Introduction

What Is Collaboration, and What Gets in the Way

If you want to go fast, go alone. If you want to go far, go together.

—Unknown

The 21st century has brought our society great new capabilities, such as landing on Mars and editing genes to treat disease, but it has also brought us complicated, intractable problems like climate change. We need to get better at coming together to solve these problems, because no one person is going to make a dent on their own. But many people find collaboration difficult and exhausting compared to working in simple teams of like-minded individuals with clear lines of authority. In my own work, I have experienced the temptation to take a narrower, more isolated path. But even when it’s difficult, the experience of working closely with someone who is very different is ultimately rewarding, and generates better answers. While not everyone is a natural collaborator, we can all adopt different behaviors and approaches to make working together better.

What’s Collaboration? And What Isn’t?

In researching this book, I’ve heard many people say that collaboration is simply “the air we breathe” and covers almost every aspect of our work. Kate Rutter, principal at Intelleto and author of Build Better Products (Rosenfeld Media), has a useful model for defining teamwork at several levels, which I have adopted (Figure P-1). She lays out the difference between cooperation, collaboration, and co-creation. At the most general level, Rutter says, is cooperation. Cooperation describes people doing things in a coordinated fashion, in a clear order, according to shared standards. She and I agree that while this is important, cooperation is very different from collaboration in that it describes work that is well understood and can be structured, sequenced, and monitored in a more straightforward way.

At the other end of the spectrum lies co-creation, where two or three people are actually making something together. They’ve got their hands in the dirt, as it were, and apply skills to something tangible, whether it’s a policy or a product. I will address this type of collaboration briefly, because there are techniques and methods you can employ for co-creation that will help you when you take their output to a wider group. Much has been written about how to do co-creation—from Sprint (Simon & Schuster) by Jake Knapp to “Pair Design”, which I wrote with Chris Noessel for O’Reilly—and you will find many ideas there to get better results.

A model for understanding what collaboration is, and is not
Figure P-1. A model for understanding what collaboration is, and is not

Rutter says what lies between cooperation and co-creation is collaboration, where a diverse group of people are responsible for an outcome, but may not all be working hands-on to build the solution. This is where this book will mostly focus: how to get alignment of purpose, how to guide smart decisions, and how to broker politics that large diverse groups will inevitably face. Collaboration at this level often involves “fuzzy frontend” thinking where both the solution and the path to it are neither obvious nor planned. Collaboration may be messier and involve leveraging very different skills in nonlinear and unpredictable ways.

Collaboration doesn’t come in one specific form, and doesn’t follow a recipe. It might be a set of people who are working independently on a common problem, sharing their work early and often to get feedback and test out ideas. Or, it may be a team of people from different business functions who go offsite for a week to hash out a new compliance framework. Collaboration can be a group of developers, designers, analysts, and product managers developing a product or service, or even a set of teams working on parts of a product or service system that needs to be coherent to those who use it.

Choose the Right Problem and Moment

Collaboration can take many forms, but at the core it’s a way to drive more innovative solutions to problems. Because it’s challenging, we need to be careful not to start throwing “collaboration” at every cooperative situation, making things that should be straightforward into complex arguments, or inviting too many people into a co-creation space and slowing it down.

Collaboration is especially useful for addressing the following issues:

Taming complexity
First, we benefit from bringing diversity to a problem, whether it’s diverse skill sets, cultural perspectives, or customers and employees. The ability to channel the experiences and skills of many people when solving a problem means you generate more potential solutions, and tests of those solutions, quickly.
Facing ambiguity
Collaboration is also incredibly useful when the challenge being faced has unknown unknowns, and there isn’t a clear, structured path forward to find a solution. In these situations, collaborations, given the right space, can help a small group of trusted colleagues feel out the unknowns from different angles.
Getting alignment
Getting buy-in from large groups of stakeholders can also be improved by collaboration. When it’s done right, stakeholders, given a chance to participate in creating the solution, will be more invested in its success.
Engaging employees
Companies spend a great deal of time and energy assessing and supporting engagement among employees. They know that workers who are intrinsically motivated and who have a sense of ownership over their work produce higher-quality work and have lower turnover rates. These employees are the profile of 21st-century workers who can think nimbly and adapt to changes because they have resilient partnerships among colleagues. These are also employees who are better suited to solving complex problems versus executing known work patterns.

