Jeff Raikes (Microsoft, Bill & Melinda Gates Foundation, Raikes Foundation)

Stories and Insights from a Business Legend

It was such a great honor to have Jeff Raikes join us at SV Icons for dinner this Monday. Jeff was the former President of the Microsoft Business Division and CEO of the Bill and Melinda Gates Foundation, and he now runs the Raikes Foundation. Hearing a wide array of amazing stories from his career and the lessons they illustrated was truly an amazing experience. Please find our main takeaways summarized below.

Key Principles/Lessons:

·      It is good to have a plan but always be open to opportunity.

·      The worst mistake you can mistake is to not make any mistakes at all.

·      Widen the scope of people you think you can learn from. You can learn from anyone: it does not have to be Bill Gates or Jeff Bezos.

·      Hire people with high growth capacity over those with more experience (in most cases).

·      Great product development is about simultaneously exploiting the key advantages of the underlying platform and having a deep understanding of your target customer and market.

·      The best product marketers can simplify their target customer, market, competitors, and product into a powerful one-sentence positioning statement.

Where Are the Biggest Opportunities for Value Creation?

·      The greatest opportunities for value creation are when you have a technology platform shift paired with a business model transformation.

What Makes A Great Leader? 

·      Great leaders are not only excellent listeners but also can distill complexity into a simple message.

·      What makes a great manager in baseball: Get along with people, help players perform at their peak as much as possible, good PR, game strategy, and get along with the front office. This applies to business as well.

How Should You Approach Your Career?

·      Approach your career like creating a business. Build assets, leverage those assets to create more assets, and repeat.

How to Interview?

·      Ask “why” questions in interviews to understand how people think.

·      Ask people to define their positioning statement. How do you differentiate?

·      Suggest pick out a highlight from their life/work experience and see if their eyes truly light up to see if they can get deeply excited about something.

·      Ask what characteristics made you successful and then compare to positioning statement to check for internal consistency.

·      Close by asking what skills you want to develop to become even more successful and seeing if have any questions for you to gauge thoughtfulness.

·      Jeff looks for people with self-awareness and growth capacity.

·      Sometimes, you must be willing to fire a brilliant employee who does not fit well with the team culture despite their high performance. Synchrony matters a lot.

How Does Jeff Approach Philanthropy?

·      Jeff practices catalytic philanthropy.

·      The core of catalytic philanthropy is to identify and solve the challenges that neither the public nor private sector will pursue.

·      The public sector won’t try to solve certain issues since the risk seems too high, and the private sector will stay away due to a perceived lack of profits (market failure).

·      By underwriting the risk for innovative interventions, catalytic philanthropists can prove out that a solution exists, enticing either the private or public sector to then invest more capital to scale it up.