Name: Ryan Hill
Role: Senior Product Manager
Background: Ryan is part of the core product team leading Yahoo Mail, where he focuses on growing engagement. With over a billion users, Yahoo is still one of the biggest email clients and continues to work hard to provide valuable ways for people to engage with their email. Ryan is a California native through and through, having been born in Los Angeles and attending school in San Diego. He currently lives in San Francisco. Aside from work, Ryan loves his various hobbies and side projects, such as photography, woodworking, and cooking.
How did you get into the PM field?
When I was younger I lived with my grandparents, and my uncle who was about a decade older would bring home a ton of “cutting edge” tech — which, at the time, was giant brick cell phones with a touch stylus stowed away in the antenna. I was in awe, and knew I wanted to work in the technology space, whatever that meant. As I grew older and started applying to colleges, I assumed that working in technology meant being a computer science major who became a software engineer. However, once I got to college, I had many people who I now consider my mentors (shout out to Don Norman) challenge this assumption by introducing me to options I didn’t even know existed.
Once I knew that fields like design, consulting, etc were potential options, I had a bit of an existential crisis. After trying many different roles, someone suggested I try product management, and described it as a way to be involved in all of the disciplines I found myself now enjoying.
Eventually, I found a product manager at Adobe who tweeted that they were looking for an intern to help for the summer. After a long process and a lot of luck, my reply on Twitter turned into my first product role, and I’ve been in product management roles since.
What skills are important to being an effective PM? How do you use them? What’s the best way to build up your PM skills?
It’s hard to give a satisfying generic answer here, as I’ve met PMs who come from many disciplines, and who gravitate towards companies that are looking for someone with their current skill set. A simple example of this — go browse product manager job listings and you’ll see a top requirement for most roles being “X years of experience in Y industry.” Ultimately the generic skills like writing a good PRD are totally outweighed by expertise in a particular field.
That being said, I think most of the effective PMs I know are able to:
- Understand the breadth of options available to them
- Ruthlessly prioritize
- Communicate complex ideas in their simplest form
I think the best way to build up PM skills is to try to sell a product on your own. It doesn’t have to be complex or even within the technology sphere — I know PMs who sell art, t-shirts, online courses, food, and more. Once you are directly faced with product problems, you quickly run into core PM thought experiments. I’m putting in a lot of effort but not getting results; what is the best use of my time? Will this improvement actually matter? What matters to me (the business?)
I often see aspiring PMs fixate on the idea of user stories and use cases, since most of their life experience is as an end-user, but that’s just a part of the puzzle. Once you switch to the other perspective (and inevitably waste a lot of time,) you deeply understand the balance between things like quality, time, money, and effort, and learn how to consider a variety of options to reach your goal.
What tools do you use most frequently in your job?
I think PMs more so than other roles have an extreme amount of both internal and external work. That is, you are trying to manage your own time, thoughts, priorities, and product ideas, while also managing team communication, tasks, expectations, and more. Because of this, the tool sets you use can be very different for yourself versus the team.
I think if you are in a big company, the “external” tools you use are mostly set. For example, I don’t particularly like Jira, but I am not going to convince the dozens of engineers I work with to use something else, so it is good enough.
Internal tools have a lot of flexibility though. Each person can decide what makes them most effective. I personally love sketching out diagrams and mock- ups (either on paper or on my iPad), typing my thoughts out in organized note- taking apps (currently using Roam Research), putting everything I can into my to-do app of choice (Todoist), and obsessively using my (Google) Calendar to set up both meetings and block off time for focused work.
What productivity “hacks” or habits do you live by?
As your scope increases as a PM, you inevitably start context switching a lot. One minute you are working with engineering to understand the current blockers and what tradeoffs can be made, then you are in a conversation with marketing potentially talking about a totally different feature set or product. To help with the constant multitasking, I really love doing what I call “business journaling.” Much like how many people take time to journal about what they are thinking or feeling that day, I do this in a business context. What problems are important today? What are my unfinished thoughts on a topic? What is currently frustrating the team? When I want to come back to a problem, it’s awesome to re-read my internal dialogue to put me back in the frame of mind to quickly dive deep into work again.
I’m also very aggressive about documenting all my tasks, and making sure that every task has a due date associated with it. For example, when I triage my email inbox, if I can’t reply to the email immediately, I will add it to Todoist with the next steps I need to take in order to reply, as well as put a date and time on it so I will get a reminder and the task won’t get dropped. I hate the feeling of wondering “what do I have to do again?” Because of how disciplined I am with my todos, it takes a lot of stress off my plate. I can trust my to-do list, calendar, and notes to be my second brain.
When it comes to communication, what works for you and what doesn’t?
I love working asynchronously. I would almost always rather have an email thread, slack message, or cloud document than having a meeting. Written communication is great for distilling rambling into a few well thought out points that people can review and consider at their own pace. It also makes addressing each topic much easier as you can refer back to what was written.
Inevitably synchronous communication takes your colleagues out of their focused flow state, and for larger groups, just wastes people’s time as they have to listen to parts of a conversation that don’t require them.
Between the salary, stocks, and administrative costs associated with each employee, let’s average that employees at large tech companies (because really, those are mostly the ones who hire PMs) cost the company $200k per year. That’s about $100 per hour of time per person (and much more for more senior employees.) The next time you schedule something like a daily sync, add up the people’s time as money and ask yourself — is this meeting a worthwhile way to spend a few thousand dollars?
What advice do you have for aspiring PMs?
If you are recently graduated or soon to graduate and are an aspiring PM, I encourage you to take advantage of APM (associate product manager) programs. I keep a list of programs I am aware of on apmlist.com, and I think new grads should apply for every single one. Most programs accept only a few applicants a year, and it is usually quite competitive.
For a sense of how competitive APM applications can be, APM List, which is just one resource aspiring PMs use, had 25k unique visitors and 70k+ unique sessions over this summer. Applying for only one or two programs means you believe that you are at least the top 0.05% of applicants, and I think that’s not a wise opinion to have.
If you have been working for a while and want to be a PM, I hear far more success stories where people transfer internally into a PM role rather than just applying to a junior PM role at a new company. All of the tribal knowledge you have about how your current company works, what the team dynamic is like, and what the roadmap looks like are all great assets that arguably could make someone inexperienced as a PM still a better candidate than an external applicant.
If you apply to be an APM and don’t get a role, it’s ok — work in another discipline at a company you can learn at, and try to follow the above suggestion to transfer roles later on.
What’s the most gratifying part of being a PM? The least gratifying?
To me, the double-edged sword of being a PM is that you get an enjoyable amount of breadth, but often an unsatisfying amount of depth. If you are someone who loves their discipline, whether that be marketing, programming, designing, etc, you will find that you don’t actually get to do those things often (or at all.) A product manager has a much more direct impact on the people who make the product than the product itself. If you deeply appreciate and enjoy your craft, being this hands-off might be tough at times.
What is your go-to jam if you need to concentrate on something?
If I am doing light reading (emails, JIRA tickets, etc) I can listen to songs where the focus is on the lyrics, but if I am writing something more intense like a PRD, I struggle to think of what words to write when I’m listening to someone else say a bunch of different words.
If I need something sans-lyrics, I like artists in the vein of dne, knxwledge, Galimatias, Balmorhea, dvsn, Justice Der, and RAC.
When I need to do something with less deep thought, some of my favorite artists are Frank Ocean, The 1975, Cautious Clay, Remi Wolf, Arin Ray, and Lucky Daye — the list is probably too long to list haha!