On “The Hard Thing About Hard Things” From a Junior Dev Perspective

I read the The Hard Thing About Hard Things by Ben Horowitz this weekend. I went into it not knowing what it was about other than being a management advice type of book by a VC whom I had heard of but hadn’t read much of. I wasn’t sure what to expect or if I would learn anything useful but thought it would be a fun read and provide some talking points with the project manager at my work who mentioned he was reading it.

The book is geared toward startup founders and passes along lessons and advice Ben picked up on while rising to and working as a CEO. It starts by telling his story briefly of how he worked at Netscape then Loudcloud and Opsware. Once you know his back story he moves onto things he believes CEOs should do, things they should know, etc.

Most of what is written isn’t directly applicable to me, a junior developer at a web agency. However there are a lot of things that I learned that will be useful for me to know not only as my career advances, but also so I can better understand the way senior managers think and operate. I won’t cover everything in the book because that would be exhausting and I have little to add for some sections other than, yep that’s interesting.

It’s very easy for me at the bottom and sitting on the sidelines watching deals get made or lost and be critical of the people involved. As with decisions made by senior employees or the CEO. I only see things from the perspective of the lowly dev and not the CEO. It put things into perspective of how much deeper many issues are that I was unaware of and all the different pieces at work that need to come together to make a startup succeed. The tough decisions that a CEO faces like one example he gave of reverse splitting the stock, laying people off, or selling the company in order to survive is incredibly difficult decision to make and one which has almost no positive ending for someone in my shoes. The CEO has to make the decision that will affect not only myself but all the employees at the company, and everyone affected will remember the decision that was made. That is a very heavy load to put on someone and is difficult to relate to for myself; however knowing what those situations entail is beneficial for me to understand as it isn’t a personal dig towards me when the outcome affects me. The decision is made to benefit the company as a whole.

There were a few times throughout the book Horowitz describes having made difficult decisions and not gotten any blow back from his employees affected by such decisions. One example I will use is the profanity case he mentioned. After his talk it sound like everyone was happy with the outcome because no one complained to him about it again. However I think he forgot the position he was in and why he wouldn’t be likely to hear that again. After the CEO comes out and says they aren’t going to resolve the complaints then it would seems more likely those people would simple just look for different jobs instead of staying there unhappy. If don’t approach the CEO again with the same complaint that doesn’t mean they fixed anything. I haven’t known of a place where people freely air their grievances to the CEO so it seems much more likely the people still upset simple moved on to other jobs or continued on there with some resentment towards Ben. He didn’t give an indication that he later followed up with those people to see if they felt comfortable with the decision.

Another point of discussion I found interesting from my perspective was when his team worked 14 hours a day every single day and later an employee told him that he didn’t mind the relentless workload and demanding schedule. Horowitz felt relieved and thought he did the right thing doing that and assumed this one employee who reached out and mentioned this represented all of the people who did such a thing. He doesn’t touch on the fact that of all the people that were ordered to work this demanding schedule, only one came forward to mention he didn’t mind it. I believe that is called the Survivorship bias. Hearing one person out of hundreds that thrived in that situation doesn’t imply even one other person also enjoyed it. Working those hours for months on end is something I have done and it is hell. I was in my early 20s with no family, for someone with kids it is simple not possible. You quickly turn into a robot or zombie where all you do is go home to sleep then right back to work. It isn’t fun and for a job that demands mental focus you face diminishing returns in those situations.

Several times in the book Horowitz talks about and emphasizes training employees both in an executive level and non-executive roles. He expects people to be hired into roles they can handle but knows you must train them in order for them to succeed in that role within your company as his expectations are different that what the persons previous employers expectations were. Also people that get promoted need training to acquire the skills necessary to move up. When employees fail to do this he takes it as a failure on himself having not provided the necessary tools to allow his employees to succeed. You cannot set high expectations but provide no guidance of how to achieve those expectations.

