Hacking Your Product Leader Career
The skills, metrics, and hypothesis-driven approach required to accelerate your product leader career.
A few years ago, I watched an Olympic gymnast deliver a speech, “How to Score a Perfect Ten.” He gave his talk while doing his pommel horse routine! He vaulted onto the horse, did a series of moves, then said, “I get 9.4 points for getting on the horse and executing the required skills.” Then, he launched into a fearless series of spins, suspended himself for a moment, and continued, “I get another three-tenths of a point for embracing creativity and risk.” For his last maneuver, he pressed himself into a full fingertip handstand, stretched his toes to the ceiling, then concluded, “I get those last three-tenths of a point through extension.”
I thought this was a fantastic metaphor for performing the Product Leader role at a world-class level. Below, I:
- list the technical and functional leadership skills required to do the job
- encourage risk and creativity in navigating your career through “career hacking,” then
- describe how I built a “personal board of directors” to get full extension in my career.
- DO THE JOB: The Required Skills for a Product Leader
As the SVP of The Learning Company/Mattel, the VP of Product Management at Netflix, and the Chief Product Officer at Chegg (a homework help/textbook rental company), I have hired, managed, and developed hundreds of product leaders. The job is hard, but I describe the role straightforwardly:
Your job is to delight customers in hard-to-copy, margin-enhancing ways.
As I evaluate candidates, I focus on two separate sets of skills: the technical skills required of all product managers and the functional leadership skills needed to grow into VP-level roles.
The technical skills of a product manager
When I interview a product leader, I ask them to force-rank their capabilities against each of these skills:
- Technical: Strong understanding of technology; work well with engineers
- Management: Light process to build things and deliver results
- Creative: Generate ideas that matter
- Business: Understand how to deliver shareholder value
- Marketing: Package & position ideas so they appeal to customers
- Design: Work well with designers; value simplicity
- Consumer science: Deliver consumer insight via focus groups, usability, surveys, behavioral data, and AB-testing. This is where empathy lives.
In interviews, I ask for examples of how a product leader demonstrates their top two skills. I also work to ensure they have all the baseline skills required, especially in consumer science skills.
The second list, below, outlines the functional leadership skills — those skills required to develop into a VP Product role. Again, I ask candidates to force rank the skills.
Functional leadership skills
- Leadership: Inspired communication of a vision
- Management: Hiring, firing, managing, and developing teams
- Strategic thinking: Developing hypotheses for how to delight customers in hard-to-copy, margin-enhancing ways
- Results-oriented: Proactive, “everybody grab a shovel” attitude to make things happen.
- Culture: Understand how to leverage culture as the foundation for light process & to build world-class organizations
- Business maturity: Great judgment about people, product, and business
- Domain expertise: Experience with the product category and stage of the company.
As before, I ask candidates to give examples to verify their top two skills. One important note: With “culture,” there are two questions embedded in the attribute:
- “Do you have experience shaping culture to enable great decision-making without process?” and,
- “Are you a good fit for the company, given its unique culture?”
If the two lists of skills above look daunting, there’s good news: you don’t have to learn all of the skills overnight. They develop over time.
The Career of a Builder
Most product managers love building stuff. I’ll ask a candidate what they did over the weekend, and they’ll answer, “I hosted a dinner party for twelve,” or “I used my short-wave radio to talk to someone in Vietnam.” These are good examples of creative pursuits from people who love to build stuff.
There’s a natural progression in a product leader’s career, starting with “build something” and culminating with “build an industry.” Below, I outline the steps, along with the skills needed at each stage:
- Build something: Basic design and management
- Build a hit: Marketing & consumer insight. Demonstrate mastery.
- Build an org: Leadership, strategy; develop teams and culture
- Build a company: Cross-functional leadership, company strategy
- Build an industry: Long-term strategy and partnerships
Looking at the list above, think about your current career stage and work examples you’d give to demonstrate your capabilities at that stage.
