In January of 2018, I joined Shopify as the Product Manager (PM) on a team that hovered between 15–20 people. Our goal was to build single sign-on capabilities for the Shopify platform. This was a complex build that involved migrating large amounts of data and would change the way that our Merchants logged in to Shopify, without disrupting any of their usual management flow.

This type of work would have impacted almost every other product group in the company, which made it a very complex problem to solve. There’s no sugar-coating it; it was one of the toughest product journeys I had ever experienced. After about six months of me joining the team, we still were not making meaningful progress to hit our goals by a specified timeline. A drastic change was needed… and that’s exactly what happened. The project was paused last August.

When a project no longer makes sense for a company, quickly folding it can be a major win. But when a project for a complex product carries on for an extended period of time and finally gets paused, it may not feel that way to people who dedicated thousands of hours to it. Some PMs may even see it as a major personal hit. That’s exactly how I felt about this outcome — even though I knew the decision to overhaul the project was the right one for the company.

There are undoubtedly other PMs who have experienced similar circumstances as I did, or will one day reach a point in their career when a project or product gets shelved or folded altogether. There were other factors that contributed to our team’s unfortunate outcome, but in this post, I will solely focus on the things that were in my control. I want to share the top five lessons that I’ve learned as a PM from my experience.

Lesson One: Be Accountable for the Size of the Team

As previously mentioned, our team hovered between 15–20 members, which is considered as a pretty big group in typical product team standards. I recognize that most PMs can only dream of having a full team, but because of our team size, I occasionally noticed that members were working on things that didn’t always directly contribute to the team’s top priorities. When they weren’t assigned to priority-scope tasks, they naturally picked-up other pieces of work to keep themselves productive. Great — Right?? Well, often those pieces of work created confusion as to what was priority-scope, and what wasn’t. To be clear, I allowed the scope to creep every time I saw a team member working on something outside of the project’s key deliverables. Keeping true to scope is the role of the PM.

In retrospect, the original scope didn’t align with the size of the team. Normally, asking for more people to help a project seems like the easy thing to do to help speed things up, but sometimes, having too many contributors can actually do more harm than good. This resulted in decreased motivation amongst the team members that weren’t directly contributing to the main focuses of the project. This also resulted in general confusion in regards to what we were trying to achieve. As a member of the team’s Leads, I needed to be more engaged in matching the project’s scope to the size of the team.

Takeaways:

• Mind the team: Take an active part in the hiring process. The hiring initiatives for the project need to make sense to you and align with project scope.
• Address concerns: Stemming from the above, voice your opinion if you feel that the size of the team doesn’t match the expected outputs.
• Direct the focus: Actively ensure that everyone is focused on the project goals. Planning sessions, retrospectives, and health checks are helpful discussions to gauge this. Ensure that each team member is working on something that contributes to the project’s success.
• Ensure health: Work with the UX Lead and Engineering Lead of the team to ensure that team health is strong. Tough, honest conversations are sometimes needed to address team health issues.

Lesson Two: Be Accountable for the Skillset of the Team

A healthy team consists of members that span across the spectrum; this includes having a variety of skill and experience. For more complex products, the most ideal team would include tenured members that have been with the company for at least several years. Even better if these members have been involved in areas of the site that have some tie-in to the product at-hand. And even better if they have developed a strong trust battery across the company.

In our case, the Engineering Lead, the UX Lead, and myself had each been at Shopify for less than a year; I can’t help but wonder if our team would have been more successful if one of us had more Shopify-specific context and proven success shipping complex products at the company. Or if there was a way for the three of us to collectively build that context more quickly to ensure we were ready to take on this project.

Apart from our newness, we were also lacking certain skill sets on the team and were hard pressed to bring in the right talent to support the product. These missing pieces resulted in the team constantly fighting an uphill battle which would have eventually prevented us from achieving product success. As the PM, I needed to escalate these skill and knowledge gaps as soon as I noticed them.

