Thursday, November 12, 2026
61% of surveyed US business owners have never had their company valued. The real cost isn't at exit — it's every day you're building something that might be worth nothing without you in the room.
Most strategic plans do not fail because the strategy is wrong. They fail because the plan is too big to run.
Published by Simple-Growth, a business coaching practice. Last updated 13 November 2026 (New Zealand time). Written for owners of established small and medium businesses in New Zealand and the United States.
ClearPoint Strategy, a strategic planning software company, analysed 20,582 strategic plans and 31.2 million records from its own platform (ClearPoint Strategy, released 20 November 2025). It found a sharp cliff: plans with fewer than 20 total goals, measures, projects and milestones succeeded 68% of the time. Plans with more than 60 succeeded just 8% of the time. Fewer than 10% of organisations completed even half of their strategic goals. ClearPoint does not name the countries, and does not define "success", so read this as a strong signal from one vendor's data, not a law.
If you have ever built a thorough, detailed, colour-coded strategic plan in January and found it gathering dust by November, this is not a discipline problem. It is a design problem.
For decades, business advice has pushed owners toward more detail, not less. Cover every department. List every risk. Map every contingency. A thin plan looks lazy. A thick one looks like leadership.
ClearPoint's report is not a survey of opinions. It is platform data tracking what strategic plans actually accomplished. And it points the opposite way from what most of us were taught: more content in the plan does not mean more gets done. It means less does.
The reason is simple arithmetic, not laziness. Every goal, measure, project or milestone added to a plan is a claim on somebody's attention. A 60-item plan is not three times harder to run than a 20-item plan. It is an order of magnitude harder, because every item is competing with every other item for the same scarce hours, the same scarce owner, the same scarce week.
This matters more for SME owners than for a large organisation. ClearPoint does not publish the size of the organisations in this dataset, so the numbers may not map neatly onto a 12-person business. But the logic holds: a 200-person company can spread a sprawling plan across a dozen departments. A 12-person business cannot. You are the department. Every line on that plan eventually lands on your own desk.
Here is what I use with Simple-Growth clients building a 90-day plan, the Rule of 20.
1. Name one real constraint. Not five priorities, the single thing most limiting growth right now: cash, customers, capacity, team, or you. Diagnose before you prescribe.
2. Choose three moves that would genuinely shift it. Not ten nice-to-haves. Three. If a move does not move the constraint, it does not make this quarter's list.
3. Give every move one named owner and one date. No "the team" as owner, a name. No "Q2" as a date, a week.
4. Keep the total under 20 items, including every sub-task you are tracking. If you are at 25, you do not need a better tracking tool. You need to cut five things.
5. Review weekly, not quarterly. A 20-item plan reviewed every week catches drift in days. A 60-item plan reviewed every quarter catches drift in months, by which time it is unrecoverable.
This is not a simplified version of real strategy. It is what real strategy looks like once you strip out everything that was never going to get done anyway.
"Kevin had a no-nonsense approach and tackled the issues head on. Accountability was the key."
— Ashley Berrysmith, Icehouse Coaching Programme
Most owners reading this already sense that smaller plans execute better. Here is why they still build the sprawling version anyway: it feels safer. A 60-item plan means you have thought of everything, so if something goes wrong, it was not because you missed it. A 20-item plan feels exposed, you are betting the quarter on three things actually working.
That is not really a planning problem. It is a confidence problem, and underneath it, an accountability problem. Without someone checking the plan weekly, not quarterly, not "when I remember", there is no cost to letting the list grow, because there is no moment where anyone asks why item 37 still is not done.
This is exactly where an outside coach earns their keep: not writing the plan for you, but being the person who makes keeping it at 20 items the accountable, uncomfortable, non-negotiable choice, every single week.
1. Pull up your current plan and count every goal, project, measure and milestone on it. Just count. Most owners are shocked at the real number.
2. If you are over 20, cut to your top three moves against your single biggest constraint. Everything else goes on a "later" list, not a "now" list.
3. Put one name and one date on each of those three. If you cannot name an owner, you do not have a plan item, you have a wish.
It is a planning limit: name one constraint, choose three moves that would shift it, give each move one owner and one date, and keep the whole plan, sub-tasks included, under 20 items.
Every item is a claim on the same owner's time and attention. ClearPoint Strategy's data shows plans with fewer than 20 items succeeded 68% of the time and plans with more than 60 just 8%. ClearPoint does not define success, so treat the figures as a signal.
Under 20 in total, counting goals, measures, projects and milestones. If you are at 25, cut five before you buy a better tracking tool.
Weekly. A short weekly review catches drift in days, while a quarterly review catches it in months, when it is much harder to recover.
ClearPoint does not publish the countries or organisation sizes in its dataset, so it may not map exactly. The reasoning, that every item competes for the same scarce owner time, applies even more strongly when the owner is the whole team.
Sources. ClearPoint Strategy, first strategic planning report: 20,582 plans analysed, 20 November 2025 (opened 13 November 2026). Testimonial: Ashley Berrysmith, Icehouse Coaching Programme feedback, verbatim.
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