Here are examples from my career:
- Build something: The first software I built was “Sesame Street: Counting Café” for Sega Genesis. It sold a dismal 400 units, but I learned how to design a game and work with engineers, designers, animators, musicians, and data scientists to build software.
- Build a “hit”: My first hit was “Sesame Street: Elmo’s Preschool,” which was a top-selling software title in the mid-’90s. I learned how to package and position a software title — a full preschool curriculum on one CD-ROM. I also kid-tested religiously to create a simple design that worked for three-year-olds.
- Build an organization: I did this first at “Creative Wonders,” an educational software startup. I had built a successful line of Sesame Street software and then had the opportunity to develop more titles based on the Madeline, Schoolhouse Rock, and Arthur brands. I learned to give up hands-on control, build a team, and define a strategy to keep the product organization focused and aligned. Based on lessons from my early days at Electronic Arts, I began to understand the culture's power to help employees make significant decisions without mind-numbing rules or processes.
- Build a company: I had a hand in building Creative Wonders, The Learning Company, Netflix, and Chegg. As you reach this level — typically a VP Product role — you define the overall company strategy. You also work closely with other functions (marketing, finance, etc.) to ensure cross-functional alignment.
- Build an industry: The streaming launch at Netflix jumpstarted today’s Internet TV industry. This stage of my career required working with partners (set-top boxes, game consoles, and HW manufacturers). I also dedicated myself to the long-term strategy of building a virtuous cycle that steadily grew subscribers, hardware partners, and content.
Another benefit of this “career as builder” model is identifying which skills you need to develop at each stage, especially if you find yourself stuck at one level. Look ahead to the next step in your career and identify the skills you need to develop to get to that stage.
2. EMBRACING CREATIVITY & RISK: Hacking Your Career
The previous list of skills and stages makes career advancement seem linear. It’s not. As an example, LinkedIn analyzed the data for how employees advance to a CEO role. The conclusion: the fastest path to CEO is a winding one — from customer service to marketing to operations to finance — which allows folks to develop the skills needed to provide cross-functional leadership and manage folks in different functions.
My career was a winding path. During a year off from college, I ran a sailing school, graduated as an English major, and then joined the mailroom at an ad agency. I eventually advanced to account services (think “Mad Men”), left to join a design firm, then developed into a marketing leader. After graduating from business school, I joined Electronic Arts as a marketer, then switched to product. Over the next twenty years, I enjoyed alternating success and failure, helping to scale both education and entertainment startups as a product leader.
Framing Your Career Hypotheses
As product leaders, we execute lots of experiments to determine what’s best. We form hypotheses, test them, then create new theories based on results.
Looking back, I wish I had taken a more hypothesis-driven approach to navigate my career. Today, I describe these career hypotheses as “forks in the road” — a series of questions you need to answer over time. For me, these questions would have looked something like this. (I bolded my eventual choice.)
- Marketing Leader v. Product Leader
- Starter (from scratch) v. Builder (help startup with a proof-of-concept to scale) v. super scaler (helping substantial companies get even bigger)
- Education v. Entertainment products
- Marketing v. Product Leader
Over the years, I did test these hypotheses via side projects, by talking with folks in roles that interested me and by occasionally diving into new positions. I joined Electronic Arts as a marketer, then moved into product a few years later, and I loved the role. And as much as I wanted to be a “starter,” I concluded I was better at helping established startups scale. (I’m a “builder.”) As for the entertainment v. education hypothesis, the answer is both — I bounce back and forth between the two industries.
The Right Metric?
If you embrace “career hacking,” which metrics should you measure to evaluate your career hypotheses? Below, I illustrate one potential answer: income. I have graphed my income over time, beginning with the J World Sailing School and ending with my current role as a teacher, speaker, and writer:
The two periods with no income correspond to my two years at business school, then a two-year sabbatical after selling “FamilyWonder” to Sega of Japan. Note that I didn’t get put in the “penalty box” after the sabbatical; my income quickly resumed its growth. It’s ok to take time off if you can afford it.
