Zen and the Art of IT Planning #cio

It's been on my reading list forever, but this year I finally got around to Robert Pirsig's Zen and the Art of Motorcycle Maintenance.  It was heavy going in spots, but it didn't disappoint. So many wonderful ideas to think about and do something with. Among a thousand other things, I was taken with Pirsig's exposition of "gumption".  He describes it as a variable property developed in someone when he or she "connects with Quality" (the principal object of his inquiry).  He associates it with "enthusiasm", and writes:

A person filled with gumption doesn't sit around dissipating and stewing about things.  He's at the front of the train of his own awareness, watching to see what's up the track and meeting it when it comes.  That's gumption. (emphasis mine; Pirsig, Zen, p. 310, First Harper Perennial Modern Classics edition 2005)

In recent years I've tested my gumption limits in trivial and meaningful ways: built a treehouse, fixed an old snowblower, serviced sailboat winches, messed around in SQL and Python, started a business. For me, gumption was the "Well, here goes..." evanescent sense of that moment when preparation ends and experimentation begins, an amplified mix of anxiety and anticipation at the edge of the sort-of-known and the TBD.  Or, like the joy of catching a wave,  it's feeling for a short time what it's like to have your brain light up an order of magnitude more brightly than it manages on average, and watching your productivity soar.

So what's this got to do with IT planning?

For a while now I've been working with both big and small companies, and seen two types of IT planning happen in both settings. In one case there's endless talk of 3-year end-state architectures that seem to recede and disappear like mirages as you Gantt-crawl toward them.  In the other, there's endless hacks that "scratch itches" and make you feel like you're among the tribe of Real Men Who Ship, but  which toast you six months later with security holes or scaling limits.

Getting access to data and having enough operational flexibility to act on the insights we help produce with this data are crucial to the success we try to help our clients achieve, and hold ourselves accountable for. So, (sticking with the motorcycle metaphor) a big part of my job is to be able to read what "gear" an IT organization is in, and to help it shift into the right one if needed -- in other words, to find a proper balance of planning and execution, or "the right amount of gumption".  One crude measure I've learned to apply is what I'm calling the "slide-to-screen" ratio (aka the ".ppt-to-.php" score for nerdier friends).

It's a simple calculation.  Take the number of components yet to be delivered in an IT architecture chart or slide, and divide them by the number of components or applications delivered over the same time period looking backward.  For example, if the chart says 24 components will be delivered over the next three years, and the same number of comparable items have been delivered over the prior three years, you're running at "1".

Admittedly, the standard's arbitrary, and hard to compare across situations. It's the question that's valuable.  In one situation, there's lots of coding, but little clear sense of where it needs to go, tantamount to trying to drive fast in first gear.  In the other, there's lots of ambition, but not much seems to happen -- like trying to leave the driveway in fifth gear.  When I'm listening to an IT plan, I'm not only looking at the slides and the demos, I'm also feeling for the "gumption" of the authors, and where they are with respect to the "wave".  The best plans always seem to say something like, "Well, here's what we learned -- very specifically -- from the last 24 months' deployments, and here's what we think we need to do (and not) in the next 24 months as a result." They're simultaneously thoughtful and action-oriented.  Conversely, when I don't see this specifics-laden reflection, and instead get a generic look forward, and a squishy, over-hedged, non-committal roadmap for getting there, warning bells go off.

Pushing for the implications of the answer -- to downshift, or upshift, and how -- is incredibly valuable.  Above "1", pushing might sound like, "OK, so what pieces of this vision will you ship in each of the next 4 quarters, and what critical assumptions and dependencies are embedded in your answers?"  Below "1", the question might be, "So, what complementary capabilities, and security / usability / scalability enhancements do you anticipate needing to make these innovations commercially viable?"  The answers you get in that moment -- a "Blink"-style gumption test -- are more useful than any six-figure IT process or organizational audit will yield.