Recommended Reading – Product Management, Startup Business, etc

Last Updated: 2021-04-02

I’ve added a wide variety of books I often recommend to my PM mentees. I like recommending more than just PM-specific books because my philosophy about PMing is to be more holistic (at least in background knowledge) to make better decisions taking the many different teams’ priorities and best practices in mind. I also recommend these same books to my data mentees because I find it super helpful to have an understanding of how product decisions are made to give more context to the data they’re working with / creating.

For example, prior to one job of mine, my analytics experience originally was just with web. Based on a great recommendation by the an Engineering leader at that company, I slowly learned more mobile development skills to better understand the reasons behind why some things just can’t be tracked or if they are the weird caveats in the data. 

That helped me:

  • PM the analytics product I was helping build much more effectively
  • understand the data I was pulling better (especially any weirdness between platforms)
  • QA the new changes better
  • help the other (real/official) PMs (and the sales, marketing, community, etc teams) better define metrics
  • define and code/implement the analytics events we’d need to implement across all client-side platforms. 

I also learned that understanding at least the fundamentals of how each part works can help me better empathize with and therefore better lead many teams in this cross-collaborative role I was in. (This is especially important when pushing back against people/groups who keep pushing to rush projects but who are further removed from the actual building/process.)

Lastly, I now see a pattern in the books I recommend: They’re often about being “real” and honest about how the product will be built and accepting the reality in order to build effectively while finding ways to push back against cutting corners unnecessarily or setting an unsustainable pace.

Product

  • Inspired by Cagan
    • Recommended by the former VP of Product at one of my jobs
  • The Art of Product Management by Mironov
    • Recommended by a Product Leader at one of my jobs
  • Everything that 37Signals / Basecamp have written:
    • Shape Up
      • Basecamp’s book about their approach to Product Management
      • free PDF copy on their site
    • Getting Real by 37Signals/Basecamp: https://basecamp.com/books/getting-real 
      • This isn’t exactly about product management, but Basecamp’s approach to software dev overall (even way back then) still guides how I approach PMing and product advice I provide to friends/colleagues. I’m highlighting this one in particular because it really gave me a ton of insight into how to really prioritize and also how to approach MVPs and building.
    • Rework
      • Overall notes on how to manage teams and yourself with a focus on autonomy, not stressing people out unnecessarily, not panicking, etc
    • It Doesn’t Have to Be Crazy at Work
      • Felt like this was the sequel to Rework – especially with leading/guiding a product or startup without panic. When the Basecamp dudes were talking about the book pre-launch, they often referred to “writing a book called The Calm Company” – would’ve been a perfect title. But I guess they changed the title because emphasizing to people that it doesn’t have to be crazy is even more important after decades of people just being told work IS crazy and stressful. Breaking out of that paradigm. Escaping Plato’s Cave.
    • Remote
      • I’m very very biased toward WFH/remote because I hate offices and office culture, but also because this was especially useful back then to maintain a lower overhead and allow for collaboration and talent no matter what the location is. Super important / needed now due to the pandemic.

Design

Design Thinking especially UX

  • The Design of Everyday Things: Revised and Expanded Edition by Don Norman  
  • Hooked by Nir Eyal
  • Don’t Make Me Think by Steve Krug  
  • Rocket Surgery Made Easy by Steve Krug
  • Ruined by Design: How Designers Destroyed the World, and What We Can Do to Fix It by Mike Monteiro

Visual Design 

  • 100 Things Every Designer Need to Know About People (Voices That Matter) by Susan Weinschenk
    • But also remember this was made in 2011 so this is a little outdated in terms of design patterns and because this was during web-only times
  • 100 MORE Things Every Designer Needs to Know About People (Voices That Matter) by Susan Weinschenk
    • Another book related to it and published in 2015

