Why It’s So Hard to Collaborate — And How Teams Can Get Unstuck

We often want to blame our colleagues when things don’t go well, but it makes more sense — and is more effective — to adjust the underlying systems, says organizational design expert Ali Randal. 

Author: Barbara Palmer       

Ali Randel

Work problems aren’t just about — or even mainly about — the shortcomings of people, said Ali Randel, a partner at organizational design consultancy The Ready.

I once worked in a high-performing department with a strong and positive work culture — with one wrinkle. Every 18 months or so, the people hired to fill one particular role either were fired or left to take other jobs. Each time a colleague left, we all considered, privately and otherwise, the ways in which those particular people may have not been the right fit for the job. Then one of the tasks that was part of that role — which conflicted with another more crucial responsibility — was shifted to another employee. Once that happened, the problem disappeared. The next person hired to fill the redesigned position thrived.

That’s a good illustration of how systems thinking works, said Ali Randel, a partner at The Ready, an organizational design consultancy based in New York, when I relayed the story to her. When things go wrong at work, said Randel during a workshop she presented at Convening Leaders 2021, our tendency is to focus on the most visible part of any scenario — people — and ask ourselves what’s wrong with them. The challenge is that work problems aren’t just about — or even mainly about — the shortcomings of people, she said. “They are also,” Randel said, “about the operating system.”

Randel and her colleagues at The Ready use the term “operating system” to describe the mindsets, values, rules, and processes that lay beneath the surface of almost everything we do at work. The operating system is organizational DNA “that is so pervasive, unquestioned, and deeply held that we don’t even notice it,” the firm’s founder, Aaron Dignan, has written.

“Operating system” also refers to a tool Dignan created — the Operating System Canvas — which he intended as road map for the reinvention of work for now and in the future. According to Dignan, many companies are mired in models developed a century ago, where leaders figured out the best way to handle tasks and then workers carried them out. It’s a system, he added, that once worked spectacularly well, but isn’t fast or flexible enough to allow companies to adapt to the complex, disruptive challenges that they now face. Dignan developed the Operating System Canvas by studying firms that successfully were pioneering new ways to work and used the patterns and best practices he uncovered to describe 12 key dimensions: purpose, strategy, workflow, membership, authority, resources, meetings, mastery, structure, innovation, information, and compensation.

In the Convening Leaders workshop “7 Change Actions: Crack the Collaboration Conundrum With Systems Thinking,” Randel demonstrated how the Operating System Canvas model could be applied the problem of collaboration — a capacity that is critical to organizations but isn’t simple to achieve, she said.

The “collaboration conundrum is the persistent and very common scenario where we all know collaboration could be better,” Randel said. “We’ve probably had multiple conversations about the things we wish were different [about collaboration] and we’ve got a lot of smart and well-intentioned people noticing things that could be better … yet it’s really hard to shift those things.”

One of the most common ways organizations collaborate — bringing individuals on different teams together to work in a cross-functional initiatives — is rife with wrong turns, Randel said. They include feeling that colleagues are handing off issues without any context or communication, cultivating a “general sense of us vs. them,” and complicating progress by sharing information inconsistently. “It’s really easy to focus on the people involved, and ask: Why don’t they just share information?” Randel said. But the operating system “usually is the biggest culprit and the biggest factor affecting the work.”

Randel highlighted a few dimensions of the operating system, like meetings, strategy and authority, to show how they can stymie collaboration. For example, even when the stated goal is collaboration, there usually is no time set aside in meetings to actually allow people to work together, Randel said. Meetings are designed to present or defend information, with “no routine built in to invite collaboration.” Strategy is crafted in silos, and there is no clear method for creating priorities, she added. And even when priorities are understood, individuals often are unsure when they are allowed to make decisions. “It’s no wonder that we get into patterns of ‘us vs. them,’ because we’re all frustrated with the way work is happening.”

Considering collaboration across a 12-part grid like this can feel a little overwhelming, Randal said, if there is something in every field that needs to change. The good news, she said, is that the tool not only identifies practices that are holding us back but makes it easy to find new practices that reflect all of the things we want to have happen.

For example, teams could add practices including:

  • Draft strategic outcomes with cross-functional partners
  • Schedule recurring meetings that allow team members to build an agenda together in real time
  • Hold a regular retrospective with collaborators and team members
  • Start every meeting with a check-in round to help cross-functional teams get to know each other

The phenomenon of widespread remote work has made understanding how organizational practices can affect collaboration even more important, Randal told Convene in an email. “When teams have clear strategic outcomes, they know what they’re working toward — and how — even if they’re working from different locations,” she said. “And when teams have an intentional meeting rhythm for coordination and retrospection, it tends to reduce the feeling of isolation, creates a regular forum for support and advice on work, and creates space to share what may or may not be working about current remote … practices.”

Concentrating on practices is likely to be more effective than concentrating on people, because “we have far more agency over shifting how we work when we look at the systems level,” she said. “No matter what we hope or dream, we can’t control the behavior of other people. What we can do is shift the practices we use.”

Find a description and download a copy of the OS canvas at theready.com/os-canvas.

Convening Leaders 2021 registrants can watch the collaboration session on-demand in the CL library until March 15. Interested in registering for Convening Leaders’ on-demand sessions? Visit conveningleaders.org.

Barbara Palmer is deputy editor of Convene.

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