I've long found myself unsatisfied with the conventional discourse of what leadership is supposed to look like in Silicon Valley technology companies. These best practices are typically oversimplified into two high-level philosophies on leadership.
The first philosophy is often characterized by first setting an overall vision; then coming up with mutually agreed upon goals, often in the form of objectives and key results (OKRs), and holding teams accountable to those results; and finally delegating and getting out of the way to allow the team to perform. Folks who subscribe to this philosophy often talk about making yourself as redundant as possible as a sign of success in the process. Fred Wilson shares this mentality in how he describes the role of the CEO of a startup:
A CEO does only three things. Sets the overall vision and strategy of the company and communicates it to all stakeholders. Recruits, hires, and retains the very best talent for the company. Makes sure there is always enough cash in the bank.
In stark contrast to this approach, the second philosophy is exemplified by the leadership style of the late Steve Jobs. It's a benevolent dictator mentality that has the leader at the top leveraging their own incredible and unique abilities, taste, and judgment to call the shots and make the most important decisions. They are often leveraging their teams as the execution arm of their will. And while scaling is the typical challenge to this approach, they solve for it through a maniacal focus on the very few products that really matter. Elon Musk and Mark Zuckerberg are also often described as leaders that exemplify this very leadership philosophy.
These two leadership approaches couldn't be more different from each other. Yet both suffer from serious shortcomings. Given this, I've always been fascinated with alternative or more nuanced approaches to leadership that could potentially provide a better way. Keith Rabois encouraged me to read The Score Takes Care of Itself by the late Bill Walsh to learn about another such way. It turned out to be a fantastic read in which Bill Walsh shares unique insights into his leadership approach from his time as head coach and general manager of the San Francisco 49ers. It provides a compelling model for tech startups today and I wanted to share my three biggest takeaways from it.
Listen: SoundCloud | PMLesson
Original Essay: 5 Paths To Your First Product Manager Role
I was recently invited on the PMLesson podcast to share the 5 most common paths to landing your first product management role. We discussed each of the following ways to break in as well as best practices for each path to increase your chances of successfully making the leap.
- The computer science graduate
- The engineering undergrad + recent MBA graduate
- The adjacent role
- The entrepreneur
- The domain expert
Video: The Style of Product Management
Slides: The Style of Product Management
Essays: The Art of Being Compelling | Engaging in Product Debates
In January I was invited to Atlassian to share my wisdom on product management with the global product organization. I decided to delve into the style of product management, covering some of the critical soft skills that are so crucial for the success of product managers. I dove into the art of making a compelling argument, a task a product manager does every week in their role, whether it's with peers, R&D team members, executives, and more. I shared 6 specific style techniques that can be used to make effective arguments. I also dove into how to engage in productive product debates, which product managers also often find themselves in. I talked about how to make these discussions effective, fruitful, and ideally enjoyable instead of how dreadful they often end up being.
Video: What is Product Management?
Slides: What is Product Management?
In January I was invited to the UserTesting Sales Kick-Off in Napa Valley to give a keynote on product management. This was a far more foundational talk compared to many I've given in the past, really trying to establish what the role is all about for those just starting to get familiar with it.
I set out to address three key questions in this session:
1) Where do product managers fit in the R&D organization?
2) What do product managers do?
3) How do product management roles differ?
Listen on: Mixergy | iTunes
I got a chance to sit down with the famed Andrew Warner of Mixergy, who's shared the startup stories of over 1000+ entrepreneurs in podcasts and videos. In this candid interview we cover everything from my entrepreneurial roots, my first two startups, as well as the story of my current startup, Notejoy.