I read. A lot. And, I’m often asked to recommend books. For business books, I find myself endorsing the same titles to people all the time. Books that give timeless advice, confer skills never learned, or have insights to deal with our rapidly changing business environments in practical ways. These are ones that made big differences for me in an overhyped landscape of business books.
What makes you effective in modern business environments? What skills were you never taught explicitly in school that you need to acquire? A good education is about learning how to learn. Most people reading this will have that. Most aspirants need guidance and material that is going to help them. This was the basis of my thinking on this list:
- Decision making
- Strategy and execution
- Managing and Delegating
- Managing and Delegating
- Finance (both corporate and personal)
YMMV, but these books had major impact for me and multiplier effects from their knowledge, productivity, techniques, or perspective that changed how effective I felt I was. I applied every one of these in my work in some way so can vouch for them being useful. If you’ve got 90 days at 10 days a book (a fiscal quarter, basically) to deeply read, digest, and apply these (and COVID is giving a lot of people extra reading time), you’ll struggle not to be the better for at least a handful of these.
- Getting Things Done by David Allen
- Atomic Habits by James Clear
- Good Strategy, Bad Strategy by Richard Rumelt
- The Four Disciplines of Execution by McChesney, Covey, and Huling
- Smart Choices by Hammond, Keeney, and Raiffa
- Deep Work by Cal Newport
- To Sell is Human by David Pinker
- Never Split the Difference by Chris Voss
- Radical Candor by Kim Scott
1. Getting Things Done by David Allen
A classic few actually read; even fewer apply. While I think no normal human could live up to Allen’s excellent organizational method, there so many key takeaways anyone can lift, riff on, and easily apply to your own productivity that you will no doubt get something here that will make you more effective.
Productivity gains compound, and help improve all aspects of delivering outcomes. The bonus from this book is despite the busier I’ve gotten over time, implementing the ideas here actually made me a calmer person with less anxiety. Why, I hear you asking? I can trust in my system. Things get out of my head, ubiquitously captured, into the system, and I have high confidence I’m not going to lose them, will review them and will get to them when it makes sense. I don’t forget things, and stuff does not sneak up on me. There’s nothing rattling around my head at midnight, which leads to better sleep, fewer worries, and lets my brain’s mental cycles work on more valuable work.
The three ideas which I think you should take away from the book:
- Ubiquitous capture
- Processing and the 4D cycle
The simplicity of Allen’s system is perhaps one of its strongest hallmarks. The system focuses on ways to deal with the crush of information (and plague the modern information workers). It completely changed the way I think about my email and task productivity (I’d also mention this epic post by Gina Trepani the former editor of Lifehacker on the Trusted Trio for email. I wrote about how I’d riffed on this and Allen’s system here). This is what I currently employ.
The first element is the idea of ubiquitous capture. Have methods to get everything in one place. Do not use your email inbox for task management (be a big fan of Inbox Zero). Getting everything in one place is harder than it sounds. Email, slack, productivity apps, note taking apps, Whatsapp/Slack/Discord, and hand-written written notes militate against cohesion. Strategies to get everything sorted so you have one Inbox(es) of info you can then apply processing to is harder than it sounds.
Process your inbox with the 4 D (Do, Delete, Defer, Delegate) cycle and move TODOs to an Action folder/tag you will process later. I personally create a TODO item in my GTD app Inbox that links back to these. For delegations and deferments, assign and put a deadline to them (in my system I put a Chaser date on these) though David Allen who used a paper and folder baed system called these Ticklers for things he would do in the future. I personally separate out deadlines and scheduled tasks from Someday/Maybe tasks I assign an ISO week to and review in that week. It sounds more complex, but effectively consists of those three: Capture, Processing, Ticklers.
Match this with a simple, modern productivity app like current industry-darling Notion, Taskpaper (which I used formerly and still think it great), or my emacs org-mode GTD setup and you’ve got yourself modern superpowers.
Getting started and into the habit is the hard part, but once you develop this as a reflex, benefits compound.
2. Atomic Habits by James Clear
And habits is the subject of the next book. This was a new read for me but had a profound effect on my quality of life outside of work (and made me more productive inside of work.). Starting off where Duhigg’s Power of Habit ends on the theoretical underpinnings of habits, Atomic Habits is a practical guide about how to both start good habits and break bad ones.
Pragmatic advice on approach is often wrong; we try to change the wrong things in the wrong ways. Habits can be modelled as a cycle:
I felt the key differentiator in Atomic was actually how he came up for a model of change based on layers. An almost Maslow-esque hierarchy. A three-point idea about outcomes (goals one might say), processes (the actual habits), and outcome about lasting habits and change, identity. It’s this last idea that differentiates the book from a sea of self-help books and its killer idea imho.
