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,” as he performed on a pommel horse. 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 360 flips and 720 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 legs and toes to the ceiling, then concluded, “I get those last three-tenths of a point for the 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 in a straightforward way:
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 required to succeed in the role: the technical skills required of all product managers, and the functional leadership skills needed as product leaders 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 the skills below:
- 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
In interviews, I ask for examples of how a product leader demonstrates their top two skills. I also do a little work to ensure they have all the baseline skills required, especially in the consumer science area.
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 superpowers. 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 naturally 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 and consumer insight
- Build an org: Leadership, strategy; developing 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 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 to work with engineers and designers 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,” my first educational software startup. I had built a successful line of Sesame Street software and now had the opportunity to develop more titles based on the Madeline, Schoolhouse Rock, and Arthur brands. I learned to give up hands-on control, to build a team, and to define a strategy to keep the product organization focused and aligned. And based on lessons from my early days at Electronic Arts, I began to understand the power of culture 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 participate in the definition of the overall company strategy. You also work closely with other functions (marketing, finance, etc.) to ensure cross-functional alignment.
- Build an industry: The launch of streaming 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: it helps to identify which skills you need to develop at each stage, especially if you find yourself “stuck” at one level. Look ahead at 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. LinkedIn analyzed the data for how employees advance to a CEO role, for instance. They concluded that 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. I ran a startup sailing school during a year off from college, graduated as an English major, then joined the mailroom at an ad agency. I eventually advanced to account services (think “Mad Men”), left to join a design firm, then slowly 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 (working at large companies)?
- 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 self-identified as a “starter,” I concluded I was better at helping established startups to 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 we sold “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— a reminder that it’s ok to take time off.
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 is 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. And, in the case of 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 flexible schedule. Note that my current job satisfaction matches my earliest career satisfaction when I was running a sailing school — I love teaching.
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 very worthy use of time.)
You can see the upward trend during my educational software years and the lower rating during my entertainment tenure (EA, Netflix). Also, 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 8, however, I try to figure out ways 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, and that has helped me to embrace a “beginner’s mind,” especially as I made career transitions. Reflecting on my past, I think my job satisfaction begins to dip when my rate of learning slows. For me, this feels somewhat inevitable at or 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 substantially 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 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 working, but I knew that I needed to fulfill both 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. speaker/workshop host outside the classroom
I spent lots of time talking to folks in roles on the list above. But in the end, I learned mainly by doing. Here are a couple of my insights and notable experiments over the last few years:
- I concluded that a CEO role would be a poor fit for me — more on 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 — I wouldn’t know if I were good at investing for 5–10 years. I also felt that the role would not fulfill my social needs: most investors looked like “lone wolves” to me.
In contrast to the early days of my career, I have been much more purposeful about exploring my “forks in the road” to discover what roles suit 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 “best fit” 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 conscious of the notion of a board of directors until I fought my way back onto the playing field after my two-year sabbatical. But 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 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, an Amherst College alumni who graduated a few years ahead of me. 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 the “dollar a year” professor of entrepreneurship 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). I said to her, “I am having 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 for three days a week.” It felt audacious, but it worked.
Establishing Your Board
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 to avoid the same mistakes they have made, 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 are extraordinarily helpful in evaluating the financial potential of startups.
- They are trustworthy. Over time, as personal chemistry develops with mentors, I share my secrets with them, and vice-versa.
- They s 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 more meaningful connection.
- Figure out how you can help them. I have had mentors who wanted to understand better the companies that I have worked for or were interested in domain expertise that I have. 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 do ask for the names of 2–3 people who may be helpful to 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.
CONCLUSION: Get on the Pommel Horse & Take Action
As an aspiring world-class product leader, here are your go-do’s:
- Do the job: Develop your product leader skills. Assess both your technical skills as a product leader, as well as 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. Given that there is no such thing as “one size fits all” for careers, build a board that provides meaningful insight, based on knowledge of you and 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 that you can 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 the article 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.
Some of my other related articles on Medium:
Visit www.gibsonbiddle.com to learn more about me, as well as my talks and workshops.
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