One Kings Lane Product VP on Career Roadmap (Part 3)

In building your career roadmap, it takes time to define your vision and assess your current state. Once you clear these major hurdles, you can start to have some fun and put your roadmap to work. After you go through some soul-searching, the next step is to brainstorm on how you’re going to execute. In other words, this is when you can start to finally ideate.

When thinking about your own career roadmap, it’s very helpful to seek inspiration from those who have made it. Said differently, these are people you admire in your field or have built careers in a way that is appealing to you. Some of you may refer to this as “LinkedIn stalking” – but trust me, it works! You can start by finding people in your network and ask for introductions to begin developing your own resources for professional development.

As you connect with mentors and advisors, be mindful of the following patterns and common themes:

  • Who are the people that I admire? What does their profile look like? For example, what positions have they held and where have they worked?

  • What skills have they developed? Furthermore, what is their personal story and how did they get to where they are now?

  • Based on these learnings, what are the gaps that I need to fill in order to get to where I want to go?

One important thing to keep in mind is to not obsess over the things that you don’t have. Ultimately, you have to walk your own path and set your career roadmap on your terms. You can use insights and inspiration from mentors to provide a guide for your career. However, you should not try to recreate or mimic anyone else’s career roadmap.

Finally, the last step in your career roadmap development process is to compile all of your learnings and to prioritize action items. It’s important to look at all of your findings from a holistic perspective to set your roadmap for success. For example, you can identify three skills to prioritize for development based on gaps in your skillset. To ensure that these skills are fully developed, it’s important to “test drive” along the way to provide opportunities for role play and feedback from trusted colleagues.

Once you have validated these new skills, it’s time to update your LinkedIn profile and put them on display for key stakeholders. Ultimately, the enhancements you make to your career roadmap need to be endorsed by decisionmakers and advisors who can validate your new skills.

In summary, you need to think about yourself as a product. As a result, it’s important to stay focused on your vision and be practical in how you optimize yourself to realize your vision. Along the way, it’s easy to get sidetracked by other people’s career accomplishments. There’s nothing wrong with using other people’s paths for perspective. However, you should never copy someone else’s trajectory and use them solely as learning opportunities.

Most importantly, be fearless and put in the necessary work to execute your vision. In the end, your career roadmap will come to life you stay committed to your goals.

Click here for Part 1

Click here for Part 2

About the speaker
Andrea Chesleigh Boxed, VP of Product and Engineering Member

Andrea is the VP of Product and Engineering at One Kings Lane, a digital-first resource for making your home an expression of your personal style. She has spent over fifteen years in Product and Tech, and has led teams at startups and Fortune 500 companies, including Rent the Runway, Zappos, Time Warner, and Verizon. Andrea is passionate about solving hard (seemingly impossible) challenges, developing simple yet delightful products, building teams of entrepreneurial critical thinkers, and creating strategic outcomes with impact. She is a hands-on leader with a player/coach style, diving into the details with her team to partner, advise, and guide them to success.

Provide your rating for this post
If you liked this post, please use the buttons to the left to share it with a friend or post it on social media. Thank you!
One Response
  1. Thanks, Andrea Chesleigh, for this succinctly condensed and informative piece. It’s practical. And from just spending minutes reading this 3-part article, I got all the tips I’ve been looking for to propel my career without having to take a full-blown course on career development.

Leave a Reply

Read more

One Kings Lane Product VP on Career Roadmap

Building a career road map provides a path for product managers to achieve goals, which starts with building a vision for long-term success

Career Roadmap: Assessing Your Current State

Assessing the current state of your skills will help solidify your career roadmap to leverage strengths and identify areas for improvement.

Product Career: Getting The Perfect Job

Set up your product career for success. Find optimal roles with companies that have like-minded colleagues and opportunities to grow.

Product Career: Leadership Qualities

Every product career is defined by learning from great leaders and applying these skills to generate results on your team.

Product Career: New Challenges For Greatness

Part of building a great product career is identifying new challenges to enhance your skills and expand your ability to create new products.

Product Career: What Are You Good At?

Product careers can be enhanced by employing skills that you pick up from other backgrounds or jobs - including many non-technical skills.

Sign-in / Register for Free

Don’t be left behind in your career. Join a growing community of over 500K Product professionals committed to building great products. Register for FREE today and get access to :

  • All eBooks
  • All Infographics
  • Product Award resources
  • Search for other members

Coming soon for members only: personalized content, engagement, and networking.