Diagnostic
CEO Test
A quick self-assessment — score yourself on four questions to check that the big things are covered.
Use this when you are worrying "am I doing enough?" — a five-minute clarity check, not a full strategy review. Be honest. The point is to spot gaps before they become crises.
The four questions
We know where we're heading
Destination is clear enough that you and the team could repeat it. Low score? Revisit the Strategy One-Pager or Six Critical Questions.
We have a clear plan on how we are going to get there
You can name the path from here to the next milestone — priorities, sequencing and trade-offs. Low score? Chart the path before adding more initiatives.
Each of my team has a plan that feeds into the company plan
Leaders can explain how their goals connect upstream. Low score? Cascade is broken — check OKRs and 1:1s before blaming execution.
I'm confident that my team can execute that plan
You trust the people and systems in place, not just the slide deck. Low score? The gap is likely talent, capacity or accountability — not more strategy.
How to score
- Rate each question 1–5. Halves are fine (e.g. 3.5).
- 1 = not true at all · 3 = partly · 5 = fully confident
- Note the lowest score first — that is usually where to focus this week.
- Re-run monthly, or whenever the "am I doing enough?" anxiety spikes.
High scores on direction and plan but low on team plans or execution confidence usually mean the strategy work is done — the org work is not.
Different funding paths — raise, profitability, debt — often look distinct on paper but converge on the same requirement: performance. If direction and plan score high but metrics are soft, the answer is rarely a new strategy doc.
Source / credit
Outstride original
Related capabilities
Related tools
Work with Ben
Want help installing this?
Outstride OS is the system behind Ben's founder coaching — pre-seed to Series C. If this page names something you are living right now, start a conversation.