Questions to Ask a Technology Expert

1.Based on what I've described, what's the highest technical risk in our current setup?

The most important diagnostic question — prioritizes where to focus attention and investment.

2.Is our current tech stack appropriate for where we want to be in 2 years, or are we heading toward a painful migration?

Early decisions compound. A forward-looking assessment now is cheaper than a rewrite later.

3.Where are we likely to hit scalability limits first, and how expensive will they be to fix?

Not all bottlenecks matter at your scale. This filters the real ones from theoretical concerns.

4.What technical debt should we be paying down now versus accepting for now?

Not all technical debt is equally costly. Good advisors know which to prioritize.

5.For a specific feature or system we're considering, should we build it, buy it, or use an open-source solution?

One of the highest-leverage decisions in tech. Specific scenarios get specific answers.

6.What would you change about our architecture if you were starting over today?

The clean-slate question often surfaces the most honest assessment of existing decisions.

7.Are there technologies or tools we're using that you'd consider risky or likely to become problematic?

Surfaces dependencies, vendor risk, or ecosystem choices that are harder to see from inside.

8.Are we using our engineering team effectively, or are there process or tooling changes that would unlock more output?

Often the most valuable question for non-technical founders — reveals efficiency gains without more headcount.

9.What should our engineering team be doing in the next sprint that we're probably not planning to do?

Gets specific short-term recommendations that are immediately actionable.

10.What would you want to review or audit before making a recommendation you'd stake your reputation on?

Reveals what additional context they'd need — and signals their intellectual honesty.