Session Prep
Technology consulting sessions are most productive when you come in with specific decisions, not just open-ended questions. These prompts help you get direct technical opinions, surface architectural risks, and leave with clear recommendations you can act on. This guide covers three core areas: assessing your current technical situation and risk profile, build vs. buy and architecture decisions, and team, process, and next steps. Before your session, prepare a brief overview of your stack, your current scale (users, transactions, data volume), and the specific technical decisions you're facing. A non-technical background is fine — a good advisor can work from business context and outcomes. Come with the specific problem at the center: a migration, a scaling concern, a vendor evaluation, or a team structure question. Focused inputs produce focused recommendations.
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.