"What would you have done differently?"

Note:  I'm simply attempting to write as often as possible about issues relating to work, not having a job and building some income opportunities.  Not much of this is really all that epic.

After closing the small business to the public for the day we drove around aimlessly for for twenty minutes.  Halfway through the aimlessness my better half asked "What would you have done differently? (at the 27-year gig)"

That question has gone through my head a few thousand times but I responded as if it were new.  "Do you mean what would I have done better to have been more successful and still there or are you asking what I would have done in a broader sense in a not-specific-to-that-organization sense?"  After some back and forth dialogue I responded more or less in the following points:

• No, there is nothing different I could have done.
• I was a progressive IT leader, quite ahead of the curve.
• The organization never valued IT.
• The organization was deal-focused (real estate).
• None of the owners were interested in IT.
• The successful ($$$) executives were those that brought in real estate (and construction) deal dollars.
• Cost-saving IT and process improvements were secondary to big-deal revenue deals.
• At the prompt of the then CEO we started a 'lean' process improvement initiative in 2006.  I led that.  We made significant progress but were derailed by the 2008 recession which slashed employees, wages and spending across the organization.  The program ended.
• While I had kept responsibility for IT while starting the lean program the recession also ut IT staff by 50% and all discretionary spending.
• The new CFO had no experience in IT, wanted to eliminate all IT-initiated spending and move strategy and spending allocation to the user community (which also lacked any meaningful IT development, spending/budgeting or strategy experience).
• The cards were dealt.

In an earlier post I was critical of the Target board of directors and C-level staff for being experts in their own disciplines, driving vertically rather than horizontally.  The organization I served likewise worked vertically within disciplines or departments or functions.  Strategic planning sessions typically involved deal people talking to everyone else about their deal plans, marketing talking about marketing, IT talking about IT, etc.  Obviously each function's focus should have been on defining and requesting resource needs from other disciplines that would make their groups successful or each department selling itself better to the others, both logical and not.  That cannot be done in an abstract fashion.  

Each department head needs to know more or less everything about their discipline and that discipline's place within the organization but each department head needs to know key performance opportunities about each other department; it might have served a good purpose to rotate executive positions for a day or week every so often.  Target did a good job of this in their lower management ranks, encouraging extensive networking and rotation of managers frequently.

• From an IT perspective I saw and developed opportunities early, but too early, as much as a decade.  That should have been a warning that I was in the wrong organization.
• I should have worked harder to find someone in the organization sweet spot (e.g. real estate deal person) to latch onto.  This started to happen in the process improvement initiative.  Also unfortunate is that real estate deal people are tenacious and goal focused...but this goal, not really the next one done the road.  I guess the opportunity would have been to latch onto a younger person who had show promise in the deal business but who also had and affinity or interest in IT/process improvement.
• I do not believe that in this organization any national or regional exposure via industry groups or associations would have been appreciated.
• My networking within the organization was decent.  Outside the organization (which would not have mattered) could have been better.

You don't become a successful farmer by simply planting and harvesting.  You need to understand biology, animal husbandry, mechanics, welding and repair, chemicals, accounting, finance, commodities, meteorology, IT, etc., etc.. and you need to find the balance.