Takeaways:

• Create an outline: Create an initial plan for the work needed to build the product that satisfies your team’s goals. Reach out to other experienced people in the company to get feedback on your approach, which will help you steer in the right direction.
• Mind the team: From there, assess the size, skill, and experience of your team — including your own capabilities. The more complex the project is, the more you will need people who have been with the company for longer; and/or who have done very similar work in the past.
• Fill the gaps: If there are knowledge gaps, put mechanisms in place to help the team to ramp up properly and quickly in those areas.
• Adjust the team: After your assessment, if you don’t believe that you have the right team, escalate and make team member adjustments. This step will be tough, but better done sooner than later.

Lesson Three: Create Robust Communication Plans

The tricky thing with complex products is that you must ensure that the people sponsoring the initiative (your Leadership team) are on the same page as you. Because they’re the ones ultimately accountable for the project, you need to align the scope with their expectations. If alignment doesn’t happen, it can be problematic.

We had a lot of scope creep on this particular product, as I mentioned in Lesson One. Our Leadership was located in Ottawa, and our product team was split between Toronto and Waterloo. So based on distance alone, you can see how misunderstanding of scope and lack of communication could easily become one of our top obstacles.

It was hard to gauge how our Leadership was feeling about our progress on a regular basis. When we synced with them in our Quarterly Reviews, there were notable misalignments that left us feeling discouraged. We thought that we were on the right track, but we weren’t in their eyes. In retrospect, I should have developed a more effective communication plan that strengthened our trust battery and surfaced true product alignment.

Takeaways:

• Plan to communicate: Develop a detailed communication plan. Get your Leadership and other important stakeholders involved in this process. Agree and commit to specific channels, formats, and a frequency of communication that keeps everyone properly informed.
• Plan to travel: If same-office proximity is not possible, create a structured travel plan to which both the Leadership and leaders of the product team can commit to meet in-person on a regular basis. Based on my experience, I recommend a monthly cadence at minimum.
• Seek to restructure: If none of the above is possible, ask if there is potential for the team to switch under a local leadership team. It’s a stretch, but worth evaluating if the plan above isn’t working.

Lesson Four: Set Project Tripwires

I joined the group back in January, but the team was created three quarters of a year before that. We were having a tough time wrapping up a milestone that had been dragging on for about eight months, albeit, a highly complex milestone that involved migrating data.

If you are accountable for a deeply technical platform-related product that touches every area of the company, it’s a pretty good indicator that you should set tripwires. A tripwire is a mechanism or an indicator that you define, and when it gets triggered, flags are raised.

For example, you should set the tripwire of ‘time’ when a milestone isn’t completed after a defined period (for me, this should have been two months). When that happens, my recommendation is to have a serious discussion with the team and make your Leadership and stakeholders aware of what is happening. Communicate the changes that you will make to the team or process to get the project back on track. Next, outline what happens if the milestone isn’t completed in three months, then four. These are your tripwires as determined by time, but you can define tripwires in whatever form you see fit for your initiative.

Creating a tripwire strategy would have helped us to course correct leading us to make adjustments and difficult decisions earlier.

Takeaways:

• Assess the landscape: Identify if your product is or could be a suitable candidate for a tripwire strategy. A few indicators are: it’s highly technical platform work, a team of over 10 people is needed to serve the project, it has many stakeholders in various offices, the solution is not easy to figure out, or there are many milestones required to get to the end result.
• Create tripwires: If any of the above is true, create a tripwire strategy, along with an action plan to resolve each contributing issue when tripwires are set off. Because each product and project is very unique, the tripwire strategy and action plan can vary tremendously. You will need to figure out the best approach for you and your team.

Lesson Five: Set Personal Tripwires

There were many of issues that prevented us from building momentum on this project; I have highlighted some of the major ones from a PM perspective. Despite these issues, I had a vision that our team would become a high-functioning machine and I worked hard to get us there.

Looking back, the project constantly felt like an uphill battle, but I held on to the belief that I could fix it all. Although I saw glimpses of improvement during my six months that gave me hope, deep down, I knew that we weren’t gaining the momentum that we needed in order to create real value soon enough. My gut was telling me this, and I internalized it.

As a result, I frequently found myself managing stress headaches. I also lost hours of sleep many nights — thinking about product details, the overall project, or specific events that bothered me. At the four-month mark, I began to recognize that I was burning out and began asking myself how much more I could take.

