Quick Answer: Before starting an AI customer support pilot, ask about automation guarantees, what happens if targets are not met, true total costs, data ownership, ongoing support requirements, and realistic timelines. Good vendors welcome these questions; evasive answers are red flags.
Most AI customer support implementations fail not because of technology limitations but because businesses did not ask the right questions before committing.
These 10 questions separate informed buyers from disappointed ones. Ask all of them. Accept only clear, specific answers.
Question 1: What Is Your Automation Rate Guarantee?
Why This Matters:
Vendors make impressive claims. Demos look perfect. But what happens when reality does not match promises?
What to Ask:
"What specific automation rate do you guarantee, and what happens if you do not achieve it?"
Good Answers:
- "We guarantee 60% automation. If we do not hit it, you get a full refund of setup fees."
- "Our guarantee is 65% containment rate measured by conversations resolved without human intervention."
- "We commit to specific metrics in writing before the pilot starts."
Red Flag Answers:
- "It depends on your business." (Every business is different, but guarantees should be specific)
- "We typically see 70-80%." (Typical is not guaranteed)
- "We do not offer guarantees because every implementation is unique." (They lack confidence)
The Oxaide Answer:
We guarantee 60% automation. If your pilot does not achieve this threshold, you receive a full refund. No exceptions, no fine print. We have delivered this for dozens of businesses and only issued two refunds—both for highly specialized technical support scenarios.
Question 2: What Exactly Counts Toward the Automation Rate?
Why This Matters:
Vendors define "automation" differently. Some count any AI response as automated. Others only count fully resolved conversations. The difference can be 30-40 percentage points.
What to Ask:
"How do you define and measure automation rate? What specifically counts as 'automated'?"
Good Answers:
- "A conversation is automated when the customer's query is fully resolved without human intervention."
- "We measure containment—conversations that reach natural completion without escalation."
- "Here is our exact measurement methodology..." (detailed explanation)
Red Flag Answers:
- "When the AI responds, it counts as automated."
- "We measure based on AI engagement percentage."
- "Our analytics show all conversations with AI involvement."
The Real Definition:
Automation rate should mean: conversations where the AI completely handled the customer's need. Not "AI said something." Not "AI was involved." Complete resolution without a human touching the conversation.
Question 3: What Is the True Total Cost?
Why This Matters:
Setup fees are just the beginning. Hidden costs emerge after commitment—platform fees, conversation charges, integration costs, and mandatory add-ons.
What to Ask:
"Beyond the setup fee, what are ALL costs I should expect in Year 1? Include conversation fees, platform fees, required integrations, and support costs."
Good Answers:
- Itemized breakdown with specific numbers
- Clear explanation of usage-based fees
- Transparent about Meta conversation charges
- Optional vs. required costs clearly distinguished
Red Flag Answers:
- "It depends on your usage." (Provide estimates based on stated volume)
- "We will discuss ongoing costs after the pilot." (Should be transparent upfront)
- "Just the setup fee and minimal platform costs." (Suspiciously vague)
Complete Cost Categories:
What Total Cost Should Include:
One-Time:
├── Setup/implementation fee
├── AI training and configuration
├── Integration development (if needed)
└── Staff training
Recurring:
├── Platform subscription (if applicable)
├── Meta conversation fees
├── Support/maintenance costs
└── Optional optimization services
Usage-Based:
├── Per-conversation charges
├── Overage fees
└── Additional channel costs
Question 4: Who Owns the AI Training and Data?
Why This Matters:
Some vendors lock your knowledge base in proprietary systems. If you leave, you lose everything. Others ensure you own your data and can export anytime.
What to Ask:
"If I decide to stop using your service, what happens to my AI training data, knowledge base, and conversation history? Can I export everything?"
Good Answers:
- "You own all data. Full export available anytime."
- "Knowledge base is yours—we can provide in standard formats."
- "Conversation history exportable within 30 days of request."
Red Flag Answers:
- "Our AI training is proprietary and cannot be transferred."
- "Data export requires enterprise plan."
