General Management and Leadership Books

  • Ask a Manager: A compendium of advice from Allison Green, author of the popular [[https://www.askamanager.org/) blog. It's in bite-sized Q&A format, covering a variety of things from how to deal with smelly co-workers to what to do if you throw up during a job interview to how you as a manager can coach people away from unrealistic goals. A good reference work that you can read and learn from in small doses. Even if you don't hit all of these exact situations (really, how many people have to deal with a bonkerballs co-worker putting curses on people?), Green's overall attitude of respect for everyone and honest conversation is a great example for us all. (Reviewed by Mike Gunderloy).
  • The Advantage: Lencioni is pretty well known for his business fables (FIVE DYSFUNCTIONS OF A TEAM et al). This is his non-fable book, a synthesis of his work and the points he made in those other books to take an overall look at organizational health and its benefits. He walks through what he's found necessary about high-performing organizations, from leadership alignment to good hiring practices to which executive meetings are necessary and how they should be structured. I found the discussion of core values (and the other types) very useful, among other things. There is a fair amount of advertising for his consulting group sprinkled throughout, but it's more "we could help you with this" than "if you want the real secrets pay us" so it wasn't annoying; between the book and the handouts on the book's website, they appear to be giving away their whole system for free. Recommended. (Reviewed by Mike Gunderloy)
  • The Best Team Wins: Heard the author on a podcast & ordered the book. I'm glad I did, even though a lot of the motivational techniques in here leave me cold. I'm an aging baby-boomer and so a lot of the things the authors have to say about those born later leave me confused. But they also match up with some of what I'm seeing at work. There is plenty of concrete advice here for motivating individual contributors and entire teams, including a long list (101!) of techniques to try. (Reviewed by Mike Gunderloy)
  • Brave New Work: Dignan digs into what some organizations are doing to change the rules, then walks through a set of chapters on evaluating "the operating system" of your own organization and possible alternatives (this is the strongest part of the book in my opinion) and closes with a section on how to run a change process. Bear in mind that this is his own work, which means it's based on actual experiences in helping places change. I've got a bunch of sticky notes to review for the future as our company grows; the sections that ask penetrating questions on topics like strategy and resources, together with the guidance on what it means to be "people positive" and "complexity conscious" seem quite valuable to me. The main question in my mind is whether these good, innovative companies are destined to be trampled by the Facebooks and Ubers of the world, but we won't know that for another decade or more. (Reviewed by Mike Gunderloy)
  • The Checklist Manifesto
  • Crucial Conversations: Skills for getting past conversations that have turned into battles. The authors bring out just a few critical skills that are designed to get things back to the point where everyone involved is contributing to a pool of meaning. They won't always work, but they do help. The main challenge I have is to remember this stuff in the heat of the moment, but as they point out, anything that moves you in the right direction is worth doing. (Reviewed by Mike Gunderloy)
  • The Daily Drucker: It took me a year to read this one, but after all, that's what it's intended to take. Bite-sized (no more than a page or two) chunks from Drucker's decades of writing on management, together with action points that can be used as springboards for thought. A lot of these didn't apply to my own circumstances as I read them, but enough things did, in fields from time management to marketing, to make it worth my while to exercise my brain on this book daily. (Reviewed by Mike Gunderloy)
  • Deep Work: I'm pretty conflicted about this one. On the one hand, I do think the concept of deep work is valuable. The idea that some things require focus & concentration to achieve, and that you won't hit that focus and concentration by accident, is useful. But on the other hand, Newport's arguments in favor of it are largely a mix of anecdote, poorly-justified pop science of the Ted Talk variety, and fallacious logic. When he gets around to arguing that social media is worth quitting, though he himself has never been deeply involved, the whole takes on the flavor of a virgin producing straw-man arguments to justify avoiding sex. (Reviewed by Mike Gunderloy)
