Becoming A Leader

  • Join a high-growth company. Growth creates VP-level roles and battlefront promotions like mine.
  • Deliver results. I spent nine months helping to sign a long-term exclusive to the Sesame Street brand, then learned to build, ship and market CD-ROM software that delivered substantial revenue.
  • Embody the culture. The behaviors that a company seeks are articulated by who you hire, fire, and promote. Despite my quirkiness, I was “on culture.”
  • Hire and train great people. Not only does a great team help you deliver results, but odds for promotion are higher if someone on your team can replace you.
  • Demonstrate leadership. There are many opportunities to lead even if you are not a formal leader. Before I became VP, I took on ownership of the Sesame Street relationship and provided direction for how a Silicon Valley startup could work effectively with an NYC-based non-profit.

Be The Leader

  • Leadership. I define this as the ability to communicate an inspired vision of the future.
  • Management. Early in a product management career, these are the skills that enable you to build software in concert with engineering, design, data and marketing partners. As you grow into a leadership role, management extends to hiring, firing and developing talent to build a successful organization.
  • Strategic Thinking. Over time, you learn to define a product strategy that articulates hypotheses about how you plan to delight customers in hard-to-copy, margin-enhancing ways.
  • Pro-active, results-oriented. As a leader, it’s your job to initiate action and change — you can’t wait until someone tells you what to do.
  • Culture. A distinct, well-articulated culture makes it easy for employees to make decisions without talking to each other. Great leaders understand the importance of culture, work hard to define it, and are role models for desired behavior.
  • Domain expertise. It’s helpful to have experience with both the product category and stage of a company. (I had a little of the former, and none of the latter, but I am thankful that Greg Bestick saw my potential.)
  • Mission, vision, and brand definition. I learned to articulate these in an inspired way that provided a “true north” for the organization.
  • Strategy, tactics, and metrics. I used these tools to translate vision into action. The strategies articulated high-level hypotheses, the tactics were the experiments, and metrics helped measure success along the way.
  • Organizational design. Beyond hiring and developing teams, I learned to experiment with organizational structures to enable highly-aligned, loosely-coupled teams to work together. There is no “right” way to organize a company, so I experimented with different structures every six to twelve months as we grew.
  • Management systems. I relied on weekly one-on-ones, weekly team meetings, monthly strategy meetings (for each product “swim lane”) as well as quarterly product strategy meetings.
  • Ask “What’s best for the company?” As an individual contributor it’s easy to be partisan, fighting for things that benefit you at the cost of others. I learned to focus more broadly on the needs of the company and its customers. An example: At TLC, I advocated for layoffs in the product organization when it became apparent that the team had grown too large.
  • Make decisions quickly. Early in my career, I agonized over decisions. But over time, I became comfortable making decisions with only 70% of the data, and consequently made decisions faster. Decision-making became easier, too, when I recognized that most of my choices were reversible if I got them wrong.
  • Over-communicate. Given the importance of alignment in an organization, and the fact that most people can only remember 2–3 things, I learned to focus on just a few “big rocks” each quarter.
  • Think long-term. Early in your career, your job is to execute the short-term projects. You learn that executing better and faster will help the company learn faster, and thus succeed. As I took on broader leadership roles, I learned to think further ahead. By operating at a more strategic level, I could help the company “skip ahead” by a quarter or two. And if you maintain a five-year horizon, you begin to learn that it’s possible to do the seemingly impossible.
  • Be you. Personal passion inspires folks. It’s also the most efficient way to demonstrate authority. Over time, I learned to channel my “quirkiness” in ways that helped me to be authentic, but also moved the company forward. An example: early in my tenure as a leader I would figuratively “head out to sea” for a few days then return to the day-to-day work with a manic level of energy. Over time, I learned to temper this behavior so I didn’t drive my team crazy.

Leadership at Scale

  • Put the tough issues on the table. Responding to adversity is critical leadership behavior. You can’t bury your head in the sand.
  • Admit mistakes. Part of the job of a tech leader is taking on risk, so you’ll make many mistakes. Admitting errors helps others to learn from them, too.
  • Be authentic. Reed’s display of humility was very “Reed-like.” Fist-pounding would not have been as effective for him.
  • Inspire through context, not control. Reed didn’t give marching orders. He inspired the team through consistent focus on strategy and metrics, and in this case, four simple words that motivated teams for years.


“If you want to build a ship, don’t drum up the people to gather wood, divide the work, and give orders. Instead, teach them to yearn for the vast and endless sea.”

Twenty-five years after skipping out to windsurf and tempering my manic “out to sea” behavior, I hope that you and your teams will find new oceans to explore — and successfully navigate the inevitable leadership challenges.

About Me

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