Juggling Between Product Manager Realities

Authors: Ivana Gimeno, Olivia Zaporzan & Marguerite Thévenin-Viallet

HOW DID WE GET TO THIS QUESTION?

In November, I remember reaching out to my colleague and fellow PM, Ivana, and telling her how consuming my Product Manager life was at that particular time. I had met with a few other PMs in the same situation, making me feel part of a group and willing to share tips on how to go through deep “delivery-mode” times. She was interested in my dilemma because she really wasn’t in the same mode as for me with her team. She had spent months working on her new squad roadmap and strategy was at the core of her day-to-day.

That’s when we realized there are different realities you live in as a PM. Sometimes, you will be focused on meeting the deadline with your team, but sometimes, you will be focused on building your roadmap and don’t yet have a squad. As we were very interested in this idea of juggling between realities, we have decided to share our experience with other PMs. This conversation was even more important in our eyes because we knew we were not alone, other PMs were also living the same experience as us. We also knew that at some point we would be in each other’s shoes; some sharing needed to happen.

We have a bi-weekly meeting for PMs at SSENSE called “Community of Practice”. We use this time to share experiences and learn from each other. Ivana, Olivia, and I decided to present one of the sessions to discuss juggling between PM realities, and introduce an open conversation to build connections and agree on best practices.

WHY WE STARTED DISCUSSING THIS AS A TEAM

There are three main reasons that triggered this discussion with our fellow PMs.

Giving visibility to this reality. Ivana Gimeno

It’s something we don’t talk about because it’s not always a defined problem.

Our initial conversation on this topic made us realize something very important: with our working remote reality over the past year or so, we’ve lost the ability to see what other PMs’ realities are. Are you running from meeting to meeting or always working very closely with your squad? Are you in brainstorming sessions or mostly sitting at your desk doing ‘thought work’? We’re so isolated in our homes that we forget that others might be going through something completely different! We’ve also had a lot of new PMs join our team in the past year; some of them might come from roles where only one reality was present, without any preparation for the differences that await them. Giving visibility to everyone in our team on what our different realities become all the more important so we’re all ready for the shift, one way or the other.

Acknowledge the ebbs and flows. Olivia Zaporzan

We should expect to live through all phases.

As PMs, one of our most important assets is empathy; we use it to understand and acknowledge the experiences of our stakeholders, squad members, and customers. We empathize, in particular, with our fellow PMs as we understand exactly what they might be going through at a given time because we have already gone through or know we will soon. From heavy periods of execution to times that are deeply strategic and aspirational, combined with the likelihood that you’ll run into those random-intense-but-super-fun-and-character-building periods where both are required — is all part of the role. Knowing that, makes these times a little more attainable and all the more fun.

Building a support network. Marguerite Thevenin

Never take for granted things that we manage naturally & transitions can be difficult.

We often read that having a good support network is important. As a PM, it helps remind me that I am not alone, that other colleagues of mine with whom I exchange a bit less, are probably in the same situation. And if I can trigger the conversation, I can learn a lot about how they deal with problems that I am facing.

The other way around is also true, I might sometimes be in a situation of success where I have found the right balance and process to meet my objectives. But other PMs might actually be struggling with situations that you know how to deal with. In this situation, sharing is key to everyone’s success. Sometimes things that seem so natural or logical to us, are not for others.

How can we build this support system within our team and help trigger the conversation on both sides?

We have identified 3 PM realities: 100% strategy, hybrid, and 100% delivery. We will explore each of them through a personal experience lens:

…this was my starting point

…this is what was difficult

…this is what I did about it

THE THREE DIFFERENT PHASES & BEST PRACTICES WE IDENTIFIED

100% strategy by Ivana Gimeno

Strategy & design work with no squad

In May of last year, I came back to the Product team after my maternity leave, and I was thrilled to be assigned to a super exciting project at the core of the SSENSE fulfillment operations. We were tasked with the full revamp of an existing system to unlock countless opportunities for growth. This meant I would spend the next few months strategizing and working closely with our business stakeholders to articulate what we’re trying to achieve and what the priorities were. It also involved working very closely with our architect to figure out what this new system might look like, at a very high level, and starting to identify risks and dependencies. In parallel, we started building a dev team, beginning with 2 very experienced engineers; we needed technical heavy lifting! However, the first thing we did was spend a very large chunk of time mapping our existing systems, identifying the gaps, and defining a clear strategy on how to build the new system without too much disruption to the ongoing operations.

Anyone who’s had to ask their squad to work solely on documentation for multiple sprints in a row knows this can be a real struggle! What was most difficult in this phase was figuring out how to measure results and drive motivation for the squad. The results were tough because the main objective for going through all this documentation was somewhat abstract for the team. We basically needed to document the entirety of our operations, even if we would only touch parts of it, which was the result of years and years of not prioritizing this type of documentation. This obviously impacts the motivation side, which would also be made more difficult by the slow progress we were making.