  • Dynamic Reteaming: This one is currently in not-quite-final form at Leanpub, but although it still needs a tiny bit of copy editing, it's practically done. Helfand draws on her own experience in several growing tech companies, as well as interviews with other coaches, managers, and non-managers, to identify some patterns of change on teams. There's thinking here about team lifecycles, antipatterns to avoid, onboarding people to new teams, among other things. I especially liked the stories of companies that have had success allowing people to choose their own teams, either as part of a major reorganization or on a regular basis. (Reviewed by Mike Gunderloy)
  • The Effective Executive
  • The Effective Hiring Manager: I grabbed this one as soon as it was available and I'm glad I did; a lot of Horstman's advice will inform my future hiring process. That said, many many people are going to hate this book because it is bluntly about doing a good job of hiring based on job fit and merit. If you're one of the people who feels diversity & inclusion must be considered when hiring, well, those words aren't even in the index. There are also other times that you'll want to bring someone in based on factors other than proven ability in job skills (hiring interns, for example). But if you want a step-by-step process that leads to efficient decision-making and removes dependence on "gut feeling", and that goes from reading CVs straight through onboarding, you've come to the right place. (Reviewed by Mike Gunderloy)
  • The Effective Manager
  • An Elegant Puzzle: Will has been a senior leader at several large software companies including Stripe, Digg, and Uber. This is his collection of "how to do it" recipes for success. I suspect it will have the strongest appeal to leaders who have come up from the software development ranks and who find people messy and uncomfortable. There is some material here on areas like hiring and culture, but the book is at its strongest when talking about things like the perfect n-step process to cold-recruit people based on their LinkedIn profiles, or how to size and reorganize teams. If you believe that management can be reduced to the same sort of science as databases, this is the book for you. I'll keep it on the shelf, but I don't think it'll be my go-to. (Reviewed by Mike Gunderloy)
  • FIRE: How Fast, Inexpensive, Restrained, and Elegant Methods Ignite Innovation: An argument that better work comes out of projects that are deliberately "fast, inexpensive, restrained, and elegant". The author comes out of the engineering & military communities, where he's certainly had lots of opportunity to observe projects that miss all of those targets, soak up money, and deliver nothing of value. But the principles apply in software development as well. Constraining things can have a wonderful focusing effect. (Reviewed by Mike Gunderloy)
  • The Five Dysfunctions of a Team:As it says on the tin, this is a "fable" and as such it can come out however the author wants. So, there's a happy ending, where the new CEO manages to build a high-performing team. Nobody wants to read a fable about the teams that crater. I'm not convinced Lencioni has identified THE way to high-performing teams, but a lot of this stuff strikes me as A way, and the connection between vulnerability and trust is, I think, more important than many small-team leaders give it credit for. So for reinforcement of that point, as well as for being a good story told well, I give it a five. I wonder, though, how many leaders and prospective leaders read this one through the warm glow of "the new CEO is so sharp, and her direct reports are such bozos...why that's exactly the way it is here!" Not Lencioni's point at all, but I'll bet it helps with sales. (Reviewed by Mike Gunderloy)
  • Flight of the Buffalo: I read this one at roughly the same time as Pflaeging's ORGANIZE FOR COMPLEXITY, and it wasn't long before I got an eerie "separated at birth" notion. Those who think this agile decentralized stuff is all new might want to dip into FLIGHT OF THE BUFFALO, now 25 years old. The central theme: that you get better leadership by helping your people grow into a flock of self-organizing geese than you do by being the lead buffalo who does everything (and thereby becomes the indispensable bottleneck to everything in the organization). An easy, though somewhat long read, it teaches a series of lessons about why and how a good leader will let go, and how to challenge your employees to succeed by delivering great performance for customers. (Reviewed by Mike Gunderloy)
  • Get Smart!: How to Think, Decide, Act, and Get Better Results in Everything You Do
  • The Goal: A Process of Ongoing Improvement: This one gets super reviews but I'm at best lukewarm about it. It's an early example of the "teach business principles through a novel" genre. In this case, the bumbling plant manager gets whacked over the head by his Israeli physicist friend until he figures out that flow through his plant is more important that keeping everyone busy. You'd think that the piles of inventory choking things off would have been a clue. There are things to learn here, but they could be taught in half the size, without the bad romantic subplot or the amazingly bad portrayal of Boy Scouts. (Reviewed by Mike Gunderloy)
