A senior person’s most valuable holding is not a set of principles. It is several hundred situations, each with what was known at the time, what was decided, and how it turned out.
Principles are what those situations compress into, and the compression loses the part that matters. Somebody who receives the conclusion cannot apply it to a case that does not obviously match, which is most cases.
Why the conclusion does not travel
Always get it in writing is a rule. It carries no information about which situations it applies to, what it costs to insist on it, or how to tell when the relationship is worth more than the protection.
The account of the specific occasion where a verbal understanding cost the firm a season, including the fact that insisting would have been awkward and that the other party was somebody you had known for years, carries all of it.
The listener now holds not a rule but a case they can compare new situations against, which is what judgment actually consists of.
Withhold the outcome
The single technique that does most of the work in this entry.
Told with the ending, a case is a story and the listener is a spectator. They will find the correct decision obvious, because they know how it went, and they will learn nothing about deciding under uncertainty.
Stop at the decision point. Here is what I knew. Here is what I did not know. What would you do?
Make them commit before revealing anything. A person who has stated a position has exposed their reasoning to themselves, and the subsequent correction attaches to something rather than passing through.
Then, and this is the part senior people skip, ask why before saying what happened. Frequently the reasoning is sound and produces a different answer, which is worth knowing and occasionally worth learning from.
Tell the ones where you were wrong
Cases where the senior person decided correctly teach the least, and they are the ones that get told, because they are comfortable.
The instructive material is the decision that went badly, told honestly: what you believed, why it was reasonable, and what you had failed to see. That teaches the failure mode, which is what the listener needs, and it teaches that being wrong is survivable and discussable.
It also establishes the only condition under which the junior person will later tell you about their own errors. A mentor who has never been wrong in any story they have told has made honest reporting impossible without either party noticing.
Uncertainty is the content
Memory tidies decisions. What was agonised over for a fortnight becomes, in the telling, something that was clear at the time.
That tidying removes the instructive element. A junior person hearing a series of decisions that were apparently obvious concludes that senior people simply see the answer, and that their own uncertainty is a deficiency rather than the ordinary condition of the work.
So the effort is to restore the doubt honestly. I did not know. I nearly went the other way. What decided it in the end was a detail I could easily have missed.
This is also where a written record earns its cost. A decision log lets somebody tell a case as it actually was rather than as they now remember it, which is a different and more accurate story.
The live case beats the historical one
Better than any recounted situation is one currently in front of you, because the outcome is unknown to both parties.
Bring somebody into a decision you are actually making. State what you know, ask what they would do, tell them what you are inclined toward and why, and then have them watch how it resolves.
Both of you find out together, and the case is genuine rather than reconstructed. This is the highest-value form available and it requires only that a senior person be willing to reason out loud in front of somebody junior while the answer is still in doubt.
Cases are perishable
A working life produces several hundred of these and no institution collects any of them.
When somebody retires, the situations retire with them. Not the technical knowledge, which is documented, but the accumulated pattern recognition about how things actually go here, which existed only in one head and was never asked for.
Writing down a dozen of them before somebody leaves is not sophisticated and it is almost never done. What was the situation, what did you know, what did you decide, what happened. A page each, in their own words, recorded by anybody willing to sit with them for an afternoon.
For an institution intending to persist, that afternoon is among the highest-return uses of time available, and the window for it closes on a fixed date that everybody can see coming.
Edited by Patrick J. Wolf, PhD