Ben’s story of raising money to take LoudCloud public while the country was still feeling the effects of the Dot-Com crash was quite intriguing. It’s a situation I tried to put myself in as an engineer there and what their perspective must have been during this time. From stories I’ve read from engineers in SV during that time the job market went from anyone who could spell H-T-M-L had a job to nothing even for experienced engineers. I have to think the employees there were quite nervous and likely quite upset their CEO led them to come so close to shuttering the business. It’s very easy to take things personally and think the person leading you is an idiot or doesn’t know what they’re doing because you only hear about the bad stuff. Like Ben said, “bad news travels twice as fast as good news”. Being an engineer there they didn’t know the massive amount of stress Ben was under trying to raise money to keep the company afloat during such cold times. We don’t see the sweat equity that goes into such big deals since as an outsider all alone at our desks we only hear about it afterwards an it’s usually only news if it’s bad news. The good news goes unnoticed but the good news is what keeps the lights on, however it’s what you expect and is therefore easy to gloss over.

Being an employee who only hears bad news about grave situations you had no idea your company faced is another topic Ben discussed at length. Confronting problems and not waiting for water cooler talk to spread the news is important to keep morale high and politics low. Eventually things get said in passing without the next person understanding the full situation and that in turn gets spread to the next person. Hiding behind obscurity and hand waving serves no one. Attacking the problem head on and making people aware of the situation right away means you can begin working to solve the problem as Ben described. Employees will want to attack the problems like he said, but they cannot if such things are clouded and only partial truths are slowly leaked out.

Constant Feedback. This is one thing Ben described as important for a CEO to do. Rather than saving everything up for an annual review or singling out people on rare occurrences, creating a constant feedback loops allows for people to take suggestions or criticisms easier. As Ben mentioned people won’t stress over the one comment they heard from him because he was constantly giving direct feedback to his employees. It created open dialogue the employees understood was not to be taken as an attack. This is not only important for a CEO but any manager to do for the people under them. If you wait and bottle it up until performance reviews it will become a greater problem and as Ben described in the Sixty Days To Live section, no road block could go more than 24 hours without being resolved because the company could not afford to lose any more time than that.


“’What’s the secret to being a successful CEO?’ Sadly, there is no secret, but if there is one skill that stands out, it’s the ability to focus and make the best move when there are no good moves. It’s the moment where you feel most like hiding or dying that you can make the biggest difference as a CEO.”


That stood out to me because it applies very well to anyone. Being great at what you do is when you are able to push through and not cower when things get bad. This is a situation everyone faces in their lives. You need to be able to make a decision when there are no good outcomes and just push through it. Like the common phrase goes, it’s always darkest before dawn.

The section after that quote is The Struggle. Another great section that is very relatable to people of all walks of life. He ends one section on The Struggle with “You may not make it. That is why it is The Struggle. The Struggle is where greatness comes from.” Everyone goes through tough times in their lives. It’s how you handle those events that shape who you are and who you will become.

Lead Bullets. This section was about having to make not only tough decisions but face the reality that there isn’t always a single answer to your problem. Opsware was getting beat by BladeLogic because their product wasn’t as good. They couldn’t simple pivot or touch up the fascia. They needed to rebuild from the ground up. Engineers face this at a more micro scale all the time. They can fix a single problem to roll out fix (adding to technical debt) but that isn’t a real answer, sometimes you just have to suck it up and rebuild.

A Good Place To Work. Ben goes into a talk with a manager about what the difference between a good place to work is and a bad place. The employee gets drilled by Ben on the differences and how his manager was creating a bad place to work. Being a young developer I really enjoyed hearing what Ben described as a good place to work. Things like: “Every person can wake up knowing that the work they do will be efficient, effective, and make a difference for the organization and themselves.” Knowing that the work I do is not all for nothing and that someone appreciates it is what keeps myself motivated and keeps morale up. At a small company which I work for this is easy to achieve. We don’t have room or time to do useless work or have useless employees. However everyone likes feedback that reassures their work is valuable. If it isn’t useful then it leads to wondering what your purpose is there. That in-turn can manifest into a self destructive employee or division.

Looking forward, I now have some understanding of what managers, executives, CEOs expect of me and what they will expect of me as I grow in my career. Of course I need to continue striving to become a more experienced software developer but there is much more to being a great employee than writing efficient, maintainable, clean code. Having an understanding now of what people at higher levels such as executives and C-suite employees expect out of their subordinates will help me navigate the ropes of my career and hopefully prevent me from stalling out.