Another potential metric: job satisfaction. In talking with folks about their careers, one of the first questions I ask is, “On a 0–10 scale, where zero sucks and ten is awesome, what’s your current job satisfaction?” Here’s a graph of my satisfaction over time:
My job satisfaction number bounces up and down and is often the inverse of income.
Self-analysis: My experience at Netflix scored a nine for a long time, but then began to slide below seven. The reality was that as much as I was the right person to help the startup to scale, I didn’t have the right skills to advance the company to the next level. At Chegg, I was delighted to help the company scale and go public but eventually felt bogged down by the slow rate of change in the education industry.
Today, I have exceptionally high job satisfaction — teaching and speaking is a lot of fun, and I enjoy my very flexible schedule. My current job satisfaction matches my earliest career satisfaction when running a sailing school — I love to teach.
Another potential metric: the extent to which your work is “good for the world.” Below is my wife’s evaluation of my work. (She has high standards and is focused on developing novel approaches to treating cancer — a worthy endeavor.)
You can see the upward trend during my educational software years and the lower rating during my entertainment tenure (EA, Netflix). Note the high rating during my sabbatical; during those two years, I spent a lot of time with my two young daughters, tutored at their school, and engaged in other community projects. And today, I have the highest rating for “good for the world,” embracing my role as a teacher and mentor.
“Make it an 8.”
So, what’s the right metric? I find the most helpful metric is job satisfaction. If your satisfaction is an eight or above, things are good. If it’s below an eight, I work to change the job or to develop skills that will make me a better fit for the role. But if six months go by, and my satisfaction is still below an 8, I start looking for my next opportunity, either within the same company or at a new one.
There are a few things that help me to navigate the long and winding road of my career:
- I got good at job-hunting. I’ve begun a new gig every 3–5 years, so I have lots of practice. In some cases, my startup ran out of funding, we sold the company, or I was laid-off or fired — it happens to everyone. Each time I looked for something new, I found the process easier. My job-hunting confidence encouraged me to leave jobs when my satisfaction fell below 8 for more than six months.
- I’m good at learning new stuff. I am not embarrassed by sucking at new things, which has helped me embrace a “beginner’s mind,” especially as I make career transitions. Reflecting on my past, I think my job satisfaction begins to dip when my learning rate slows. For me, this happens at around the five-year mark.
- I’ve been well-supported by a “board of directors” that includes both peers and mentors. These high judgment individuals improved my odds for success when evaluating new opportunities.
The advice I would give to my “younger self?” Be bold. I should have been more aggressive about pursuing my passions earlier. I wish I had experimented more quickly with new ideas via side projects and had been braver about taking on new opportunities when my job satisfaction fell.
My last few years of “Career Hacking.”
Since 2015, I have done my best to follow my own advice. After Chegg went public, I concluded that I didn’t want to take on another full-time product leader role as I had a strong “been there, done that” feeling about the position.
I could afford to stop work, but I needed to fulfill my sense of purpose and social needs — two things that jobs satisfy. Last, I needed enough structure in my life that I would not “bounce off the walls” or drive my wife crazy.
Below, I list my “career” hypotheses — my “forks in the road” over the last few years of my career. (I indicate my eventual choices in bold.)
- Product leader v. CEO
- Full v. part-time role
- VC/angel investor v. board member v. advisor/mentor v. teacher
- Teach in classroom v. talks/workshops outside the classroom
I spent lots of time talking to folks in roles on the list above. But mainly, I learned by doing. Here are a couple of experiments and insights over the last few years:
- I concluded that a CEO role would be a poor fit for me. (More about that later.)
- I engaged in three-year-long, part-time product “Executive-in-Residence” roles at fast-growing startups. These roles kept my skills sharp, provided structure, and fulfilled my social needs.