The importance of this step was not enough to clarify results to be measured and drive motivation, so I needed to be creative. To drive motivation, the first step was to clarify the objective and focus on why it would be important for the success of the team. Then came finding a way to structure the work to make the task less daunting and being able to measure our progress and our success. Turns out the approach I selected is one that we often talk about as PMs, but doesn’t always come intuitively when you’re deep in the weeds of a problem: break it down and iterate!

• Clarifying the objective of the documentation phase seemed clear for me, and with the support of our Architect, we were able to make it clear to the team as well. We could start working on the new system right away, but we would be going in partly blind. Biting the bullet and focusing on documenting the current state would have the added benefit of giving us a clear understanding of how things work, identifying the biggest gaps in the current processes that we could improve with the new system, and help us structure the work ahead of us.
• Breaking it down can seem quite simple, but in this case, we had the added challenge of a large number of dependencies with other teams. Since the product we were working on was central to the operations, we needed to make sure that the way we broke it down made sense to other teams and that the documentation we were creating could be leveraged across the organization. Each piece of the process that we broke down then became a milestone for us to reach, and the relative size of them drove how many of these sub-processes we focused on during each sprint.
• Iterating meant a bit more for our team than just organizing our work in 2-week sprints. We had clear milestones to reach each time, but we made it clear that our different documents might not ever be “final”. With each sprint and each new process we were looking at, we might uncover more information that could be useful and would need to be added. So, while we had sprint objectives, we continuously worked on the same documents in parallel to make sure we were capturing all of the information we found.

Hybrid by Olivia Zaporzan

Strategy, design work and delivering the roadmap with a squad

In October, I started my SSENSE journey as a PM on the Productivity squad. Productivity partners closely with Studio. Our squad’s work centers primarily around the tools used to create and support a sound and scalable Studio operation; our aim is to ensure we execute content (visual and copy) efficiently, accurately, and maintain our quality standard. Around this time, my team was kicking off two large initiatives for the upcoming year: the discovery work for Preflight, an image file management tool, and the translation work required to enter the Korean market. This meant two things. First, our team would be heavily involved in the Korean content process, facilitating the translation of our entire SSENSE catalog into Korean and the optimization of our end-to-end translation process at SSENSE. Second, I would be driving the discovery and planning of two large milestones around the same time. A strategic thinker’s paradise.

Year-end came quickly with our markdown period combined with one of our heaviest months of high traffic launches. High Traffic Launches put us in the role of actively managing bugs or glitches that occur that pose a risk to studio operations or content production/display. This requires us to be: adaptable to change, meticulous in problem-solving, and sharp in delivery to ensure all goes smoothly and as planned. As a PM, this also requires a strict executional mindset. Because of the season combined with where we were strategically within our roadmap, I found myself having to pivot several times a week from a deep strategic mindset thinking to quick-problem solving/delivery mode (ie: a deep thinking brainstorming session to ensure a bug fix is addressed and root cause found). Never 100% in one camp, but always somewhere between 50/50% to75/25% in both. How do you lean into that type of challenge combined with the aspect of being a newbie?

My answer to this test was by leaning on my experience with prioritization & pivoting, and finding a friend in my newly built network:

Prioritize & Pivot:

• Rigorous prioritization is something commonly referenced in Product practice. This helps us make the best decision given the circumstance. We prioritize based on assessing a task’s value (benefit/impact) vs effort (cost/complexity/risk). Common questions we ask ourselves in these situations: What holds the greatest value right now? What can be pushed? What needs to be addressed first? I leaned into my experience leading and executing large initiatives and put my prioritization framework in place.
• By focusing on my backlog and prioritizing risks, I was able to understand what required my immediate attention and focus, and what could be addressed at a later date. This framework allowed me to make decisions to help my squad and the business succeed.

Find a friend:

• Finding friends in Product (and in my experience, generally anywhere at SSENSE) is as easy as it comes. The willingness to collaborate, intelligence to relate and passion for the work is outstanding. As a new hire, I was paired with a transition partner to support my onboarding. He was a tremendous support in helping me to understand the product and the people, continually providing sound advice. He also succeeded brilliantly in creating a relationship of extreme approachability which made it comfortable for me to ask questions and express any vulnerabilities. This helped me to quickly establish expectations and deliver on them. A key to helping me make decisions on what to invest in and what to push, both strategic and execution. It also provides a great sounding board to relate to the circumstance I was in. When in doubt, find a friend.