- Unclear ownership terms in contract
Why This Matters for Pilots:
Even during a pilot, you want assurance that success does not create dependency. If the pilot works, you should be able to continue with the vendor or take your learnings elsewhere.
Question 5: What Happens After the Pilot?
Why This Matters:
Some vendors use pilots as sales funnels into expensive contracts. Others provide clear, fair options for continuing or not continuing.
What to Ask:
"What are my options after the 21-day pilot? What does ongoing operation cost? Is there any lock-in?"
Good Answers:
- Clear pricing tiers for post-pilot operation
- No lock-in or long-term commitment required
- Self-managed option with minimal ongoing cost
- Ability to upgrade or downgrade based on needs
Red Flag Answers:
- "We will discuss options when you see the results."
- Minimum contract length required to continue
- Significant price increase after pilot period
- Pressure to commit during pilot
Post-Pilot Options Should Include:
Typical Post-Pilot Paths:
1. Self-Managed ($0-$200/month)
├── AI continues running
├── You handle updates
├── Basic email support
└── No lock-in
2. Managed Support ($500-$1,500/month)
├── Ongoing optimization
├── Knowledge base updates
├── Priority support
└── Performance reviews
3. Exit Option
├── Export all data
├── No cancellation fee
├── No long-term obligation
└── Clean transition
Question 6: How Long Until Customers Interact with AI?
Why This Matters:
Vendors sometimes quote "deployment" times that mean technical setup, not customer-facing operation. You need to know when real results begin.
What to Ask:
"On what day of the pilot will the AI start responding to actual customer messages? What happens in the days before that?"
Good Answers:
- "AI goes live with customers around Day 10-12."
- Clear breakdown of setup vs. live operation time
- Explanation of what happens each week
Red Flag Answers:
- "Depends on your preparation."
- Vague timeline without specific milestones
- "As soon as possible" without commitment
21-Day Pilot Timeline Example:
| Days | Activity | Customer Exposure |
|---|---|---|
| 1-7 | Setup, verification, training | None |
| 8-10 | Internal testing | Team only |
| 11-14 | Soft launch | Real customers, monitored |
| 15-21 | Full operation | All customers |
Question 7: What Support Do I Get During the Pilot?
Why This Matters:
Self-service pilots with documentation-only support have significantly lower success rates than pilots with dedicated implementation support.
What to Ask:
"What level of support is included during the pilot? Who do I contact if something goes wrong? What is the response time?"
Good Answers:
- Named implementation contact or team
- Same-day response guarantee for issues
- Proactive monitoring and optimization included
- Regular check-ins scheduled
Red Flag Answers:
- "Email support with 24-48 hour response."
- "Documentation and knowledge base available."
- "Support tickets reviewed weekly."
What Good Pilot Support Looks Like:
- Dedicated implementation manager
- Daily conversation review during soft launch
- Same-day fixes for issues
- Weekly optimization calls
- Real-time Slack or WhatsApp access for urgent matters
Question 8: What If My Business Is Different?
Why This Matters:
Every vendor has success stories. But your business has unique aspects—industry regulations, complex products, specific customer expectations. You need assurance the AI can adapt.
What to Ask:
"Our business has [specific complexity]. How does your AI handle this? Can you share examples of similar businesses you have worked with?"
Good Answers:
- Specific examples from similar industries
- Explanation of how complexity is addressed
- Honest assessment of fit ("This might be challenging because...")
- Willingness to discuss before commitment
Red Flag Answers:
- "Our AI handles everything."
- Generic case studies not matching your industry
- Dismissive of your specific concerns
- No references available
Common Complexity Factors:
Areas Requiring Discussion:
Industry-Specific:
├── Healthcare (HIPAA, medical advice)
├── Financial services (compliance)
├── Legal (confidentiality)
└── Education (student privacy)
Operational:
├── Complex pricing structures
├── Custom product configurations
├── Multiple service locations
└── B2B vs. B2C differences
Technical:
├── Required integrations
├── Multiple languages
├── Legacy system connections
└── High volume periods
Question 9: How Do You Handle Sensitive Situations?