- I gave 5–10 product leadership talks/month. These talks demonstrated to Stanford that I could teach an entrepreneurship course. In the end, however, I chose to teach outside the classroom where I can iterate much more quickly (v. wait for the next semester to begin).
- I rejected the VC/Angel route. The learning cycle was too long for me — five to ten years — and I doubted that the role would fulfill my social needs. Most VCs looked like “lone wolves” to me.
In contrast to the early days of my career, I was more purposeful about exploring my “forks in the road” to discover what roles suited me best. Today, my job satisfaction bounces between 9 and 10 — hacking my way into a non-traditional career has been very rewarding.
3. EXTENDING YOUR CAREER: Build your Board
Career hacking requires a series of relatively quick decisions to determine the “best fit” roles for you. You need to be self-aware about your skills and what fulfills you, plus you need to evaluate many different roles and industries. Given that no one possesses complete self-awareness, it‘s a bad idea to go it alone.
I wasn’t deliberate about forming a board of directors until after my two-year sabbatical when I had to fight my way back into the career world. At this point, I set up two conversations/day with past colleagues, role models that inspired me, entrepreneurs, VCs, recruiters, and people whose judgment I valued to figure out “what’s next?” In the end, there were 5–10 people I consistently kept in touch with to help identify my career path. You can think of these folks as my personal board of directors.
Here are a few examples of how my board helped me over the years:
- I understood that I needed a strong sense of purpose and enough structure in my life not to drive my family crazy. I learned this from Joel Jewitt, a fellow Amherst College alumni who graduated a few years earlier than I. I met Joel during my sabbatical, and he shared the story of his “retirement” at age 40. He detailed the “intervention” that his young kids and wife staged for him — begging him to go back to work — and this story had a lasting impact on me.
- Irv Grousbeck is an entrepreneurship professor at Stanford. Irv invented the cable TV industry and also graduated from Amherst College — thirty years ahead of me. During one conversation, he looked at me and said, “Gib, can I be honest with you?” After a hesitant “yes” from me, he continued, “You seem too nice to be a startup CEO.” The feedback resonated with me, and in a single moment, Grousbeck released me from the notion that I had to be CEO before my career ended.
- In my last few years of career hacking, it took me a bit to get going. I took a long walk with Patty McCord (former head of HR at Netflix) and said to her, “I have a hard time finding non-traditional roles.” Her reply: “Just tell them what you want.” Shortly after that conversation, when recruiters called, I responded, “I’m willing to take on a product leader role, but only if I can work three days a week.” (I was able to do this with Life360, Metromile, and NerdWallet for a year at a time, starting in 2016.)
I have maintained a personal board of directors for fifteen years. Here’s what I have learned:
- Invest in good times. It sucks when you only reach out to people when you need their help. Do it persistently and consistently — in good times and bad.
- Encourage honesty. Your board’s job is to help you to see your blind spots and to identify suitable vectors for you. Sometimes they need to be brutally honest with you — accept their feedback.
- Listen carefully. I can still repeat dozens of career conversations that fundamentally impacted my career. Your board is there for you — listen to them.
- Refresh/upgrade often. Navigating your career requires different skills at different stages. Your peers and mentors will “age out,” and you’ll need new board members to navigate the ever-evolving landscape of a hi-tech career.
- Seek diversity in both thought and experience. This practice helps cover your “blind spots.”
My board of directors includes both peers and mentors. Here’s what I have learned in recruiting both:
- Reach out to peers for mutual support. Peers navigate issues similar to you and help you avoid the same mistakes and vice-versa.
- Seek peers in similar functions, stages, and companies. Peers in similar roles deliver timely, relevant insight.
- Keep in touch with past colleagues. Make an ongoing effort to stay in touch as you switch from one company to another. LinkedIn makes this easy.
I seek the following attributes as I evaluate mentors on my board:
- Extraordinary judgment. These individuals have demonstrated phenomenal decision-making through ongoing, high-level career success at world-class companies.
