If at First I Don’t Succeed, There’s Still Time

I’ll try just about anything twice. Hairstyles (to bald, or not to bald?), relationships (oops), Jack In The Box (OK, that’s a lie – fool me once, Jack…). They say the definition of insanity is doing the same thing and expecting a different result – they also say it’s the most overused cliché of all time – but I aim to try to force a different result. What was it about the first time that didn’t work out? What’s changed since then? How can I use that information to cheat the expected results?

I’ve never liked tests. I say that knowing that I’m the rule, rather than the exception. In University I was an expert at finding 25-hour-long days so I could cram for just a little longer than everyone else. Not just because I wanted to outperform everyone else, but because procrastinating was, effectively, a sport.

The problem with that, is that it always worked. My hand was never slapped away from the cookie jar. I’d get my grades back, breathe a sigh of relief, and then watch another episode of The Wire, clean the house, or Google Nauru’s chief export (phosphate, in case you’re wondering), rather than prepare for the next test. In the long run, the only thing I was really testing was my blood pressure.

Out of all of this came some good, whether directly or indirectly. Turns out, I love testing myself and trying out new things. The shamefully large number of apps on my iPhone is proof of this. But so what? The so what is that I now find myself in a situation almost daily where I need to try something new. Or I need to use something I’m already familiar with to do something I’ve never done with it.

From Slack to Google to MailChimp, we use a TON of tools at the office (embarrassingly few of which are hammers and levels to hang art). We’re always trying to find the best and simplest way to get things done. The less time we spend tripping over ourselves and our process, the more time we can spend making cool stuff. The idea development is where the magic happens – which is, coincidentally, the second-most overused cliché of all time (thanks, MTV Cribs). Some of the magic that I’m responsible for is ensuring that all of the ideas and plans and dreams get put into action.

Enter: the tool shed. It’s filled with all sorts of communication, project management, design, and other app-goodness, but it’s not limited to paid software. We also consider the systems that we use to be tools – example: we stole the idea of a daily morning standup from the SCRUM project management system. So, when I talk about tools, I’m referring to any of the things that we try to implement to get stuff done better or faster.

The biggest and most important tool? By far, our project management software. So, that’s where I’ll start off.

As a team, we’ve tried a large handful of project management software systems to help us stay on task. I’ve personally tried several dozen in search of the holy grail. What I’ve found in my painstaking (‘tis but a scratch) searches is that there may be no such holiness at the end of the quest, but there are a few perfectly good grails, and plenty to go around.
Before I travel too far down this metaphorical trail (and lose anyone who was born after 1988), what that means is I’ve circled back on apps such as Asana, dapulse, Teamwork, Trello, and Wrike, which I had previously deemed inadequate for our team. The cold, hard reality is that “adequacy” boils down to our own commitment to use and manipulate the tools to our own advantage. Was Asana really too simple? Was Wrike really too complicated? What can I do to strip these apps down to their core and get from them what’s going to get us producing the best work we ever have, at the quickest pace we ever have, without using that 25th hour? Start testing, reimagining, committing. Getting everyone on board to just do it. (The third-most overused cliché).

Over the next few weeks and months, I’ll be using this space to let you in on the process – which ones end up producing Slack-like levels of results and liberation from archaic technology (sorry not sorry, email), and which ones should be steered clear of. Check back, and feel free to shoot me your favorite by tweeting at me – @EfFDotLowry or @JunctionYVR.

Written while listening to Jamie XX’s “In Colour” (just as good, if not better, on the 87th spin) and drinking Alhambra cervezas (this batch tastes a little… gasoliney).