  • Grinding It Out
  • How F*cked Up Is Your Management?: You can read the title two ways: "how fucked up are these idiots I report to" or "how fucked up is my own management style". I think the second reading is much more productive. From the editors of The Co-Pour (https://mfbt.ca/), (and a lot of the content started there), this book takes a hard look at some common management and geek ideas and rethinks them. Think you're doing enough for diversity? Think your unlimited vacation policy is a benefit? Think again. (Reviewed by Mike Gunderloy)
  • How to be an Inclusive Leader: An excellent guide to those of us trying to navigate the tricky and confusing waters of diversity & inclusion in the workplace. Brown draws on her large experience in the field to provide a framework for thinking about where you are on any particular dimension of diversity, from unaware through aware and active to advocate. She also makes the point very strongly that this is not a simple linear journey, and that you should be prepared to move back and start over more than once. I expect I'll be reading this one again in the future, both for the framework and for the concrete ideas about what to do if you really care about these areas of life. (Reviewed by Mike Gunderloy)
  • How to be Happy at Work: I ran across this one thanks to the How To Be Awesome At Your Job podcast, and picked up a copy. It's a lot more academic than I had expected: even though this is aimed at a popular audience, McKee has plenty of research background and she pulls in a lot of work she's been involved with in the past, notably on emotional intelligence. There's no magic spell to be happy, of course, but there are techniques that can help in many circumstances, and she makes a nice organized presentation of them. I personally got the most value out of the discussion of hope at work and the value of having friends, even though I'm not one to easily make friends. It's nice to see an empowering set of ideas in one place, though I'm not 100% sure I'll have luck putting them into practice to change things outside myself. But one of the messages here is that changing yourself is a good starting point. (Reviewed by Mike Gunderloy)
  • Influencing Virtual Teams
  • The Innovator's Hypothesis: "How cheap experiments are worth more than good ideas" is the subtitle here, but be warned: if you're in a small startup, you may not have the same definition of "cheap." Schrage has clearly worked with a bunch of big companies, and his idea of a radically streamlined process is to give a team of 5 people 5 days to come up with a portfolio of 5 experiments that take no more than 5 weeks and $5000 each to run. But even if that's too rich for your small-scale blood, the basic notion that actually getting out and DOING things trumps just THINKING about them is worth internalizing. And who knows, you might even pick up some brainstorming ideas that you can apply to your own experimental practice. (Reviewed by Mike Gunderloy)
  • Lead Inside the Box: A framework for thinking about leadership in organizations based on a matrix that balances leadership capital invested vs. results obtained. I'm not currently leading a team, but this one was valuable to me from the other side of the table: I did some deep thinking about which of my behaviors at work are causing my boss to invest unwarranted amounts of his leadership capital. I came away resolved to change a few things, and that's about all I can expect of any book. (Reviewed by Mike Gunderloy)
  • Lead Like an Ally: A Journey Through Corporate America with Proven Strategies to Facilitate Inclusion: Let me just say this right up front: it took a hell of a long time to get it through my own personal thick skull that "I only want to reward the best performers and I'm not going to lower my standards in the name of diversity" is (a) stupid when the rules are designed to make it easier for some people to do their best than others and (b) offensive in that it assumes people who don't look like me are not as good as me. I get it now, though, at least some of the time -- though I still catch myself falling back on comfortable technocratic assumptions that were baked into my thinking back in the days when you could also safely assume that every engineer worth anything also smoked cigarettes. Julie Krantz's new book is an attempt to help leaders of all sorts (but primarily male middle managers, because there are so many of them with problematic behavior) see the problems with this vein of thinking and learn to be more inclusive about their leadership. The book is short and to the point, and leads the leaders through a journey towards a more inclusive style and true allyship using a synthetic story that captures many of the issues women (and other non-majority employees) face in today's workplaces, even many of the ones that pat themselves on the back for their D&I initiatives. Each chapter gives a part of the picture, then analyzes the warning signs (not all of which I saw!) and gives concrete advice on what leaders can do better. Highly recommended for anyone in a leadership position who cares about this stuff, which should be every leader. (Reviewed by Mike Gunderloy)
