Ercole de’ Roberti: The Miracles of St Vincent Ferrer (1473)
"… We might just be setting ourselves up …"

The pathway between any two places never runs in anything even vaguely resembling a straight line, yet in my mind, when I envision a journey, I seem only capable of imagining straight-ish lines. My experiences, then, diverge from my plans, continually surprising me. This result probably has most to do with a personal limitation, not precisely a lack of imagination, but a limited one, and the inherent difficulty of plotting curves using only straightedges. I thought I'd long ago immunized myself against shock or surprise when encountering these divergences, but I apparently had not. They get me pretty much every time.

My "discovery" that nobody ever appreciates an accurate plan marked a huge leap in my maturing as a project manager. I'd noticed that by far the most accurate forecast would be one prepared after finishing the project, since only then would one ever have access to the actual data, and afterward, everyone involved could readily assess its correctness. But beforehand, nobody would be likely to accept that post hoc plan as in any way acceptable, for its track would seem altogether too Wending, not nearly efficient enough looking. Organizations often perform retrospectives to produce what they refer to as Lessons Learned, but few learn very much of anything from these exercises, if only because the most profound insights seem somehow non-representative, one-offs unlikely to represent repeating patterns. These variations from plan seem more like accidents boogering up the data than accurate portraits of likely future experience. The Lessons Learned white paper gets published but few read the result and even fewer believe it.

There's a balance aching for someone to achieve it. Completely fictional plans rarely pass muster, but utterly accurate ones never get approved. Author Peter Block characterized the typical conversation between any sponsor and their project planner. The sponsor always asks, "How much will it cost and how long will it take?" The planner never responds as he should if he was trading in the truth and nothing but, which would be some variant of, "This effort will cost more than you'd ever willingly agree to spend and take longer than either of us would ever find acceptable." Yet this assessment more often ultimately proves accurate. We would rather be lied to than receive this truth. We insist upon becoming willing partners in another grand deception. We mostly author our own disappointments.

But for the period before our bubbles burst, we're almost Gods. We're foreseeing, reveling in whatever we've conceived. We seem to be having it our way, a heady experience, indeed! Our anticipations follow rules of order stricter than those enforced by any parliamentarian, and at first, divergences always seem rare. How does an effort go off the rails? The same way one goes bankrupt, very slowly, then instantaneously. We might maintain certain contingencies, but these, too, will very likely prove inadequate. We might just be setting ourselves up so that we're cornered into conditions where our reactive intuition has to kick in, what some refer to as 'wisdom.' Only after the planning proves wanting do we seem to accept the necessity of dead reckoning, and its inevitability, and rediscover our hidden mastery of it again. Then we become human.

©2021 by David A. Schmaltz - all rights reserved

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