Inside the Mind of a Product Leader with Yahoo Sr PM

This week Product School hosted Derek Kwan, former Senior Product Manager at Yahoo and now COO at ReSci, for an #AskMeAnything session. Derek discusses different aspects from his personal experience as a PM, such as analyzing competitive markets, validating success and more.

Derek Kwan Former Senior Product Manager at Yahoo

Meet Derek Kwan

Derek is a technical Product Executive with more than 17 years of experience building and scaling products in AI, marketing, B2B SaaS, e-commerce and BI. He has a proven track record going to market with successful products in different companies and he is proficient in turning underutilized assets into successful products.

Derek on His Career and Personal Experience

How was your journey in becoming a PM?

My journey to PM was a little all over the place, and I probably wouldn’t recommend it even if it eventually had a good outcome. I honestly didn’t know what I wanted to do for a while in my 20s, and bounced around various jobs. As I started to get more career focused, I went from Analyst to QA to reporting developer and then to product management. This long and winding road absolutely made me a better PM as I got so much exposure to other areas of the business. But these days, there is so much information and education out there that you can just kind of learn things that way and then go for jobs.

Poker possibly doubled my capabilities as a PM, and you can read some of that in “Build Startups like a Poker Player”.

What’s the most controversial PM-related topics you have come across in your career?

I think waterfall vs agile is certainly a controversial topic, as everyone seems to have a very adamant opinion about what is best. Prioritization that leaves behind a lot of tech debt can be controversial, as there are no hard rules or perfect answers on how to balance those, it’s highly dependent on the organization and company goals. Depending on how you give feedback to others, those can get controversial too. But your job as a PM is to navigate all of these situations elegantly and professionally, and lead where you may have no direct authority. That’s the job.

What are some of the overlaps when working with a Scrum Master?

I have worked at big companies where I can lean on Scrum Masters, and worked at startups where I need to be the Scrum Master. Overlap abounds in PM, PJM, SA, and a bunch of other new titles that have come up in the past few years that are frankly a little confusing to me. But generally, product managers should be focused on users and solving users’ needs as their core responsibility. Scrum Masters ensure organization. efficiency and progress in projects. Product managers can’t ignore those things, but can lean on good Scrum Masters to handle it and do their best to support them. Scrum Masters should still be knowledgeable about the product and users on which they are managing projects.

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Understanding Success, Strategies, Algorithms and the Competitive Market

What frameworks do you apply to validate the success of a new product? How do you assess if a new business opportunity is better than the existing product at your company?

Generally, you want to take some time to learn “analytics”. Having a good sense of how data works will then help you make decisions around KPIs. Learn databases, learn a little SQL, and at a minimum, understand the inputs and outputs of systems. From there, KPIs can be situational, but they are a blend of measuring user behavior, some type of conversion metric, and company goals.

As an example, working on a feed in a social media app would include measuring things like time spent on feed, likes, comments, shares, clicks, bounce rates, etc. Building a SaaS reporting feature might include things like page visits, number of reports run, and help desk complaints.

For new business opportunities, you have to account for a number of factors: revenue impact, level of effort, strategic alignment, urgency, risk. After objectively scoring feature A vs feature B, you can arrive at some conclusions. But sometimes, your product instinct may have to override that analysis. No one ever asked for an iPhone.

What are the things to look out for when defining Go-to-Market needs and strategies in specific countries? 

At the end of the day, it’s always understanding your users first. How do users in a different market behave vs another market? Maybe there is way higher penetration of mobile devices. Or extreme lack of high speed internet. Or government regulations that may restrict your entry.

But I would recommend starting with opportunities before you start thinking about how an idea may not work. Everyone thought Uber and Airbnb would never work when they first got started.

What things are mandatory in keeping a product innovative?

You have to solve problems for users 5-10 years in the future. Close your eyes, think about what the world looks like in 10 years, and ask: what’s missing? What problems are users facing now?

Don’t only try to address things they are asking for, but think about how you can make their lives better in ways that no one is thinking about.

Also note that many many innovators and contrarians and slightly weirdos. If everyone thinks your idea is great, it might not be that innovative. If everyone thinks your idea will fail, you might be onto something.

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How do you attempt to remove human bias in the design when creating algorithms for ML/AI products?

In general, ML / AI will give you optimal outputs for specific things. But domain knowledge and business rules have their place to make those outputs useful for users. So generally you should start with fewer rules to let the AI / ML provide optimal outputs, and then tweak things as you go to improve the performance and usefulness of your algorithms.