  • Lead Right for Your Company's Type
  • Lead Yourself First: An excellent book focused on the importance of solitude to leaders - though that could just as well have been cast as "the importance of finding time to focus." While many leaders get that time through being away from everything (running, vacationing, or just closing the office door), others may be able to focus just by a change of setting away from the everyday noise. I'll be chewing on this one for a while, especially as I have fallen deeply into the trap of instant response to everything myself. (Reviewed by Mike Gunderloy)
  • Leaders Eat Last: The basic idea here is simple, clear, and worth knowing: one of the prime jobs of a leader is to encourage a "Circle of Safety" in which every employee can do their best. Unfortunately that simple idea isn't up to carrying a 300-page book. There's a great deal of pop biochemistry and potted history and references to things like the Milgram studies (which have since had their moment in the revisionist glare) thrown in, none of which I found especially illuminating. The whole thing strikes me very much like an extended TED talk; you have the feel while listening that you're learning Important Things, but when it's all over, there isn't a whole lot to hang on to. (Reviewed by Mike Gunderloy)
  • The Leaders Pocket Guide
  • Make Your Bed
  • The Making of a Manager: A nice addition to the shelf of management books aimed mostly at the software industry (though certainly some of the techniques here will work in other industries as well). Julie Zhou is currently a VP at Facebook, but she still remembers what it was like to be a new & clueless manager when the company was much smaller. Her target audience is precisely those who have suddenly found themselves in management. The sections on dealing with your first three months are great, and the sections on good meetings, good hiring, and good O3s all stand out as well. Recommended if you're early on the management track, or thinking about heading in that direction & wondering what you're in for. (Reviewed by Mike Gunderloy)
  • A Man for All Markets
  • Management 3.0
  • The Manager's Path: This one traces a typical career progression for software engineers, from individual contributor to mentor and team lead, and then on into successively higher levels of management ending up in the C-suite. The author has made that journey herself, and offers advice based on her own career -- which, you ought to keep in mind, is just one data point, albeit an extended & successful one. This book was most valuable to me in terms of seeing what I didn't want to do in the future. It's worth reading at least as far as you aspire to go, and then skip forward to the last chapter on team culture. (Reviewed by Mike Gunderloy)
  • Managing in the Gray
  • The Mom Test: Really helpful tool kit for customer learning conversation (reviewed by Daniel Baily)
  • No Hard Feelings: A leadership book that stepped out of my usual comfort zone and made me think, which is about all I can ask. The authors dig into the uses (and some of the misuses) of emotion at work, arguing that in the modern workplace selective vulnerability is a necessity. I'll likely come back to this one in the future when I hit some situation that I can't quite work through on my own. (Reviewed by Mike Gunderloy)
  • Once an Eagle: At 1200+ pages, reading this one was a serious commitment - but worth it. The story of Sam Damon, professional soldier from WWI to the VietNam era (and secondarily of Courtney Massengale), it tries to show by example what leadership looks like, as opposed to simply executive ladder-climbing. The portrayal of the necessity of a moral backbone, and care for one's subordinates, is well-done. No wonder they're still reading this one at American's military academies. (Reviewed by Mike Gunderloy)
