
Optimization is a powerful tool. It is also frequently
misunderstood.
Most optimization problems assume the objective function is known,
stable, and agreed upon. In operational contexts, that assumption
often holds. In leadership contexts, it rarely
does.
Leadership exists precisely because the problem is contested.
Trade-offs are real. Values collide. Consequences unfold over time
in ways that no model fully captures. What appears optimal in the
short term may prove strategically fragile over a longer
horizon.
Yet many organizations now behave as if leadership were primarily a
matter of selecting the best option from a ranked list. The harder
work—framing the decision itself—quietly recedes into the
background.
This was one of the central questions that led me to write A
Return to Strategic Leadership as a business novel rather than
an analytical treatise. Frameworks are well suited to optimization
problems. They are less effective at revealing what happens when
the objective itself is uncertain.
When leaders confuse optimization with strategy, judgment does not
disappear. It is exercised upstream, embedded in assumptions about
what is being optimized and whose interests are prioritized.
Accountability becomes diffuse even as decision velocity
increases.
Optimization improves execution. Strategic leadership begins when
optimization no longer answers the question—when judgment is
required because accountability cannot be delegated.
There is a growing belief that advanced systems have reduced the
need for human judgment.
In reality, judgment has not been removed. It has been
obscured.
Every AI-enabled decision reflects prior human choices: what data
to include, which variables to prioritize, how outcomes are
weighted, and what trade-offs are deemed acceptable. These
judgments are embedded upstream, long before a recommendation
appears on a dashboard.
One of the reasons I chose a narrative form in A Return to
Strategic Leadership: Judgment in the Age of AI was to make
this hidden judgment visible. Stories expose where decisions
actually happen—through people, incentives, and institutional
pressures—rather than where organizations claim they
happen.
When judgment is hidden inside systems and processes,
accountability weakens. Decisions begin to feel inevitable rather
than chosen. Responsibility becomes harder to locate, even as
consequences remain very real.
This invisibility creates a false sense of objectivity. Leaders may
believe they are “following the data” when, in fact, they are
endorsing a chain of assumptions they did not personally
examine.
Leadership requires making judgment visible again - surfacing the
choices embedded in systems and being explicit about which ones you
are willing to own.
In the age of AI, the hardest leadership work is no longer
analytical. It is judgmental in the truest sense of the word. AI
can inform decisions, but it cannot assume responsibility for
them—and strategic leadership begins where that responsibility is
owned.