Hiring Guide
Technical decisions made early have a long half-life — the wrong architecture, stack, or vendor choice can cost years of refactoring. Whether you're a non-technical founder or an engineering team looking for an outside technical review, here's how to find and evaluate the right technology expert.
Use these in an intro call or first session to quickly assess fit and expertise.
1.Given what you know about our stack and stage, what would you be most concerned about?
Why it matters: This reveals how quickly they can pattern-match from limited information. Senior technical advisors will immediately identify 1–2 real risks.
2.How do you decide between building something custom versus using an off-the-shelf solution?
Why it matters: Build vs. buy is one of the highest-leverage decisions a technical team makes. You want someone with a principled framework, not a reflexive preference either way.
3.Tell me about a technical decision that turned out to be wrong. What happened and what would you do differently?
Why it matters: Every experienced engineer has made significant mistakes. Advisors who can talk candidly about their own failures are more trustworthy.
4.How would you approach evaluating my current codebase or architecture?
Why it matters: You want a structured thinker. A good technical reviewer will describe what they'd look for: code quality signals, test coverage, dependency risks, scalability bottlenecks.
5.What's your opinion on a specific technology choice we've made or are considering?
Why it matters: Ask something specific and technical. You want an informed opinion, not diplomatic hedging.
Technology consulting sessions are highly practical. Your expert will quickly get up to speed on your technical context, ask the right diagnostic questions, and give you direct recommendations — not a 50-page report. Expect frank opinions, trade-off analysis, and actionable next steps you can act on immediately.