There are lots of tools for collaborating online.

Google Docs is perhaps the go-to standby for sharing text and spreadsheet documents. Evernote shared notebooks are another way of sharing files and text documents. And of course there’s Dropbox as a sort of shared hard drive in the sky.

In practice, the amount of actual collaboration that occurs on these platforms varies.

More often I find myself using Dropbox, Google Docs and Evernote to share stuff with other people. But there’s rarely much collaboration.

These applications are great at solving the problem of access to documents, but they don’t do much for collaboratively working with others.

I suspect this has something to do with the way the documents and relationships with potential collaborators are structured. Once a word processing document has been started, the next people along might feel less like creating anything than editing. Perhaps go in and make a couple quick cleanups.

Making a wholesale restructuring of someone else’s shared document assumes a whole different level of collaboration and working together. If you are close colleagues, or in a business relationship that is defined by this level of collaboration, then going into their text documents or spreadsheets is alright.

But if the nature of the relationship isn’t so clearly defined as collaborative, it’s trickier. For example, the relationship between an agent and a client might be assumed to be collaborative, but in reality it isn’t. Maybe the client isn’t holding up their end of the collaboration, or maybe the agent’s idea of collaboration is really, “I’ll show you stuff and you’ll say yes or no.”

In these situations, where the structure of the relationship isn’t truly collaborative, the formality of standard text documents and spreadsheets may hinder true collaboration. No one wants to offend the other person by “messing up their work.”

It’s as if there’s some sort of hidden relationship between the structure of our working relationships and the structure of the documents our working relationships produce.

As the importance and structure of collaboration in our relationship increases, the ability to work together on structured documents like word processing files also increases.

This presents a challenge for new collaborative relationships: How do we work together to make something, or learn from one another, when we don’t know each other well enough to confidently “mess up” one another’s text documents?

In technology and marketing, when we have an interesting problem to solve and want to work on it with multiple people, it’s very rare to start out with a spreadsheet or text editor. Only once a problem is clearly defined do spreadsheets and text editors get hauled out, so that something can be made.

But when we start on the challenge we start somewhere else.

Whiteboards, the place for creative collaboration

In tech and marketing, whiteboards are the place where creative things happen. If not a whiteboard, then a large sheet of paper. These things are givens in the tech and marketing worlds. Entire rooms are devoted to these kinds of things.

One of the things I do when evaluating tech and marketing strategy for a company is determine their capacity for creative work. There are many things that go into this, but the best shorthand is probably the size of the largest whiteboard in their building.

If an organization doesn’t have a large whiteboard, then how are they working together? The whiteboard provides a physical space for collaboration. If there’s not much physical space to collaborate in, then only one person is going to work on it at a time. If the physical space to collaborate in is small, the ideas produced in that space are also likely to be small.

The tools we use have an impact on the work we make. This is a sort of corollary to “when you have a hammer, every problem is a nail.” When you don’t have a whiteboard, your culture doesn’t collaborate. When you have a small whiteboard, your culture solves small problems.

Last week I was in Orange County and stopped in to have lunch with Justin LaJoie. He showed me around Zillow’s Irvine offices, where he works. One of the things he made sure to point out was that an entire wall of the conference room was painted with whiteboard paint. The entire wall was a surface for collaboration.

An organization outside the real estate industry that I met with recently also had a whiteboard in their conference room. But it was small — two people could not stand side-by-side in front of it — and hidden in something like one of those TV cabinets. It was as if someone knew they needed a whiteboard, but wanted to make sure that it was as difficult and frustrating to use as possible.

These two organizations, in the way they used physical space and surface in their facilities, communicated two vastly different approaches to problem solving and collaboration.

One of them must be solving highly structured or pre-existing problems with little collaboration, and the other must be working on new or unstructured problems collaboratively.

Whiteboards in digital space

I’m always on the lookout for tools and apps that help me solve unstructured problems. This is because unstructured problems are the most interesting and lucrative to work on. Once a problem becomes structured then it’s only a matter of time before it’s outsourced to trained labor, turned into software, or turned into hardware.

I was totally psyched when Mike Bowler Sr. showed me a digital whiteboard tool called Realtime Board. It takes all the non-structured problem-solving fun of a whiteboard and stuffs it into a cloud-based web application.

While I personally prefer to use a real whiteboard with real people in person, the reality is that many of us are collaborating across vast distances and at different times of day. Web-based digital tools are useful to deal with this reality.

Realtime Board lets you do all the stuff you want with a whiteboard: write, draw, paste pictures up and so on. It gives you a digital space to collaborate. The big drawback is that it uses Flash, so you’re limited to desktop or laptop machines (A sign that, as great it is, HTML5+Javascript isn’t all the way where we’d like it to be yet).

How might a tool like this be used in a real estate practice? You might paste in pictures of houses or neighborhood maps. You could include lists of properties looked at, including images of things that worked or didn’t work for the customer. You can throw in text documents or PDFs if they are important.

Some creative disciplines use something called a “mood board” to post pictures that point in the right direction for a style or feeling. A worker in these fields might paste in images from magazine, for example, to help set the right mood so others collaborating on the project get a good sense of the direction. If you’re focused on “lifestyle” as part of your process then you are already familiar with this methodology (I hope).

Perhaps the use of a shared digital whiteboard would be useful for some real estate challenges. It seems to me that many times there is a collaboration occurring between customers and agents.

Collaboration is not for everyone. But for some customers, the creative experience might be rewarding, and deepen their relationship with the agent.

Gahlord Dewald is the president and janitor of Thoughtfaucet, a strategic creative services company in Burlington, Vt.

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