Product School hosted Chester Staley, Product Leader at Microsoft for an #AskMeAnything session. Chester answered questions transitioning into Product, how to analyze data, and advice on career development.
Chester is an experienced Product Manager skilled in programming, software development life cycle, data analysis, and user interface design. He is currently working at Microsoft, managing the security implementation and attestation of over 200 individual applications and 40k users. Prior to this, Chester had a long experience at Boeing, starting as a Junior Business Analyst and becoming Product Manager after eight years.
As Product Manager, he led the global development team implementing Robotic Process Automation solutions to Boeing Commercial Airlines Finance and was responsible for comprehensive transformation Executive Council (e.g., CEO) software used to manage and run enterprise operations. He holds a Business Administration and Information Systems degree from the University of Washington and an MBA from Seattle University.
What’s the best route to get into business/operations/supply chain Product Management at Microsoft. What are your suggestions for someone just starting out?
I’ve always found that the best path to success for moving functions is doing projects outside your current RAA. Several of my Product Management roles were instigated by my participation in either hackathon-type events or special projects.
Most people will tell you to just apply, but I have always done projects outside of my current space first. This is for two reasons:
- It affords the opportunity to showcase what you can do to people in that space.
- It’s an easy excuse to network.
After doing these things, I’ve literally had interviews that have only lasted 30 minutes and they offered me a position, all because they knew me and already knew what I can do.
What is the most challenging task being as Sr. PM at Microsoft, and what are the greatest assets being at Microsoft?
The best way I can answer this question is that it’s a double-edged sword and honestly its’ probably a similar answer to most companies. The people is one of the biggest challenges as well as one of Microsoft’s greatest assets:
WHY CHALLENGING: As PM, one of your core skills is to galvanize people to follow you, your vision, your epic, your user story. You need to get buy-in from devs, designers, stakeholders. The larger the company, the more teams, and people you are trying to convince to come with you on this journey.
WHY AN ASSET: Company’s like Microsoft are filled with some of the most intelligent people around. You can learn something from everyone. I think for me when I started accepting the fact that I probably had more to learn from my peers than teach them, only then I started seeing these huge advantages.
Check out: The Skills Product Managers Need in 2021
What’s the most challenging but rewarding part of being a PM and can you tell us what your experience has been so far working at MS?
It’s has to be delighting users. Users are challenging to satisfy, but when you do it’s the best feeling in the world. My experience at Microsoft has been an education at scale. Its is a company that has the potential to reach everyone in the world and more importantly help them. I think the opportunity to do that is my biggest driver.
According to you, what are the top qualities a PM must have?
In my opinion, the qualities a PM embodies are the most important, the resources you can explore and get as needed.
1. Lead – You need to be able to get people to buy in and follow you. All the while, not having them report to you.
2. Curiosity – This is the biggest one, that spans so many areas. User research, technical research, stakeholder values. This is a black hole of things and I get that, but you have to be curious and always learn.
How should a candidate from developer experience try for PM interviews?
I’ve worked with Devs who wanted to transition into PM and I have always had the stance that if you’re willing, I’ll give you a shot. In my experience, I would have my devs take on an epic and flesh out all the user’s stories for that epic and then I coach them through any gaps they may have from a user perspective.
My best answer is if you have a PM you’re working with right now, ask them to do this. It will give you hands-on experience fleshing out an epic from a roadmap and developing user’s stories so you’re seeing and doing things from the PM point of view, not just the dev point of view.
You might be interested in: How to Get a PM Job at Microsoft
I’m looking to transition from Cloud Architecture to Product Management. What would be learning curve look like? Is this an easy transition?
It doesn’t have to be. If you come from a technical background in a specific space like Cloud Architecture try to be a PM in that space to learn the natural operating rhythm for PMs. Getting hands-on developing user stories from a PM point of view is the building block to hone your skills as a PM first and then if you transition away from cloud architecture you can then lean on those PM experiences in that cloud architecture space.
How do you resolve conflicts with senior stakeholders on feature prioritization?
This challenge never goes away and if anyone tells you there is only 1 answer, they’re lying. I can share what I’ve done in the past.
A lot of my prioritization is spawned from data, as such, I’ve relied a lot on telemetry information regarding product usage to drive where dev efforts have gone. For instance, I worked on an Enterprise Performance management (EPM) application which had half a dozen pages in an MVP state, through telemetry data we found that our customizable tile design dashboard was the most frequently used page, so I used that data to convince stakeholders that development on our other pages should be put on hold to fully mature our customizable dashboard feature in order to continue to increase on-board on our application.
Would it be easier to transition into Product in Tech companies by leveraging data analytics skills and Lean six sigma experience?
I would say your data analytics experience would probably be more useful in the tech space. Speaking from a PM lens, a lot of our decision-making is backed by data. I’m sure you’ve heard the term data-driven decision making, it is your analytics skills that would come into play most in the PM Space. It’s all about convincing stakeholders, your devs, and designers that what you want to develop is the right thing to develop and a lot of time they want you to show them the data proving to them why.
What would you recommend to people who are transitioning from PM role for web to PM role for mobile apps?
I have limited exposure to the mobile app development space, but we did try to launch a mobile version of our EPM system in one of my previous roles. I would say two things with regards to this space.
1. The languages, a PM who is technically proficient, creates more proficient development teams. Why? because they can anticipate the programming challenges ahead of time and do some of the research that normally an engineer would have to do in terms of a spike.
2. Design, be very sensitive to design. In that same experience, so much of our onboarding depended on the usability of our mobile app and look and feel via mobile. Work closely with design and make sure you are hypersensitive to the user experience.