How to go from managing projects to leading teams? (Interview Valeria Castelli, Outfittery)

Valeria Castelli has worked at Eastpak, Trivago and now Outfittery. In this interview, she reflects her learnings throughout the journey.

Hey Valeria! How did you get into product work?

Being Italian, I’ve always been quite interested in fashion. During my marketing Masters in Milan, I started as a Junior Marketing Manager at Eastpak. I was doing a lot of competitor analysis there, especially on the e-commerce site and the online brand presence. After graduating from my Masters, I loved the idea of working abroad and with these previous experiences in the digital world, I also knew that I wanted to do something digital. The next step was to apply. I got a job at Trivago in Düsseldorf, where I would first start as a project manager and later – since I had experience in dealing with different stakeholders and organizing the AB tests – was asked to join a new team as a product manager.

How did it feel being a product manager compared to being a project manager before?

It was a bit of a tough start. Because as a project manager you always have a plan. If there were some problems on the project, I updated the plan and it still was quite stable all in all because I knew well what was going to happen. In product management, however, I didn’t know how long discoveries would take. Especially in a data-driven product, e.g. machine learning algorithms, where there is a lot of uncertainty at the start. There are a lot of unknowns. And that’s tough when you come from a position where you’re used to having all under control.

In addition, as a product manager it wasn’t about managing the project in first person anymore, but more about empowering people to do the best and just be there to provide context, answering questions, asking questions and challenging others. I wasn’t the only one involved in the decision-making process anymore. Now it was with a group.

So you felt that leadership was required?

Yeah, exactly. Which was very challenging at the beginning because I never saw myself as a leader before. But I started to like the challenge of developing into this mentality to be empathetic, to listen more, to be patient. There are a lot of valuable qualities you get out of this job.

You just mentioned qualities, which trait is most relevant to you?

Something I learned the hard way is being patient. In this job role, you really have to be patient if you don’t want to be overwhelmed by chaos. For me, it’s about communicating the right goal-focused urgency while having emotional control. And that’s something I’m still working on. But I think this is the biggest trait for product managers, or at least what I try to work on the most. Sometimes things don’t go as they’re supposed to. Sometimes you have to be the person bringing the bad news. E.g. it might be that a project is stopped after three months of work. That’s though and it’s especially tough for your team. And then it’s important to be able to control your emotional response and be the rational person. Always inhaling before saying anything helps. Patience is the biggest quality for me.

Another important quality would be time management. Being mindful of other people’s time and trying to make the best out of it. On the other side, it’s equally important to also defend your own time. Sometimes, as a product manager, you’re the one person that everybody goes to. And that’s okay but it might prevent you from focusing. So I like to set expectations with other stakeholders and set a blocker of time for me to focus and to get things done. Sometimes I need to understand myself and decide whether I need a home office day, book a meeting room for myself or put the headphones on so that nobody bothers me. Also, I sometimes disable Slack notifications to focus better.

How is doing product work at Outfittery today different from how it was at Trivago?

It changed quite a lot for me because at Trivago, I was working more with the customer-facing product and at Outfittery I’m working with internal products. At Outfittery, we have fashion stylists in-house, they pack the boxes for our customer according to their preferences. I’m responsible for the tool that stylists use to pack the boxes, which is also powered by some machine learning algorithms. So my product is still customer-facing, but this time my customers are in-house and I know their names and faces. That’s a big difference. Also in a smaller company as a product team, we can work cohesively together in an easier way, because communication is faster and it’s just less complicated to bring all the user perspectives to the table, including internal users. We exchange a lot and it’s great to have the full picture from all the different views.

What does it mean to be a Product Owner?

As a Product Owner, I’m mainly responsible for making the team work together, prioritizing and support. But this extends to different areas:

One very important part for me is to spend time with the users, to understand them, and to see where they are struggling. I do a lot of product discovery and user research.

A second big part is stakeholder management. This could mean listening to the stylist leads telling me what we could do to improve our internal product. In another case, it could be other product teams launching a new feature and they need this feature to be reflected on our stylist product too. These constant dialogues with different stakeholders provide an important understanding of not just the user but also where we as a company are going and that’s a big one for me.

The third big part comes with the team. Now with knowledge gained from one stakeholder, I have to think about the next step. How can I make the team aware of their input without overwhelming them? How can we test? How can we prioritize? What can we do to have the biggest impact? So it’s about filtering, adjusting, and enabling the team to work on things that have the highest impact.

