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Discovery Question Bank - CloudCRM Pro

Overview

Version: 2.0
Last Updated: 2025-01-09
Purpose: Comprehensive question repository for effective discovery conversations
Target Users: Sales Representatives, Solution Engineers, Customer Success
Best Practice: Use 15-20 questions per call, adapt based on persona and situation

Universal Opening Questions

Rapport Building (Choose 2-3)

  1. "I saw you recently [achievement/news]. How has that impacted your team?"
  2. "How long have you been at [Company]? What brought you there?"
  3. "What's the most exciting initiative you're working on right now?"
  4. "I noticed you're connected with [mutual connection]. How do you know them?"
  5. "What's been keeping you busy these days?"

Context Setting (Use 1-2)

  1. "What prompted you to take this meeting today?"
  2. "What's your understanding of CloudCRM Pro so far?"
  3. "What would make this conversation valuable for you?"
  4. "Before we dive in, what questions are top of mind for you?"
  5. "What are you hoping to accomplish in the next 30 minutes?"

Business & Strategy Questions

Company Overview

  1. "Can you give me a 30-second overview of your business?"
  2. "What's your company's primary value proposition?"
  3. "Who are your main customers?"
  4. "What markets/verticals do you serve?"
  5. "How would you describe your company culture?"

Growth & Goals

  1. "What are your top 3 business priorities for this year?"
  2. "What's your revenue target for this year? How does that compare to last year?"
  3. "What's driving your growth strategy?"
  4. "Where do you see the company in 3 years?"
  5. "What could prevent you from hitting your targets?"

Competitive Landscape

  1. "Who do you consider your main competitors?"
  2. "What's your key differentiator in the market?"
  3. "How do you typically win against competitors?"
  4. "Where are you losing deals and why?"
  5. "What market changes are you seeing?"

Current State Analysis

Sales Process Questions

  1. "Walk me through your typical sales process from lead to close?"
  2. "How many stages are in your sales process?"
  3. "What does your ideal customer profile look like?"
  4. "How do you currently qualify opportunities?"
  5. "Where do deals typically get stuck in your pipeline?"
  6. "What's your average deal size?"
  7. "How long is your typical sales cycle?"
  8. "What's your current close rate?"
  9. "How do you handle contract renewals?"
  10. "What does your sales methodology look like?"

Team Structure

  1. "How is your sales team structured?"
  2. "How many sales reps do you have? Plans to grow?"
  3. "What's the breakdown between hunters and farmers?"
  4. "How long does it take to onboard a new rep?"
  5. "What's your rep turnover rate?"
  6. "How do you currently train your team?"
  7. "What's your sales management structure?"
  8. "How do territories/accounts get assigned?"
  9. "Do you have sales engineers/solution consultants?"
  10. "How does marketing support sales?"

Technology Stack

  1. "What's your current CRM system?"
  2. "How long have you been using it?"
  3. "What other sales tools are you using?"
  4. "What marketing automation platform do you have?"
  5. "How do these systems integrate?"
  6. "What's working well with your current setup?"
  7. "What's not working or missing?"
  8. "Who manages your CRM today?"
  9. "How much are you spending on your sales tech stack?"
  10. "When does your current contract expire?"

Data & Reporting

  1. "How do you currently track sales metrics?"
  2. "What are your key performance indicators?"
  3. "How often do you review pipeline?"
  4. "How accurate is your forecasting?"
  5. "What reports do you rely on daily/weekly?"
  6. "How do you measure sales productivity?"
  7. "How clean is your current data?"
  8. "What data do you wish you had?"
  9. "How do you share insights across teams?"
  10. "Who needs visibility into sales data?"

Pain Point Discovery

Productivity Challenges

  1. "How much time do reps spend on administrative tasks?"
  2. "What manual processes slow your team down?"
  3. "What tasks do reps complain about most?"
  4. "Where do you see wasted time in the sales process?"
  5. "What could reps do more of if they had time?"

Revenue Impact

  1. "What percentage of leads never get followed up?"
  2. "How many deals are lost due to poor follow-up?"
  3. "What's the cost of your elongated sales cycle?"
  4. "How much revenue leaks through your pipeline?"
  5. "What's the impact of inaccurate forecasting?"

Operational Pain

  1. "What keeps you up at night about your sales operation?"
  2. "Where do you see the biggest inefficiencies?"
  3. "What would you fix first if you could?"
  4. "What complaints do you hear from the team?"
  5. "What's your biggest competitive disadvantage?"

Quantification

  1. "How much is this problem costing you annually?"
  2. "What's the impact on rep productivity?"
  3. "How many deals are affected by this?"
  4. "What would solving this be worth?"
  5. "What happens if nothing changes?"

Desired Future State

Vision Questions

  1. "In an ideal world, how would your sales process work?"
  2. "What would 'great' look like 12 months from now?"
  3. "If you could wave a magic wand, what would change?"
  4. "What capabilities do your competitors have that you want?"
  5. "What would transform your sales organization?"

