1. Company Mission, Strategy & Finance
Use these to gain a deeper understanding of the "big picture" and business stability.
Values: "What are the company values and how does the company ensure it’s upholding them?"
Vision: "What direction do you see this company heading in over the next few years?"
Goals: "What are the current goals that the company is focused on, and how does this team work to support hitting those goals?"
Trajectory: "What is the projected trajectory for the company?"
Industry: "What is exciting about [X] industry? Did you have exposure to it before starting here, and will a lack of experience hold me back?"
Competitors: "Who are the company’s principal competitors?"
Financial Health: "What are the growth goals and the strategic plan to get there? What are the key milestones for the next year?"
Funding: "Is the company funded and by whom? If not, are there opportunities for funding if the business breaks even in the future?"
The Exit: "Do you see the company ultimately being acquired or going public? When might that happen?"
Stability: "What are the company’s plans to combat the current/impending economic downturn?"
2. Artificial Intelligence (AI) & Innovation
Crucial for modern roles to see if the company is leading or lagging.
Workflow: "What AI tools are currently integrated into the team's daily workflow (e.g., Copilots, automated testing, or content generation)?"
Ethics: "What frameworks do you use to evaluate the ethical implications or bias in the AI systems you build or use?"
Training: "Does the company provide upskilling for employees to keep up with the fast pace of AI advancements?"
Policy: "Is there a formal internal policy on using Generative AI (like ChatGPT) for company projects or sensitive data?"
Strategy: "Is the company looking to augment human roles with AI, or is the goal to automate specific functions entirely?"
3. Tech Stack & Engineering
Best for technical interviews and CTO conversations.
Deployment: "How do you integrate and deploy changes? Is it CI/CD?"
Maintenance: "What percentage of maintenance needs to be done every month?"
Tech Debt: "What is your tech debt, and are you doing anything to address it?"
Security: "How quickly can you respond to security issues in the code or dependencies?"
Buy vs Build: "Are you trying to build everything in-house or working with newer technologies?"
Stack Details: "What programming languages, frameworks, and libraries do you use and why?"
Data: "What kind of databases do you use and where is the data stored?"
4. Culture, Leadership & Inclusion
Use these to gauge the work environment and management style.
Feedback: "What was the last change you implemented based on employee feedback and the impact it had?"
Failure: "How does your team deal with production failure? What is the first thing you do when things go wrong?"
DEI: "How does the leadership team hold themselves accountable for diversity, equity, and inclusion goals?"
Safety: "How are differing opinions or conflicts handled within the team?"
Environment: "How would you describe the work environment—is it typically more collaborative or more independent?"
Values in Action: "How do you maintain values like teamwork with remote work? Can you describe an example of when communication shaped an important outcome?"
The Fit: "What kind of person thrives at your company? What’s different about working here than anywhere else?"
Leadership Style: "How would your team describe your leadership style? How do you like to delegate tasks?"
Conflict Resolution: "If a staff member comes to you with a problem, how do you usually address it?"
Accessibility: "Would your CTO/founders be open to having coffee with an entry-level person?"
5. Roles, Responsibilities & Career Growth
Ensure the role aligns with your personal development.
The Job: "Can you tell me more about the day-to-day responsibilities and the team I will be working with?"
Onboarding: "How do you successfully onboard remotely? How can I impress you in the first 3 months?"
Performance: "How will my performance be measured? How do you monitor the performance of individual team members?"
Support: "What is your approach when an employee is underperforming vs. exceeding expectations?"
Development: "What formal/informal mentorship and professional development opportunities are offered? Is there an allocated budget?"
Shadowing: "If I am interested in practicing a newly acquired skill, could I shadow someone to learn more?"
The Path: "What do you imagine is the career path for someone in this role? How do you define career growth here?"
6. Location & Remote Work
Logistics that define your daily quality of life.
Flexibility: "Is there flexibility in place of work? Is the current remote policy here to stay?"
Hybrid Nuance: "I see multiple locations listed; is this role specific to this location or can I work in others?"
The Office: "What is the office space like? Is parking provided/paid for?"
Life Balance: "What does work-life balance mean to you as a company? Do you offer flexi-hours for things like school drop-offs or traffic?"
Isolation: "Isolation in remote work is real. What strategies/systems are in place to prevent that? Would I meet members of other teams in a virtual water cooler?"
Home Setup: "Does the company assist employees with a home set-up, including equipment?"
7. Salary & Benefits
Best for Recruiters and HR Managers.
The Number: "What will the salary for this role be?"
Benchmarking: "How do you benchmark your salaries? How does the company think about remuneration in general?"
Structure: "What is the cadence/timing for performance reviews? Who runs them?"
Perks: "What benefits are offered, and how does this impact Cost to Company? Are benefits compulsory or can I pick/select?"
Incentives: "Are there any bonuses or pay incentives? Are they guaranteed or performance-based?"
8. Specialised by Company Types
Startup Companies:
"Do you have investor backing?"
"What is your roadmap in terms of future projects?"
"How does the business plan around the current unstable economy?"
Consulting Companies:
"Do you already have a specific project/company that I would be working with?"
"If I am not happy in a project, is there flexibility to move to a new one?"
"What are the average lengths of projects?"
"Would I be required to work on technologies I don’t have exposure to yet?"
The Final "Must-Ask" Question
Before you leave, always ask this to clear any doubts:
"Based on our conversation today, is there anything about my background or my fit for this role that gives you pause or that I can clarify further?"
