Lessons learned scaling design teams

4 min read
Aarron Walter
  •  Apr 10, 2017
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When you’re part a fast-growing company, it can often feel like the challenges and breakthroughs you’re experiencing are unique to your team and organization—that these are problems you have to solve together, for your company’s unique position.

In some ways, that’s true. But that doesn’t mean we can’t lean on the experience of others as well.

Being part of MailChimp’s growth from 6 employees to 550 in 8 years, and now witnessing similar growth at InVision, has afforded me a unique perspective on the stages companies, teams, and individuals go through as design scales. I’ve paired that experience with insight I’ve gained from interviewing dozens of design leaders on their growth and challenges, and distilled it down to some hard-earned lessons I shared with O’Reilly Design Conference attendees in March. Today, I’d like to share them with you.

Aarron Walter presenting at the O’Reilly Design Conference. Image courtesy of O’Reilly.

Inflection points of a growing company

It can be hard to navigate the territory of a scaling company, especially when no one has a map. It turns out there are clear transition points along the way, and knowing where they are can give you perspective when things look more dire than they are.  

In general, the following stages represent distinct inflection points on a company’s growth journey:

  • 1-30: The organization feels like a family. Everyone is doing multiple jobs. Communication is constant and effortless because you know everyone in the company. Decisions are made quickly, and are often founded only on hunches, but that’s okay. The product is in its infancy and the to-do list is clear.
  • 31-50: More people have been hired to help relieve the pressures of wearing too many hats. Hire well, as these people will hire many more and have a big influence on your culture. With more people comes the need for better communication.Twitter Logo You’re starting to explore process. The team is mostly comprised of generalists still.
  • 51-200: Big changes are happening, and they often feel awkward. You no longer know everyone in the company, and you may not know who to speak with about basic issues. Chances are you and others will have to move to new roles to keep the company moving forward. You’ll have to hand over your previous projects and team to new people, which can be hard. There are more meetings and formal processes. You can no longer base your strategy on hunches as there’s too much at stake. Define your company values now to guide the growth of the culture.
  • 201-750: More big role changes for many. Some of the people who’ve been with the company from the beginning will be leaving and a new guard will take charge. The company has shifted from innovation to optimization. The product is mature, and now you need to stabilize everything to continue growing. The company has many more specialists who will introduce new capabilities. With so many teams now, you’ll need connector people who can bring them together and can communicate institutional knowledge.
  • 750: Culture and values are well defined. They can be changed still, but it’ll require a lot of effort to move things. Beware of teams and individuals putting self-interest in front of the company’s interest.

Andrew Crow, former VP of Design at Uber, saw insane growth in his tenure. Just as they got a handle on their workflow, more people would be added to the team requiring a retooling of both org structure and process. He likened it to bringing water to a boil, only to add more water and drop it back down again.

“Clear and consistent communication can reduce FUD.”

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As roles change and responsibilities shift you and your colleagues will undoubtedly experience FUD: fear, uncertainty, and doubt. Recognize that this is normal. Reorgs mean FUD, but clear and consistent communication can reduce it.  Leadership can ease the turbulence by communicating changes early and often, and normalizing the emotions people are feeling.

Giving up your LEGOs

As your company grows, you’ll inevitably have to shift roles and rethink your identity. Molly Graham, a veteran of rapid scale and an operations master, has sage advice for surviving periods of rapid growth. Give up your LEGOs—the project or role that has defined your work.Twitter Logo

“If you personally want to grow as fast as your company, you have to give away your job every couple months.” –Molly Graham, VP Operations Chan Zuckerberg Initiative

Giving away your job to someone new is a difficult thing to do. Your attachment to the work or skepticism of your successor’s ability to fill your shoes may make you leery of change, but you’ll be needed elsewhere in the company. There are new mountains to climb and more opportunities for growth for both you and the company.

Letting go can be liberating.Twitter Logo It’s exciting to learn new things and expand your skills. It’s much easier to let go of your precious LEGOs when leadership helps you see that the next batch of LEGOs are even better.