Then the last one is managing the backlog. It’s about formulating tasks, encouraging the team to have knowledge sharing sessions, allowing them to spend time with the user. Giving them as much context as possible so that we together can make better decisions instead of me being the gatekeeper.

How do you encourage knowledge sharing between teams?

We have knowledge sharing tasks with accountability partners and these are even parts of our KPI. So, for example, one task could be that by the end of the quarter, everybody should have a proper understanding of the overall user experience or of the other teams around us. Knowledge collaboration helps a lot in making context tangible for the team and it also leads to greater transparency.

Let’s switch to the other side. What is your biggest take in dealing with stakeholders?

The biggest one for me is asking why. As a PM, people will inevitably come to you and say: “Oh, I have the idea of the century. Let’s do it.” And maybe it’s indeed a good idea, maybe it’s not. The point is, you don’t know yet and you cannot blindly say yes.

What helps is having a simple decision-making framework that shields you from receiving lots of requests at the same time. Because we need to prioritize, we need to understand what’s important, what’s urgent, and what isn’t. As early as possible.

So one way to do this is by asking: “Why?“. I like to ask the person to guide me through the process: Why do you think it’s a good idea? Why do you want it to be done? Why now?

Repeating this also subconsciously educates your stakeholders at the same time to be prepared for that question. If you keep asking people the same question, at a certain point, they will learn that if they come to you, they already need the information. And you get the other person to realize themselves whether it’s a good idea. Asking them the question that your team might ask you later, saves you and everybody around you a lot of time.

In fact, it also keeps your relationship with this person intact. Having this dialogue keeps things transparent. Maybe the team is already working at something and this person could help. Either way, you don’t judge a person’s idea immediately while also having a smart filtering shield.

How do you manage switching between team, stakeholders, users, the product?

It can get overwhelming sometimes. But other than that it’s great because this mental effort helps you to keep the bigger picture in mind and to not just think in the business perspective, user perspective, or in the technical perspective.

The bigger picture helps to realize that making good money isn’t sustainable if we’re losing a lot of retention because the user says our product is a mess. Reminding myself that my goal is building something sustainable that makes the user and the business happy is a good motivator for becoming comfortable with switching so fast.

For that, it’s also very helpful to be able to let go and let the experts do their job. In my role, I have to be the one that trusts in another person’s expertise. Some are the experts for the user experience, others in businesses goals, and the team is the group of experts for building the solution. I rather try being the support role for the team and ask questions like: How can we make this possible? How can we deliver this on time? Letting the experts do their jobs helps a lot in switching contexts.

What is something you focus on to make sure you get better?

My way to level up is through feedback. At Trivago, we had a very feedback-driven culture. Every two weeks I had a feedback meeting with my previous leads through 1:1s. And then we also did “360 evaluations”, two times per year, one of which was mandatory. Other than that you’re always encouraged to ask your peers and teammates for feedback and say: Hey, is what I’m doing correct? Is there something that I can improve on? What can I do to be better?

I’ll share an example. I wouldn’t say I’m a control freak but I like to know where things are running, you know? And so sometimes my team would say they appreciate the fact that I always try to be on top of things and to think ahead. But sometimes I have to let go and let other people do and drive the balance between where you need to let things go, and where you need to actually take the control. So I tried to listen to this feedback had to push myself to be less controlling and to let things go. To improve on being the enabler for the team.

I have regular sessions with my team and like to also ask them general things like how life is going and whether I can do more for them. This dialogue helps to come along, trust and also understand that everybody is different. With closer ties, we can be clear with each other to do our best work together.

CSG* recently merged with Outfittery. What is it like to have teams from another company joining?

Yeah, the merger happened in June. That’s what we’re working on right now. We can see daily how people react when moving from one company to another environment. The biggest takeaway here is having empathy and trying to understand where the other person is coming from. It’s very helpful to put yourself in another person’s shoes rather than judging blindly from the beginning. What did they learn that may be helpful for us now? Being empathic also helps to build a better personal connection between each other, and then go forward as a team.

Team at the summerparty after the merge of both companies

Final question, as an Italian working at a fashion company, what is your biggest fashion tip?

Oh, well, I would say use Outfittery because you can have a personal stylist, a little marketing here. But the most important thing is to just try to understand yourself. That’s it. Not what’s in the trend but what really fits your personality. Being yourself is the best fashion tip I can share.

Thank you very much Valeria!

This interview was recorded on the 31th of June 2019.

*CSG included then the brands of Modomoto, Box40, Box31 and The Cloakroom

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