Software

  • Mythical Man Month by Brooks
    • It’s an old book, but the overall concepts for managing expectations and being realistic about teamwork still rings true. 
    • My major takeaway from the Mythical Man-Month essay in this collection of essays is that management can’t just go “oh let’s just hire a bunch more people asap to help us hit the deadline.” Realistically, management needs to understand that whether the deadline is successfully hit depends on how early more hiring occurs and also that the whole team realistically needs to slow down a bit to successfully, thoroughly onboard the new team members. 
      • If onboarding is not taken seriously (or at least attempted), then you’re setting up everyone for failure, especially the new team members. 
      • Also, allowing your team to slow down their pace in order to write documentation is a great investment that helps speed up that onboarding.
      • Management needs to have their expectations managed – hiring more people won’t be an immediate increase in productivity. Everyone needs to budget some slowdown time during onboarding so that the teams can then be much faster longer-term without burning out.
  • Code Complete Second Edition
    • I keep restarting this book and haven’t completed it yet because it’s such a massive, daunting tome. So I can’t give an actual “co-sign” for it from personal experience. However, it is ALWAYS in the software development must reads lists and the comprehensive look at software development (what kind of project/product management style to follow, unit testing!, etc) is relevant in a bigger picture view no matter what language or framework is used. 
    • Also from a community/historical perspective, since everyone supposedly reads this, it gives us insight into why devs might make certain decisions in their architecture or workflows
  • Pragmatic Programmer
    • Same as Code Complete 2
  • Designing Data-Intensive Applications: The Big Ideas Behind Reliable, Scalable, and Maintainable Systems by Martin Kleppmann

Business

  • Crossing the Chasm by Moore
    • Recommended in a marketing class I took and also always recommended by both product and marketing people
    • Especially useful for early stage startups because it’s about getting people to adopt a new product/tool/etc
  • The Hard Thing About Hard Things by Horowitz
    • I learned about this book at my my first startup / tech job. I decided to borrow one of the copies that the CEO had, so I could get an idea of what startup founders/CEOs and especially those who eventually become VCs think. 
    • While these kinds of books sometimes read really self-congratulatory, they still do really give interesting insights into the thought processes, prioritization, feelings(!!), etc that founders and VCs face. That has helped me try to not only better understand companies and leadership decisions more holistically but I think also helped me be a more compassionate coworker and advisor/helper. 
    • Shit’s scary, and we’re just doing our best (with caveats w/r/t actual immoral, greedy decisions of course).
  • Lean Startup
    • Everyone always mentions this book, and tbh it’s because running lean and trying to focus on MVPs+iterations really is the way that most startups can best function in an ever-changing landscape and to further their funding runways. 
    • I’m also biased because for many projects/companies I’ve worked on, I’ve constantly reminded management the importance of iterating and just getting an MVP out there first to prove parts of the major changes they wanted to launch – if at least to give a product that has less complexity for QA testing during each release and why tons of complexity in each release means the team has to make sure to regression test even more and that bug fixes are tougher (due to not knowing which of the 100 major changes in this single release actually caused the bug) – so it’s better to iterate and test and iterate and test smaller changes each time to get to the big major change safely coded and thoroughly tested
  • High Growth Handbook: Scaling Startups From 10 to 10,000 People by Elad Gil

Misc

  • Saltwater Buddha
    • I’ve been really enjoying this memoir especially with seeing concrete examples (via the author’s experience learning to surf) of how Zen Buddhism and mindfulness practices can help with common new-to-this experiences and also keeping calm under intense pressure(s) you have absolutely no control over. Totally relevant for PMing.
  • Creative Confidence by David and Tom Kelley
    • I’ve started reading this this weekend, and I’m already loving it. One of my design friends recommended it to me because it’s about how to enable yourself to become more creative. David Kelley founded IDEO, which is basically THE design/innovation firm that all UX designers want to work at or be – at least in the Bay Area / Silicon Valley. Tom Kelly is David’s brother and does a lot of leadership work on the various business sides.