We’ll cover each of these issues in more detail next.

Taming Complexity

Paul Ford, a well-known serial, solo entrepreneur, recently founded his own studio, Postlight, helping clients realize new product concepts. “As you grow in the industry,” he says, “you learn you can’t do it all. Especially now, with tools as they are more robust, it’s basically impossible for one person to ship a truly innovative product anymore. The tech stack is so vast, you need to be able to tap into everyone’s strengths.”

It’s not just our tools that have gotten more robust and varied; the wicked problems we face have gnarled root causes demanding varied viewpoints and specialty skills. In his excellent TED talk, “When Ideas Have Sex”, Matt Ridley points out that ideas are never just born de novo but are always an evolution sparked by someone else’s ideas and solutions. He considers the creation of something as prosaic as the computer mouse and all of the intricacies involved in creating it. Even the most competent maker on earth couldn’t single-handedly pull off creating one once you consider not just the making of circuit boards and buttons, but also the petroleum refinement needed to make the plastic and the firmware to control the interaction with the computer. We can and must stand on the shoulders of giants.

When problems have many intertwined causes, or solutions require novel skills and materials, it’s critical to be able to bring a diverse group of people together to be productive.

Facing Ambiguity

Many teams do just fine with a well-understood problem where each person can cooperate and do their part. But when the challenge doesn’t have a clear answer, people start to fear failure and doubt their ability to contribute. Collaboration helps us deal with the unknown by harnessing the diversity of skills and experiences in the team to test out ideas and mitigate risk. And the more diverse the team is, the better able they are to see ambiguity from many sides and create better understanding by using their various perspectives to shore up a fuller picture.

When you face unknowns or tackle something novel, you need to be able to blend the skills and perspectives of a group to avoid pitfalls that you can’t see.

Getting Alignment

It’s tempting to think that what you need from teams and leaders is agreement. Josh Lovejoy, now Principal Design Manager at Microsoft, says he learned the hard way that “getting to yes” is a real trap, because when you ask for agreement, you may get it just so you will go away. True alignment requires time and space to air out differences and make sure that what we’re agreeing to is more fleshed-out than a few bullet points or truisms. When we allow a group to wrestle appropriately with a problem, their mental pictures start to actually resemble each other and the friction they experience decreases. Even when alignment is difficult to achieve, the discussions around making decisions, provided they are healthy, can make the entire group smarter.

When decisions span many types of people, getting them to participate helps build a shared understanding of the situation and how to proceed.

Engaging Employees

But collaboration isn’t just about the ability to channel lots of different POVs and types of expertise. Reid Hoffman, the founder and executive chairman of LinkedIn, knows the value of healthy teams means more than just low turnover. He sees the trust between employees as a competitive advantage because they can deploy their expertise at faster and faster rates to get better solutions. His new book with Chris Yeh, Blitzscaling (HarperCollins), spells out this relationship in case studies across industries and differently sized organizations, where a key part of the answer is enabling engagement.

When an organization needs to build camaraderie and a sense of mission, supporting collaborative work gets people more deeply engaged. But there are forces at work in most business contexts that make collaboration something that doesn’t happen simply by putting people together.

What Gets in the Way of Good Collaboration?

Collaboration isn’t something that is easy to do. It goes against our human nature in some ways, and it conflicts with many aspects of corporate culture. Very often, what passes for collaboration is what I call “collaboration theatre,” where people work side-by-side on the same problem without actually combining their talents. Sure, we get real people together in a room and ask them to write stuff on Post-its. We send out surveys to hear what our peers and employees think. But often all of that activity is really just masking the same old ways that companies always make decisions, where “experts decide” what’s important, what’s working, and who’s right.

Tom Chi, a product development luminary, described his first day at what would become Google X at the Google Sprint Conference in October 2018. Chi was thrilled to join a team of brilliant people from all different backgrounds that had been assembled by Sergey Brin to work on the Google Glass concept, among others. During the first few hours of the day, the team began a debate over what color the display for the device should be. The color choice would have implications for what material would make up the surface of the display and how much power would be needed. After a hour of intense debate, the issue was decided. Brin, Google’s founder and Silicon Valley genius, asserted that the color would be red. His rationale was clear: red photons have the lowest energy level, and thus would take the least power to project and would cast the least energy on the retina. Also? It’s always red in sci-fi.