Thankfully, Shopify staffs full-time Coaches, and I began scheduling sessions with one of them when I needed someone to be a rational sounding board for me. My Coach helped me to simplify the deeper people problems I was facing on the team and we developed ways for me to manage those complexities. And although coaching relieved some of the craziness and helped me to gain more control at work, I began doing research for additional support from an external therapist because I knew I wasn’t operating at my best. That said, I should have never let my mental health get to that point.

I thought that I could fix it all … but sometimes things can’t and shouldn’t be fixed. Now I know that I need to lean into those intuitive thoughts and feelings to develop a plan for knowing when my well-being is in trouble.

In short, I didn’t trust my gut and I should have. Doing so would have resulted in me calling out issues sooner. It would have forced difficult, but necessary conversations. It would have resulted in the final solution (to put the project on pause) to surface months before it actually did.

Takeaways:

• Acknowledge YOU: Listen to your intuition. These might start as barely noticeable thoughts inside your head, but if you are able to recognize these subtle cues, this is precisely the point in time that you need to accept them as meaningful emotions and potential precursors.
• Create tripwires: Just as you would with ‘Project Tripwires,’ identify the personal tripwire indicators that would raise red flags to you that a change is needed.
• Gather your people: Share these tripwires with the people around you that you trust the most. Ask them to help you remain accountable for your own tripwires. For example, if I still have noticeable concerns about my headaches in one or two months, that’s a tripwire that I need to take seriously — what is my action?

Always Be Mindful of Complex Products

The most important lesson I’ve learned is to treat complex products with a higher degree of awareness and sensitivity. Major issues can lurk underneath the surface and aren’t always straightforward to resolve when they eventually do surface.

Keeping these five lessons in the back of your mind is an excellent place to start, but complex products can be very unique with different issues. The biggest piece of advice that I can give you is to exercise awareness and to call out potential roadblocks when they are small. If left unaddressed, they could grow into massive obstacles that lead the entire project to fall flat.

And if all else fails and the unspeakable happens, my final takeaways are:

• Gather your people: Share your experience with the people that you trust. Leverage these friends and family for support and as your rational sounding board. Ask for guidance from those who’ve been there before.
• Illustrate your experience: Share your story so that the people around you can learn the lessons that you’ve gained.
• Move on: The good thing about being a PM is getting many opportunities to tackle cool and complex products. Every initiative will help you grow as a PM. Don’t forget about your downfalls, but don’t hang on them either.

Hopefully, my tips will help you to better navigate a project for a complex product and help you overcome potential adversity.

Are you currently working on a similar project? Please don’t hesitate to reach out to me. Let’s chat!

Reiterate shares insights into the craft of product, so the rest of us can learn and get inspired. Follow Reiterate for more pieces like Erin’s.

The Hard Thing About Complex Products & How I’ve Grown as a PM was originally published in Product @ Shopify on Medium, where people are continuing the conversation by highlighting and responding to this story.

To start off, a bit of context…

In this post, I’m going to riff off of Sheryl Sandberg’s latest theme — resilience. Of course, my perspective on resilience only runs as deep as the environment and background in which I grew up. To be clear… I was born and raised in a middle income household. I’ve been given every necessity in life (and many would argue, more). I’ve never battled any notable health issues. And I’ve always lived in safe neighbourhoods in some of Canada’s most thriving cities. I really haven’t had it that bad — my problems have been of the first world variety. So you might be asking, “Who the hell are you, Erin, to write a post on resilience??” That’s a great question that I don’t have a good answer for, but I have thoughts on what it means to be resilient. Bear with me.

I’m well aware that many people have much greater tales of resilience than I do. Those people inspire me and help me to put my resilience in perspective. That said, I’ve been thinking a lot about my resilience muscle in the past month. I’ve recently encountered a downfall (more on that in another post) and was a little surprised that it didn’t bother me as much as it should have. A couple days after it happened, I sat there thinking, “Should I be more worried about what just happened? Or, should I be worried that I’m not that worried? What’s going on inside my head?… or not going on? Am I losing my marbles? God, I need to keep those marbles!”

Obviously, a great time to unpack.

