Creating Clarity from Chaos

Question [01:16] What inspired you to start a career in tech? Did you maybe have any family members working in tech when you were growing up?

Chris [01:22] I didn’t have any family members that were working in tech per se. I really had more of a natural interest in business, which eventually led me to tech.

I really love the idea of providing a product or service that helps people. I’ve always gotten excited about the core concepts and fundamentals of business in general. In my late teens and early twenties, I actually had my own company doing event management and production. And we were doing everything ourselves, myself and a small group of friends, and learned a ton through that. I was really sort of operating in a PM style role without realizing it.

And that became the catalyst to being interested in technology and being interested in the tech field in general. And even in that early time, this is sort of late nineties/ early two thousands, I realized that tech was a huge accelerator and we were harnessing the power of email distribution, email lists, message boards, digital advertising…and all of that sort of sparked my curiosity to how technical things work. Which eventually led me down the path to work at a tech company.

Question [02:37] Your background is in software engineering, and then you made the transition to product while you were at Amazon. So what’s it like to transition from one to the other while you’re in the same company?

Chris [02:57] I’d love to talk it through. I think I’ll take it from two angles. There’s my specific path and then kind of general advice that maybe I would give for folks who were thinking about a transition.

My specific path was a little unique, as most people’s are. For me, I started in the product world. I was a product manager at a couple of tech startups early on in smaller companies. I became a PM at Microsoft, had a great time there and learned a lot and really sunk my teeth into product management.

And then I moved down to San Francisco, worked for Amazon music. I was initially a PM, then a senior CPM at Amazon, and transitioned into software development, software delivery management, and then became a senior engineering manager at Uber.

And now up here in Zillow, I’m leading a product engineering group in Seattle. So that was my path and I had that transition point from PM to engineering and then sort of back. But I never really left the product space.

The engineering work that I did was very focused on the product side, very much customer facing features…And I think for folks that are thinking about a transition, then maybe you’re in an adjacent career. I think if you can do it at the company you’re currently employed by, where you have rapport and you have a good sort of understanding of the company norms and the practices that run the company, it’s a much easier transition to make. I found that at Amazon, they were very willing to do internal transfers, and most companies are.

So that’s definitely an option, and we even have some programs here in Zillow that allow folks who are in a completely different career to go through a training program and then start off with software engineers. There’s a lot of these different types of programs that exist at companies. But I think that if folks are considering this, it’s really a matter of stepping back and thinking holistically about what it is that really drives you and what it is that you’re passionate about. What are the times at work that were the most exciting times to you, that you really felt alive, that you felt like everything was firing on all cylinders..and go deep on that.

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What specifically, what was the challenge at that time? Was it a technical challenge? Was it a problem that you were solving? Was it a customer issue that you were fixing? Was it a big launch, and then feeling the satisfaction of knowing that the customers are actually using your product now? And then sort of work backwards from that into what roles are available within your company, or maybe other companies that could allow you to do more of that? Cause that’s when you’re going to do your best work, when you’re feeling passionate and excited about what you’re doing.

Question [09:56] What was your experience when you went through traditional university? Did you leave prepared for a product career or did you have to kind of pick things up along the way as a graduate?

Chris: [10:19] It’s definitely a bit of a hot topic these days, given the extremely high cost of education, and the school debt that so many young people are taking on. So I think it depends, is what I would say. For me it did help in some ways, in the sense that undergrad gave me some time to figure out what I wanted to do. And then I got into a technical MBA program, which helped me. But I would say that’s kind of the slow, and expensive, and less efficient route to get the skills that you need to be successful in a PM or technical role. Everything that’s taught in schools is available online, at a fraction of the cost or potentially free.

And you can typically go a lot deeper online as well. The depth of information that’s out there and the variety of people you can learn from, and that diverse perspective that you’ll get through a lot of online content is something that I don’t think universities match too well these days.

So I think it depends. I think if you’re young and unsure and you can afford it, a university can be a great option. It’s a great environment for learning. But if you’re past your typical college years, or you already have an undergrad degree in something unrelated, there’s so many great options out there, including bootcamps. They’re another really great way to get the skills you need to enter the technical workforce

And that could be a coding boot camp, a product bootcamp, a data science boot camp. There’s a variety of those out there today. Um, in fact, I should mention that I actually took a couple months sabbatical and did a coding bootcamp. I wanted to go deeper on my front end technical skills. I was already an engineering manager at the time. I was definitely different profile than a lot of the folks that were in the program, but I decided, ‘Hey, I want to take some time off and just really go deep and really sharpen my skills.

Question [12:49] What other kind of free kind of resources do you recommend to people who want to learn?

Chris [13:10] Of course in addition to The Product Podcast, I should start there, it’s a great podcast! There’s a lot of great resources out there. I spent a decent amount of time on Medium. I find that there’s a lot of really great topics and publications and authors out there that are willing to share their experience, and can bring a really diverse perspective to a given topic. I just find that to be a really great forum for information and more bite size information as well.

Twitter can be a great resource as well. One approach is to set up a separate Twitter account with just the folks that you want to follow. And you can Google for lists of good product people, engineering people, infrastructure, people…whatever area that you may be focused in, and get a really nice list of folks to follow that way.

And then Instapaper and Pocket are really good applications to save a lot of the articles you may find as you’re browsing and read when you have time.

So those are some of the tools and resources. And then I think books are another great way. There’s a great book summary service out there called Blinkist, which I subscribed to for a few years. It’s a great way to get a digestible version of a business, or product, or technology book in a very short condensed format that you could read in 20 minutes or so.

In terms of full books that I’ve read semi recently, Inspired by Marty Cagan is a great overall end to end product management book. Great way to think about the customer that he outlines there. Meaure What Matters by John Doer is another book that goes through the OKR framework, which is used a lot of tech companies and a great way to set and measure success.

And then finally, what I’d say is another area to really think about as you’re trying to ramp up skills and build some expertise is to do a side project. I think side projects are great way to force you to learn. They also become potentially a big asset for you when you’re interviewing as it’s something to talk about. [Something] that’s tangible, it’s in the world, and going through the experience. And so building something from scratch, whether you’re writing all the code yourself or doing all the design yourself, or outsourcing parts of it, using services like Fiverr and Upwork to get things done and actually building and launching something on your own, becomes a really great way to build skills as well.

Question: [21:47] When hiring, what are the sorts of things that you really look for in an ideal candidate for a product job?

Chris [21:58] Beyond the basic descriptions and qualifications for the role, if I’m interviewing there’s a couple of things I’m really looking for in a PM role specifically. So examples of strong ownership, examples of having a bias for action…being able to work well in a team environment is very important. And then I would say examples of high judgment, which is a little more subjective, but I think this can be in strategy, this can be in roadmap choices, prioritization of features, design choices, product strategy. And I’m looking for examples of how people have been challenged and how they were able to make good judgment calls that ended up being the right decision for the customer or the right decision for the company.

To summarize, I’m looking for people that are problem solvers, people that can deal with ambiguous problems and figure out what needs to be done, how to do it and how to measure if it was successful.

Thank you, Chris, for talking with us today!

We’ll be back next week with Sudha Mahajan from Microsoft, with even more of the latest insights from the Product Management world.