When working with highly technical products, do you often have to study the technology yourself to make communication with the team easier? How deep should PMs technical understanding be in your opinion?

Absolutely. Your first 30 – 60 days of any PM job should just be consuming yourself with learning your users (talk to them!), learning the tech, and learning priorities. At a minimum, you need to understand the inputs and outputs, but knowing that you need to translate business needs into technical requirements, and technical concepts to business users, should give you some useful guidelines on how deep you need to go.

Has there been a time where you needed to make product decisions where there wasn’t a clear competitive landscape? How did you navigate these waters and drive successful decisions?

I guess not really personally, but just remember that you are trying to solve user problems the best way you can. Leaning on competitive analysis is important to see what others are doing, but don’t let competitors build your products for you, or you will just build commoditized products. With that in mind, you probably don’t need to sweat competitive analysis for opportunities with fewer competitors, but sometimes that is a signal that the opportunity (today) is lower demand. But build for the future!

When building products, how important is it for you to compare with competitors? Do you invest a long time checking what features they have?

While this is necessary, I would certainly put the importance below understanding your users deeply and thinking through the best ways to solve their problems. This method tends to breed more innovation and avoid commoditized solutions, as well as “chasing your competitors”. Just note you don’t need to reinvent the wheel on everything though.

What do you do when there is limited or no data available for a particular project?

I’m going to answer this question by posting one of my talks for Product School! “Being OK with Ambiguity”.

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What strategy do you use while making conscious decisions to build products when different customers ask for different solutions, such that this also convinces all customers?

One big thing that all PMs can learn to do better is saying “no”.  

But generally, you need to score all of your features for a range of things, like revenue impact, strategic alignment, user need, urgency, risk, etc. This type of objective scoring will take into account a number of factors which can help you more accurately select what to work on.

At the end of the day, you want to build things that work for the most amount of users. But you can get creative with features sometimes and “kill two birds with one stone”, and often you can solve some user problems in a slightly roundabout way that is better than nothing. So the decision doesn’t always have to be binary.

Recommendations for a Successful Career

Any book recommendations? 

  1. Cracking the PM Interview
  2. The Design of Everyday Things
  3. Zero to One
  4. Build Startups like a Poker Player! (my book).

You might also be interested in: The Product Book By Product School.

How to ace a product manager interview? Any tips or important things to focus on?

I would recommend the book: Cracking the PM Interview, not only for interviewing, but just for understanding product management in general. It’s an amazing resource. There is also a great YouTube channel called “Exponent”, which does mock interviews. 

Product School also has a wide range of great videos from PMs who give great interview tips. In general, don’t jump right into answering questions without clarifying the problem, laying out your approach and strategy. And always focus on users!

You might also be interested in: The Ultimate List of Product Manager Interview Questions

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What do you think it takes to be a great PM? Is the combination of Data Science, ML & Product enough to be an end to end product manager something still missing?

The best PMs are extremely user focused. They understand the big picture and strategy of what they are building and why. They are extremely execution driven and can move dependencies along quickly to get things done. And they are quantitative in measuring success.

Knowing ML is useful if you’re going to be working on ML products, but I wouldn’t say it’s a requirement. Focus on the broad range of skills first, and then narrow down what you actually want to work on.

Thoughts on PMs moving across industries? What should be the focus in how they present themselves?

I think PMs moving across industries is absolutely necessary if we ever seek to innovate. Those that have been doing the same thing for a long time will often develop blind spots, and expect things to work “like they always have”. People coming in from the outside with a certain amount of ignorance for history will come up with those off the wall ideas that can sometimes lead to big innovations. But never excuse yourself from learning about those users and that history.

Then there is the problem of getting an interview. This one is a little bit tougher as you’re trying to convince recruiters and hiring managers to pick your resume out of the giant pile. Customizing your background (without lying) to target specific roles is always a good idea. Plenty of resume tip resources out there for this.

What advice would you give to a PM aspirant who wants to make a switch in product management space?

This one is tough, as it’s hard to get your resume noticed without PM experience. I would try one of a few things:

  1. Go after internships or something like Google’s APM program. Study study study for these interviews!
  2. Stalk people like me on LinkedIn and ask for help.
  3. Aim for some roles you don’t think you can get anyway, do your best to customize your resume, and write a cover letter to convince them.

All of these will be an uphill climb but you need to fight for what you want!

Want to learn more from experienced Product Managers? Join our upcoming AMA sessions!

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