Why This Matters:
AI that responds to complaints inappropriately, mishandles urgent situations, or provides incorrect information on sensitive topics can damage customer relationships and create liability.
What to Ask:
"How does the AI handle complaints, urgent requests, and sensitive topics? What triggers immediate human escalation?"
Good Answers:
- Configurable escalation rules based on your requirements
- Automatic escalation for defined sensitive topics
- Complaint handling protocol with human follow-up
- Audit trail for all escalated conversations
Red Flag Answers:
- "The AI is trained to handle all situations."
- No escalation capability discussed
- "Customers do not complain to chatbots."
Escalation Categories to Define:
Should Trigger Human Review:
Immediate Escalation:
├── Complaints or dissatisfaction
├── Safety or health concerns
├── Legal or compliance topics
├── Requests for manager/supervisor
└── Explicit human request
Monitored Escalation:
├── Complex multi-step requests
├── High-value transactions
├── Returning customers with history
├── Topics outside AI training
└── Unusual patterns or requests
Question 10: What Does Success Look Like for You?
Why This Matters:
Vendors' incentives should align with yours. If they only care about closing the deal, support may disappear after payment. If they care about results, they will invest in your success.
What to Ask:
"What makes a pilot successful from your perspective? What percentage of your pilots convert to ongoing customers? Why do some fail?"
Good Answers:
- "Success means you hit targets and want to continue."
- Transparent about pilot-to-customer conversion rates
- Honest about scenarios where pilots do not succeed
- Focus on your business outcomes, not just their metrics
Red Flag Answers:
- "Success is when you sign up for ongoing service."
- Unwilling to discuss failure scenarios
- Only focused on positive cases
- Conversion rate significantly higher than industry norm
Aligned Incentives Look Like:
- Performance guarantees with refund options
- No pressure to commit during pilot
- Focus on proving value, not selling features
- Willingness to recommend against pilot if fit is poor
Bonus Question: Can You Tell Me When NOT to Use Your Service?
Why This Matters:
Honest vendors know their limitations. They will tell you when a competitor might be better, when AI is not the right solution, or when your business is not ready.
What to Ask:
"Be honest—what types of businesses should NOT use your service? When should I look elsewhere?"
Good Answers:
- Specific scenarios where they are not the best fit
- Honest about technical or business limitations
- Recommendation to prepare first if not ready
- Suggestions for alternatives when appropriate
Red Flag Answers:
- "We are perfect for everyone."
- Cannot identify any limitations
- Dismissive of competitive alternatives
- Pushes forward despite stated concerns
Using These Questions
Before the Sales Call
Share this list with the vendor beforehand: "I would like to discuss these 10 questions during our call." Serious vendors will appreciate the preparation. Unserious vendors may avoid the call.
During Evaluation
Score answers on a 1-5 scale:
- 5: Clear, specific, aligned with your interests
- 3: Adequate but vague in places
- 1: Evasive, unclear, or misaligned
Any question scoring below 3 warrants follow-up or reconsideration.
Comparing Vendors
Create a simple matrix:
| Question | Vendor A | Vendor B | Vendor C |
|---|---|---|---|
| 1. Guarantee | 5 | 3 | 4 |
| 2. Measurement | 5 | 2 | 4 |
| ... | |||
| Total | 45 | 32 | 38 |
Numbers remove emotion from vendor selection.
Conclusion: Questions Reveal Character
How vendors respond to these questions tells you more than their marketing materials.
Good vendors:
- Welcome tough questions
- Provide specific, written answers
- Acknowledge limitations honestly
- Focus on your outcomes, not their sales
Problematic vendors:
- Evade or deflect questions
- Give only verbal promises
- Claim to be perfect for everyone
- Pressure for quick decisions
The 30 minutes spent asking these questions can save months of frustration and thousands of dollars in failed implementations.
Ready to ask these questions?
- Schedule a pilot consultation and ask anything
- Read the pilot program comparison guide
- Understand our 60% automation guarantee
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