Interviewee 1
Company: n8n · Date: 10/02/26 · Recorded? Y (Zoom, permission given at start)
1. Company
Notes: n8n, workflow automation company. Historically used to “connect various systems together, move data around, much like Zapier.” Now popular for building agents “that you can, you know, then talk to from Slack,” and “that’s how we’ve really grown,” starting early 2025.
Size: “now more than 400 people,” up from “a bit below 100 people when I joined in the beginning of… 2025.”
Stage: rapid growth.
Customers (his side): core product, not enterprise. “solopreneurs and… SMBs type of users.”
2. Role / ownership
Notes: Works with two teams in the “ecosystem domain,” building out integrations so people building agents can “give these agents tools to work in the software that they use at work,” e.g. Slack, HubSpot. “The teams that I work with take ownership of this integration ecosystem.”
Who he works with: “a very typical SaaS company.” Works “very close with a design peer and an engineering manager,” and each team has “anywhere between 4 to 6 engineers.” Currently across two teams, “which isn’t the norm.”
Users: continuous discovery, “a couple of user interviews, usually every week.”
Decisions: his perspective is “most upstream from whatever we build,” meaning “bringing in the company strategy,” driving “problem discovery,” “trying to spot patterns… what competitors are doing, going through customer feedback,” and “sizing opportunities.”
Split: “I’m driving most the problem discovery, whereas design is driving most during solution discovery, and then engineering is driving most during delivery, but it’s always all of us kind of involved.”
3. A day in the life
Notes: Days “tend to be very meeting heavy.” Walked through Wednesday as a typical day:
- Two catch-ups with other PMs (one enterprise, one on the agents product) “to kind of do some early alignment” on an area that overlapped
- Stand-ups with both teams, “back to back”
- 1:1 with his engineering manager
- Call with product marketing “to align on upcoming launches”
- Product and design session to “share very half-baked ideas… to riff off of each other’s ideas”
- Lunch, then a user interview
- Afternoon: monthly company-wide dogfooding. “we want to be our own best customers,” automating your own tasks and finding bugs
About 7 things before the afternoon, almost all meetings.
Mental work: “really lots and lots and lots of micro decisions just flying at me.” Ties this to AI: “five years ago, I was able to work 6 to 12 weeks ahead of what the engineers were thinking about. And now… it feels like sometimes I’m a day ahead at best… really making lots of in-the-moment decisions. And I think that’s where most of my mental energy goes.”
4. The good
Notes: “Generally… I feel very confident and secure in my workplace every day.”
Specific example: Tuesday this week, a retro with one of his teams. The team is “absolute… world-class at what they do, but at the same time… kind, humble human beings.” Also “lots of fun at work.”
Has worked with this team “about a year, if not more,” so there’s “really good rapport.” They can “celebrate the highs as a team” and he has “absolutely no problem flagging… stuff that didn’t go well and getting kind of energy from that.”
Building together: sessions where they “riff on stuff… look at a prototype together, see how it feels… discuss… trade-offs… design engineer and myself in the room… co-creating, shaping a solution together. I think those moments, they are really lots of fun and very human.”
I summarized it as “the time you enjoy most is human connection.” He agreed: “I think that’s fair to say.”
5. The bad
Notes:
Transactional Slack across the org: “communicating… in Slack across the org… with people that are far removed from me, where… we’ve grown so fast that I’ve never met them, and it’s like the 1st day, 1st time they need something from me… those are the cases where things tend to be like very… transactional.”
Two teams = no time to think ahead: “I’m serving… two teams right now, and that… means that I have even less time to work ahead, and to kind of think ahead.”
AI FOMO: “I’ve never seen a… greater… spread of FOMO across this industry where every day a new AI tool is taking off.” “everybody seems to be chasing their 15 minutes of fame and forgetting about the basics of building good products.” What he struggles with is “reminding myself to not buy into that FOMO so much” and going back to “what do we know our users need… what’s our unfair advantage.”
Engineering outpacing product/design: “the productivity increase has been so insane compared to other functions, like product and design.” A sustainable ratio of engineers to PMs is “4 at max, maybe 3.” “It’s really, really hard to get in front and have some time for rigorous thinking, like higher altitude thinking… those million micro decisions… that’s the symptom of that.”
Decisions have to be “shot from the hip… very quick judgment decisions.”
How he deals with it now: “Working nights and weekends.” Thinks it’s “a bit of a temporary thing” because the two-team setup “will not be the case for long.” Also “good old meeting free Friday stuff, like blocking off… days… or afternoons for focus time.”
6. Else
Notes:
What he’d most like to stop doing: making decisions “shot from the hip” without time to think, and working “nights and weekends” to catch up.
