How a Sr. Product Manager Turned Customer Criticism into a Winning Strategy for iPhone Support

Published Monday, August 31, 2026
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INTERVIEWER

Interviewer

In all of the projects that you worked on. Sometimes I mean, not that often with stuff I've worked on, clearly never, uh, but sometimes you get negative feedback, uh, from customers. That, uh, and it's pointed and specific that drives, um, an improvement process or a change in the product, etc. So, when you think back on, you know, just the last 10 years or so of your career. What's a piece of difficult customer feedback that you had to incorporate into a product, service offering or whatever?

CANDIDATE

Candidate

Yeah, um, we delayed shipment of iPhones. Um, sorry, uh, You know, if, if you're an iPhone user, I apologize. One of our, our customers at Pivotal was, uh, TSMC, um, which is a, a key component in the supply chain for iPhones, um. And they were telling us, uh, the, the product I was working on at the time was Cloud Foundry at Pivotal, and I was responsible for Windows and .NET support, um, which was a, a very small business at the time that I took it over. Um. With like 4 or 5 customers, um. And we found that that like we were getting feedback of this isn't working, it doesn't perform, uh, it crashes all the time, like nothing works. Why did you sell us this thing? Why did you ship this? We should switch back to Apprenda, which was uh by and large our only competitor. Um. That was hard to hear. Uh, it was less hard for me because I was very new to the team. Like this is my, my 3rd or 4th week, uh, at the company, um, but it was hard to hear for the team. Uh, and what we did was we, you know, we worked off hours, we got on the phone with Taiwan, um, we screen shared and worked through individual issues, uh, and I would say like there were two things that we changed broadly speaking. Um, from a technical perspective, uh, we started recommending that our customers not domain join those machines, um, because the domain join was applying lots of corporate policies that were screwing up all the stuff that we had built, and it was impossible for us to test. Happy to go into the, the technical solution, but like I don't think anybody cares. Um, the other thing we learned from a process perspective was that expectations with our customers had been set incorrectly. Um, they had been sold a product that was fully mature and ready to go and could handle all their needs, um, but it was like a V.9, like it was almost a V1, um, and almost ready to go. Uh, so we started resetting expectations. Um, I started having weekly calls with all of our customers. Uh, at the time it was 44 or 5, and then it, it grew, uh, and it became weekly calls with our top 4 or 5 over time, um, where I was talking to them about our roadmap, what was coming next, um, their requests, what they'd like to see, challenges they were having, all, all this stuff. Um, this is Uh, uh, with the blessing of the account teams, um, but having those conversations was super helpful to me to understand like where we should go and what problems we need to solve. And I think it's, it's a really excellent model for enterprise products. Um, you should know, or I believe that you should know as a PM who your 1st 5 users are gonna be. Um, consumer or enterprise, frankly, like you, you should know who the first couple are gonna be. Uh, and in enterprise where that may be a significant percentage of your users or, or at least measurable, um, you should know what they want. And giving a couple of select customers access to the roadmap to understand what's coming, giving them input to the roadmap and letting them Like help you shape it, builds trust with the customers. They know what's coming, they know the status of everything and, and like the dates and if stuff slips and and all those things, um, and it allows them to feel like they have skin in the game, so that they do go install the new version right away or like start using the new feature and they give you feedback on it. Um, and that was like an incredibly helpful process change that we made, uh, based on having, you know, those early really negative interactions with, with like TSMC and Boeing was, was one of our other early negative customers.

Interviewer Insight

this is a very good starting point for an answer to this type of question. The connective tissue could be strengthened by being more clear about what the specific asks were from customers, how those came in to the product team, and how the product team ultimately landed on delivering something else. In this case it comes across as having first started building the dashboards and then through their use of the product in development the product team realized they were building the wrong thing. There is a lot of process being hidden in this summary answer that would be great for demonstrating the skillset of the candidate.

INTERVIEWER

Interviewer

So, at the risk of asking an extremely pointed question, but because you weren't the p.m. responsible for the product, I know I'm not gonna offend you, I'm gonna offend someone who might be a friend of yours. With so few customers, how the fuck Excuse the language. Were they surprised that things didn't work? Like, uh, that, that to me is when I hear, oh, you know, early products, only 4 or 5 customers, like there's no excuse for shipping and then being surprised that things don't work. So how did that even happen?

CANDIDATE

Candidate

So, um, I'm reading between the lines a little bit. Um, Cloud Foundry is a large, complex product. Um, at the time, the minimum deployment was something like 35 virtual machines in your environment. Um, so like more complex than Kubernetes is today. Um. The product was well established. It was like a year and a half into market, um, and like was doing $40 million ARR and growing. Um, so these customers were using it for Java applications. When we came in and said we have a new feature that will also run Windows applications. It was sold or they assumed or probably both that the Windows quality level was going to be the same as the Java quality level. Um, so it was like an extension or a new vertical within an existing product. So all the existing sales contracts and stuff were already there, like the relationships were there, um. some combination of assumptions and explicit, you know, misselling of the quality.

INTERVIEWER

Interviewer

Got it. And when you say Windows applications, you really mean .net.

CANDIDATE

Candidate

These were actually .NET on Windows at the time, yeah. OK, as it, well, today it's .NET on Linux a lot of times, so yeah,

INTERVIEWER

Interviewer

fair, fair, fair. I'm trying to think. I'm, I'm mixing questions I had. OK. Um. So in terms of the customer advisory board, which is what I'll call it. Did you, it sounds like this was a new process for, for your company, if I'm wrong, tell me, but, uh, how did you get buyoff on, on a customer advisory council?

CANDIDATE

Candidate

Um, I didn't. I just did it. Uh, So I, one of the great, one of my favorite parts of this role at Pivotal was that I was the only PM in New York when I started. Uh, I was working on Windows, which meant that literally no one wanted to talk to me cause nobody cared, um, cause, you know, Silicon Valley is a little Linux, uh, focused, right? Nobody likes Windows. Um, I saw that as an incredible opportunity because Uh, for internal like LOB applications, it's something like 40% of the market. Uh, it's a huge, huge market. Um, so I thought that was great. Nobody bothered me. I got to do my own thing. What I did do was clear it with, uh, each of the account teams for the accounts that I wanted to, to include, um, and made sure that they were involved in the process because I, I don't want to piss off enterprise account teams. Um, When my boss found out, uh. I didn't call it a a cab or anything. I called it like I'm having regular calls with a couple of customers, um, uh, each individually, so they didn't know about each other, uh, and like it didn't even cross his radar as a thing to worry about. Uh, so I, I just kind of went for it.

Interviewer Insight

What is great about this answer is the nuance of differentiating between type of alert and whom would be working on the alert. This is a high degree of Customer Obsession. What would take this answer from really good to great would be more exposition on how the team got there.

Expert Assessment

Interviewer assessment - would be used in a hiring meeting

The specific answer block for this leadership principle was a great start for the candidate. There was a high degree of Customer Obsession on display with regard to how the candidate framed the processing of inputs from the customer and turning those inputs into positive outcomes for the customer. What really stood out more than anything else were two very nuanced points. First, the understanding that the product should organize content based on who was solving the problem, not based on type of alert, and second, that it was more important that the product make their customer look good to their ultimate reporting chain. These are subtle items which can make an enormous difference in the success of a product.

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