High-Impact Discovery Questions for Selling to CEOs in Professional Services

Summary:

Uncover strategic goals, align with client delivery needs, and qualify faster with questions tailored for service firm executives.
When selling AI or Analytics platforms to CEOs or Partners in consulting, discovery is all about outcomes, margin, client satisfaction, and operational scale. Effective questioning uncovers decision criteria tied to both internal optimization and external service delivery.

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Here’s a curated set of 30 questions designed for early discovery, qualification, and deeper value exploration, especially when selling automation, forecasting, or strategic intelligence solutions.

Early Discovery (Understand context + hook interest)

What are your top growth or operational priorities this year?
What metrics are you tracking to assess project profitability?
Where do inefficiencies exist in your service delivery or resourcing?
How do you currently track client engagement or satisfaction?
Are you facing challenges scaling operations or standardizing processes?
What’s your biggest blind spot in understanding delivery performance?
How does your team currently handle reporting or dashboards for clients?
Are you exploring automation to reduce manual project work or reporting overhead?
What insights do you wish you had about team capacity or project risk?
How do you currently forecast revenue from long-term or retainer clients?

Qualification (Uncover priorities, buying signals)

What would success look like from implementing an analytics or AI solution?
Are there specific areas (e.g. utilization, forecasting, margin) you’d want to improve?
How do you currently make decisions about scaling client delivery?
Who else on your leadership team influences tech purchases or platform selection?
What’s your timeline for evaluating or implementing operational improvements?
Have you tried internal tools or spreadsheets to solve these issues?
What limitations are you experiencing with your current systems?
How often do data delays or inconsistencies affect client delivery or reporting?
Is the budget already approved or under discussion for analytics investments?
Are you expecting significant growth or team changes in the next 6–12 months?

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

What’s the cost of under-utilized billable resources per month?
How confident are you in the accuracy of your project or pipeline forecasts?
What’s your average client churn rate, and what factors drive it?
How long does it take to identify delivery risks once a project starts?
How do you currently analyze profitability across different service lines?
What impact would real-time insights have on your client decision-making?
How much time is spent each week preparing internal or client reports?
What would a 10% increase in average utilization mean to your bottom line?
What visibility do you have into underperforming projects before they escalate?
If you could automate one strategic insight or reporting workflow, what would it be?

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How Pepsales AI Helps

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Pepsales AI helps sales teams ask the right questions, faster. It delivers intelligent, role-specific, and industry-aware discovery questions in real time tailored to the context of each deal.

What it delivers:

A library of proven questions per industry, persona, and product
Smart prompts that adapt to buyer role, objections, and stage
Embedded coaching and insights to guide better conversations
Automation of discovery prep, no more guesswork

Whether you’re prepping for a demo or coaching new reps, Pepsales AI ensures every conversation starts strong and gets to the real need, fast.

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Ready to unlock higher-quality discovery conversations?

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Get Early Access to the Pepsales AI Discovery Copilot
Equip your team with questions that uncover real problems, build urgency, and close more deals.