A changing product

Just as the company changes with scale, so too does the thinking around the product. For a product to mature you’ll need to continuously change the way you think about its evolution.

We can map the evolution of product thinking into 3 stages:

Stage 1

Early on, new features are like low-hanging fruit on a tree—they’re easy to see, easy to reach, and should be harvested as quickly as possible. Priorities and direction tend to be clear at this point. The product is immature and you’ve got a lot of work ahead of you. You move fast just to get basic features built.

Stage 1: When the product is still nascent, priorities and direction are clearest. Features are low-hanging fruit to be plucked as quickly as possible.

Stage 2

Rapid development inevitably leads to some rough edges. The product may not be as usable as it should be, and it’s likely to have some gaps in functionality that can be deal breakers for some of your customers. It’s time to refine to prevent churn and shore up defenses against fast following competitors.

But what refinements are most pressing? The fruit is now higher in the tree, and a little harder to reach. You’ll need to talk to customers, and watch them use your product to know where to invest your energy.

Stage 2: As the product matures a bit, it will become clear that rapid development has lead to some rough edges. You’ll need to refine the product to be more usable and robust enough to meet the needs of customers.

Stage 3

Your product is maturing and hopefully stabilizing. Core features and integrations are built, and now it’s a little fuzzy what to do next to make another innovative leap forward. New ideas are harder to come by—the fruit is at the top of the tree. Your next big idea probably won’t come from internal brainstorming, but from studying your customers and the market more carefully.

Visit customers in person to observe how your product fits into their life.Twitter Logo It’s unlikely that a customer will tell you what feature or product they need. You’ll have to spot a problem they’re unwittingly suffering through to find your next big idea.

Stage 3: Product ideas are hard to come by. Observe customers in person to discover your next product idea.

Shifting priorities

Priorities will shift as your product matures and your customer base grows. Speed is essential as you build out core features. The product will change dramatically, but with a small customer base the disruption is minimal. Rapid change is exciting to your early adopters.Twitter Logo

“Speed is essential as you build out core features.”

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But middle-stage customers won’t tolerate an ever changing UI. They’ll have something new to learn each time they use your product, which slows down their workflow. Where speed was once a virtue, it’s now a vice. You’ll need to be much more thoughtful and incremental when you introduce change to the product.

Slowing your roll can be a buzzkill for many in the company, but there’s a silver lining. Though the product may advance more slowly, your work will be far more influential because you now have more customers in the product.

Typically, as your customer base grows, your speed and rate of innovation needs to slow as you shift your focus towards optimization. But with scale comes greater influence on a large audience.

This is where the importance of constant quality improvement comes to fore. Your ideas may be great, and highly influential, but if they’re buggy and inefficient, you’ve got problems.

You need to start formalizing a refinement process—something at MailChimp we called “Guns forward, guns backward.” That might mean having a team dedicated specifically to product refinement, constantly sanding off the edges.

“The best product companies in the world have figured out how to make constant quality improvements part of their essential DNA.”Phil Libin, former CEO of Evernote

We’ve talked about process, product, and your own role. Now let’s look next at lessons to be learned in hiring and management.

Your legacy is the people you hire

Growing a company from 1 to 100 to 300 and beyond is not easy, and you and your team will face countless challenges, big and small, on your journey.

Imagine yourself on a beach, retired, contemplating your legacy. Is it, “I made this thing that changed 6 months after I left”? Hopefully not. That’s why hiring is the single most profound impact you, as an individual, can have on your organization’s success. The people you hire will be your legacy.Twitter Logo

Hire people, not skills

That doesn’t mean just choosing the best people with the right skills. It means identifying those individuals who have the potential to grow into something bigger. Companies that have low churn and a great success rate have mastered this skill, and it involves looking at both hard, “technical” skills as well as soft skills.

