The Career Strategy Framework by James Gray

Edition 2 – Newsletter Purpose

Last week I nervously clicked the publish button on the first edition of this newsletter with no expectations. I was completely surprised by the colleagues who reached out to me after many years. What a gift – thank you! 

This newsletter aims to share ideas influencing how to manage a career and learn from others through the open conversation available in each post. It is unlikely you will find ground-breaking research, but my experience is that many of us lose touch with actively managing our careers in the hustle and bustle of a work week. Consider these editions as reminders that spark an action to invest in the essential product of your life – you.

For colleagues who remember me from my Microsoft days, they know this topic of career strategy, and advocating for colleagues to take ownership of their careers is not a new passion. In 2008, I sought best practices for managing a career, sharing techniques with my team members, and a whole-person perspective applicable beyond Microsoft. I concluded after much research that there were so many topics that a framework to pull and organize ideas together would be valuable. My curiosity led me to stub out the Career Strategy Framework with seven core ideas that have surprisingly stood the test of time:

  • 1 – Know Yourself
  • 2- Target the Unique Opportunity
  • 3 – Plan the Journey
  • 4 – Learn Continuously
  • 5 – Sell the Value
  • 6 – Connect Intentionally
  • 7 – Decide Consciously
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Running a career strategy workshop at Microsoft in 2015

Throughout my years at Microsoft, I had the opportunity to run workshops, speak at events and work with small teams and colleagues one-on-one using the framework concepts. Microsoft was a test bed to experiment with these ideas and see how people used them. The many stories and experiences are what I remember from my time at Microsoft. 

When Covid hit in 2020, it was an opportunity to re-assess my path and review the decks and notes I created at Microsoft. Presenting the framework ideas was facilitated through a PowerPoint deck, and it would require me to explain it. This was not a scalable approach to sharing ideas with a broader audience. I used the weekends to begin translating concepts into words to describe the framework. Warning: I am a tech guy, not a prolific writer. I write like I build software products – iteratively in sprints, not fully complete, with bugs (typos, grammar), with new features (new ideas), ideas I may change or deprecate, and with experimentation to improve the product (reader feedback). The Career Strategy Framework is a 15-year-old beta product that spurs my creativity, acts as a forcing function to improve my writing, and spreads good karma that may be helpful to people. It’s an art hobby that I continue to shape.

The framework is a set of mental models with recommended actions to operationalize the strategy. These mental models are not sophisticated AI models, but loading them into your memory can consciously influence your daily decisions to manage your career. You will be surprised that there are often many daily opportunities to use these ideas proactively. As the primary audience, I started formulating mental models as conscious reminders for myself. It’s painful when I go back to read an idea that I did not follow! Generally, we know what we need to do to manage our careers, but we often prioritize other urgent initiatives higher. 

So What’s In It For You?

The core value proposition of the framework is to help people articulate their stories and engage stakeholders to help them achieve their dream. It’s about feeling intentional and confident about your career direction, given that there are limitless choices. It’s about making conscious decisions aligned with our purpose, career, and broader aspirations. The career story can include the following:

  • Clarity around who you are.
  • The talents you bring to your craft.
  • Your value proposition.
  • Aspirations for future roles.
  • Development plans and help needed from others.

It’s simply packaging yourself as a product and engaging investors who believe in your product to support your development and dream. I often thought about what could create more leverage than optimizing the overlap of business needs and employee needs – a simple concept but rarely used based on my experience.

I have seen this work in the wild and the results it can bring for both employees and managers. For example, I worked with a leadership development program within Microsoft where selected employees would tell their stories in front of a small panel of executive sponsors to learn more about their development path and progress. I have seen this work in one-on-one meetings to engage manager feedback and gain support for career aspirations. The simple call to action is that you need to do the work to craft your story. Remember, leaders, are not mind readers. If you can’t articulate who you are and what you want, it’s unreasonable to think your leader or mentors can effectively support your direction. I have seen career strategy plans formulated into various mediums, including decks, docs, and videos.

Would you buy a product if you needed more clarity about what it is, its value, and its brand characteristics?

Challenging Leaders to Up Their Game

The feedback I often got from colleagues I worked with was that managers needed to be more ready to engage with this level of career ownership and create the right environment for collaborative career discussions. If you are a leader, I would like you to consider your approach to developing talent within your organization. Are you familiar with career aspirations and roadmaps? When was the last time you discussed career strategy and coaching with your directs? Are the competencies and expectations clear for a promotion? Have you been able to provide resources to support employee development plans?

Why Spend Time on This

People ask me why I spend time on this topic. First, it’s my responsibility to manage my career and realize the rewards most vital to me. I need to learn how best to do that. It’s a complicated topic that math and physics can’t explain, so I am curious to explain it. Second, most leaders need to improve at creating the right environment and processes to develop talent and seeing an employee as the hero, not themselves. I strive for this to be a differentiator for me. The number one responsibility of a leader is to put the best team on the field and help people grow to create value for the business and themselves. It’s that simple.

Love and Believe

Love and believe in your product. Each of us has a unique value proposition to sell and deliver through our hands and minds. Today’s tumultuous environment requires that you reconfigure your product using existing skills or new skills to position a value proposition that is relevant and in demand. You may be lucky to have multiple products, each with a unique value proposition and buyer. You are the product manager of your career.

Thanks for listening to the back story, and I hope these periodic reminders will help you. I look forward to sharing ideas and having you join the conversation over the weeks ahead.


For people who enjoy reading books about strategy, philosophy, self-help, product management, and career management -> see my online book collection.


Thanks for reading this newsletter edition. Many of us lose touch with actively managing our careers in the hustle and bustle of a work week.

Consider these editions as reminders that spark an action to invest in the essential product of your life – you.