- Outcomes - what you get
- Processes - what you do
- Identity - what you believe
Effectively layers of change need to descend from the identity change, not the actual goal you are shooting for (eg. running a 5k or a marathon is not as important about the identity change you actually want below that, that of being a runner. How do you become a runner? By running… etc.). The ultimate form of intrinsic motivation is when a habit becomes part of your identity. I am this, rather than I want this. True behaviour change is identity change. And your habits are embody your identity. You are what you do.
Every action you take is a vote for the type of person you wish to become.
I highlighted passages all over the place, and applied them directly to plans, starts, and fixes. Great book, very helpful. Read critically, and do make notes and try applying ideas. I would be surprised if you saw no practical benefit or upshot in your life if you apply even one idea from this book.
3. Good Strategy, Bad Strategy by Richard Rumelt
Strategy is an abused word. It conjures up near-mythical images of genius CEOs moving chess pieces, or generals commanding soldiers on a battlefield. The capital T truth is that strategy is a woefully underappreciated and anemic area in most companies and far too many businesses confuse tactics with strategy. Worse, companies often make fluffy mission statement and then tick their strategy box and move on to executing poorly.
Why is strategy important? Priorities and decisions. It’s about where you are trying to get to. It helps determine actions and guide execution. Far too many companies lack any strategy. Ask sometime what your company strategy is of a random sample of people. If it can’t be succinctly articulated by at least five individuals the same way then you don’t have one (or it’s so poorly communicated it’s a non-starter ). Clear strategy allows good decisions when you are not around, and is a pillar of a strong organizational culture.
Rumelt has clear guidance:
- Figure out where you want to go
- Have an honest assessment about where you are
- Have a legitimate plan to path from here to there
- Communicate this simply to every person in the org
After that it’s all execution which leads to our next book.
4. The Four Disciplines of Execution by McChesney, Covey, and Huling
When good business books get written, sometimes style and hype gets them lost in the noise. “4DX” has some fantastic ideas that everyone should try to apply (and imho better than alternatives like the Measure What Matters). Unfortunately, the book makes itself out to be a panacea for every problem rather than fixing key issues organizations often have about strategy, prioritization, and course correction. Also, because the authors consult, they gloss over non-happy paths where their approaches may have disconnects. That said, some great, pragmatic ideas to focusing on how to create change and change processes in organizations.
Execution is everything. Companies that do have a legit strategy or are trying to change, go wrong focusing on the wrong things or the crisis of the day, then lamenting Q4 results. 4DX has a process, especially in places with a strong BAU (Business as Usual) culture, that helps new courses take precedence. Focusing on how to get people to action tasks that will drive strategic priorities and results is what this book is about.
Perhaps, besides its recognition of BAU being the biggest impediment to change, it’s key contribution is the idea of lag indicators that happen over time versus lead indicators: What you can do which will have impact and basically let lag indicators hit your strategic targets. I also feel this is a much better system than annual OKR planning which most people poorly understand, is difficult to communicate and coordinate, perpetuates corporate silos, and leads to goal padding.
5. Smart Choices by Hammond, Keeney, and Raiffa
Fundamentally, the quality of your life will get dictated by the decisions you make (and in some cases, decide not to). Any incremental improvement in your ability to make better decisions pays back massive dividends.
Actually, I don’t really like this book, but find it’s the best in a field of titles focused on decision making and essential for people who recognize they lack any sort of process or framework for making decisions in a coherent, logical, balanced way. It’s a bit overly complex so difficult to internalize or communicate to people easily, but as a primer on how to think about decisions and a methodical process for making them I haven’t found anything better. Much like personal finance, separating substance from hype in this area of publishing is hard.
The techniques laid out are good, though the writing is bad. I like to think I have a good decision making process and even I came away with a pair of techniques I had never seen to enhance the way I look at (and especially compare) outcomes.
It’s a bit of a hard slog, but worth the effort if you even pick up one thing to improve your decision making efficiency and capabilities.
6. Deep Work by Cal Newport
This title has a simple premise: most people are doing unproductive “busy work”. Being able to take time to do deep, critical thought work is a super power. In fact, as you get into higher management, one of the biggest challenges (I find) is to carve aside time to think deliberately and deeply about issues, resolutions, and actions to move challenges forward.
Deep Work advocates techniques for finding time by controlling calendars and interactions better. Counterintuitively, applying it made me vastly more productive at my last company (and made me think taking my role remote to be more remote and de-emphasize a litany of low-value meetings and administrivia.).