Defining ‘resilience’…

Sheryl Sandberg, Facebook’s famed COO, had a bout with resilience in losing her husband not too long ago. Without having read her new book, I opened up my laptop and Google’d ‘Sheryl Sandberg resilience’ and found this quote…

“The seeds of resilience are planted in the way we process the negative events in our lives.” — Sheryl Sandberg

The important word in Sandberg’s quote is ‘seeds’. It implies that resilience is derived from human development and growth. In other words, a person doesn’t become resilient easily and/or over a night of sleep.

To go along with that, I Google’d the dry definition of ‘resilience’ to hopefully uncover any nuances of the word that I wasn’t aware of before. Here’s what I found…

re·sil·ience

rəˈzilyəns/

noun

1. the capacity to recover quickly from difficulties; toughness.
2. the ability of a substance or object to spring back into shape; elasticity.

As the word ‘resilience’ is increasingly becoming a term used to characterize a person as it relates to their work, the definition above doesn’t entirely address the multi-dimensionality of people and what it means to be career-resilient. To give an example… would you ever characterize someone who experiences a career downfall, gets back up, and goes through the same motions again and again (same mistakes and same downfalls) a ‘resilient’ human being?

Interesting. According to the dry definition of resilience, that person would, in fact, be resilient. But I would argue that this person isn’t resilient at all. Sure, they are one-dimensionally resilient, but as human beings gifted with the abilities to deeply process events into complex thoughts and understandings, we are not one-dimensional and therefore the dry definition of resilience isn’t accurate in my mind.

People can ‘recover’ and ‘spring back into shape’ as, say, a rubber band that has been extended to max capacity would. But hopefully, we are vastly more sophisticated than rubber and we should emerge stronger, more intelligent, and MORE resilient than before. And that is my definition of human resilience — the capacity to recover quickly from difficulties and emerge to a higher level of resilience. Rubber bands can’t do this.

In my experience, there are a handful of steps that make up the process to build career resilience.

1. ACKNOWLEDGE that a negative event has occurred and assess how it made you feel.
2. CHOOSE to believe that things will get better despite the negative event that just occurred.
3. IDENTIFY the breaking points associated with the past negative event + STRATEGIZE how to mitigate them in the future.
4. TAKE ACTION to ensure, to the best of your abilities, that the negative event never happens again.
5. EXPERIENCE numerous or many negative events of differing natures/scenarios. Repeat — go back to Step #1.

Going through the above process isn’t easy! It involves a lot of awareness, a bit of work in figuring out a complex problem, and a mountain of courage. But as humans who want to grow emotionally stronger and psychologically smarter, we must.

My path towards resilience…

When I was a little kid, I was obsessed with swimming. At the age of 10, I often woke up in the morning having dreamt of swimming and winning medals the night before. At the age of 12, I decided that I wanted to make the Junior National team. I always stared at the older National Team members in awe as they wore their red National Team parkas on the pool deck. I listened to their stories about travelling to far away countries to compete and represent Canada. I wanted it all (and more!), so I began working hard… really hard. I set goals for myself and I practiced and trained as much as I could. While other kids were sleeping before school, I was in the pool training over and above regular practices. While other kids were playing or watching tv during the weekends, I was running around the neighbourhood to build up my cardiovascular fitness. While other kids were getting their first jobs over the summer months, I attended yoga classes, joined the canoe club, and enrolled in ballet programs. Oh, and of course… I kept running.

When I was 14 years old, long story-short, I didn’t make the team. My dream for two solid years came crashing down. I was devastated. I can remember that summer was characterized with a lot of crying and me sometimes feeling so bad about my life that it was a struggle to get up in the morning and breath. It was such an awful scene that it was embarrassing. I had zero resilience.

Thankfully, I had the best role model — my mom. She scraped me off of the floor and pushed me back into the pool. Well, she didn’t actually push me because… that would be child abuse, but we identified where I needed to be better and we moved onwards and upwards from there. And even though it was my mother who forced me to pick myself back up, I can confidently say that I wouldn’t be the same person I am today without her help during that difficult time. That was my very first big fail. I ended up making the National team the following year when I was 15. And I made the team every single year after that until the year I retired. Sure, there were many ups and downs during my National Team years, but my first experience with failure was the hardest. It was my very first step towards resiliency.