Chi, having just left Yahoo, found himself feeling uncomfortable. This kind of decision-making—from smart, senior people with no real evidence, only conjecture—was the kind of thing he wanted to leave in the past. So he advocated strongly that, before the team committed to that decision, they try something out. And they did. Within the first day they had a super-crude prototype that they could use to project a paragraph of text onto a display to see what worked. The results were unanimous. Red was the worst color, by a long shot.

The decision-making approach where one expert decides based on great assumptions is what Chi calls “guess-a-thons,” and you’ve undoubtedly encountered them yourself. In a guess-a-thon, smart people have really smart reasons and confidence behind their guesses, which makes them seem indisputable. But as the team saw, there was a lot to dispute. As it turns out, Brin was right, in a way: red photons do have the lowest energy potential of the visible spectrum, which means when you try to focus on them out in the world or in a room, they become overpowered by every other color of light, making them impossible to read.

Collaboration theatre and expert-driven guess-a-thons set teams up to fail for all the right reasons. And the stronger the leader, the worse the effect, since they are trusted to use their talents and power to guarantee greatness for the team. But one person, no matter how powerful, can’t drive people to a solution when the problem is complicated and ambiguous. Actually harnessing the power of many different people takes more than a strong leader; the team itself needs to be engaged and supported.

So what’s going on that makes us resort to theatre instead of real collaboration? To master collaboration, it’s worth understanding what gets in the way, specifically in a business context.

The Environment Favors Independence and Individualism

We talk about our teams at work, but in many ways, business is a solo sport. We are evaluated and rewarded individually. We often compete with peers for an ever-shrinking number of more valuable positions. This model carries perverse incentives for individuals to garner attention for themselves for work that was performed by a group. For managers, come performance review time, it can often seem like your employees were all carrying out 10 different, yet very similar, efforts that each succeeded because of one person’s heroic efforts. Being independent is appealing because we are rewarded individually so it’s easier to stick to a silo or a solo effort, rather than get into a situation we can’t fully control.

The business context doesn’t do much to help teams be open and trusting with each other, either. Teams are often assembled by outside management, with little attention paid to helping them overcome the interpersonal dynamics that come with bringing diverse perspectives together. The focus tends to be on a team’s output, so we label those who show progress by any means necessary “high performing teams,” without attending to whether the collaboration is actually healthy.

Our business environment also challenges teams to use space productively. Open office plans, originally designed to promote collaboration, turn out to have the opposite effect. Collaboration isn’t something that is done face-to-face, side-by-side, 100% of the time. We need to find ways to give people some time away, as well as ways for teams to be effective even when members are remote.

The tools we use to collaborate can also be a challenge if they are too constricting or too chaotic. Teams can hide behind tools that are meant to support open communication. We send an email or a Slack message rather than have a face-to-face or even phone conversation where we might work through issues more efficiently and entertain more complex ideas.

To make the conditions for collaboration supportive, we can focus on who we include, and how, to make sure a team develops the trust needed to bridge gaps and have breakthroughs. We can also set up their space and tools such that they enhance the team’s ability to build a shared understanding and vision.

We Start with Unclear Objectives and Structures

Enterprises spend billions on setting up and tracking progress with metrics. These efforts likely give those at the highest level at least some understanding of what’s happening, but many of these metrics are too focused on the short term to be useful for those facing a complex, ambiguous challenge. Metrics are also chosen for their ability to be measured rather than for their appropriateness. Often the indicators we’d like to see for a collaboration aren’t available to us. Matt LeMay, author of Agile for Everybody (O’Reilly), also points out that collaboration suffers from having “invisible ROI.” He says that “trying to prove the contribution that healthy collaboration makes to an outcome is impossible, because we have no control group to compare it to. We don’t know what would have happened if we hadn’t worked together.”

Rather than just following metrics, teams need clear objectives to steer their efforts. But creating clear objectives for an ambiguous problem isn’t something many business people have mastered. It’s natural, LeMay says, for people to offer up overly specific solutions as a starting point, but it can be a trap if the team doesn’t know how to back up to the underlying vision that the effort is looking to achieve.

