With more than 15 years of tech experience, Andrea Chesleigh has led product teams that are committed to delivering great experiences for consumers. There's a fine line between learning from successful leaders in your field and directly emulating their careers. Andrea outlines the best way to leverage professional mentors in putting the finishing touches on your career roadmap.

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
Array VP of Product and Engineering
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.

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