Covering two teams back-to-back (two stand-ups, double the context switching).
Follow-up: he offered to answer more over email (“very happy to answer them over email”), so send him this question.
Possible pain points I heard (how often each happens, and how they deal with it now):
- Can’t stay ahead of eng; “a day ahead at best” (used to be 6–12 weeks); Daily: “micro decisions just flying at me”; Decides “from the hip”; nights and weekends
- No time for “higher altitude thinking”; Ongoing, worse with 2 teams; Meeting-free Fridays, focus blocks
- AI FOMO distracts from strategy; “every day a new AI tool is taking off”; Self-reminders: user needs, “unfair advantage”
- Transactional Slack with people he’s never met; Not asked; None mentioned
- Meeting-heavy days; Most days (“these days”); Dogfood afternoons are the only hands-on time
Interviewee 2
Company: Oracle · Date: 10/02/2026 · Recorded? Y (Zoom, permission given at start)
Role note: Interviewee leads UX design for Oracle’s CX applications rather than holding a PM title. In his words: “Part of my job is product management, but I don’t own the product management aspect.”
1. Company
Notes: Oracle: “primarily a database company and an infrastructure company, and it also has applications.” About 40 years old. Started with core databases that other companies built applications on, then built its own applications, then cloud infrastructure.
His division: Fusion Applications, “cloud applications which customers can customize.” These cover ERP (finance), supply chain, HCM (HR), and CX (sales CRM, CPQ, marketing automation, service).
He leads “all of CX applications that include sales, marketing service.”
Example: even at Stanford, reaching prospective students with automated or personalized B2B email, or a service rep using software “to help troubleshoot.”
AI: “now everything is getting transformed because of the AI layer.” CX is “the front office layer,” so “the opportunity to transform this… is immense.”
Stage: established. Customers include “Macy’s and Ferrari and the Porsches of the world.”
2. Role / ownership
Notes: Leads “the user experience design for all of these applications.” His goal is making sure the experience is “seamless… reducing as much friction as possible,” so users get their job done “in a way where they also feel satisfied.”
Works closely with the development team, “which help execute it.”
Shares ownership with PM on “why this feature needs to be done, who this is for, and is it even gonna work.”
Also works with go-to-market, user research (“if we need to fill a gap in our understanding of certain personas”), the design system team (“that design system is never done, it’s evolving”), and the user assistance team (copy and consistency).
Manages design leads who each own a vertical (service, sales, marketing, order management).
3. A day in the life
Notes:
Planning: “Even before I get to look at my day… very high level goals are known” for the quarter and the next six months. Most important part of his work is making sure “my team’s priorities are aligned with the products’ priority” (e.g., rolling out AI features; CPQ, sales and marketing right now). When planning his week, he looks at which areas “need further alignment” and more cross-functional collaboration.
Early-career lesson: meet cross-functional stakeholders “so that you can disagree in private so that you can agree in public.”
Most of his week goes to aligning “the priorities, the goals, and the OKRs” and making sure “the meetings on my calendar are reflecting that.”
Team rituals: Regular 1:1s with design leads to check alignment and “cross-functional troubleshooting,” and to find “places where maybe design is not being heard as much as it should be.” Team meetings for “dissemination of information from all these other sync ups.”
Reviews: “many of the meetings are scheduled based on just reviewing stuff that is getting shipped, or stuff that is getting designed.” “Product reviews, design critiques, a lot of time goes into that.”
Typical day: decides which reviews he needs to attend, preps (reads the “Confluence page” for product requirements, sees what designers built), then attends. “If there’s no agenda, I would rather cancel those meetings.”
Thinking time: Protects time for “hands-on thinking work,” e.g. a strategy doc mapping the end-to-end process “from a marketing exercise to all the way to sales and quoting and service” and back to “upsell, cross-sell.” “Instead of looking at these products in silos.” “I put in meetings with myself so that I’m able to get those things done.”
Tools: “I have a to-do that I track. But it’s really rudimentary. I just keep it in my notes.”
Reviews the next day’s meetings, may “decline certain meetings, or just add certain meetings… calibrate back to my objectives.”
Decisions: Many are “already taken,” like design-system-level ones. But when reviewing flows, B2B data is huge (“the shape of data is so huge”), and “in agentic patterns, we may not have that pattern yet.” Claude Code and Codex are “very individualistic single player kind of exercises… you’re throwing it over the wall, and someone else is reviewing it,” while design got used to collaborating in Figma. He decides to push design system and product to prioritize collaborative patterns. “If it is not in code, then it does not exist.”