Fast forward to today. Having gone through, what feels like, a million downfalls (and some outright fails), the way that I absorb and react to these difficult events in my career has changed dramatically. I’ve learned to place them in a larger and more colourful context. This bigger picture is painted by having a more complex life (ah, the life of an adult!), but mostly painted by past experiences and having had the opportunity to have lived through (and survived!) a million career downfalls. And yes… I did use the word ‘opportunity’ in there — that was intentional. I also used the word ‘million’, which was not intentional and obviously a dramatic exaggeration.

I’ve learned how to grow from negative events. Today, I have career resilience and I don’t perceive downfalls as the outright ‘failures’ that I once did when I was a teenager. They are now a stepping stone for me to become a more intelligent and resilient (being the key word here) professional. And I’m definitely not saying that I’m 100% bonafide resilient today— I’m far from it, but at least I’m a whole lot farther than I was at 14 years old.

If you have any thoughts on resilience or on this post, please leave a comment!

And thanks for reading.

1. The user’s account becomes a marketing channel:

When a company is in its nascent stages, founders and marketers stick to traditional, digital and non-digital channels when it comes to marketing activities. For the most part, focus is directed towards getting new customers. But as the customer prospect pool shrinks and the company looks for more ways to generate higher revenues, the existing user base will become a resource to harvest.

The user’s account suddenly becomes a very attractive channel for marketers to upsell. This is always a tricky area for the Product Manager who is accountable for all things behind the Login screen. Of course, it’s your job to be the voice of the user, but you also can’t be the blocker of the company’s financial goals.

A user’s account should remain a safe haven where they can login, quickly do the tasks they need to do, and leave. Any marketing elements that you inject inside a user’s account should be non-obtrusive, personalized, and relevant. When marketing in the account is done wrong, the customer is left frustrated — you’ve crammed an undesirable experience into a place that they feel belongs to them. In some cases, you’ve lost their trust because they perceive that you don’t care about them nor their experience on the site. At its worst, you’ve got an angry customer who is a step closer to churning.

Takeaways:

When the first signs of marketing requests arrive on your plate, decide where you are going to draw the line and outline, in detail, what too much marketing looks like in the customer’s account. Make sure you have strong reasoning behind your decisions so that you can help the leadership and marketing teams understand your point of view (and the user’s point of view). Ideally, you will have qualitative and/or survey data to back you up. And then… stick to it!

2. Design elements, copy, and tone across the brand’s various sites become misaligned:

It is so easy to lose control over a brand’s communication and design elements, and especially as the company’s team grows in size. Two different teams could be sitting in the same room for the same brand and STILL overlook variances in communication and design. I have witnessed this firsthand! At my previous employer, our teams sat at the same long table and, at times, we still strayed from each other. The Commerce team on one end of the table and the Self Serve team on the other. We had our heads down when things got busy and when it was time for demos with our senior leadership team, found that we had treated certain design elements totally differently.

(Embarrassing and awkward laugh. My bad… apologies to all of those involved!)

If left unchecked, a plethora of tiny misaligned details between a company’s sites can grow into two very different brand experiences. And as a company scales, teams become dedicated to different sites (ex. the account site, the marketing site, the support site, etc.). These teams are often in different buildings, and sometimes in different cities. This is where communication and opportunities to share progress of work breaks down. A misaligned and broken brand is an easy opportunity for a competitor to grab the customer’s attention by flaunting a unified and easily digestible experience. Brand is one of a company’s most important assets and employees need to put their best foot forward in creating a unified experience.

I have found that content writers are often freelancers. This means that there is a revolving door of talented people who are potentially injecting their own writing style and tone in various parts of the site. Again, with a barrage of small inconsistencies and different tones, the brand suffers.

Takeaways:

Having people dedicated to creating and upholding a content/communications playbook, a brand playbook, and a library of design elements. Make these sources of information as detailed as possible including examples of what is okay and what is not okay. Weekly mandatory demos, UX reviews, and brand touchpoints are key in catching any creeping variances and keeping the brand consistent.

