What was the hardest PM skill for you to develop? Why?

The short answer for me: consumer science and a proactive, results-oriented mindset. For PMs in general: creativity and leadership.

Below, I summarize the product and leadership skills required of a product leader. Then I reveal which skills were hardest for me to develop, along with the skills that most product leaders struggle to learn.

Product skills

  • Technical: Work effectively with engineers

  • Management: Light process to deliver results

  • Creative: Generate ideas that matter

  • Business: Deliver shareholder value

  • Marketing: Package and position ideas to make the product relevant to consumers

  • Design: Work well with design; value simplicity

  • Consumer Science: Insight via qualitative, survey, data, and A/B tests; empathy

Leadership skills

  • Leadership: Communicate an inspired vision of the future

  • Management: Hiring, firing, and developing teams

  • Strategic thinking: Form hypotheses to delight customers in hard-to-copy, margin-enhancing ways

  • Results-oriented: Proactive, do whatever it takes to deliver results.

  • Culture: Good fit; understand how culture provides the foundation for great decisions and enables companies to scale without heavy-handed process

  • Business maturity: Good judgment around product, people, and business decisions

  • Domain expertise: Experience with category and/or company stage

My product challenge: Consumer Science

My communication skills and ability to work well with others make building relationships with technical, design, and marketing partners straightforward. While I have a natural empathy for customers and enjoy qualitative research, I lack the math and statistical expertise to be fluent in AB test design, execution, and analysis.

I have to force myself to learn as much as I can about data-driven decision-making as it doesn’t come naturally to me. Reed Hastings, the CEO of Netflix, once gave me a “Statistics for Dummies” book as a holiday gift. Reed distributed twenty copies, so I wasn’t the only one who needed help in this area.

My leadership challenge: Proactive, results-oriented

It’s hard for me to maintain a proactive, results-oriented mindset. I am very thoughtful and deliberate, but I’m not strong at thinking on my feet. Consequently, I pair poorly with very proactive, results-oriented startup CEOs— we drive each other crazy.

The toughest product skill for PMs: Creativity

Creative skills are a bit binary— you have them, or you don’t. When recruiting, I look for candidates with lots of ideas who love to build stuff. When I ask what they did last weekend, my ears perk up if they tell me they hosted a dinner party, built a treehouse, or landscaped their backyard. If I ask them how to make my product better, they have a long list of ideas.

The good news is that not all product manager roles require that the PM over-index on creative skills, though they are beneficial for inventing new products or launching startups.

I have experimented with “wild duck” creative leaders for all-new product categories and ideas. Sometimes these individuals develop the other product and leadership skills on my list. Sometimes they don’t. But I always find it hard to “train” creative skills, which is why I initiated the wild duck experiment.

It helps to create an environment where folks can comfortably share ideas, and I have successfully given product leaders increasingly challenging projects to help build their confidence and creative skills. As they deliver more impactful results, these product leaders become more confident about sharing and executing new ideas.

A controversial point of view: I don’t think psychological safety leads to breakthroughs. You need a very demanding environment with clear standards and a willingness to raise the bar to accomplish world-class results. (Steve Jobs, Elon Musk, and Jeff Bezos come to mind— all three obsess over details and are constantly raising the bar.)

The toughest leadership skill: Leadership itself

Similar to creative skills, I find leadership to be a somewhat inherent skill. I was the captain of my high school ski team and was an offshore yacht racing skipper at sixteen. I ran a sailing school to help doctors, lawyers, and business leaders to become accomplished sailboat racers when I was twenty. After two months in Alaska, I was nominated to be a National Outdoor Leadership instructor. Through these activities, I learned how to inspire, build and organize teams to deliver results.

During an interview, I ask candidates for examples of their leadership. Answers range from on-the-job leadership examples to running a fundraiser for “Wake up Narcolepsy” or organizing a roadside litter pickup effort. No matter the example, these candidates demonstrate their confidence to make decisions and to live with their consequences— both good and bad.

Leadership is more coachable than creativity. If I have a strong individual contributor who demonstrates the confidence and willingness to lead, I encourage them to focus on the following skills:

  • Always be recruiting. Exec teams give bigger projects to the leaders they know can execute and quickly put teams together to deliver results. During rapid growth periods, I encourage leaders to spend one to two days/week recruiting. When they inevitably receive a battlefront promotion, they have someone ready to replace them.

  • Don’t be fazed by your first-time management experience. You already know how to do your new report’s job. Quickly pass on everything you have learned so that this individual can succeed in the role, too. The faster you groom your replacement, the faster you advance up the career ladder.

  • Be clear about your product vision, strategy, metrics, and the projects that tie to each strategy. This is how you learn to communicate an inspired vision of the future. Thankfully, product strategy is a practiced art.

  • Leaders lead. Learn to put your neck on the line and to offer your opinion when asked— and occasionally when you’re not. If you can’t answer the question, ask lots of questions until you form an opinion. Learn to debate ideas to sharpen everyone’s thinking. (To learn more, read my “Leaders Lead” essay on Medium.)

  • Be you. Everyone is different. The challenge is to be a leader in an authentic way — it shouldn’t feel contrived. This is the area you need to experiment with the most.

Become a “learning machine” and then share what you learn with your team so that others benefit from your knowledge. For twenty years, I hosted weekly sessions on various product and leadership skills. My teaching skills helped me a lot as I hired, trained, and developed talent within my product organizations. To learn more about this, see Richard Feynman and his notion that the best way to learn is to teach.

Be patient. You have 30-40 years to establish your career. In the long-term, anything is possible.

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