This is an art—not a science. It sounds simple, but the most valuable thing you can do when assessing soft skills is to simply spend time with a person—get to know them. It’s easy to fake your way through an hour or two of interviews. It’s a lot harder to do so on a multi-day, multi-person immersive experience.

“When hiring, identify people who have the potential to grow into something bigger.”

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One core skill to look for? Adaptability. You have to change in your role—giving up your LEGOs, remember?—so the people you hire will have to change too.

Diverse team perform better, so as you review candidates be careful not to gravitate people who are too similar to you. Different perspectives will help you and your team see problems from different angles, and will help you empathize more effectively with the many customers who will use your products.

Scariest of all can be hiring someone who is smarter or more experienced than you, but that’s what you have to do to level-up your team, and to leave it better than when you found it. It’s also a great opportunity for your own personal growth.

Keep your standards high

If you must become more comfortable hiring those who are better than you, you must also avoid becoming comfortable with mediocrity in your hiring.

Consider this: Mediocrity begets mediocrity.Twitter Logo

When you hire someone who’s pretty good, because you have a timeline to complete a product and everyone says you need to move faster—someone who can get on board quickly but may not be the best—their mediocrity will become a problem sooner or later.

“You cannot hire top talent with mediocre people.”

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It will attract other less-than-great people, and tell your team that mediocre work is okay. It’s an insidious problem that brings the whole team down, because you cannot hire top talent with mediocre people.

Communicate—always, in all ways

If you’re hiring, you’re probably managing too, and delving into good management is a blog post (or several…) all its own. Here are the top lessons I’ve learned, though, both in my own career and in speaking with other leaders in design.

Get stakeholders involved early and often. Bad things happen when people feel left out. We all know the chaos that can erupt when you get far down a product path and realize you didn’t involve key stakeholders like engineers, executives, or marketers. Not only does it lead to bad feelings all around, it also jeopardizes your work which may get derailed by skeptics or transformed into something much different than you’d expected. Involve stakeholders in design reviews regularly to make sure they stay in the loop. Regular communication about the design is far superior to a grand reveal.Twitter Logo

“Bad things happen when people feel left out.”

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Get good at conducting 1-on-1s. 1-on-1 meetings with each individual contributor are key to the care and “feeding” of the people on your team. It’s their time to ask questions and get feedback, so don’t cancel or clog up the conversation with status updates. This is the time to talk about their needs, their career path, and how you can help them maximize their potential.

Your team wants a place where they can grow, get feedback, and learn how to do better work. Getting good at 1-on-1s will help you hire the right people and build the next generation of leaders at your company.

Grow comfortable with changing processes. Time and again I hear the same question: Centralized, distributed, hybrid—what’s the best design team structure? The truth is, there’s no answer because it depends on the stage of your company’s growth, and your goals. Each team structure comes with pros and cons.

Let go of the idea that a team structure is permanent; what’s more important is knowing your company’s primary goals right now and optimizing to help your team work towards them. When you reorg, your team share with them the benefits and trade-offs to destroy the FUD that occurs when reorgs happen. They need to hear how change helps the company and helps them do their best work.

“Know your company’s primary goals and optimize to help your team work towards them.”

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Spread the knowledge

As designers, it’s tempting to shroud design in mystery. This is born out of fear—fear that if others are involved, you as a designer may not be as valuable.

The truth is, you are not magical alone. You will be magical—and more valuable—if you involve more people in the design process, and make design less of a black box. Doing so shows others the true, deep value of design.

Sometimes as a designer, especially when you’re working alone, it can feel like you’re the star at the center of the universe, when you’re actually just a piece of the constellation. It can be disconcerting to adopt that mindset, but also exciting—because you realize you’re part of something much bigger.

When design is a black box, it’s hard to see its value.Twitter Logo When it’s transparent, the value becomes more apparent to all. As a company grows designers must build social capital with many teams to help usher products through the many phases of development.

Get to know the other people on your team who influence and shape your product, from every team. Because at the end of the day, what we’re doing here is a team sport.

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