  • One Mission: This one was an inspiring read as I think about our company's management structure and how it might get through a round of growing pains. It's a follow-up to Team of Teams, continuing to dig into how lessons from the Special Operations Task Force run by General Stanley McChrystal can be applied to the fast pace of today's business. Fussell makes a case -- I think a convincing one -- that no matter how good your managers are the "solid-line hierarchy" of an organization isn't enough to keep up any more. The best managers act as information pumps, collating information as it moves up the organization and sending it back down to other subordinates who need to know. But this is an inherently slow process, and one subject to communications breakdowns as messages get passed multiple times (remember your childhood game of "telephone."). On the other hand, a purely decentralized organization with no managers, a la holocracy, is incapable of large-scale coordination (this is my interpretation, so blame me rather than Fussell if you're a holocracy fan). The solution proposed in this book is to overlay a network of "dotted-line relationships" between small teams, recognizing that there are individuals in the organization who are well-connected. That's not new. What is new is seeing management's task as making sure those individuals communicate regularly, that the entire organization is included, and that key connectors are empowered to decide things even at the expense of breaking the organization's rules. There's a lot more here, and I find it all pretty convincing. I'll be recommending this one for a while, I'm sure. (Reviewed by Mike Gunderloy)
  • Only the Paranoid Survive: This is Grove's book-length argument that one of the main features of successful upper management is to recognize "10" factors that lead to strategic inflection points. Recognize and seize these opportunities, and your company can thrive; miss them at your peril. Overall, it's a pretty good read, and gave me a way to think about my position in my current company (I'm one of the Cassandras). I wish that there was more concrete advice on telling signal from noise, but that's part of the challenge: figuring out which factors matter, and which are immaterial. There's a final chapter on treating your own career as a mini-enterprise which I found pretty uncompelling (it has the feel of something tacked on later to enhance sales), but overall I'm glad I read this. (Reviewed by Mike Gunderloy)
  • The Optimistic Workplace: There are a bunch of themes intertwined here, on the way to a better workplace. There's an argument that management is better replaced by stewardship; there's a notion that work need not be a soul-sucking trade of time for money; there's evidence that optimism encourages people to perform better. There's also a 90-day plan for stewards who would like to implement these ideas in their own workplaces. While I don't expect to be personally executing on that plan any time soon, I did appreciate the reminders (and evidence) that things improve on many fronts if you act like you're dealing with adults who want to do their best, instead of getting sucked into an endless cycle of politics and distrust at work. (Reviewed by Mike Gunderloy)
  • The Power of Full Engagement: The central argument here is that if you're busy and focusing all your attention on time management, you're doing it wrong. The authors argue that energy management, specifically various analogs of interval training that allow you to push yourself and then recover, is even more important. The argument is buttressed by a bunch of anecdote and case studies where they were able to successfully turn lives around, though it's unclear to what extent the stories they tell are composites rather than actual individual successes. I generally like the central idea, but I dislike the attempt to put everything into a neat crystalline structure, where what is said about physical energy is perfectly echoed in discussing emotional, mental, and spiritual energy. In my experience, life isn't that pretty. Much of the book also feels like padding or advertisement for their services. But the notion of building rituals to recharge yourself is, I think, an important one, and if you've never stumbled across it on your own that makes this book at least worth skimming. (Reviewed by Mike Gunderloy)
  • Principles: I put this one in the category of "total systems." From the inside, Ray Dalio has written down, in a logical and ordered fashion, all the things that he thinks contributed to his own success and that of Bridgewater Associates. Whatever else you say about this, it's objectively true that he's made a boatload of money following this recipe. (The book also contains a biographical section as background, but that's pretty dull and self-congratulatory). His principles run from "Embrace Reality and Deal With It" to "Don't Overlook Governance" and give a set of tools for life & work. He comes to the conclusion that an idea-based meritocracy is objectively the best way to organize a workplace, and it's very clear that he's used these tools to select people who agree with him to turn Bridgewater into a machine (his word) that functions very well in the world of finance. If you accept his premises, then Dalio's principles explain everything. This I think is the prime characteristic of a total system: