Product Tips for a Startup vs Big Company with Microsoft Senior PM

This week, Product School hosted John Shotton, Senior Product Manager at Microsoft, for a special #AskMeAnything session. John recognizes that in Product Management, context is everything. A startup PM doesn’t approach a product the same way a big company PM does, so he addresses problem-solving from both of these perspectives!

Meet John

John Shotton, Senior Product Manager at Microsoft

John Shotton is a Senior Product Manager with a strong background in building data-focused products. He is currently working at Microsoft, leading freemium upsell growth for Microsoft 365 and Onedrive. He is also the Co-founder and Lead PM at Nuggets, a computer software company he helped create in 2021. John also previously worked as a PM for Data and Analytics at HP.

What technique do you use to define user persona and to segment them? Do you think segmenting persona based on demographics as a primary factor is a good approach?

There are two different answers. One for larger companies and one for startups.

For larger companies, there are already predetermined customer segments (e.g. demographics like location, economic status, age, etc.), and you just go with those, especially for more mature products.

As far as startups go, you need to be more specific. Don’t use demographics, but instead envision your dream customer, what they are like, what they need, and build around that. Big companies try to hit as many people as you can, but when you’re just getting started, build specific products for niche audiences.

group of people in white shirts, all standing and looking down at their phones

What signals from users do you look at the most when considering how to get people to upgrade to the paid versions?

Great question. Signals that I use? 1) Frequency of “free feature version” use and 2) looking at number of clicks on various paywalls. Basically, I’m looking for the places where people hit pain in the free version and just dig in a little more there.

How should I get started when transitioning into Product? Is it tough to get entry level PM positions?

Build your own product (e.g. an app). You build an app, launch it, grow it, and you’re set for PM roles. That’s what I did basically. I never had an entry-level PM position.

Which books would you suggest for critical thinking and design thinking?

The Build Trap is a fantastic book for product thinking. For design thinking, I really liked Design of Everyday Things, although it’s slightly dated. For critical thinking though, I honestly think an engineering background, in general, is the best way to develop that. Or any way you can learn how to break problems down into their most fundamental concepts. 

For other book recommendations: 10 Free eBooks For Your Product Manager Library

person sitting on bed, in darkness. there is a shaft of light coming in through a window above illuminating the book

How can a PM prepare for a different type of industry/company completely unrelated to their current company?

That’s a good question. I think, at least from my experience, just spending time to understand the customer base. Prioritization and stakeholder management skills translate over to other PM roles super easily. Just learn to understand your new customer base and build from there.

We often talk about building products with fail fast approach, get feedback and be ready to pivot based on customer response. If that is true, how do you build the product roadmap? What is the timeline?

So I love this question, but I’m gonna give a slightly controversial answer. Product roadmaps for startups and big companies are totally different. Startups, you don’t even think about a roadmap. You just prioritize what you think are fantastic features for customers by max potential impact, and then just build build build.

But for large companies, product roadmaps sometimes are on the months to years frame. These are done and prioritized based on market/user research and lots of stakeholder negotiation. By the time your product roadmap is finalized, it will look completely different than the one you started with.

Check out: The Difference Between Startup PMs & Big Corporation PMs

I’m a marketing manager at an aviation company and certified PMP with a data background, looking to become a PM at a tech company. Do any tech companies offer programs for mid-level PMs to get started? 

Tbh, Product Management is something you just kinda figure out on the fly. The fact that you have PMP and formal marketing experience is a huge leg up. I didn’t have any of that. I just have kinda been winging it. (pun intended)

Microsoft does have some internal training for PMs and whatnot, but the best way to get experience in my opinion is reading books on Product Management, and then directly applying those concepts in your current role. I do think that Microsoft loves people with data backgrounds, so I would just apply to data-related PM positions online. That’s what I did, and I eventually landed this role.

underbelly of a backlit plane flying overhead

How do you respond with product changes quickly when you identify a new market segment? Most companies get stuck in multiple sprints of dev cycles to create new plans/packages to drive conversion from freemium to paid.

“Quickly” is tough tbh. You are absolutely right that companies get stuck on cycles trying to optimize upsell, Microsoft included. In a startup setting, you just make the decision to pivot and build something different. Full send and no second-guessing that.

But at a large company, you have to do two things at the same time. You have to “test” or experiment on the side the product changes (which takes a while in and of itself) while running your current product set. Once you prove that this change gives a strong signal in your new market segment, then you can roll it out broader. However, the larger the company, the smaller you can change at any given time.

My top level execs are purely focused on revenue generation. The tech team can’t build new features fast enough for them, and there’s low team morale because of things not working out despite the effort put in. What would you do in this situation?

I wish I had a good answer for this, but I don’t know, unfortunately. However, the main thing you must do as a PM is to talk to the executives to make them have a product mindset and a developer-friendly mindset (which is a tall order). If the execs don’t get it, then you’re in for a longgg ride.

Read next: Why Do Product Managers Quit?

There are 2 approaches to doing user interviews: 1) ask a bunch of questions to figure out pain points, and 2) form a hypothesis and use the interviews to validate it. Which do you recommend? Is there a better answer to ‘What should we build next that would yield the highest ROI for our users?’

Honestly, that’s one of my favorite roles. Cofounder/first PM. You have quite an exciting time ahead of you!

Ok, you may not like this answer, but although “1” is more correct in approach, I recommend doing approach “2″. Here’s why imo. When you’re at a small stage, you still don’t know what users will resonate with the most. It’s honestly faster to just use your gut intuition to crank out MVPs of features and validate them than doing the user interviews first.

Especially at a small scale, users don’t know what they want, so you’re still going to have to go through multiple iterations of features anyways. Just build build build.

For the last question you have, don’t bog yourself down with the highest ROI. Shoot for great ROI but built fast. Then you can optimize from there.

person in white shirt sitting at table strewn with writing tools. This person is holding a phone to their ear and looking down at the table

What basic tools should a PM know to carry out data analytics and measure KPIs for digital consumer products?

Power BI/Tableau or any good data visualization tool. You already know how to read data, but what’s more important is being able to communicate your data in such a way that most stakeholders can understand your pov in 5 sec or less.

Any final tips?

Honestly, if I had to give one piece of advice to Product Managers, it is basically to trust your gut. Sometimes we all get bogged down with hundreds of sources of data, conflicting user interests, differing stakeholders. Just go with the flow, and if you’re wrong, it’s totally ok! you can correct your mistake. But it’s better to trust your gut, execute, and get it wrong than to not do anything at all. This goes for PM jobs, applying to PM jobs, and your career as a whole. Thanks for the great questions, everyone!

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