Highlights from the Product Hunt AMA with Steven Sinofsky

Steven Sinofsky is currently a Board Partner at Andreessen Horowitz. Through his work at A16Z, Sinofsky sits on the board of Everlaw, Product Hunt, and Tanium. Steven also currently serves as an advisor to Box.

Prior to his work in venture capital, Steven worked at Microsoft for more than 30 years. From 2009 to 2012 Sinofsky was the President of the Windows Division at Microsoft. His responsibilities as President of the Windows Division included maintaining, improving, and marketing Windows, Internet Explorer, Outlook.com, and SkyDrive.

Steven Sinofsky

In March of 2016, Steven joined Product Hunt for an AMA. You can read the entire AMA here. Below are a few of our favorite questions and answers.

Can you give us a story or an insight into what it was like working with Bill Gates?

It was so long ago — that’s always the tough part of talking about it. We were kids so to speak (I was pretty much your age then). So anything I say sounds so weird when I think about it. But it was an amazing experience at an amazing time at the company. I do love to share this story even though it is first person to some extent because it has so much of what can be incredibly fun to be at the right place at the right time working for the right leader http://www.businessweek.com/1996…

What are some of your favorite questions to ask founders at the early stages? From that, what questions do you like to see answered as a startup grows and what do you like to challenge the team on?

I really love to learn the path that founders took in life. I love to hear how they got started in technology, what jobs they had (paid or otherwise), what their family tech scene was like, how cofounders met and more. I think I naturally do this with people I meet anyway but it is especially fun when connecting a story like that to the creation of a product and company.

The most interesting questions are always about scale and growth — there are no easy answers. Well a better way to say that is answers are everywhere, but picking the best answer is where all the fun and challenges can be.

Sinofsky likes to learn about the path founders have taken in life.

What’s something you used to fervently believe that you now see as fundamentally misguided?

Actually related to the Thiel question. I spent a long time deeply believing in the production of documents as a “thing” and how much effort an individual should put into formatting and preparing information (at work especially). Now I am convinced that doing that is almost always misguided and tools should change to reflect that.

What’s one piece of advice you constantly find yourself giving?

Balancing breadth v. depth. There’s a time for depth and a time for breadth. The “advice” (ugh hate that) is not that one is better but to make sure at any given time the right one is being done.

What do you enjoy the most in the process of making a product and why?

I enjoy the full “360 experience” of making a product. I love the genesis moment, the planning, the execution and execution lulls, and the deciding when to release (when the most effort goes into doing the least amount of change). I don’t have a favorite phase and get super excited at each step.

What are the most interesting product trends you’ve observed? One thing I’ve noticed is that new apps are switching over to chat UIs — what do you think about this?

When something becomes big then every app/product/service converges on that thing. Everything looked like a word processor in the 80s, email in the 90s, then a browser, then a photo sharing tool, and now a messaging tool. These things are categories and then ingredients — think of the fact that fancy text is everywhere, you end up “browsing” in most apps, photos are as common as text, and so on. Right now we are seeing this play out with machine learning techniques. I think we will see ML applied to everything and eventually be a key part of everything.

Sinofsky believes one of the next big tech trends is Machine Learning. Photo credit to Toptal.com.

I’d like to ask the famous Peter Thiel question: What important truth do very few people agree with you on?

Well I don’t know if it is “important” in any metaphysical sense, but I get a lot of pushback from a lot of people over my views on the transition we are undergoing with computing devices. I’ve definitely held a belief for quite some time that we are undergoing a massive shift and while everyone agrees on mobile there’s not as fast an agreement on what it means for all the other computers we use ;-)