100% delivery by Marguerite Thevenin

Delivering the roadmap with a squad

As an e-commerce company, Q4 is a key quarter for our company. Markdown periods in the Fall/Winter season are happening all over the world. It’s the highest traffic season and it requires weeks of preparation. Last year, on top of regular efforts, we also launched a new department, Everything Else™, which encapsulates homewares, activity, technology, and pet wear — we also introduced exclusive shopping benefits for our top clients. As the PM managing the website upper-funnel, I was impacted by all three initiatives. The deadlines were fixed and we had to deliver on time. For about two months, we were with my squad 100% in delivery mode, our only goal was to release the three initiatives on time and safely.

How can we meet expectations? This was our main struggle. The 3 initiatives were on different parts of the stack and would require different skills and knowledge. I clearly joined at a very sensitive time, leaving no margin of error.

My solution to go through a time of delivery is hardcore prioritization.

Prioritization of my backlog: when you need to deliver something, my squad becomes everything. Being in harmony with my developers is what helped us achieve our target:

• Readiness and anticipation: I make sure all requirements, open questions with the business, UX needs are resolved before I enter the delivery mode.
• Visibility: I make sure everyone clearly understands what we are working towards, what is at stake and what is required from them.
• Listening: This is even more important during delivery because little things can mean bigger things as this is a very stressful time. I have to make sure on a daily basis that developers & QA feel heard and understood and that the issue being raised will be solved, whether in the short or medium term.
• Focus: During these Delivery modes, I usually assign one developer to one specific project and specific PR reviews. We review the ownerships on a daily basis to focus their energy on one thing instead of being spread out. Although during hybrid, the team can have one similar sprint goal, when in Delivery we have 3 initiatives and 1 team, we need to build sub-working groups.
• Daily goals: After the stand-up, I shared all the PR I wanted to merge on that day as well as what I would hope to QA by the end of the day.
• End date and aftermath planning: I do not believe that we can ask someone to work on a deadline in delivery mode forever. Setting the end date of the craziness, ensuring my team will have time afterwards to do some deeper technical work and clean-up was key to our success. The main reason is that in delivery mode, we have to cut corners but we don’t want to pile up technical debt. Planning during the delivery time for the next phase was very important for us.

Prioritization of my skills:

• Fill in the gaps: When it comes to Delivery, my only goal is to meet our target. To do so, I try to fill in the gaps where I see process flaws. For example, we noticed that during Retrospectives, PR reviews were often a pain point. Between the time it is published to the time it is deployed in QA, it can sometimes take up to a week. When we are in delivery mode, we don’t have a week to wait on. I was thus following up on all published PR, assigning them to specific developers for reviews, pinging the developer in charge when the PR was approved and ready to be merged, pinging QA when the PR was deployed, doing status updates 3 times per day with all of them… This is not my initial job as a Product Manager, however, when we are in delivery time, we need to identify the gaps and find solutions very quickly and the solution can often be to find someone to fill in the gaps. Note: by filling in the gaps, I don’t want to step on anyone’s toes, and RACI needs to be super clear, roles & responsibilities aligned with my Developer manager and Tech Lead on everyone’s expectations, again, team harmony is the most important.
• Deprioritize strategic work: The issue comes when I start filling the gaps as a PM and going outside the role is when you will do overtime. This is not the goal because Delivery is a very stressful time and adding more stress will lead to burnout. It’s therefore important to make it very clear to everyone, including your stakeholders that your time and focus on delivery is very important and the reason why. This allowed me to deprioritize working on strategy, so that I could focus on the important things (“let’s circle back in X weeks”). I am also very lucky to have an excellent relationship with my manager who supports me 100% and helps me by jumping on some more strategic conversations so that I can focus on the delivery.

WHAT WE CAME UP WITH AS A GROUP

As we mentioned in the intro, we decided to host one of our Community of Practice meetings on this topic because we thought this was a very good conversation to have with the entire Product team. The meeting was a great success, and we were able to drive an amazing conversation with the group. Here are a few ideas our team came up with, we hope you might find some of them inspiring:

Creating a dialogue:

• Having a visible status somewhere so other PMs in the same situation can chat
• Hosting more Community of Practices to deep dive on each phase
• Booking recurring meetings based on each reality to regularly share knowledge

Process:

• Documenting a RACI for the squad depending on realities with clear roles & responsibilities
• Optimizing schedules depending on realities
• Sharing and oversharing the business context so the squad knows the business, so they are more autonomous when it comes to execution

CONCLUSION

Juggling between realities is part of the Product Manager life, it requires quick adaptation and high focus. The intent of this article is not to help you deal with a specific reality, it is more to acknowledge the realities and encourage you to build a dialogue with your fellow PMs to create your own best practices, based on your work context.

Editorial reviews by Deanna Chow & Liela Touré.

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