“It felt like you just told a life story!”

How 17 months in a startup got me so many things to share

Recently, I had a chat with an old-time colleague who is now the director of product in a growing startup. As he is currently preparing for an organization scaling (26% more to hire), he was interested in managing more than five Scrum teams.

I was part of a fast growing design team during which the organization had to undergo two scaling stages, so I started with “The product team grew from two scrum teams to eight, roughly speaking”. Then he asked inspiring questions! Didn’t expect that my answers were useful to him, so I decided to write them here (not a transcript of the conversation).

How was the organization structure?

When I joined, there was one product director, who oversaw multiple product managers. My team worked closely with these teams, but there was another design team who worked on communication and advertising projects, working closely with marketing teams. Both design team leads reported to Head of Design, who reported to CEO. As of that time we didn’t have a C-level design / UX person, as the organization structure didn’t indicate that need (or yet). You know, a CXO or CDO needs to have a broader scope than just leading designers and working on “operational design”.

Note that the product director was more business oriented, unlike you who is really product oriented. So were the product managers. Design and Engineering worked like an agency to these product teams. It’s like they were our clients and we supply designers and engineers to work on solving their business problems.

How was the transition during the scaling?

Before I joined, designers didn’t participate in a scrum team. They used to run meetings, inviting product managers to bid for designer’s resources for their projects. After I joined, we tried to do it every two weeks as if it was our internal sprint.

The first scaling was three months after I joined. The co-founders wanted to restructure the product teams to be more efficient, so agency systems were no longer practiced. It also needed a physical reorganization with the spaces, where designers and engineers sit together with product teams. We had to hire more designers, since the number of designers were not sufficient (due to a large discrepancy in skills) to distribute them among the product teams. It took roughly three months to do a lot of hiring and mentoring until we had a set of skillful designers in each product team.

The second scaling was only seven months after the first scaling. Due to new business initiatives, a new product director was hired, building two scrum teams to begin with. Within three months we had to adapt with so many hiring even more intense than the previous scaling, as there were no longer just one product director. Fortunately, this time was around college graduation, so we managed to get fresh graduates with good potentials before they found a job somewhere else. Our recruiter was very helpful!

How did you manage the transition to ensure that designers were ahead of product development?

Each product team adapted differently. There were two remarkable product managers whose team adapted quickly. One got really interested in UX that she attended a UX course. Her understanding of UX made her immediately rearrange her team, so designers got involved from the beginning. The other one was the only product manager whose background is product research (although in a completely different industry), so it was easy for him to switch to UX mindset. He also did a rearrangement of the team with iterative process (“hardcore” scrum) together with everyone. They both adjusted within the first month. It took six months for the slowest team to adapt to having designers fully included in the scrum team.

At the beginning of each quarter, product managers sit with their team of designers and engineers to share the quarterly roadmap and arrange project execution. Priorities were usually set at this stage, but it was still open for adjustments during the quarter. What is important during this stage is to estimate man hours. For example, a designer said that the projects in the upcoming quarter would take him 1.5 times of his capacity, indicating the need to hire or assign a new designer to the team.

I worked closely with product managers in order to find out their needs for designers, but since I got to understand the scope and goal for each project I also helped with the strategy part here and there, e.g. what design activities needed for a project or how to confirm that a problem was real. Sometimes I played a backup designer to help a less skillful designer, or worked on side projects outside the sprint planning.

After all, what is better, the designers to sit together with product teams or as an agency?

Definitely to sit with the product teams, because of two benefits. First, they got to really know about the product (unlike in the agency setting when they weren’t part of the discussion behind the Why of the design task). Second, it’s beneficial for their growth as designers, because they learned more due to intense collaboration with engineers and product managers. The UI designers got to know the engineering behind their design and then able to ensure an implementable solution. The UX researchers got to know deeper about their product and then able to propose a product concept to solve customer’s problem.

Didn’t having many new people joining slow down the product teams to keep executing what they needed to do?

New designers were able to adapt quickly, because of the direct placement within close proximity of their product teams. They started with working on an ongoing sprint and learned on the go. Within each product team, designers sat next to each other, so this was also helpful for a new joiner (communicating in designer’s language).

In the first scaling, we didn’t have a proper mentoring system. Only with weekly meetups of each designer type, e.g. UX Researchers meetup, UI Designers meetup, they shared findings and experiences and howtos among each other.

In the second scaling, due to many fresh graduates, we asked the mentors (designers with Senior title or close to Senior) to be accountable to what their mentees did (this was communicated to the relevant product managers). Product managers could ask the mentors for help when the new designers couldn’t help due to insufficient skills. In certain cases, the mentor sat with them for a day per week during the designer’s first two weeks.

