Why is cross-functional collaboration so hard? (And how to fix it)

Alexandre Omeyer
Alexandre Omeyer
5 min read
I explore the challenges of cross-functional collaboration and how we can overcome our human limitations to improve team synchrony, efficiency, and project success.

Leaders usually get the potential of nailing cross-functional collaboration. But most of us aren’t achieving it.

Why’s that the norm? Why is cross-functional collaboration so tough, despite a shared understanding that companies that get this right perform better?

The reality check of working together

Before we get specific, I want to flesh out the reality that humans, despite our advanced evolutionary communication skills, are designed for something other than this kind of teamwork. 

We can’t remember everything we need to, because we have fundamental cognitive limitations. We can’t share everything we could, because we have output limitations. We get decision fatigue, and we are innately biased by our perspective. We end up with varied interpretations of shared goals, misalignment and even conflict.

The point is, great collaboration isn’t default. It has to be nurtured, with intention.

Cross-team collaboration tools in an office

Case in point

Tool wars

We dream of every team harmoniously using the same tools. Everything in one place. But it’s a far cry from reality.

Your engineering team uses Jira to track project progress, but your marketers won’t use it – it’s clunky for marketing tasks, so they use Monday, which is far more flexible. Meanwhile, the design team insist their Trello board is sacrosanct. And fair enough, the other team’s tools are overkill for their use case. Sure, everyone’s using Slack, but in practice, a lot of the collaboration on specific tasks and projects is happening within these other tools.

Lost in translation

As we scale, we tend to notice unique practices, cultures and even languages springing up across different teams. The endgame for that kind of fragmentation is that customers will find that different parts of your infrastructure don’t look like each other, don’t work the same way, and don’t work together.

Silos – of both people and information – develop naturally. Preventing them from doing so is like swimming upstream – but it’s crucial. Once we have silos with unique cultures evolving within each, we get exponentially more duplication, misalignment, and frustration.

Navigating the office in the cloud

To me, the debate is essentially settled that the option of remote work is both better for everyone and here to stay. Remote work makes space for humanity and inclusion. Enforced face-to-face office work suits those who seek control, but few others.

But these days, you can’t just stroll over to a co-worker for a quick chat, or clear up a question over the water cooler. Maintaining synchrony requires adaptation beyond just video conferencing.

When we get it right, distributed workplaces are just as powerful breeding grounds for innovation.

Remote work collaboration

Getting collaboration with tech right

When it comes to tech collaboration, there are two possible scenarios. 

In the first, our technology landscape is a chaotic mess, with teams struggling to navigate a maze of different tools and platforms. Information is scattered everywhere, making efficient collaboration almost impossible. 

In the second scenario, technology acts as a unifier. Even though there are multiple data sources, the activity and information that matters is surfaced to whoever needs to see it. Information is centralised, gaps between teams are bridged, and team’s work becomes harmonious.

How I’d do it

First things first: centralise your tools. If you or your people play hide-and-seek with data and resources, you’ve got technical debt for your internal infrastructure. You’re probably not going to get everyone using the same software, but you can A) aim for a 'single source of truth' and B) leverage smart tech to surface key activities and outcomes.

Get your transparency culture right. Prioritise visibility. Encourage teams to share not just their successes but also their challenges, roadblocks, and learnings. Automate that, if you can.

Invest in shared understanding. Speak the same language, align on common goals, and understand the roles of different teams. It isn’t enough to iterate the goals at quarterly meeting or pop them in a doc. A shared knowledge and understanding of direction need to course through the veins of the whole collective organisation.

Bridging the gap with collaboration tools

I said earlier that humans aren’t wired for collaboration in the workplace, and are limited in how much we adapt.

Some tech can be a hindrance. But today, some communication tools can surpass what humans can do. By a fair bit, too.

AI is ready for this

Humans may not be evolved for workplace collaboration. AI can be.

Humans can’t, even in principle, keep up with everything that happens in real-time and remember it all.

AI can do all that. It can form long-term “memories”, constantly review goals, watch any channel, and decide what matters and what to share.

I’m building a tool called Stepsize AI with my team at Stepsize.

It might not be an actual magic wand, but it's close. It…

  • Sends you updates about exactly what you care about, in the format and level of detail you want
  • Alerts you when something demands your attention, such as a bug affecting a key client, or urgent action to meet a compliance deadline
  • Deeply understands the context of your projects and goals
  • Answers any question you have about your updates with a context-aware response you can take action on

The last word

Navigating scattered information across a multitude of tools, ensuring visibility, and fostering shared understanding is an uphill battle. 

Human limitations make this challenge even steeper. That's where technology, specifically AI, steps in, to help diverse, multi-functional teams successfully collaborate.

I’m building Stepsize AI with my team. It’s an AI companion for software projects.

Stepsize AI integrates with your existing tools, creating impactful, actionable updates for any situation, bridging gaps between teams and reducing the cognitive load. It provides real-time updates, alerts on critical issues, and delivers context-aware responses.

It’s like having an omniscient team member who never sleeps, constantly monitors every channel, and understands what matters to your projects.

I’d love to hear what you think of it.

Request exclusive beta access.

Never trawl through Slack, Jira or GitHub for updates again.

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I explore the challenges of cross-functional collaboration and how we can overcome our human limitations to improve team synchrony, efficiency, and project success.
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