Founder of Goodspeed
Why the Right Questions Matter
Before you list the questions, it helps to understand why structured questioning matters. Asking the right things in the right order protects your budget, exposes weak candidates early, and anchors the relationship in clarity.
A thoughtful discovery conversation does three things at once:
Filters for genuine Claude expertise—not just generic AI or LLM experience.
Surfaces assumptions early so scope, budget, and timelines don't drift.
Reveals how the developer thinks—their reasoning process is often more telling than a polished pitch.
Red Flags Poor Answers Reveal
Weak answers usually share common patterns—vague project descriptions, buzzword salads, or reluctance to discuss failures. If a developer can't explain why they chose Claude over another model for a past project, that's a signal worth paying attention to.
Here's what one of our clients said: "We asked three agencies the same five questions. Only Goodspeed walked us through the trade-offs instead of selling us features. That conversation alone told us who to hire."
Tip: Write down your top 10 questions before any discovery call and ask every candidate the exact same list. It's the fastest way to compare apples to apples.
Questions About Claude Experience & Track Record
With the foundation set, here are the four categories of questions every serious buyer should run through. Each group targets a different risk area—talent, technical fit, process, and long-term support.
You need to confirm the developer has shipped real Claude projects—not just tinkered with the Anthropic SDK.
How-to: Ask "Can you walk me through a Claude project you shipped in production? What was the scope, what model did you use, and what would you do differently?" Push for specifics on token volume, latency, and costs.
Questions About Architecture & Technical Approach
Claude projects live or die on architecture decisions—model selection, context management, tool use, and evaluation.
How-to: Ask "How do you decide between Sonnet and Opus for a given workflow?" and "How do you structure evals before shipping an agent?" Strong developers will reference concrete frameworks, not hand-wave.
Questions About Process, Timelines & Communication
The best technical team in the world will fail you if they disappear for two weeks between updates.
How-to: Ask "What does a typical sprint look like? Who will I talk to day-to-day? How do you handle scope changes?" Confirm you'll have access to the actual builders—not just a project manager relaying messages.
Here's what one of our clients said: "Every Friday we got a demo, a cost breakdown, and a clear list of what was shipping the following week. It removed the anxiety of 'what are they actually building?'"
Questions About Handover & Ongoing Support
If the agency walks away and you can't run the system, the project isn't really done.
How-to: Ask "What does handover documentation include? Do you offer post-launch support, and at what rate? Who owns the prompts, evals, and infrastructure?" Get the answers in writing before you sign.
Evaluating Technical Depth
Evaluating Cultural & Commercial Fit
Evaluating Risk & Accountability
Final Thoughts
The questions you ask before hiring a Claude developer are the single cheapest insurance policy available. A 45-minute conversation can save you six months of rework—if you know what to listen for.
Recap of Core Steps
Prepare a fixed question list covering experience, architecture, process, and support—and ask every candidate the same thing.
Evaluate answers for specificity, not polish—real builders reference real trade-offs.
Put the answers in writing as part of the scope so promises carry over into the contract.
Next Steps
Smart questions only work if you also know the warning signs and common pitfalls to watch for.
For deeper insights:
Read How to Identify Red Flags When Hiring a Claude Agency to spot trouble before you sign.
Check 6 Common Mistakes to Avoid When Hiring a Claude Agency to avoid the traps most buyers fall into.
The right questions turn a sales pitch into a technical interview—and that's exactly what you want. Go in prepared, listen carefully, and trust specifics over slogans.
If you want to see how a transparent discovery process feels in practice- book a free consultation with Goodspeed.
Written By
Founder of Goodspeed