from the inside, it is complete, an explanation of the entire world, and you need nothing else. The problem comes when you realize that there are many conflicting total systems out there: Ayn Rand, L. Ron Hubbard, Karl Marx, and Malaclypse The Younger are among others who have produced complete explanations for the world. They can't all be right at the same time. I'm sure there are things in here that will influence me moving forward; some of his ideas on exposing and settling disparate points of view, for example, seem useful (though the description of meetings at Bridgewater, with real-time "dots" micro-feedback from participants, is frankly horrifying). But I can't imagine buying into the premises to the point where I'd be happy in an organization run 100% by Dalio's Principles. (Reviewed by Mike Gunderloy)
  • Quality is Free
  • Radical Candor
  • Resilient Management: A short (just over 100 pages) book for new engineering managers. I know many managers who should read this. Unfortunately most of them probably won't, because Lara focuses on all the squishy stuff about building trust and helping your team and getting past the forming and norming stages, rather than on cookbook recipes for managing projects and figuring out velocity. If you're managing people rather than robots, and especially if you're not already familiar with things like the BICEPS model, or the difference between coaching, sponsoring, and mentoring, I can't recommend this one highly enough. (Reviewed by Mike Gunderloy)
  • Start With Why
  • Strategic IQ: Wells pulls together a lot of different threads here to try to examine the idea that some firms are better at identifying and executing profitable strategies than others - or, in his language, they have "high strategic IQ." His taxonomy of approaches and pitfalls led me to reflect that I think I've seen every single one of the dysfunctional low IQ behaviors he identifies during my career -- and I'm not sure I've ever worked at a firm that would make his cut for "high." After looking at the idea of strategic intelligence, he discusses ways that firms can improve their structures and their people to compete better. It doesn't all quite come together into a coherent whole for me, but there are plenty of thought-provoking ideas: more than enough to justify buying a copy. (Reviewed by Mike Gunderloy)
  • Switch: How to Change Things When Change is Hard: A lot of people find this inspirational; I felt it was at best ho-hum. The Heaths provide a reasonable framework for change management, though far from the only possible framework, and if you need to organize your thinking their Rider-Elephant-Path paradigm may be of help. But they are masterful at jumping from particular just-so stories to sweeping principles, and I'm past appreciating that style. One to read once, but probably never again. (Reviewed by Mike Gunderloy)
  • Thinking in Bets - I didn't have too high a hope for this one: a book on how to make decisions written by a professional poker player. I expected some variation of "know your opponents and learn how to bluff." Well, I was wrong, and also pleasantly surprised. Annie Duke has a lot of things to say about making better decisions, chiefly by trying to avoid some common mistakes (like depending on hindsight or wishful thinking) with the help of friends. She pulls together everything from John Stuart Mill to the poker table to make these points, and it's an engaging read with a lot to think about in the end. (Reviewed by Mike Gunderloy)
  • The Toilet Paper Entrepreneur
  • Turn the Ship Around!: A True Story of Turning Followers into Leaders - Marquet was a successful captain in a nuclear submarine, which is a rather more high-pressure job than most of us have. He credits his success to pushing decisions down the chain of command as far as possible, and has gone on to a consulting career promoting this "intent-based leadership" idea. The book is an easy read, taking you through the (poor) state of morale and performance on the Santa Fe when he took over to the better state he left it in. One nice thing is that he calls out his own missteps and failures, as well as his successes, while boiling his experience down to small chunks. The questions ending each chapter provide a good set of topics for any budding leader to reflect on. (Reviewed by Mike Gunderloy)
  • Why Leadership Sucks
  • Your Oxygen Mask First: This one is from an executive coach, and largely directed at executives so busy that they need a short, no-nonsense checklist of things that they should be doing (or that they should stop doing). Despite that, Lawrence is big on making sure you have a life outside of work, as well as at driving hard while you're working. I'll likely read selected chapters a second time, paying attention to the end-of-chapter exercises as I do so. (Reviewed by Mike Gunderloy)

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