end up with "The Pheonix Project" (whose author is apparently making a nice living as a snake oil process consultant, according to friends who have dealt with his appearance in companies) which is the "software factory" mess of the 1980's rewarmed and shoved out the door again. Rather, go read Deming's "The New Economy" (just ignore the section on intrinsic/extrinsic motivation).

I'm not really following your criticisms on The Phoenix Project... Can you elaborate?
I didn't attempt to make a detailed criticism. Basically, it's the naive application of Goldratt's "The Goal" to IT. People have been trying to model IT processes on manufacturing for decades. Still doesn't work. The opinion of several engineers that I respect very highly who suffered from the author's consulting services makes me discount his work entirely.

If you read farther in Goldratt, the sequels to "The Goal", he refines the notion of constraints in very interesting ways that leave the factory floor. I don't think the author of the Phoenix Project ever got that.

Goldratt is excellent for optimising processes with well defined goals.

This is ofen true in business software.

If you want to optimise a learning process, The Principles of Product Development Flow is more relevant.

The two books (The Goal vs The Principles of Product Development Flow) give very different, seemingly opposite advice.

Would you mind expanding on how your friends suffered? What went wrong etc. Sounds interesting.
I haven't done a detailed debrief with them, so I can pass on an opinion and experience that I respect, but I can't expand without conjecturing.
What Every Body is Saying: An Ex-FBI Agent's Guide to Speed-Reading People [1]

This book has allowed me to understand what the people around me are saying, without even saying a word!

"Read this book and send your nonverbal intelligence soaring. Joe Navarro, a former FBI counterintelligence officer and a recognized expert on nonverbal behavior, explains how to "speed-read" people: decode sentiments and behaviors, avoid hidden pitfalls, and look for deceptive behaviors. You'll also learn how your body language can influence what your boss, family, friends, and strangers think of you."

[1] https://www.goodreads.com/book/show/1173576.What_Every_Body_...