Saturday, October 27, 2018

2018-10-27 Saturday - 10 Lessons from Sailing, for IT



Recently I had some work done on my mast - and I took some time this morning to ponder some of the lessons I've learned from sailing (either through direct experience, or by studying the historical accounts of the voyages of others)...and how those might apply to the world of IT...

1) Preventive Maintenance: On a sailboat, preventative maintenance is a lot like taking care of Technical Debt in IT. Avoid or ignore it at your peril. A mast failure, when sailing in storm conditions - much like a performance/load failure for your IT systems. It all comes crashing down.

2) Keeping a Weather Eye: Means to monitor the horizon for developing weather conditions. Within the world of IT that can mean observing closely which projects/areas of IT are gaining/losing funding, organizational restructuring, and whenever new external third-party IT vendors are being introduced into the organization.

3) Sometimes You Must Tack: On a sailboat, you must often tack (change course) to reach your target destination - because the wind changes direction, or you are trying to make way against a current that is not in your favor. Your career, much like the track of a sailboat - will rarely run on a straight path for very long. Often, you may find that you need to sail away from your destination, or even sail backwards. In your IT career, this can take the form of willingly taking what might appear as a demotion (lower job title, less pay) - so that you can make "headway" in gaining new skills and experience - as well as gaining important connections.

4) Faster Doesn't Always Win (or Finish) The Race. If you focus only on speed in sailing - you are much more likely to experience catastrophic failure of essential equipment - or, your crew will become exhausted and burned-out to the point of making catastrophically bad decisions. Same goes for your IT staff.

5) Compasses Can Lie. On a boat, the accuracy of your compass can be skewed by magnetic declination and/or magnetic deviation. So too, in IT - While you may have your 3 or 5 year IT Roadmap all planned out - and you may have your Key Performance Indicators (KPIs) established to help you measure your progress and alignment with your plan - your "compass" can be skewed by underlying market forces, or competitors bypassing your strategy entirely by focusing on something that is even more fundamentally important to your customers.

6) You Need A Course Plotted Out. Leaving the harbor on a boat for a leisurely afternoon sail is fine - but if you expect to cross great expanses of open ocean - you will have to contend with weather patterns, shipping traffic, and currents - and you need to plan for enough provisions, fuel, and electrical power management to keep your crew healthy, happy, well fed - and all of your essential systems operational. Often in IT, we see a pattern of constantly changing priorities - and poorly charted courses - with apparently no thought to the sustainability of making any voyage - nor any intent in reaching a destination. You'll soon find your "crew" abandoning ship as soon as the first habitable "island" appears on the horizon.

7) Things Break, Have Contingency Plans. Before embarking on a long voyage, the prudent skipper has already charted a primary course (and alternative courses to safe harbors), laid on sufficient provisions, and has gone over the game plan for making the voyage with the crew. But preparations for making a voyage don't end there. The prudent skipper has also planned for various emergencies that may arise - emergency pumps, emergency locator beacons, a life raft, emergency provisions, an emergency watermaker, signaling devices, solar battery chargers for emergency communication gear, etc. Within IT, having third-party relationships established - to provide supplemental staffing in case key team members are lost could be part of your contingency plan - or ensuring that you have active-passive fail-over strategies for your cloud-hosted infrastructure. Or implementing abstraction layers over a cloud-vendor's specific implementation of a particular service - so that you may more easily swap out another cloud service provider's service - without requiring rip-and-replace throughout your application architecture.

8) Expertise, Competence, Passion - Beats Size, Every Day. Given the choice to crew aboard a small ship, or a huge mega yacht - it all comes down to who else in onboard. The size of the ship - or the number of crew - or the fancy amenities offered onboard are of little concern - what matters is whether the selected crew members brings the right mix of expertise, competence - and passion. Without those three things, a ship can breakdown in the middle of a voyage and become a floating prison - or a floating hell. With those three things - even a small ship with a good crew can make a faster passage than a huge crew who forever fights among themselves - shirking their duties - and finding fault rather than pitching in and doing the tasks at hand that need doing. Ships that must make long voyages must be run as efficiently as possible, that means you cannot afford to have dead-weight onboard - consuming resources, but not adding to the operation of the ship. There are many analogies in this - in the way many IT organizations are often mismanaged.

9) Selection of Crew and Crew Cohesion. On a long voyage - the fit, temperament, and cohesiveness of the crew is vital and of paramount importance to the success of the endeavor. For a master treatise on leadership, the importance of crew selection, and the importance of leadership in maintaining crew cohesion - you can do no better than to read Ernest Henry Shackleton's own written account of the 1914 voyage of the Endurance to the Antartic, "South: The Story of Shackleton's 1914-1917 Expedition"

10) Sometimes Your Ship Sinks. No matter how diligently you plan, no matter how much care and attention you give to the maintenance of your ship - sometimes catastrophically bad things will happen - after which, events unfold in ways that you cannot manage (for example, the rate of water ingress may exceed the capacity of your pumps to keep up with the inflow). That's when your planning and approach to voyage preparation may spell the difference between hoping for rescue, or rescuing yourself. I always prefer to have a sailing dinghy on deck, in lieu of a life raft (for several excellent historical accounts of why this is my preferred choice, please see: The Voyage of Bounty's Launch; Dougal Robertson: Survive The Savage Sea; 438 Days: An Extraordinary True Story of Survival at Sea; Adrift: Seventy-six Days Lost at Sea; Once Is Enough). Within the world of IT, a Death March Project is a comparable event - but so too are much slower scenarios of your own personal "ship" sinking - such as being pigeon holed into roles (for years, or decades) that don't allow you to be exposed to new technologies, learn, grow, and gain in responsibility.

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