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Why is collaboration so freaking painful?

October 4, 2024

Ahhh cross-functional collaboration— it’s university group assignments all over again and no one is here for it. Why do we find it so hard?

Breaking the Stereotype (Spoiler: It’s Not Just Corporates)

Startups are supposedly the pinnacle of teamwork, where everyone is a multi-tasking ninja solving problems 24/7. Meanwhile, corporate teams are stuck in endless meetings, trying to break down silos without a real conversation in sight. But as I’ve discovered, both can be equally terrible (or awesome) at collaborating. Startups often descend into chaos because no one’s quite sure whose job it is to do what, while corporates get bogged down in red tape and PowerPoints that never seem to end. The truth? It’s a universal pain point.

1. Perfectionism: Where Great Ideas Go to Die

Picture this: you’ve got a brilliant idea, but instead of sharing it with your team, you sit on it for so long that by the time you present it, someone else has already moved on to the next big thing. Perfectionism is a killjoy for collaboration.

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2. Trust: Or Lack Thereof

Teams from different departments often treat each other like frenemies in a reality TV show: polite on the surface, but secretly plotting how to steal each other’s snacks. Without trust, collaboration turns into a game of “who’s going to mess this up first?” rather than a productive exchange of ideas. So instead of treating the HR team like they’re from a different planet try going out on a whim and find something you have in common that you can all get behind.

3. Bridges and Connectors: The Unsung Heroes

If trust and communication issues are the problem, bridges and connectors are the solution. These are the people in your company who somehow manage to speak Marketing and IT—kind of like corporate bilinguals. I know these peeps well. One was a former boss who had to ‘translate’ my advice to the IT team. They’re the ones who can translate “I need this by EOD” into actual human language and make sure the right people are talking to each other. In startups, everyone’s a connector because, well, there are only about six people. In corporates, you need someone to play matchmaker between departments.

4. Leadership: The Puppet Masters of Collaboration

As with so many things, collaboration starts at the top. Effective leaders encourage open communication, set clear expectations, and go out of their way to collaborate with their own peers. They know that collaboration isn’t just about getting people in a room (virtual or otherwise) but actually creating an environment where people feel safe enough to speak up, pitch in, and where needed, disagree.

Beware of 'Collaboration Drag'

Too many meetings, too many stakeholders, too many Slack or Teams messages about things that could have been resolved with a single conversation. Collaboration drag is the silent killer of productivity. So how do you avoid it? Streamline the process. Clear roles, clear goals, and a collective agreement that nobody needs another “quick sync.”

Collaboration May Be Hard, But It’s Not Impossible

Collaboration can be more than a lame group assignment—sometimes it’s amazing, sometimes a total disaster, but almost always necessary. Whether you’re in a startup or a corporate giant, the key is to create trust, encourage communication, and accept that perfection is overrated.

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You don’t want to speak up until your idea is flawless, but collaboration is about brainstorming, not brain-straining. If everyone’s waiting for their ideas to be 'just right', then EVERYONE JUST ENDS UP WAITING.
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