What brand owners actually look for in a freelancer is rarely what freelancers think it is.

She didn't come in looking to talk about work. But the conversation went there anyway, the way the best ones always do.

She'd been in the house before so we knew she had good taste and an eye for creativity. One of those regulars who arrives with something on their mind and leaves having said more than they planned to. Our favourite kind of person. She ordered without looking at the menu and settled into the corner seat, within 10 minutes we were somewhere interesting.

She runs a brand. Mid-sized, considered, an operation where every decision carries weight because there isn't the budget to make the same mistake twice. She's worked with freelancers for years and has built the brand off some incredible talent. She said this herself. People whose work she'd recommend without hesitation.

We asked her what she actually looks for when she brings someone into her world and the answer got us mid-pour.

She didn't mention portfolios or rates. She picked up her cup, thought about it for a moment and simply said communication. Every time. Without exception.

Not the kind of communication that arrives in a well-formatted project proposal or a polished onboarding document. The kind that happens in between. The message that arrives on a Tuesday afternoon saying things are on track and here's where we are.

The question asked before it becomes a problem rather than after and the moment where the freelancer says I've hit something I didn't expect. ‘Here's how I'm thinking about it’. Does that work for you. That kind of communication. The kind that makes a brand owner feel like they're part of the process rather than waiting at the end of it for something to arrive.

She told us about a designer she'd worked with for years. Not the most technically gifted person she'd collaborated with but the one she trusted most completely. 

The reason was simple. She always knew where things stood. There was never a moment of uncertainty about the project and the timeline. The designer had made a habit of keeping her informed in a way that felt natural rather than administrative, like a conversation rather than a status update and over time that habit had built something that no portfolio could have built on its own.

We asked what happened when communication broke down.

She smiled in the way people do when the answer is obvious. The relationship ends, she said.

Not dramatically but with a difficult conversation. You just stop reaching out. You find someone else. And the talent that was there, the real ability that brought you to them in the first place, becomes irrelevant because the trust that made it usable is gone.

The coffee went cold somewhere in the middle of that so we gave her a fresh shot and left her to it. She stayed all morning and ironically. Met one of her freelancers that day. 

The best freelance relationships she'd had, she said before she left, felt like having someone on the inside. Someone who understood what she was trying to build and kept her connected to it even when she was too busy to ask. That feeling, she said, had nothing to do with the work and everything to do with how the person chose to show up around it.

We wrote this down before we forgot it.

Shot of the good stuff.