Technical Deep Dive Playbook

A structured 90-minute plan to assess technical depth, problem-solving skills, and execution focus.

Primary Objective

Go beyond titles and resumes. The goal is to determine if Candidate is a hands-on technical leader who can architect, manage, and deliver projects, or a high-level strategist. We need a "player-coach," not just a coach.

Session Agenda & Timeline

1

Phase 1: Rapport & Context Setting (15 mins)

Establish a collaborative tone. This is a peer-to-peer technical discussion, not an interview. Share your own recent challenges to build trust.

2

Phase 2: Project Deep Dive (30-40 mins)

Ask Candidate to choose a recent, complex project. Drill down from "what" to "why" and "how." This is where you test for real-world experience.

3

Phase 3: The Collaborative "Whiteboard" Challenge (30-45 mins)

Present a real-world, open-ended problem. Observe his thought process live. This is the most crucial phase for assessing practical skills.

4

Phase 4: Alignment & Wrap-up (10 mins)

Connect his skills to the company's needs and gauge his excitement for hands-on work.

Phase 3: The Whiteboard Challenge

Scenario for Candidate:

"An e-commerce client wants to add a 'Frequently Bought Together' feature on their product pages, powered by AI. They have millions of products and transaction records. We have 3 months for an MVP. Let's sketch out a plan. How would you approach this? No need to code, just talk me through your thought process, from data to deployment."

What to Look For:

  • Clarifying Questions: Does he ask about data availability, performance requirements, or budget constraints before jumping in? (Sign of a senior engineer).
  • Problem Decomposition: Does he break it down into logical chunks? (e.g., 1. Data Ingestion/ETL, 2. Model Selection/Training, 3. API Service, 4. Frontend Integration).
  • Tech Choices & Justifications: Does he suggest specific technologies (e.g., Python with Pandas/Scikit-learn, a vector database like Pinecone, a cloud function for the API) and explain the trade-offs?
  • Execution-Minded Thinking: Does he talk about milestones, potential roadblocks, logging, monitoring, or how to phase the rollout? (Crucial indicator he can deliver).
  • Scalability & Pragmatism: Does he consider how this will perform under load? Does he suggest a simple model for the MVP and a more complex one for V2?

Key Probing Questions

Use these to guide the conversation during the Project Deep Dive (Phase 2).

To Assess Technical Decisions:

"Why did you choose Tech Stack X over competitor Y for that project? What were the key trade-offs?"

To Assess Problem Solving:

"Tell me about the single hardest technical bug or architectural challenge you faced. How did you specifically go about solving it?"

To Assess Project Management:

"How was the work planned and tracked? What was your role in estimating timelines and unblocking other developers?"

To Assess Pragmatism:

"What piece of technical debt did you knowingly take on to meet a deadline, and how did you plan to address it later?"

Post-Session Evaluation

Immediately after the call, score Candidate's responses on a spectrum to form a clear picture.

Technical Depth:
High-Level Deep & Detailed
Execution Focus:
Ideas & Strategy Tasks & Delivery
Problem Solving:
Abstract Structured & Practical

Red Flags to Watch For:

  • Consistently uses "we" and struggles to explain his specific, individual contributions.
  • Relies heavily on buzzwords without explaining the underlying concepts.
  • Avoids answering questions about failures or challenges.
  • Shows little curiosity about your current tech stack or challenges.