Finding the Career Path for You

Joey Lei

Sr. Product Manager II at HashiCorp



Many people think of a career path moving in one direction: from an IC role to a manager and then an executive. Many career paths do end up this way, but as I was executing my career path, I found that a linear ascension won’t always yield personal and professional satisfaction. In fact, I had to pivot through different roles to get where I wanted to be. It is my belief, pivoting through different roles is what offers the highest level of advancement for a product management path.

"A linear ascension won’t always yield personal and professional satisfaction."

Several years ago, I was a successful product manager who transitioned from a product development & engineering career path, and successfully led execution of a product roadmap. I identified my personal interest and goal was to build an idea from conception to launch.

At the time, I believed that I needed to be at the top of an organization to become strategic and paint the vision for the company’s core products, so I found an opportunity to translate my experience and transition into a product management leadership position at a smaller company.

As a PM leader, I was accountable for creating a vision, defining a product roadmap, and delivering results with a handful of reports and across a broader cross functional team. However, I found I had added more additional responsibilities that did not put me on my course to personal satisfaction. I found myself overwhelmed with additional unplanned responsibilities.

Actions taken

I found that 90% of my managerial job was managing expectations in and outside my team. Some call this, “managing up, down, and laterally.” Some call this “office politics.” Some call this “alignment.” It is 100% necessary in a leadership role to be empathetic to the needs of others as well as your own team, and negotiate limited available resources towards your objectives.

"90% of my managerial job was managing expectations in and outside my team."

Although it was an important role where I indeed learned a lot about servant leadership, it actually wasn't my desired goal with this position. Originally, I had wanted to focus on leading a team to build a technology strategy and utilize emerging technologies to build products and services that met underserved customer demands. Turns out, I found I was more interested in the “build and innovate” aspect of product management.

I concluded that I was in a constant divide for time between my own aspirations and the expectations of the role, and I couldn't enable success for myself and my direct reports. I felt that I had bitten off more than I could chew, and it was inhibiting my job performance. Ultimately, I made the decision to downsize to a smaller scope. My transition to a smaller scope involved me moving into an individual contributor (IC) role where I could let a more seasoned product management leader manage the company’s organizational interests and allow me to focus on technology innovation.

Looking back, what I recognized in my career path was that taking the leadership role was 100% necessary. Often, the leadership position will give you more opportunities to expand your skillset than can be found in an IC path. So if you are facing a decision to take a leadership position or a higher IC position, evaluate not what looks better, but what will offer you a unique learning opportunity, put you in a position to deliver high impact, and give you ample opportunity to explore and challenge yourself.

Lessons learned

  • Transformative success requires trying out different career paths. Like any product, measuring your own personal success metrics (ie. happiness, compensation, feeling of accomplishment) are essential for you to know if you are on the right path.
  • Don’t mistake this for being conservative. It's hard to obtain transformative success staying in one path. Unless you take additional risk, for example, consider taking more ownership than what might be realistic. However, this is a fine line because you won't be successful if you take too much or too little ownership. Be sure to measure success/failures and pivot before or when you’ve reached a threshold.

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Joey Lei

Sr. Product Manager II at HashiCorp

Leadership DevelopmentCommunicationEngineering ManagementTechnical ExpertiseEmerging TechnologiesCareer GrowthCareer ProgressionSkill DevelopmentIndividual Contributor RolesLeadership Roles

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