New: Capture and analyse in-person meetings with Pepsales AI
Read MoreRead More

High-Impact Discovery Questions for Selling to CTOs in Healthcare

Summary:

Surface security gaps, infrastructure inefficiencies, and compliance risks with tailored questions designed for complex healthcare environments.

‍

Healthcare CTOs face stringent regulations, high patient data sensitivity, and the need to secure IT systems while enabling digital transformation. Effective discovery helps you align with what matters: strengthening cybersecurity, optimizing IT infrastructure, ensuring compliance, and supporting clinical and operational efficiency. Use these 30 questions to drive productive discovery that resonates with healthcare CTOs.

‍

Here’s a curated set of 30 discovery questions spanning early discovery, qualification, and deep needs analysis, perfect for tools focused on cybersecurity, IT operations, and regulatory compliance.

Early Discovery (Understand context + hook interest)

  1. What are your top IT priorities this quarter cybersecurity, digital transformation, or infrastructure optimization?
  2. How do you currently monitor security and compliance across your healthcare systems?
  3. What challenges exist in protecting sensitive patient data across departments?
  4. How much time does your team spend managing alerts, incidents, or manual IT processes?
  5. Which IT and cybersecurity tools are currently in use?
  6. How do you ensure compliance with healthcare regulations like HIPAA, HITECH, or local standards?
  7. Are there visibility gaps in your IT infrastructure that concern you most?
  8. How do you collaborate with clinical, operations, and finance teams on IT initiatives?
  9. What processes exist for onboarding new IT staff and training them on security protocols?
  10. How do you prepare for audits, regulatory reviews, or cybersecurity incident scenarios?

Qualification (Uncover priorities, buying signals)

  1. What outcomes would justify adopting a new cybersecurity or IT management platform?
  2. How do you evaluate ROI for IT tools in healthcare environments?
  3. Are there specific KPIs (system uptime, threat detection rate, compliance score) that matter most?
  4. Who approves IT or cybersecurity investments CTO, CIO, or Compliance?
  5. What is your expected rollout timeline for new IT systems or processes?
  6. Are you exploring other tools for network security, data protection, or infrastructure automation?
  7. How well do your current tools integrate with EHR, ERP, or other healthcare systems?
  8. What budget cycles or constraints impact IT tool adoption?
  9. What internal challenges prevent faster adoption of new cybersecurity tools?
  10. Are there risks with maintaining current IT systems that you’re trying to mitigate?

‍

Deep Needs Analysis (Tie value to goals, quantify pain)

  1. How much time does your team spend on manual monitoring, reporting, or incident management?
  2. What is the operational or financial impact of IT inefficiencies or security incidents?
  3. How do manual processes affect regulatory compliance and audit readiness?
  4. How do you monitor third-party or vendor risks in healthcare IT systems?
  5. How much effort is required to ensure consistent IT practices across departments?
  6. What would improved visibility into IT systems mean for clinical and operational efficiency?
  7. How do you measure the impact of IT initiatives on patient care and organizational performance?
  8. Are there missed opportunities where better automation could improve security or system performance?
  9. If you could automate one major part of IT monitoring or compliance reporting, what would it be?
  10. How would real-time visibility into IT and security risks change decision-making for your team?

‍

How Pepsales AI Makes Discovery Smarter

Pepsales AI empowers healthcare CTOs to ask the right questions, faster and more effectively. It delivers intelligent, role-specific, and industry-aware discovery prompts in real time tailored to each IT and security context.

What You Get:

  • A ready-to-use library of proven questions by persona, industry, and product
  • Smart prompts that adapt to objections, buyer roles, and IT/security stages
  • Built-in coaching to help CTOs lead more impactful conversations
  • Automated prep no more guesswork before discovery calls

Whether you're evaluating a new cybersecurity platform, optimizing IT infrastructure, or ensuring regulatory compliance, Pepsales AI helps every conversation start strong and get to the real need, fast.

Want to Drive More Impactful Discovery?

‍Arm your team with questions that uncover IT pain, build urgency, and reduce organizational risk.
Get a free trial of the Pepsales AI Copilot

Ready to shorten your sales cycle and win more deals?

Increase win rates by 50% and double your team’s productivity.

Get a Demo
See in Action
Free Trial
No credit card