Prioritization: Asked if he struggles with it: “All the time.” Rule of thumb: “it’s okay to not chase for perfection.” “Not taking a decision sometimes is more harmful than to delay a decision… in this world where generation is so easy with AI… you can always… change the decision.” Most product teams struggle with “analysis paralysis.” “It’s not prioritization until it hurts” (from Yahoo; they put it on a mug).
Communication: “My philosophy is to do as many one-on-ones as I can. Also, it’s a scale issue.” 1:1s help him understand “what is the driving force in this person’s mind.” This comes from design school (“one-on-one interviews rather than… a group setting”). Groups work “when you have to feed off ideas of each other,” like product reviews and strategy brainstorms. Oracle’s own marketing team uses the product (“our best access to our users”), so he interviews the marketing manager and specialist together.
4. The good
Notes:
Yahoo prioritization story (his “one good example”): At the end of each quarter, product, design and engineering listed what they needed to work on, each with “why… who’s asking for it.” Usually the VP would draw a line. “But this VP did it in a different way. He said, you know, all of you have a good reason… tell me what are 3 things that you’re not gonna do. And that pivoted the conversation.” Knowing what you won’t do “ultimately determines what your team can focus on and what they can actually ship with quality.”
What energizes him: close cross-functional collaboration, which he called “good friction… the more we have those conversations… actually helps us build a better product.”
At the end: “I think it also helped me clarify a few things for myself.”
5. The bad
Notes:
Slow strategic decisions he doesn’t own: “the biggest source of pain point is when… some of the decisions are being taken too slowly… there are certain things I don’t own.” A platform decision “taken 2 years back, and I opposed to that. Now, 2 years down the line, we are realizing, maybe that was not the right direction.” He couldn’t share specifics.
How he thinks about it: “the decision is not in our hand, but… how soon can we correct them? And… can we even accelerate?” In “a large matrix organization, these decisions can really harm,” unlike a startup that can “move fast… and get a product market fit a lot more easily.”
Collaboration in silos: “Everyone is a builder… the how of building has become… a lot more easier. Why you need to build something and whom you’re building for… are the harder questions.” “Many of these conversations are happening in silos, not so much in collaboration.” He’s “specifically spending a lot of time on that.”
LLM overconfidence and noise: “these LLMs tend to have a far more confidence than… they actually have.” Real needs “you can only get… by actually interviewing the user.” “The noise in the system is just far too much.” “We are moving away from user-centered design to self-centered design.”
6. Else
“What’s something you do every week that you wish you didn’t have to?”
Notes: “you have to justify that product quite a lot to many different levels.” He wants to “reduce a little bit of this show and tell at different levels… run in smaller teams and actually ship the product and then let users sort of figure it out,” and be “more focused around customer feedback than this matrix stakeholder feedback… stakeholders are not our users.” “But I understand it’s part of the necessary aspect of the job.” “Just because someone has a higher title doesn’t mean that they know better.”
Possible pain points I heard (how often each happens, and how they deal with it now):
- Justifying work up many levels (“show and tell”); Weekly (his Q6 answer); Accepts it as “necessary”
- Slow or wrong strategic decisions he doesn’t own; Not asked; example from 2 years ago; Influence and pushing back, then “correct… and accelerate”
- Prioritization; “All the time”; Don’t chase perfection, “3 things you’re not gonna do”
- Collaboration happening in silos with AI tools; Ongoing; “some teams are doing better than others”; Pushing for collaborative design patterns
- Protecting thinking time; Daily; “Meetings with myself”; cancels meetings without agendas
- Tracking to-dos; Daily; “really rudimentary. I just keep it in my notes”
Submission reflection
What felt awkward / what I wish I’d asked: I often found myself combining multiple questions together, such as: “What does a typical day in your life look like? For example, what was yesterday like? Or, if it is hard to properly represent how you spend your time with just a day, give me an overview of how you split up your weeks.” I would try to combine so many thoughts into a single prompt, either because I was worried we were running out of time or because I thought of better phrasings as I went. I had a list of written out questions, but I tended to want to specialize into a specific thought as we went. I wish I had been more consistent with the questions I asked and specifically that I asked about productivity tools, but now I know more about what to ask in the second round!
Reading idea I used: There were a couple ideas from the reading that I found beneficial in prepping for my interviews. Firstly, your team is everything. The people you collaborate with make or break your success, and you should really quantify your success with how you make the people you work with feel. The CORE reading also mentioned collaboration as a key aspect of PMing (not part of the acronym, but important nonetheless). This idea led me to ask both interviewees: “Who do you collaborate with and in what ways?” The other idea was the importance of prioritization, both for yourself as a PM and for your team. This led me to also ask my interviewees about how they prioritized their work.
AI use disclosure: I used Claude to source quotes from the transcripts to best evidence my notes, as well as assist with formatting.
