Six Question Sets Test Judgment, Contact, Leadership, Candor, and Transitions

Choose one or two of these sets for the criterion you are testing. Ask for past evidence before hypothetical confidence.

Test Business and Technical Judgment#

1. Tell us about a technology decision that clearly changed revenue, cost, risk, or strategic choice. What did you know when you decided?
2. Describe a technically sound proposal you rejected because it was wrong for the business. What was sacrificed?
3. Tell us about a business commitment you challenged. How early did you raise the issue, and what alternative did you offer?
4. Describe a time you chose a reversible step instead of a complete solution. What did you learn?
5. Tell us about a decision where waiting for more evidence was the wrong choice.
6. What technology investment did you stop after supporting it initially?
7. Describe a vendor decision where the cheapest or most capable option was not the best choice.
8. Tell us how you have connected technical debt to a business decision without turning every engineering concern into executive urgency.

Follow-ups. Authority, options, cost of delay, who disagreed, evidence, actual contribution, result, second-order effects, and later learning.

Test Technical Contact#

1. Choose a system that mattered to your business. How did you maintain contact with its real condition?
2. Describe the last major incident you reviewed deeply. What did you learn beyond the immediate cause?
3. Tell us about an architecture decision where respected experts disagreed.
4. How did you know an internal platform was useful?
5. Describe a migration you decided not to complete.
6. When did a metric produce the wrong conclusion?
7. What technical subject did you need to learn as an executive, and how did you build reliable judgment?
8. What do you personally inspect now, and what have you deliberately stopped inspecting?

For builder roles, add a realistic technical exercise. For enterprise roles, test cross-system and capital reasoning. For physical roles, test interfaces, lifecycle, suppliers, and evidence.

Test Leadership and Delegation#

1. Which leader did you hire who changed what your organization could do?
2. Describe a senior hire that did not work. When did you know, and what did you do?
3. What work once depended on you and later did not?
4. Tell us about a capable person who strongly disagreed with you and stayed effective.
5. How have you built a senior technical career path separate from management?
6. Which recurring meeting or governance mechanism did you remove?
7. Describe a reorganization whose intended benefit did not appear.
8. How do you distinguish a leader who lacks support from one who lacks capability?

Test Candor and Executive Influence#

1. Tell us about bad news you delivered later than you should have.
2. Describe a board or CEO decision you disagreed with but then executed.
3. When did you change your recommendation in public?
4. Tell us about a peer relationship damaged by a decision. What did you repair, and what remained unresolved?
5. Describe a time you had accountability without control. Which mechanism did you change?
6. What important risk did your organization accept after you made it visible?
7. Tell us about a customer promise you stopped or changed.
8. When has your public technical story become too optimistic, and how did you correct it?

Ask Both Sides About a Founder Transition#

For the incoming candidate.

• How would you learn why the founding architecture and organization evolved as they did?
• What authority would you require if the founder remains a technical executive?
• Describe a time you worked with a founder or expert with greater social authority.
• How would you respond when an engineer bypasses you for the founder’s opinion?
• Which decisions would you want the founder to retain?

For the founding CTO.

• Which work gives you energy, and which work do you perform mainly because the company needs it?
• What future decision authority do you want?
• What would make a new CTO useful rather than threatening?
• Which knowledge and relationships are dangerously concentrated in you?
• What behavior by the CEO, board, or new CTO would make the transition dishonest?

Ask Fractional and Interim Candidates About Scope and Conflicts#

• Which decisions can you own with the proposed time and access?
• Describe an engagement you ended because internal capability had grown.
• How do you prevent clients from waiting for your next available day?
• Which conflicts of interest can arise across your clients, vendors, or investments?
• What is the internal execution role you require?
• What would trigger a full-time recommendation?
• If you may become the permanent candidate, how will that affect the role you design?
• What artifacts and relationships remain after you leave?