HOW TO COLLABORATE PT 1 — THE SOFTWARE VORTEX

Are you in charge of your software, or does your software push you around? If you’re on a team of creatives, don’t let your tools dictate your decisions.

Read on to find my five rules for using collaboration software

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Remember when you were assigned to work on a group project in sixth grade? You were probably in one of two camps. Either you were relieved to share the spotlight, and thus deflect a measure of attention, or you wished you could simply do your own thing and not have to deal with everyone else’s needs, mediocrities, and divergent goals.

Collaboration comes with opportunities and perils, but unless you work alone on a mountain peak, you’re going to have to contend with it one way or another. 

I’m breaking this blog into two parts. This month concerns software, that modern boon and bane. Next month I tackle the harder and more vital part, the endless and eternal challenge of working successfully with others. 

But let’s talk about software first, and the irony of starting with software is that even a conversation about electronic tools requires a starting statement about working with other people. 

Say you have a project that’s big enough to require more than your own two hands. That means you need a team. 

Let’s say you have a good team, everyone skilled and motivated and collaborative in the best possible ways. You know immediately that many people on your team will have good ideas and you want to ignite the great power of your mental collective. You meet in groups, you set up email threads, you share documents. But inevitably— and often shortly after getting started— the whole group starts to yak and gripe about which collaborative software package they should use be using instead of the one they have.

We’ve all been there. Slack? Teams? Google Workspace? There are endless options, and this can become a never-ending discussion.

Electronic collaboration acts like a siren song, or at least a promise of Shangri-La. Unless deployed intelligently the tools themselves can also suck time like a gravitational well. But there’s no sense in denying the obvious: software makes complex things solvable. Smart creative teams long ago learned that there is no right tool. There are just better and worse options. Are they powerful? Sure. Are they useful? They certainly can be. Very few modern projects of any appreciable size can operate without them.  Handled properly collaboration software can make skyscrapers soar. Handled poorly, it can rain endless storms of distracting text alerts like clouds above an unstoppable flood. 

SET LIMITS ON ALERTS. This should be Rule #1 for software utilization. No matter what you may believe about your own abilities, nobody except a machine can actually multi-task successfully.  We may confront multiple simultaneous challenges, but we address them each one at a time, switching from one to another in rapid succession in ways that makes us think we’re handling them simultaneously.  As the saying goes, life is just one damned thing after another.

LESS IS MORE. The value, of course, is that collaboration software is brilliant for capturing and sharing information. You may have a million tasks to do, one after another, and for that you should lean on Rule #2 for good software utilization: rely on the fewest software tools possible to keep your task management organized, but not so few that you can’t do the work you need to do. Avoiding unnecessary tool creep will be essential to keeping your team streamlined and free of spending too much time just managing the tools themselves. Purpose-built collaborative tools are vital for managing tasks lists, but be cautious that you don’t lean on more tools than you actually need.

SHARE IN REAL-TIME. That leads me to Rule #3. If you trust your team (and you should think of getting a new team if you don’t trust ‘em!), make sure you’re working with software that enables real-time collaboration and shared editing privileges. For myself, I love how certain tools enable me to collaborate in real time with a video production team. We can develop shooting plans, lighting schemes, add notes, tweak schedules, and basically capture all manner of ordinary work-a-day or hare-brained wild-blue-sky ideas that will help to make our work better. This is only possible if everyone on the team understands the goals and understands the tools.  Many real-time information sharing solutions risk provoking counterproductive distractions from deeper, more meaningful work. When you update your work, the whole team benefits by having immediate access.

SAVE WHAT YOU NEED File Rule #4 in a database named after Borges’s “Library of Babel”. (Or, maybe save this rule outside the library, ‘cause otherwise you might search the shelves until the end of time.) The rule here is one you must internalize whenever you interact with your software. Save what you need, and save it regularly and religiously. But don’t save stuff that you’ll never use, because you’ll soon have more digital detritus than you can possibly imagine.

This is the problem of data creep, and it can bog a project down. Modern software, especially powered by new artificial intelligence tools, makes this especially perilous. When everything can be stored in files, groups, clusters or other modules, the tendency is to record everything, process everything, and try to keep track of everything. Truth is, how many meeting summaries from AI-processed meetings are you really likely to use for reference? Beware that a tool’s super-human abilities to store data doesn’t instead drown you in data you’ll never use. (Want a scary story to remind you? See also: the paperclip maximizer problem.)

Software-mediated collaboration is inherently cold. Even in the brave new world of AI powered tools, none of them function like human bodies filled with blood. Software tools may be vital,  but the process of using them is not entirely human. They’re called “artificial” for a reason. After two millions years it still makes evolutionary sense for working groups of creative people to cluster in real life around a piano or a dress-maker’s manequin or a monitor on a movie set. Software sends us to isolated laptops, with intermediation run through glass screens. It can add layers of inefficiency by creating veneers of comprehension, while deeper, more meaningful comprehension remains elusive. Creative work must not conform to restrictions imposed by tools, no matter what the project.  Your idea matters much more than the mechanism by which you bring it to life. Software can eat the soul of good work if the team isn’t careful, with participants fiddling with settings as much as they may be working on bringing new ideas to life.

In fact, fiddling with settings is always easier than doing the actual work of creating anything new. It’s easier to change the font of your MS Word document than it is to write a good paragraph. Ask any writer why he or she struggles to write, and often you’ll hear that good writing is simply hard, as Nora Ephron once famously declared. If the tool doesn’t serve the project, drop the tool immediately and look elsewhere.


SUBSTANCE MATTERS MORE THAN STYLE. Feature creep is a problem, but there’s even a bigger, more pernicious risk that looms. That’s Rule #5. Beware the potential for weak ideas to rise in prominence just because they might translate more easily to the polished rectangular screens of virtual collaborative space. We all want to believe that the cream of good ideas will always rise to the top, but software intermediation sometimes encourages us to promote simplistic choices. Simple ideas are easier to transform into slide bullets, which in turn are easier to understand than actual dialogue about more complex concepts. Online meetings populated with easily distractible, disembodied talking heads are often just gatherings of people only paying a smidge of real attention anyway. Online meetings are not great places for deep creative probity. Online meetings are good for exchanging schedule information, and straight-ahead, blunt concepts. We all try to use online meetings for all sorts of other stuff every single day, of course—and that’s not going to change— but don’t kid yourself. Online space is not a good way to travel towards collaborative creative excellence.

In online meetings, good ideas may not always emerge in the brightest colors, the boldest speech, or the easiest shapes. To make sure you and your team aren’t missing the best ideas because you’re inadvertently selecting the easiest to understand, encourage your team to resist multi-tasking, hard though that may be. Keep meetings as short as possible—that’s always a big help. Recall how you’d typically want to collaborate if you were having this meeting in the real world. If your personal style ports to virtual space, terrific. If it doesn’t (and if you’re being really honest with yourself, it probably doesn’t) you need to reconsider your relationship to the tools you’re using. 

This is all a big challenge, of course. It crosses boundaries between assurances pledged by the technical marvels of smart software and the always complex, profoundly promising, sometimes exasperating experience of interpersonal relations. How ideas germinate, grow, and thrive demands serious consideration, especially among creative leaders who will influence how teams ultimately choose to proceed. 


That should give you a good reason to come back next month, because the human side of collaboration is the subject of Part II. Check it out when it goes live on March 2nd. 

@michaelstarobin

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