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The Hard Thing About Hard Things

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Introduction

I have had this book recommended to me many times over the last couple of years. It generally tends to rank high on book lists, reviews, and recommendation algorithms. I finally had a gap in my planned books so picked it up. This book was unusual in the amount of vulgarity it had, unexpected rap quotes to kick off chapters, and various other little strange things. Perhaps this would have been normal if I had learned more about the author Ben Horowitz before reading.

Memorable Ideas

I'm going to structure this article in less of a summary, and more of a list of things I'd like to remember about the book. In this way if I review this article a few years from now I can use it as a quick reference. The book as a whole was solid, but there were a few keys which stuck out for me most.

Struggle

While working through difficult things (managing companies, saving a company from financial ruin, delivering on difficult projects, etc.) the struggle is the way. Struggle is a common theme throughout the book. Although this feels like a Ryan Holiday-esque cop-out, it's valid and true. Sitting and accepting that pain, agonizing through the hard parts, and not quitting is how you make it through.

In my past I've seen similar things. There were various points in the Software Factory's growth stages where it would have been easier to quit. One point was after working for years to get our new approval process "approved" only to have someone in the UK say "Yes, but it isn't approved globally" despite us including exactly that in the work. It felt like we were starting from scratch and quitting looked like a solid option.

Ben makes a point that great CEOs often will attribute their success to "not quitting" while lesser CEOs talk about their brilliant strategic choices or powerful leadership. This rings true despite it feeling like nothing more than an anecdote.

hard things image

Communication

He talks about how communication is absolutely critical. When in chaos you have to communicate all the time. Lack of communication is a key roadblock to grinding out of a difficult situation. No matter how much you think you're communicating, it isn't enough.

I've experienced this while giving trying to internally evangelize for Software Factory during the first 3-4 years. One year I stopped counting at 150 separate 30-60 minute "show and tell" sessions with people, managers, or teams. In my mind I had said the same words and stories dozens or hundreds of times. I had used the same anecdotes, showed the same demos, and answered the same questions until I could do it in my sleep. And yet... I would end up with new people and teams each week that would ask "Sorry, what's the Software Factory?" It was maddening.

Now I'm experiencing this as a manager where things that are clear to me, and that I feel like I've shared, still end up confused across the team. This idea of over-communicating and sharing more than you think you need to is really powerful.

Peacetime vs. Wartime

He discusses an idea at length related to being a Wartime CEO or a Peacetime CEO. This stuck with me not because I plan on being a CEO (ever), but because taking stock of the business situation you are in should drive behaviors. In the last 5-6 years throughout this phase of my career I've seen both kinds of times. We're currently in peacetime where funding is growing, opportunities for change are abundant, hiring is hard but possible, etc. In these times we need to be looking for smart growth, expansion, and preparing for the next bad time.

Around a year ago we were deep in re-org / transformation. Our team's future was uncertain, growth was impossible, spending was minimized, and the future looked bleak. We had to focus on survival, ruthless prioritization, and doing our best to be efficient and delivery with very little resources.

Having experience from each mode to draw on is really useful. Understanding how and when to switch modes is critical. I'm also constantly thinking of the size of our team and skill sets to determine if I could justify keeping everyone during the next downsize/re-org/downturn.

Wrap-Up

Overall, this is a solid book. It was worth a listen and had a lot of good tips. It was heavily slanted towards people at the executive leadership level and most of the stories were from Ben's time as a CEO. I think most of the lessons learned were easily transferable to various other levels if you looked for them. The three points above are my key takeaways I'd like to have easy reference to and the items I want to keep in mind as I move forward in my career.

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