A 12-question diagnostic for founder-CEOs of tech middle-market firms ($10M–$100M ARR). Built from 40+ operator engagements. Your answers don't leave this page.
Answer honestly. Your score doesn't leave this page (we don't store it). Built from 40+ engagements with tech middle-market firms.
1. How many decisions per week require your sign-off?
Pricing exceptions, team hires, customer escalations, vendor contracts, roadmap calls.
2. What % of your closed-won pipeline closes without you in the room?
Discovery, demo, negotiation, or final close. The lower the %, the higher the bottleneck.
3. When was the last full week you were unreachable?
Real unreachable. Phone off, no Slack. Not 'on a flight.'
4. How many of your direct reports could run the firm for 30 days without you?
Honestly. Not 'they could try.' Could they run it.
5. Do new hires get onboarded by you or by a documented system?
If onboarding ROI tracks with your calendar availability, that's a system gap.
6. Can your CFO close a month without your input on revenue recognition?
Bonus points if there's an FP&A model the CFO actually owns.
7. Is your customer success leader empowered to issue credits and renegotiate terms?
Without checking with you. Within a published policy.
8. When something breaks in production at 2 AM, who is paged first?
If it's the founder, that's a problem.
9. Do you have a written succession plan reviewed in the last 12 months?
PE buyers ask for this in week one of diligence.
10. Have you taken 2+ consecutive weeks of vacation in the last 18 months?
Real vacation. Out-of-office responder, no email.
11. What % of your management team has equity vesting beyond the next 12 months?
Retention math matters. Cliff dates don't lie.
12. Could a buyer's diligence team interview your leadership without you in the room?
If the answer is 'no, they'd get the wrong story,' that's the bottleneck.
0 / 12 answered
Why this diagnostic exists
Most founder-CEOs we work with describe their constraint as "growth has stalled." When we look at the engagement closely, the real constraint is structural: the founder is on the critical path of too many decisions, and the firm cannot scale past their personal calendar. A buyer's diligence team will price this risk into the multiple — typically 1–3 turns of EBITDA depending on the depth of the dependency.
How the score is built
The 12 questions aren't equal. Decision-velocity questions (sign-off load, succession plan, diligence interviewability) are weighted 1.5×; lifestyle questions (vacation, on-call) are weighted 0.8×. The total maps to one of four bands and routes you to the pillar of work that's most likely to move the number.
What to do with the result
The result is a starting point, not a verdict. If your score lands in Critical or High, the right move is rarely "hire a COO" — it's first mapping every founder-owned decision and engineering the systems that replace each one. We've taken firms from Critical to Exit-ready in 9–18 months. The pillar page linked from your result has the playbook.
Run the diagnostic against your full leadership team
Most founders score better than their team does. We facilitate the multi-respondent version inside a 14-day operator-led diagnostic.
