From Level Up’s Fractional CTO executive practice: Questions to answer before you hire your first full-time dev, CTO, or agency.
UX
1. What’s the critical path UX flow, and have we tested it with real users on real devices yet?
2. What’s the fallback UX going to be if a critical internal service fails? And what about external services?
3. Have we defined empty states, loading states, and edge cases for every view?
4. Are we building for mobile, desktop, or responsive, and why?
CI/CD
5. How are we going to manage secrets and env config across stage, QA, and prod?
6. When we say CI/CD, do we mean delivery or deployment, and why?
7. Are we going to be deploying blue/green or canary? Who’s watching the metric dashboards when we rollout? And what are those metrics BTW?
8. What’s our rollback plan? Are we talking feature flags, or redeploying the last known-good build version?
Dev
9. What’s our data model, and how opinionated are we going to be about things like schema evolution?
10. What’s our identity provider? Or are we rolling custom auth?
11. What’s our data retention policy if a user requests full deletion? Soft deletes, full deletes…or just kind of ignoring for now?
12. Are we practicing TDD, or retrofitting failure tests whenever bugs surface?
13. Are we doing Gitflow, GitHub Flow, trunk-based, feature branching? And are PRs mandatory?
14. If so, who’s reviewing them? Do we need 100% unit coverage for our 1.0 release, or are we prioritizing integration tests?
Ops
15. What’s our default cloud region, and why? Are we accounting for pricing differences, UX latency, PII/GDPR compliance… or did we just pick what’s closest to HQ?
16. How are we forecasting and monitoring our cloud spend, and do we have billing alerts for unexpected spikes?
17. What’s our high availability, backup, and disaster recovery strategy? N+1 instances, app load balancing, multi-AZ, multi-region? And for which layers? Presentation, Application, Data?
18. Do we have autoscaling configured, or is everything going to be running 24/7/365 to be ready for monthly peak traffic bursts?
19 .Are we provisioning resources manually by clicking around in the web console, or using infrastructure as code from Day 1?
20. How are we monitoring uptime? Is anyone on-call?
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