My story starting as a product manager at Microsoft Word to becoming an Operating Partner at Costanoa Ventures

I landed at Stanford thinking I wanted to be a communications major so I could be a TV anchor but soon realized there were far more interesting things to study while there. I wound up majoring in Political Science when a professor pointed out I was three-quarters of the way through the major already but found my real passion in Organizational Behavior, which I got my masters in.

When I graduated from college, Microsoft was the best company in the country to work for. I applied while I was in school and got lucky enough to have my resume chosen for an interview. Apparently, my internship at the largest coffee and chocolate manufacturer in Germany caught their eye, and after their tough interview process (which I thought I bombed!) I got offered a product manager job at Microsoft. No other company at the time was willing to hand you as much responsibility straight out of school, and I liked Seattle so jumped at the chance to learn something new.

I wrote about what I felt served me best my entire career in “A Better Way” I always sought another, better way to do what was being done.

When I started I was the most junior product manager at Microsoft, which meant I got the collection of jobs no one else really wanted. In my case, that included overseeing direct mail and end-of-life-ing a soon obsolete Word for DOS. The direct mail team came to me with the last creative concept they’d used asking what I wanted to alter for the next piece. I asked, “Have we thought about interviewing customers who already upgraded to promote their reasons why in their own words?” It was a novel idea at the time. The presumption back then was those in the industry could say it better than ordinary users. “No, we haven’t done that before, but I guess we can interview a few users,” offered the direct mail lead. It resulted in a totally new direct mail piece that was the best performing Wave 4 the team had done.

The guy who handed Word for DOS off told me, “You’re babysitting its end-of-life. You shouldn’t have to touch anything.” But when I looked at its packaging, it was a complicated design which was expensive to produce. I met with the packaging team to see if we could simplify it, got approval, and within months had shaved over $1M in total costs from the product’s bottom line. The guy who had done the handoff asked me, “Did someone tell you to do that?” “No,” I replied, “it just seemed like the obvious thing to do.”

It’s only in hindsight and working with thousands of others in the interim that I realized looking for a better way isn’t obvious to many people nor is being in the habit of challenging assumptions. The world needs all types, so I have no judgment for those who don’t work this way, but I will say for those who aspire to create, regardless of background, skills, or where you apply them, this fundamental way of questioning the status quo is important for creation. And creation is what’s essential for true innovation — which is finding something that is a truly unique, novel solution.

Know that challenging the status quo does not mean challenging reason, facts themselves or doing so merely for the sake of being contrarian. It means taking as a given facts and constraints as they are and pushing for a better, smarter way through them.

So, no matter what you do, ask “Is there a better way?” and just do it! You might be surprised where it could lead you

It is impossible to keep up with everything, but I’m a huge fan of Stratechery by Ben Thompson and Wait But Why by Tim Urban. The range of topics they both write about and their ability to unpack and explain extremely complicated things is unparalleled. And Tim is also very funny; his blog posts both changed my point of view and gave me new ways to gain perspective on my own life, broad industries (like space and solar) aside.

When I interview job candidates, if they can’t genuinely own a mistake or failure, then I don’t feel they are self-reflective enough to adapt and learn quickly. In technology, the learning curve never ends, so this skill is essential. You can never feel ‘done.’ It is really hard to be your authentic self earlier in your career, and you sometimes have to ‘age up’ in how you act. But the more open you can be to learning, failing and being wrong, the faster you will succeed. It is counter-intuitive, but ask questions that reveal you don’t know something. And own what isn’t great. You’ll appear far more mature and people will share more that can accelerate your learning.