- Broad skills & network. I have VCs and CFOs in my network, for instance, because I have found they help evaluate startups' potential.
- They are trustworthy. Over time, as personal chemistry develops with mentors, I share my secrets with them and vice-versa.
- They are candid and caring. Like Irv Grousbeck, my mentors share critical feedback with me because they care about me and my long-term career success. But candor without caring, or vice-versa, isn’t sufficient. You need both.
Finding and developing mentor relationships
The most common question I get about building a board is, “How do I connect with mentors?” Here’s what I’ve learned:
- Don’t ask them to be your mentor. You need to nurture the relationship until, at some point, they become your mentor.
- You don’t get what you don’t ask for. Dare to reach out to people who inspire you via LinkedIn and other resources. One out of ten times, you’ll get a “yes.”
- Strengthen weak links. Mentors can be school alumni, folks who share your interests, or leaders from past companies. Over time, figure out ways to get to know them better to develop a meaningful relationship.
- Figure out how you can help them. I have had mentors who wanted to understand better the companies I have worked for or were interested in my domain expertise. Some of my mentors have even asked me for help finding internships and jobs for their kids.
- Be clear and realistic about what you seek. In the last couple of years, I have targeted professional speakers, asking them how they got keynote gigs or whether they believe writing a book is helpful. Don’t bother with vague questions like, “Know any good jobs for me in SF?”
- Do your research. If a person has written a book, read it. If they’ve produced podcasts, listen to them. These are opportunities to give them feedback — a simple way to begin a mutually beneficial relationship.
- Be both patient and persistent. The people you seek as mentors are busy. Keep your emails crisp, and if you get a response, follow up quickly.
- Know and adhere to business conventions. Understand the mechanics of the two-sided intro, for instance, so that you demonstrate both your discipline and knowledge. Don’t ask for a job in an “informational interview,” but ask for the names of 2–3 people who may help you as you extend your network.
In the long-run, I don’t find much difference in how you develop and maintain peer or mentor relationships — the lines begin to blur. In both cases, maintain these relationships with updates, notes on topics your board may be interested in, or an occasional invite for coffee or Zoom call.
CONCLUSION: Get on the Pommel Horse & Take Action
As an aspiring world-class product leader, here are your action items:
- Do the job: Develop your product leader skills. Assess your technical skills as a product leader and the functional leadership skills required to grow into a VP role. Stay focused on your superpowers to position yourself for best-fit roles, but occasionally “shore up” key weaknesses that blatantly stand in the way of success.
- Embrace creativity and risk: Hack your career. Outline the critical hypotheses in your career, and find ways to test them. You can test hypotheses through jobs, side projects, or informational interviews with folks in roles that interest you. Let job satisfaction be your guide, and consistently work to “Make it an 8.”
- Extend your career: Build your board of directors. There’s no such thing as “one size fits all” for careers. Build a board that provides meaningful insight based on your board members’ knowledge of you plus their perspective on different functions, career stages, and industries.
I will leave you with one final thought — what I call the “2 a.m.” test:
What ideas do you find yourself engaged in at two in the morning? Is there something you are so passionate about in your work life that you can’t not do it?
The answer can provide a career hypothesis to explore and begin to test tomorrow. How might you test this hypothesis via side projects, informational interviews, or by connecting with someone who works in this area? Be bold.
I hope you found this essay helpful, and I’d love it if you could give me feedback on this essay by clicking here. (The survey has three questions and only takes one minute.)
Thanks for reading this 2 a.m. missive, and many thanks to Flori Fischetti, Shaun Young, and Dan Balcauski for their editing help.
Read my daily “Ask Gib” newsletter about Product Management on Substack.
My Other Product Management Articles on Medium:
- How to Define Your Product Strategy
- Netflix’s Customer Obsession
- How to Run a Quarterly Product Strategy Meeting
- Hacking Your Product Management Career
- Leaders Lead
- How to Find a Great Job
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