Teaching the Career Strategy Framework at Microsoft

Mental Model

The person who learns the most in any classroom is the teacher. Passively taking a course or reading a book is the first step. If you want to learn a topic at a deep level, then teach it to others. The challenge of teaching and sharing your knowledge will force you to learn the ideas with clarity to easily explain them to others. Thinking about the questions you will get from your students will identify areas that require further learning on your part.


The person who learns the most in any classroom or teaching experience is the teacher. If you really want to develop deep expertise and stand out as a recognized thought leader, then “teach it”.

You will need to understand the topic or domain at a deeper level. Material and concepts will often need to be synthesized and simplified for others to understand. Your uneasiness with the type of questions you may get will drive you to think about the area where you need additional study. The deadline of an upcoming presentation or lecture will act as a forcing function to accelerate your learning.

An Example in Practice

During my career at Microsoft, I became curious to learn how to demystify managing a career and teach others to do the same. What became a small curiosity blossomed into giving workshops, speaking at events, and coaching people one on one. I learned all of this by teaching it and learning what worked and what did not. Much of what I learned and taught at Microsoft formed most of the content in this online course.

More recently, I am a guest lecturer at the Columbia Business School Executive MBA program for a course in product management. This has been a unique opportunity to synthesize my years of experience into digestible ideas that can be easily understood by students with limited knowledge and time.


1 – Start a blog.

Identify a topic you are curious about – it could be work-related or not.

Write a post on a single idea – keep it short and simple.

Publish often.

2 – Teach a topic via a webinar.

Find a meetup or online community that could benefit from your expertise.

Send an inquiry to the group organizer to get on the speaker list.

Promote a free webinar where your audience visits – LinkedIn, Facebook, YouTube, etc.

Deliver the event and request feedback to improve your next gig.

3 – Teach a class.

Sketch out a curriculum you are curious about teaching others.

Promote your class and secure students on a free or paid basis.

Deliver your content and note areas that require you to up your game.

Use questions from students as a method to refine your material and delivery.

4 – Author an online course.

Think about where you already have expertise but need to go deeper.

Organize and publish your content on an online course platform.

Engage with students to learn where they have questions and need more help.

Adjust and extend content.

Add other related courses over time.

Invest the new income.

5 – Write a book.

Write a free, short e-book that can provide value to your audience.

Use the e-book as a lead magnet to grow your email list.

Identify a theme or topic to which you have unique knowledge to contribute.

Consider self-publishing as a method to author a book you always dreamed about.

Publishing quality, valuable content is more important than perfection.

6 – Present a topic to your organization.

Offer to give a “brown bag” talk within your workplace.

This will show leadership to create a learning culture.

Surprise people with your depth and breadth of knowledge.

7 – Teach via a podcast.

Offer your expertise to a notable host with a following.

Prepare and give your knowledge generously.

Start your own podcast to practice sharing your ideas in small doses.

Post consistently to grow your expertise and audience.

8 – Make something.

Build that something to make your dream a reality.

Create a side hustle to learn by doing.

Teach others how they can make and sell something unique that adds value to the life of others.

Experiment With This

Ease into teaching with something small:

  • What topic(s) do I want to master that I could teach others?
  • Offer to give a brown bag lunch discussion on a topic where you have the skill and would be valued by your colleagues.
  • Write a post on LinkedIn to get your ideas out there and get feedback from others.
  • Record a short instructional video to post on YouTube.

Engage people who share in interest:

  • Teach a live experience to help people learn a craft or skill such as Airbnb Experiences.
  • Contact learning institutions for an opportunity to teach a subject where you have expertise.
  • What how-to or instructional online course could I develop that would force me to learn the content at a deeper level?
  • Is there a domain, topic, or problem space in that I want to become a thought leader?