Most executives talk about technical debt as an engineering problem. It is not. It is a strategy problem dressed up as a code problem.
The test is simple. Pick a strategic question your CEO might ask on Monday — which products are growing fastest in which segments, which customers are at risk, which channels are profitable. If your platforms cannot answer that in a week, your strategy is being throttled.
Resolving platform debt is rarely about a single replatform. It is about identifying the three to five data and integration choke-points that block decision velocity, and investing there first.
Done well, this is the highest-leverage investment a CIO can sponsor — and the easiest one to defend to a board, because the language is strategy, not infrastructure.