I figured I’d write down some of the books I frequently recommend to people in a blog post so I can update it over time and send people back to it. Put vaguely in order of usefulness/importance but don’t expect me to think that heavily. Links to Amazon Kindle (US) listings, but for Australians who like paper books (I usually read the Kindle copy and buy a paper copy if it’s good), I recommend Booko to compare prices.
Keep in mind the one big lesson I’ve learned about business books: if you get through it and feel you aren’t learning any more or it is rubbish, just put it down. Life is too short to read rubbish books – particularly about business.
A fable (fictitious story) about a manufacturing plant, but the principles are hugely applicable regardless. A great reminder on what businesses really are about, whether it’s a ‘startup’ or SME. Great easy and quick read.
The number of people who tell me this is their #1 book in business is starting to get ridiculous. But it’s a good book to introduce you to managing people, and hopefully step back from doing everything yourself.
Another fable, quick and easy to read. A good reminder of the three basic things you can do to motivate your team: set clear goals, give praise, and give criticism – all without delay and overthinking.
As a stats nerd, I loved this book. It gives a good structured way to think about intangibles and estimates and a way to think about quantitative numbers where you do not have all the data (which is … pretty much always).
As a book, it’s deeply on the spectrum and very ‘quant hedge fund person way of living life’, but the book makes some very good points along the way. Don’t take it as a bible on how to live your life though or risk being super weird.
The Rockefeller habits are really more designed for SME-like businesses but there’s a lot of meat in here for anyone. I like his one page strategic plan model and some of his thoughts on hiring and meetings. Like “Who” on hiring practices, this is a very prescriptive book so best read as something you take away the parts you think are most relevant to you.
I like this in particular for its comments on technical founders, but also the focus on building systems and minimising single points of failure (usually the founder). A little bit dated IMO but a lot of people still swear by it. Built to sell is very similar.
Some see this as the biblical tome of startups (I prefer Horowitz TBH). It’s still a good read though.
A bit more of a political piece than anything else, the team behind Basecamp write a good story about how you can do business differently. Good even if it’s just to see an alternate viewpoint to the ‘growth at all costs’ and VC funded model of startups.
While people often don’t think of it, Automattic is actually the biggest remote-only team (I believe!) in tech. A good primer on bigger remote teams and how you can manage them as told through the story of WordPress.
Biographies / business histories
Much like High Output Management, this is one that frequently comes up as people’s favourites. Absolutely worth a read.
One of my favourite tech startup books. Well written and honest look at the early days of one of the Valley’s most famous investors (these days).
Fascinating story, really shows the impact of the ‘reality distortion effect’ that Silicon Valley loves so much. Also god, what a horrible mess.
I quite like this story of Moz. It’s quite honest, and tells another good story of the less-spoken-about path of not taking VC funding and gunning for growth at all costs.
Story of Pixar’s trials and tribulations. Some good lessons on people, but I mostly read it as an interesting history of a non-tech company.
This is one of the histories that I feel is a bit revisionist and indulgent at times, but a good background. I actually think going back and reading the annual letters to shareholders 1997-present is more interesting – you can also read The Billionaire and the Mechanic for the story of Larry Ellis’ obsession to win the America’s Cup – I think it’s in some ways quite a similar story.
Everyone loves Buffett in investing land. This is a cheap combination of the annual letters to shareholders from Berkshire from the start (you can obviously get them for free though!). I actually partly like them and Bezos’ letters much more because of the incredibly good writing style even more than the contents. Both good ways to look at how to write your thoughts down clearly, concisely and persuasively.
Another book that is lessons told through fiction/fables. Good basic primer on change management, and Kotter wrote one of the empirical tomes on change (Leading Change, also recommended). Everyone knows a ‘NoNo’.
Another on change management told through a fable. A bit more personal-change focussed than Kotter’s book.
It can get a little bit repetitive and military-styled (after all that’s the point), but a good book about developing talent. Kind of similar to Extreme Ownership, but that’s a bit more about general leadership than leading change per se.
Goals and OKRs
Big fan. The quintessential book on OKRs – what they are, how to implement them etc.
Another fable (you can see my love of these…). This one about OKRs and how they align teams. Pairs well with John Doerr’s book above.
Marketing / Strategy / Product
Not a book but a blog post (some books should be blog post length…). I think Ben is 100% on the money about this component of market strategy and segmentation. If you’re not a Stratechery reader/subscriber (you should be!), I also recommend most of his Concepts articles.
One of my favourite books about the strategy and customer lifecycle, and gives some good advice on how to get beyond the early adopters. Every time someone tells me their growth is plateaued, I send them to (re)read this book.
I love this model (maybe it’s my inner consultant). Kind of goes well with Play Bigger in terms of talking about category creation, but I find the strategic view of BOS far better thought out.
It’s controversial how ‘right’ this book is, but it’s hard to have a section on strategy in tech spaces without at least one Christensen book. A little revisionist at times.
This is one of those books the HBR tries to shove down your throat but I actually thought it was quite interesting. Alongside blue ocean strategy, one of my favourite theory-of-strategy books.
I found this a lot more relevant to consumer companies (B2C) but still worth reading. Much better than all the growth hacking bullshit published these days.
I like some parts of this book, but it also strays a little into the hand-waving tech solutionism at times. But it’s the best I’ve found on category creation to date.
Suitable for SaaS companies selling bigger ticket items (ACV > $10k), a great read about a very specific system for sales. A+ intro to selling stuff.
More about inside sales (slash sales via inbound marketing / ‘content marketing’), this is the book I recommend to SaaS founders who don’t have their own outbound sales teams (ticket size isn’t big enough)
Human resources / hiring
This gives you a very prescriptive method for how to hire people. I see it as one of the books I wouldn’t quite follow to the exact letter, but for people who like very structured and prescriptive approaches, it’s great.
(I am not a designer in the least, but these are books I recommend to understand a few of the parts of the puzzle).
NB: probably better bought as a hardcopy. Weird to include a book on forms as my #1 design book, but everyone has forms, and most people do them terribly (me included!).
I love books on ethnographic research, and this is one of the best IMO. If you enjoy this book, you should definitely read Chipchase’s Field Study Handbook which gives you a cornucopia of techniques to use.
(Also buy hardcopy not digital). I love Tufte’s approach to designing things like graphs. Love love love. It’s a pretty old book but a great primer on visual communication.
I actually found this a better introduction to UX than Don’t make me think, but that’s probably because it is a bit more about techniques than theory. Worth reading Don’t make me think sometime though.
This is a very nonexhaustive list, but I had to put it somewhere.
This trilogy is fantastic, and I think well worth reading. I really enjoyed it, even if people’s reactions to it are a bit polarising.