I’m surprised putting Deep Work in here but the fact is, it had impact. And resonates. Most of the successful people I know struggle as they move up. A they get too busy, it becomes harder to get actual work done that isn’t giving or receiving information (emails, meetings, calls, docs).
Possibly difficult to implement. I found a lot of pushback to having a Deep Work day for myself at my last company, and even more so when I advocated it for my senior leaders even though their roles' success was heavily reliant on producing results only possibly with deep work. Old style companies still have a butts-in-seats approach to management in a lot of places. Much like remote work, it needs to change.
7. To Sell is Human by David Pinker
Until I actually closed deals and forced into the role, I had a dim view of “sales guys”. Now it’s much, much more nuanced between good sales people and bad sales people. Pinker explains the difference, and why change is shifting sales people to have to be good and on the side of the customer.
The fact is, everyone sells. If you think of sales as getting someone to part with resources for something of value, we all do it. In jobs, with friends, in school, even kids with parents. If you’ve ever seen truly talented sales people close deals, they make it look effortless. But it’s not (trust me). The conception of sales as a slightly shady, used-car type negotiation where someone is the loser and someone gets ripped off has changed. Good sales people solve problems for the customers and get compensated for that solution.
Why is this shift happening? Transparency and better information. The internet has created information symmetry in a formerly lopsided game in favour of the sales person. People are better informed and have as much knowledge of pricing, deal structure, features, liabilities, and benefits as most sales people.
This means there are new ABCs of selling:
I think Pinker does an amazing job here helping you think about how you should think about Sales. And about what you need to do to be more successful at it. Of all the “sales” books I read while I was actually handling business development, this was the book I found the most helpful.
8. Never Split the Difference by Chris Voss
Negotiation, much like decision making and selling, is one of those underrated core skills that affects the quality of your business and personal life. One of the key lessons to learn is that many things that do not look like a negotiation often are.
At some point, deals get down to negotiating. The old school way of doing this laid out in MBA-school classics such as Getting to Yes; make win-win deals, what is your BATNA (Best Alternative to a Negotiated Agreement) etc provide sensible, logical, rational frameworks about how deals should be made.
Humans don’t work this way. Rational, Economic Man is a game-theory myth since behaviour, culture, and impressions of fairness often trump outcomes academic theories predict.
Chris Voss was a lead hostage negotiator for the FBI and an expert in figuring out how to negotiate high stakes situations for positive outcomes. Lives were often on the line. His book is revelatory and packed with good advice and techniques to understanding sides, determining what is counterparty-important, de-escalating, and using techniques such as mirroring and labelling to help arrive at positive outcomes. Much like Pinker’s To Sell is Human, I feel this book helps you understand how you should be looking at things like negotiations to help arrive at better outcomes.
This book is not some academic treatise, but a practical handbook and toolbox of what has worked in real life negotiating situations. More tactics than strategy, but packed with effective tools and techniques.
9. Radical Candor by Kim Scott
Scott is famous for creating the Learning to Lead at Apple program and also priming Google on how to have its people lead talented people.
While I feel the book is slightly “Silicon Valley” there is great material in here you can use if you have never had to think about career progression for your people or organizational design.
As an example, her three-conversation, lightweight framework on career conversations, I stole almost wholesale and applied to great impact with my teams in my last role (our HR department had no framework). Key thing here is to take away ideas that will work in the context of whatever business culture you are operating in to make it better for both your people and the company.
Overall, an enlightening read though what I really want to see from Scott as a sequel is a guidebook on how to mint leaders and create a “Learn to Lead at …” program from the ground up for organizations that can’t afford a professional People Operations function or are simply not focused on how critical leadership development is for future success as a company.
If you’ve never read any of the books on this list, I’d recommend giving yourself the goal of 90 days and a book every ten days to slam through them if you feel any of the areas I outlined in my rationale are an issue for you. See COVID as an opportunity to focus regained commute time on yourself. I’m also curious to hear from people who think I’ve missed major areas, disagree deeply that there are better books or feel like “Title X” really should be on the list or have issues with the nine I did choose. Would love to hear back from you. You can always ping me via @mention on twitter @awws. I do hope any one of these titles you may pick up ends up helping you out and improving your life.
Some of you will have noticed that I have not mentioned books on Finance and Delegating/Managing. I am going over past titles now to try and pick just one in a follow-up post more aimed at people in larger company roles. I felt all these titles were applicable to anyone in business whether an owner, manager or employee, and small companies or large.