High-Impact Discovery Questions for Selling to COOs in Healthcare

Summary:

Surface operational inefficiencies, spend visibility gaps, and compliance risks with tailored questions designed for complex healthcare operations.

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Healthcare COOs face strict regulatory requirements, multi-departmental coordination, and the need to optimize operational costs while maintaining patient care quality. Effective discovery helps you align with what matters: streamlining approvals, improving spend visibility, reducing manual processes, and driving operational efficiency. Use these 30 questions to drive productive discovery that resonates with healthcare COOs.

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Here’s a curated set of 30 discovery questions spanning early discovery, qualification, and deep needs analysis, perfect for tools focused on operational spend, process automation, and financial oversight.

Early Discovery (Understand context + hook interest)

What are your top operational priorities this quarter cost control, process efficiency, or resource optimization?
How do you currently track operational spend across departments and facilities?
What challenges exist in managing budgets for clinical and non-clinical departments?
How much time does your team spend on manual approvals, reconciliations, or reporting?
Which financial or operational systems are currently in use?
How do you ensure compliance with healthcare regulations in spending and procurement?
Are there visibility gaps that make it hard to forecast operational budgets accurately?
How do you collaborate with finance, procurement, and clinical teams on operational decisions?
What processes are in place to monitor vendor contracts and compliance?
How are new operational staff onboarded or trained on spend and compliance policies?

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Qualification (Uncover priorities, buying signals)

What outcomes would justify adopting a new spend management or operational efficiency platform?
How do you evaluate ROI for fintech tools in healthcare operations?
Are there specific KPIs (cost savings, compliance adherence, process efficiency) that matter most?
Who approves operational or spend management tools Operations, Finance, or IT?
What is your expected rollout timeline for new operational processes or platforms?
Are you currently evaluating other platforms for spend management or operational efficiency?
How well do current tools integrate with your ERP, EHR, or finance systems?
What budget or procurement cycles influence new technology adoption?
What internal challenges slow down adoption of new operational tools?
Are there risks with maintaining the current manual or siloed processes that you’re actively trying to mitigate?

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

How much time do teams spend on manual approvals, reporting, or reconciliations that could be automated?
What is the operational impact of untracked or unmanaged spend?
How do manual processes affect compliance and audit readiness?
How do you monitor vendor performance and contract adherence?
How much effort is required to forecast operational budgets accurately?
What would improved visibility into spend mean for operational efficiency and cost control?
How do you measure the impact of operational initiatives on overall healthcare facility performance?
Are there missed opportunities where better spend management could improve resource utilization?
If you could automate one part of operational spend or approvals, what would it be?
How would real-time operational visibility improve decision-making for your team?

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How Pepsales AI Makes Discovery Smarter

Pepsales AI empowers COOs 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 operational 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 operational stages
Built-in coaching to help operational leaders lead more impactful discussions
Automated prep no more guesswork before discovery calls

Whether you're evaluating a new spend platform, streamlining approvals, or improving operational efficiency, 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 operational pain, build urgency, and move spend management initiatives forward.Get a free trial of the Pepsales AI Copilot