Of course we managed to hire designers with some experience, too. Those with sufficient experience could independently take care of themselves in the adaptation. They had better communication skills, too. They just needed a place to ask about how things work, and it was clear where to ask, thanks to the mentor and the weekly peer meetups.

How did you manage with on-boarding so many designers at once?

The first day of a new joiner was to directly meet their product team, had a chat with the mentor and me, and physically settled. On the second day, there was a session with Head of Design to ask questions about the design organization and culture as well as product branding.

I used to run weekly sessions with all designers before the team got so big. We shared team updates and a topic to learn weekly. In addition to the weekly session with their peers, this weekly session with different designers from multiple products helped them understand the situation for adaptation.

Who was the designer’s line manager?

It was me. They didn’t report to product managers, because the product managers were mostly business oriented. Their growth focus is toward business goal fulfillment, so they didn’t have sufficient knowledge on growing designers with skills that contribute to design quality (which in turn help fulfill the business goal).

We also explained this reasoning to new joiners in product teams, who happened to work in a different startup previously. Many startups have Design as part of Product or Engineering, because they have a limited scope of design. To them, design is just efficiency or ease of use, not including the qualitative or value-based experiential factor, so it could be done even within engineering team.

How did you ensure that designers can influence product innovation?

By keeping the design team separate from the business-oriented product team. I was also glad to find that the co-founders promoted the culture of challenging each other’s ideas from the beginning. Everyone was encouraged to throw an idea or challenge others’ and we made sure this was communicated to new joiners (via Head of Design’s session).

Was innovation driven by top-down or bottom-up?

Business-driven innovation was top-down, as these decisions came out of board meetings. However, since we started to have the multiple directors of product, each director was more approachable for discussions about results of understanding market and customers.

We tried to pair one design lead for each product director. This pair can meet once a month to discuss problem discovery and discuss design strategy. That’s why it was difficult to hire additional product design leads because this person has to be able to formulate strategies leading to product innovation.

One of the signs of the readiness toward the bottom-up innovation drive was how the CTO got into customer experience. Just because we shared with him a comprehensive list of UX researcher’s projects on understanding customers, he came up with a system architecture draft that supports customer experience. I am still amazed until now.

Were you able to do real research?

Not toward product innovation yet. What do you mean with real research?

I mean, the research you did previously during your PhD.

Academic research? Of course not! Isn’t that the stereotypical view some people have on someone with a PhD? In the beginning, someone said to me, “What kind of research are you going to do here? Are you going to slow down this organization?” That’s an inappropriate remark. Obviously I knew that I was going to work with a startup (and it wasn’t my first startup experience), so “try and reflect” is the way to do. The designer’s way.

Did you work with KPIs?

Yes, but qualitatively, not with numbers. We came up with the KPIs together with product managers. Right after the first scaling, the company hired a senior expert in HR (people operations). This guy was very knowledgeable. I asked him to help with the facilitation of the meeting on designer’s KPIs.

What’s an example KPI?

For example, to a UI designer, one of the KPIs is to have an implementable design. This means that the designer has to do the work with engineers, so when he/she presents his/her design to the product manager, the implementability is already there. This is an acceptable quality of such a KPI. A better quality, for example, is when a product manager remarked “This designer went out of his way to produce a complex yet implementable user interface that led to a delightful user experience (according to the feedback from our customers).”

How did you set a boundary of your responsibilities?

Every six months all employees had a formal goal setting session with their direct managers, but in practice I changed my responsibility every three months. Things were moving too fast. In this case I had to have intense sync opportunities with my boss, because he was the one doing the communication about my changing role. This didn’t happen only with us, but also in other teams (or due to new team formation). We could create our own role or job title and change it after a couple of months or so.

Isn’t it easy to lose focus, managing so many people at once?

Of course! The last time I handled the team, it was 20+ people. I felt like exploding LOL. So when the product teams got split into four groups and we decided to hire a design lead for each group, I practically left the other three groups and stuck to one. A senior designer was promoted to lead designers in another group, and the other two groups had a senior designer each. I met with them weekly in order to catch up (one-on-one sessions). I couldn’t actually work on their design problems anymore. When we met, they could share some issues with me, their own solutions, and I could only help with some advice or just a sounding board.

There must have been so many frictions during this fast growth! How did you deal with it?

Yes, when things are chaotic, communication needs to be strong. Just a few glitches can cause frustrations here and there. For example, a new joining product guy didn’t get introduced to me until almost 2 months! To him it felt like he didn’t have any designers assigned to his team after so long asking (the wrong person) for it.

