Strategic Debt Estimator
A composite estimator of the strategic debt your team is carrying. Output: a debt score plus the payback order that clears it fastest.
Who it’s for: CMOs and heads of strategy who feel the weight of unfinished decisions but cannot name the number — and need one to defend the paydown work in a planning cycle.
- 01
Not a messaging tweak — a structured review of category, ICP, and differentiator. 0 = this quarter. 12 = a year or more.
This quarter6A year or more - 02
How many places say different things? 0 = none found. 10 = at least one contradiction on every key surface.
Aligned5Contradictory - 03
Pricing model, ICP, naming, tier structure — any of the above surface in leadership meetings more than once a quarter? 10 = yes, regularly.
Settled5Re-litigated - 04
Ask five reps the same question. 1 = word-for-word agreement. 10 = five different answers.
Identical5Diverged - 05
1 = it is written down and discoverable. 10 = no one remembers, or only one person does.
Documented5Lost
You are not in trouble. Put a positioning review on the calendar for the next cycle and make sure new decisions get written down in a findable place.
Read it honestly, not charitably.
The metaphor is literal. Strategic debt carries interest — every quarter it stays on the books, another campaign gets taxed by the unresolved calls underneath it. The score is a proxy for how much of this quarter’s execution is going toward paying yesterday’s interest.
Weight your highest-scoring input first. A 9 on “re-litigated decisions” with everything else at 3 is a different problem from a 6 across the board — the first is one rock to move, the second is a systemic review.
The score is directional, not precise. Use it to justify a paydown sprint, not to report a number to the board. “Our strategic debt is 68” is less useful than “here are the three specific decisions we have been re-arguing every quarter.”
Three moves you can make this week.
- Move 01
Pick the single highest-scoring input. Spend one week closing the top contributor to that input — not all of it, the one that would drop the score by two points.
- Move 02
Write down the decision you close. Put it somewhere a new hire can find in 30 seconds. The Strategic Decision Log is the format.
- Move 03
Re-run this in 90 days. If the score moved less than 10 points, the paydown was too ambitious or too shallow. Pick a smaller rock next time — and actually ship moving it.
Why these questions, in this order.
Five inputs because strategic debt shows up in five predictable places: review cadence (how long since the big questions got re-examined), consistency (how loud the contradictions are), settled-or-not (how often the same decisions resurface), rep variance (whether the team has a single story), and memory (whether the past is discoverable).
Weights favor review age and contradictions because both compound quietly. A six- month-old positioning review is not visibly a problem until marketing, product, and sales start accumulating drift at different rates. By the time the drift is obvious, the review needed to happen three months ago.
What this calculator deliberately misses: the market. A team running in a fast- moving category accumulates debt faster than a team in a slow one. Translate the score through your market clock — in a 90-day category cycle, a 50 this quarter is tomorrow’s 70.
Run the full Strategic Context.
The shared memory that makes every other tool smarter over time.