3. The company attracts new and different customers:

Companies grow over time and pressure to continue increasing revenues year over year builds. It becomes more difficult to scale catering to the same target market. From this, new products and services geared towards new target markets emerge and each time that happens, the business gradually becomes more complex. When more functionality, more products, and more users make their way into a site, the team accountable for the site will begin to feel an entirely new level of pressure. They must now uphold the site in the most simple way possible even as the company becomes very ‘un-simple’. Maintaining simplicity is perhaps one of the most difficult things to control for a Product Manager. You need to consider the various types of users of your site and the different types of functionality (or products) that each of them use. And then you need to consider the various levels of comfort and understanding that they each have with websites and tech in general! They each have different needs and simplifying all of that into one solid experience is a monster of a challenge.

Takeaways:

Take a look at all of your different types of users. There will be various ways to categorize them, but find a way to section them into definable groups. For example, at my last company, the large majority of customers were single-account users (one customer per account). The much smaller minority were multi-user accounts (a family or a small business using one account). You could say we used the 80/20 rule. I’m not saying that this is the right approach for every product, but it served our team well to optimize the site’s UX for the largest customer base.

So… figure out which users are the most important to your business and clearly define why. Then, build the site for them. We focussed our energy on building a great single-user account experience because we were confident that if we created a great site for them, the business would continue to grow. And it did!

That said, don’t break the experience for the other users. Perhaps certain flows might be a bit awkward for them, but the experience should never be flat out bad or broken. They are people and they matter too. But I suggest putting your best foot forward for your primary users, whoever that is for you. Don’t try to be everything to everyone because that strategy NEVER works.

4. Frequently asked questions, aka FAQs:

Creating and updating site FAQs for your product are the last thing on any Product Managers mind when things are getting busier and more complex. Well… I speak for myself. haha.

However, FAQs matter tremendously. If the business has shifted strategy in any way and you, as the Product Manager, need to reflect that shift in your product, well-written and accurate FAQs could be the second last resort for your customers (the last one being a costly call to your Support Centre). In my experience, as a company grows and becomes more complex, users rely on FAQs to help navigate the company. A strong FAQ section or entire FAQ site could save your company millions of dollars in avoided support calls. If your company is serious about reducing those calls, metrics and goals around effective FAQs should be created and watched carefully.

And although writing FAQs may feel tedious and painful, this type of work needs to be perceived differently. FAQs and any other types of support material are part of the complete product package.

Takeaways:

Dedicate 1–2 hours monthly to take inventory of everything that is about to be shipped. Schedule some time with a copywriter (or do it yourself) to update your FAQs. In the same vein, schedule regular touchpoints with the person who is your conduit to the company’s Support Centre team. Make sure this team always has the necessary information and training materials to support any updates or changes to the product that your team ships. Make it a habit — book a recurring block of time in your calendar for these activities.

Conclusion:

Experiencing a company scale from the perspective of a PM has been one of the most interesting areas of learning for me. Facing these obstacles for the first time and finding ways to overcome them has allowed the teams I’ve been a part of to be resilient and successful. It has helped me, personally, be a stronger PM with a heavier toolbox of skills and insights. Hopefully, you will have the opportunity to leverage some of the above takeaways if you are part of a growing company.

Comments and feedback are welcome. Happy scaling!

Here, you can read about my experiences, thoughts, and learnings as they relate to the tech industry, the discipline of digital product management, marketing & branding, leadership… and my life.

Being a female in the tech industry (and a relatively new mother) is tough. I’m sure that you’ve come across some of the pretty sad stats about women in tech. Reading and thinking about these stats affects me once in a while, being both a start-up founder and a product person in the bourgeoning tech scene of Toronto. That said, I feel good about my career and being where I am. I get paid to do something that I love doing and I try to shift any frustrations that I might have about being ‘female in tech' towards my family as well as creating better products and experiences for other people. There’s a lot of power in channeling shitty energy into the stuff and people that you love. A lot of this Medium will be inspired by that. Aaaaand there will be a few random subject posts here and there (because I can’t help myself sometimes). For example, I love pizza.

Just kidding… I won’t write about pizza.

Or will I???

Thanks for stopping by and I hope you enjoy the reads. It’s one of my goals to get back into writing and knowing that I have even the smallest audience helps me put finger to key. And of course… comments are welcome!

Erin