Collaboration can also be misunderstood as a freeform exchange of ideas, as embodied by the basic brainstorming meeting. Ideas are expected to be unleashed in a room full of people and the breakthrough made self-evident. In reality, open-ended brainstorms and free-ranging explorations are not very productive, and without any structure, people can fall into conflict, or conflict avoidance, very easily.

To help teams crack problems with unknown unknowns, we need to focus on framing the problem, stating objectives that describe outcomes (not outputs), and watching for leading indicators of longer-term success. Providing just enough structure and guardrails to help a team feel safe and have room to maneuver helps keep people focused.

Expertise and Experience Dominate the Solution Space

Chi’s guess-a-thon is the perfect example of how tempting it is to let experience and expertise rule the day. By giving over a decision to a specialist or expert, we may be helping ourselves avoid taking the blame if it turns out to be wrong. And then we hand it to a team to run with the expert’s guess, which, because they know more than others, never gets revisited as the possible culprit when things fall apart.

Business has already acknowledged that things are more complex, as evidenced by its shift into more specialization and investments in technology. But it hasn’t surrounded the specialists with the tools they need to get and share different perspectives. In most enterprises, the industrial age principles about division of labor and efficiencies are still in play. Leaders know what matters, and what success will look like when they see it. Workers fill in what’s in between, never coloring outside the lines. Alan Cooper, author of About Face (Wiley), calls this “working forward” as opposed to backward, where leaders define what success looks like and leave the path for how to get there open to exploration and experimentation, not expertise. This open “whitespace” is key to getting teams to tackle complex problems and solve systemic issues that no single skill set can address.

One of the reasons we rely on experts is because we want to avoid conflict and criticism—both giving and receiving it. By deferring to the HIPPO (the highest-paid person’s opinion) in the room, we let ourselves off the hook if there’s a mistake.

But by giving in to experience and expertise, we miss an opportunity to share our work in early stages, making it accessible and understandable to others. It’s the process of showing work in progress that helps us test our ideas and become aware of our assumptions. And when we begin to hear from others about how our work is being received, we start to get real data about our progress, instead of our wishful thinking.

Teams can better explore innovative solutions when they have the ability to open up constraints, have healthy discussions about solutions, and get real, actionable feedback on how well their solutions work.

Ineffective Communication Causes Conflict

Building a common understanding among a potentially large and diverse group requires a great deal of communication. Many organizations know this, and have developed whole positions and systems to manage information across levels. But maintaining the flow of information can be time-consuming, and not very effective. I’ve noticed that as organizations scale, there’s a tendency toward communicating status over outcomes because it’s easier to manage and standardize.

A lot of communication also favors making decisions over transmitting knowledge. Josh Lovejoy ran efforts at both Amazon and Google to create standard design systems across very large teams. He points out that the typical approach to decision-making—where a series of short meetings focused on the highest priorities drive outcomes—doesn’t help with decisions that are complex or nuanced. It means we choose the problems and solutions we can show progress on quickly. It means we bury those things we can’t fit into our packed schedules until they inevitably erupt into crises.

Communication is also challenging when the participants aren’t one size fits all. One of the biggest pitfalls I’ve seen is when teams are sharing with key stakeholders who haven’t been intimately involved all along. Key stakeholders are often very powerful and influential, so teams seek their approval and endorsement without actually building any real understanding of the challenge and solution.

At the same time, some people aren’t well suited to hashing questions out in a real-time, face-to-face situation. Different collaborators need different ways to explore ideas, provide feedback, and make decisions. The typical approach to gathering people around a table and holding a discussion may leave some perspectives unheard.

Leading collaborators communicate effectively by being transparent with those who are not deeply embedded in the effort so they stay aware enough to be useful and comfortable with what’s happening.

How to Help Teams Avoid and Overcome Obstacles

As you’ll learn throughout this book, there are steps you and your teams can take to avoid or overcome each of the obstacles just described (see Figure P-2). You can create or adapt your environment to be more inclusive and trusting, and use space in ways that promote better interactions. You can provide the right type of direction that teams need to manage their time, understand progress, and judge success. Help people be more creative and open to others’ ideas so that your collaboration delivers on outcomes and doesn’t just implement simple solutions that don’t move the needle. And finally, you can improve the communication within the core group, and with key stakeholders, to reduce friction and keep people aligned.

Ways to support collaboration
Figure P-2. Ways to support collaboration

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