I raised the communication issue quite a number of times. The HR expert guy started a team called People Development, whose task among others is to coach employees on professional development. Leadership communication is one of the training topics I proposed for them to have.

Wasn’t it such a different work from your previous academic research?

You know what? This particular experience is more rewarding than academic research! In a startup you’re expected to do research (reading, experimenting, reflecting) every day, due to the ever-changing nature of the work. I love taking new challenges, the reason I used to enjoy my PhD. But I can find new challenges anywhere, not just in academic research.

A new joiner in our team used to study Clinical Psychology and consider to do a PhD, until she experienced product management in a startup. She found that working in a startup is a constant learning experience, as stimulating as doing academic research. I couldn’t agree more with her!

What did you learn the most from this experience?

People growing, organizational design, and communication skills! For communication skill, there was this phrase we used, “setting the stage”, because it’s important for every team leader to set stages for team members. We should not be tired in communicating which stages are owned by whom. We reminded each other to make the effort and not to be discouraged by the need to repeat stuffs like a broken record.

For organizational design, try this book “Organization Design for Design Organization” by Peter Merholz & Kristin Skinner. These I learned from my former team members who bought the book after I left. The team leads also attended a workshop by Kristin. FYI Peter is the co-founder of AdaptivePath (one of the world leaders in design consultancy).

How long were you there?

17 months.

Wow, it felt like you just told a life story!

Scaling a startup, in a highly competitive industry like e-commerce, is definitely faster than in a more niche industry or solving a specific problem with not so many players in the industry. When the business grows out of market competition not out of innovation, you need to scale the whack out of it. I am grateful for that whacking experience.

Some e-commerce startups will eventually be a leader in the market, where the organization will have more space to breathe in order to take care of innovation. In one startup, “director of product” might mean someone leading business development, while in another startup “director of product” means someone leading product innovation.

At the end of the above conversation, we discussed our three common observations:

1. Introducing UX into an organization who knew zero UX needs two things: knowledge spreading and creating proofs. By showing more projects developed with UX understanding that cause a real delight to customers, we create more proofs that get more people to switch to UX mindset. The first step is to get the first few people to join the UX club and recognize them as the pioneers (spreading their exemplary actions).
2. In many internet startups, Product Managers or Product Owners are more business oriented. They focus more about the business development than the product development. How to fit designers in the product team is a matter of structuring the team differently. Bigger vs. smaller team, ratio of engineers to designers, and whether the designers report to Product (product people with design experience) or to Design (design people in management).
3. In many organizations, the product strategy is often the result of business strategy but not the other way around. A way to make product strategy be influential to business strategy is to create a separate team, e.g. “product innovation” or “design strategy” team, which will act as a bridge, a middle entity in the organization. This team works on innovation projects collaborating with multiple teams (to obtain various inputs instead of just customer feedback).

As a side note, my former colleague joined the 30-people startup as a UX Manager, who introduced UX understanding and promoted Scrum practice in the organization. As he learned that the startup needed to understand their customers deeper, to expand their services, he proposed a product innovation team. That’s how he transitioned into Director of Product. The “UX team” that he used to manage, who is doing the technology design (UI), merged with Technology team (reporting to CTO). He is taking a new challenge having the product innovation team as an independent team (that middle entity).

His product innovation team consists of product researchers as well as people from different backgrounds e.g. finance, marketing, design, engineering in order to solve customer’s problems with innovation. I mentioned to him another book bought by my former team members, “Sense and Respond” by Jeff Gothelf & Josh Seiden, which is exactly about what his team is currently doing: sensing and responding. I wished him the best in this now 150-people startup ready to scale.

I see him as an example of the natural transition of someone doing UX to doing product innovation or strategy. When doing UX you are constantly faced with customer feedback, which many times surprises you and makes you passionately curious about solving their problems. You will no longer see the product on its own. You will end up thinking about services, and that leads to strategy and innovation, where it’s not only about designing the product right, but the right product for your customers.

It was nice to summarize my 17 months in a 75 minutes chat! I really thank him for asking me those questions.

Thanks to the startup guys: the co-founders (including Head of Design and the CTO) for all the inspirations and for believing in me, the recruiter for all the quick moves, the two early-adopter product managers, the two approachable product directors, the head of HR for coming to the rescue, the senior designer who took the challenge to take care a group of designers, the clinical psychologist turned product manager, the other design lead and senior designers for all the sharing during the chaos, and all designers for bearing with my tough love! :)