Book Review by Jessica Rees: The Hard Thing About Hard Things

Editor’s Note: This is the ninth book review we are publishing as part of our Get Paid to Read contest. Last week, we published You Can Be a Stock Market Genius by Joel Greenblatt which was reviewed by Ronaldo Jenkins. 

This week, Jessica Rees reviews The Hard Thing About Hard Things by Ben Horowitz. Jessica Rees (Gomez) is a serial entrepreneur, public relations and communications consultant with nearly two decades of experience in business. She has worked with celebrity clients, publicly traded companies, venture capital firms, and Silicon Valley technology startups.

If only any entrepreneurial-minded person could call on Ben Horowitz as a mentor, ally, and dare I say, a friend in business. That would be the dream for anyone interested in developing technology and a technology business. Horowitz’s now decade-old book, The Hard Thing About Hard Things, offers at scale a friendly and intimate mentorship around creating a good company, technology, and culture from startup through IPO and beyond. Even if one has no interest in the entrepreneurial journey, I would suggest that the book offers valuable wisdom on developing mature leadership and succeeding as an executive within a Silicon Valley technology company. His book about business is a testament to Horowitz’s current hard-won respect as the best kind of venture capitalist, the kind who knows what it takes to build a business.

The Hard Thing About Hard Things is an autobiographical testament to experience applied, offering frameworks and methodology with personality. Horowitz sets the tone of many of his chapters with iconic rap lyrics from the nineties. His raw admissions help you understand that leadership requires one to grapple with their own integrity while making hard decisions for oneself and those around them. I appreciate the transparency of stress throughout pivotal moments in his entrepreneurial journey. It is a realistic nod to the reality of the extreme pressure a founder/CEO is under, juxtaposed against the victory laps often seen in the media. 

This book covers the practicality of how to structure an organization, hiring considerations for various roles, and the development of executives. In a lot of ways, he articulates how to talk about some of these problems in ways that make them easier to solve, like emphasizing how managers should also train their people. Horowitz puts valuable language on how to build company hierarchies, politics, and how to avoid potential pitfalls. While there are countless business gems in the book, I’m going to highlight three unique insights still extremely relevant in 2024 for both CEOs and executives called management debt.

• What is Management Debt? Like technical debt, management debt is incurred when you make an expedient short-term management decision with an expensive long-term consequence. Examples given were “putting two in the box,”  overcompensating a key employee because she gets another offer, and not offering any kind of performance feedback process. 
• Example one, putting two in the box means having two star employees contend for the same critical leadership role. Horowitz details all the ways in which splitting the role sounds tempting because you believe you can keep both stellar employees by giving them both the roles by putting two in the box. He warns you will be incurring a management debt with a high price by trying to keep both. On the surface, you believe their skill gaps will complement each other, and together they will be able to cohesively steer the department. In his example of an engineering department led by an operationally strong person and a technically strong person, he shows how splitting roles makes every engineer’s job in that department more difficult. The split role slows decision-making and will run into power problems, such as whether one of these people can override the other’s decision. Furthermore, accountability becomes murky. Eventually, as things get busy, those once clear lines will fade, and you will more than likely run a department with two priorities and inconsistent measures for success. Horowitz goes on to explain that in the end, management debt and interest will be expensive because ultimately you will have to put one person in charge of the department. 
• Example two, overcompensating a key employee because she gets another job offer is a sure way to get your entire engineering team to look for outside offers. An excellent engineer gets another job offer that is higher than any salary of your current engineers, including your best engineer. Do you match or let the engineer go? The engineer is working on a critical project, and you can’t afford to look for another engineer, so you match the offer. You save the project, but you pile on the management debt. The engineer will tell their close colleagues they decided not to leave the company because they matched the offer. Now slowly, the entire engineering team will find out that to get a proper raise, the engineers need to seek outside offers and threaten to quit.
• Example three, not offering feedback or performance reviews. This form of management debt is taken on when management feels like everyone is happy and doesn’t want to rock the boat with improvement feedback. It will make the company feel like a big corporation. The management debt for not implementing a feedback system becomes evident when an employee’s performance declines and management is unsure if anyone even told the employee what they should be working on.

In short, Horowitz concludes that often the best, most experienced CEOs pay their management debt upfront by making hard organizational decisions right away. Choosing the person for the role, cutting the project, or implementing the system. 

Overall, Horowitz’s book is a welcoming “real talk” session for the business community. Not only is this book important for its practical advice, but it also colors the historical context of the time that has shaped the foundation of power in Silicon Valley today. He translates his own mentor’s sage advice from the likes of famous business coach Bill Campbell, now known for his own best seller Trillion Dollar Coach: The Leadership Playbook of Silicon Valley’s Bill Campbell. Horowitz also mentions business dealings with other important internet moments at the time, like the rise of AOL, a story AOL founder Steve Case documents in another good read, The Third Wave: An Entrepreneur’s Vision of the Future. The Hard Thing About Hard Things still offers timeless business advice and is a must-read for those interested in the technology ecosystem.