Vetting senior cloud consultants: the five questions that matter

Why résumés are the wrong starting point

A résumé tells you where someone has been. It does not tell you what they built, what broke, or what they would do differently. In cloud and DevOps roles especially — where the work is inherently messy and context-dependent — the gap between "was present during a migration" and "led the hard parts of a migration" is enormous and invisible on paper.

These five questions are designed to close that gap in thirty minutes.

The five questions

1. "Walk me through the last time something you built failed in production. What broke, how did you find out, and what did you change?"

This question is not a test of competence — it is a test of honesty and self-awareness. Anyone who has shipped real production work at a senior level has a clear, specific answer to this question. Vague answers, or answers that focus entirely on other people's failures, are a signal to probe further.

2. "What did the architecture look like on day one of your last major engagement, and what did it look like when you left? What drove the changes?"

This surfaces judgment. Good senior architects make dozens of non-obvious decisions between initial design and steady state. If the candidate cannot explain what changed and why, they were probably not the decision-maker.

3. "Describe a time you told a client or a stakeholder something they did not want to hear. How did you frame it, and what happened?"

Senior consultants are paid, in part, to give honest assessments. This question separates people who can do that from people who manage upward by telling comfortable stories. The answer should include the specific thing they said, not just "I was transparent."

4. "What would you not use [the technology we are hiring for] for, and why?"

Every serious cloud architect has a clear view of the tool's failure modes. If someone cannot articulate where Azure Fabric falls short, or when Kubernetes is overkill, or which workloads should not be on the public cloud, they are selling the technology rather than understanding it.

5. "What does a good handover look like from your perspective?"

Consultants who are building a dependency — consciously or not — give ambiguous answers to this question. Consultants who are genuinely trying to leave the client in a better position give specific, concrete answers: what documentation they produce, how they train the internal team, what the 90-day support arrangement looks like.

The answers that should end the conversation

Walk away if a candidate:

• Cannot name a specific failure or defends every decision they have ever made
• Describes their last engagement in terms of activities rather than outcomes
• Has never told a client anything they disagreed with
• Frames all technology as universally applicable
• Has no view on what a good handover looks like