Human Resources & Benefits

  • Is this a public or privately held company?
  • How long until benefits (health, dental, vision) begin?
  • What is the 401(k) match, if any?
  • Would it be possible to maintain my current 4 weeks of vacation time, or negotiate an accelerated accrual schedule?
  • What are the standard working hours?
  • What is the company policy on hybrid or remote work, and how is remote collaboration supported (VPN, SSO, security tools)?
  • What opportunities exist for professional development — certifications, workshops, or conference attendance?
  • Does the company have a policy regarding outside consulting or side projects?
  • How often are performance reviews or check-ins conducted?
  • What opportunities exist for internal promotion or career growth?

Information Systems & Infrastructure

  • Do you host your own web servers, or are they cloud-based?
  • Which programming languages, frameworks, and platforms are actively in use?
  • What project management and collaboration tools are used (e.g., Jira, Azure DevOps, Microsoft Project)?
  • Does the company have an internal intranet or knowledge base?
  • Is there a dedicated DBA or database team?
  • Are network administrators responsible for updates across all servers, including web servers?
  • What rights and freedoms do developers have on their own machines?
  • Which databases are currently in use (SQL Server, PostgreSQL, MySQL, etc.)?
  • If publicly held, what is the current SOX (Sarbanes–Oxley) compliance process?
  • How is system and data security handled?
  • Which cloud platforms and deployment practices are used (AWS, Azure, GCP, Kubernetes, CI/CD pipelines)?
  • How is infrastructure-as-code or automation handled?

IT Applications & Development Practices

  • How are development teams organized? (e.g., by platform: backend, web, mobile, etc.)
  • What percentage of applications run on modern frameworks (e.g., .NET, Java, open-source)?
  • What hardware and software setups do developers typically receive (laptops, dual monitors, docking stations, etc.)?
  • Is there an opportunity to shadow or train with other departments (sales, marketing) to better understand business processes?
  • How are decisions about product direction or technical priorities made — and who’s typically involved in that process?
  • Are open-source tools and frameworks (e.g., Git, Docker, Kubernetes) encouraged?
  • What source control system is used (e.g., GitHub, GitLab, Bitbucket, Azure DevOps)?
  • Which IDEs or development environments are standard, and how often are they updated?
  • How does the company handle code reviews, QA, and deployment?
  • What specification and documentation processes are in place?
  • Do developers have access to MSDN or equivalent subscription kits?

AI & Emerging Technology

  • How is AI being incorporated into workflows (development, support, business processes)?
  • What’s the company’s policy on using generative AI tools in daily work?
  • Are there ongoing initiatives exploring automation or machine learning?

Security & Compliance

  • How does the company approach cybersecurity and data privacy?
  • Are there compliance frameworks we work within (SOC2, ISO, HIPAA, etc.)?
  • How are employees trained on security best practices?

Team & Culture

  • How large is the team I’d be joining, and what are their roles?
  • What is the manager’s leadership style?
  • How does the team communicate day-to-day (Slack, Microsoft Teams, email)?
  • How does the company support diversity, inclusion, and work-life balance?
  • How does the team handle crunch periods — is overtime common or avoided?
  • What are the biggest challenges the team is currently facing?

Onboarding & Growth

  • What does the onboarding process look like for new hires?
  • Is mentorship available during the first few months?
  • Are certifications, advanced training, or conference attendance supported?
  • What does career progression look like for this role over the next 2–3 years?
  • Where does leadership see the company in 3 years?

By asking these questions, I aim to ensure that the role is not only a good fit for my skills but also aligns with my values and long-term goals. A successful interview should help both sides decide if we’ll thrive working together.