Success Criteria

  1. "How will you measure success?"
  2. "What metrics need to improve?"
  3. "What would make this project a win?"
  4. "What ROI do you need to see?"
  5. "What would failure look like?"

Requirements Gathering

  1. "What are your must-have features?"
  2. "What are nice-to-have features?"
  3. "What integrations are critical?"
  4. "What customizations do you need?"
  5. "What are your security requirements?"

Change Management

  1. "How does your team typically adapt to change?"
  2. "What's worked well in past implementations?"
  3. "What hasn't worked in the past?"
  4. "Who would be champions for change?"
  5. "What resistance do you anticipate?"

Decision Process Questions

Stakeholders

  1. "Who else needs to be involved in this decision?"
  2. "What's important to each stakeholder?"
  3. "Who has veto power?"
  4. "Who's the economic buyer?"
  5. "Who would be the executive sponsor?"

Evaluation Process

  1. "What's your evaluation process?"
  2. "What are your decision criteria?"
  3. "How will you evaluate vendors?"
  4. "Are you looking at other solutions?"
  5. "What would make one vendor stand out?"

Timeline

  1. "What's driving your timeline?"
  2. "When do you need to make a decision?"
  3. "When would you want to go live?"
  4. "What could accelerate the timeline?"
  5. "What could delay the decision?"

Budget

  1. "What's your budget range for this initiative?"
  2. "How does your budgeting process work?"
  3. "Is budget already allocated?"
  4. "What would happen if the perfect solution was above budget?"
  5. "Who controls the budget?"

Risk Factors

  1. "What concerns do you have about changing systems?"
  2. "What could derail this project?"
  3. "What happened with your last CRM implementation?"
  4. "What internal resistance might you face?"
  5. "What would make you stay with status quo?"

Persona-Specific Questions

For Enterprise Decision Makers (COO/VP Sales)

  1. "How does CRM impact your strategic initiatives?"
  2. "What board-level metrics are you responsible for?"
  3. "How do you see AI transforming sales?"
  4. "What's your vision for sales operations?"
  5. "How do you balance growth vs. efficiency?"
  6. "What's your biggest competitive threat?"
  7. "How are you preparing for economic uncertainty?"
  8. "What keeps you from sleeping at night?"
  9. "How do you measure sales transformation success?"
  10. "What legacy would you like to leave?"

For SMB Champions (Sales Managers)

  1. "What's your day-to-day like managing the team?"
  2. "What takes up most of your time?"
  3. "How do you coach your reps?"
  4. "What visibility do you need into pipeline?"
  5. "How do you identify at-risk deals?"
  6. "What would help you hit your number?"
  7. "How do you onboard new reps?"
  8. "What's your biggest management challenge?"
  9. "How do you forecast today?"
  10. "What tools do your reps actually use?"

For Technical Evaluators (IT Directors/CTOs)

  1. "What's your current tech stack architecture?"
  2. "What are your integration requirements?"
  3. "What security standards must we meet?"
  4. "How do you handle data governance?"
  5. "What's your API strategy?"
  6. "What are your uptime requirements?"
  7. "How do you manage user provisioning?"
  8. "What's your backup/disaster recovery plan?"
  9. "What compliance requirements do you have?"
  10. "How do you evaluate vendor security?"

Industry-Specific Questions

SaaS/Technology

  1. "What's your current MRR/ARR?"
  2. "What's your CAC and LTV?"
  3. "How do you track product usage?"
  4. "What's your churn rate?"
  5. "How do you handle trials/POCs?"

Manufacturing

  1. "How do you manage channel sales?"
  2. "What's your distributor network like?"
  3. "How do you handle complex product configurations?"
  4. "What's your quote-to-cash process?"
  5. "How do you manage territory planning?"

Financial Services

  1. "What compliance requirements do you have?"
  2. "How do you ensure data privacy?"
  3. "What's your risk management process?"
  4. "How do you handle relationship mapping?"
  5. "What regulatory changes are impacting you?"

Healthcare

  1. "How do you maintain HIPAA compliance?"
  2. "What's your referral management process?"
  3. "How do you track physician relationships?"
  4. "What EMR/EHR systems do you use?"
  5. "How do you manage formulary changes?"

Professional Services

  1. "How do you track billable hours?"
  2. "What's your project pipeline like?"
  3. "How do you manage resource allocation?"
  4. "What's your proposal win rate?"
  5. "How do you cross-sell services?"

Closing & Commitment Questions

Temperature Check

  1. "Based on what you've heard, how well do we align with your needs?"
  2. "What resonates most with you?"
  3. "What concerns do you have?"
  4. "What questions haven't I asked that I should have?"
  5. "How does this compare to other solutions you've seen?"

Next Steps

  1. "What would you need to see to move forward?"
  2. "What's the logical next step from your perspective?"
  3. "Who else should we include in the next conversation?"
  4. "When would you like to reconnect?"
  5. "What would prevent us from moving forward?"

Commitment Questions

  1. "If we can demonstrate value, what would prevent you from moving forward?"
  2. "Assuming we meet your requirements, what's your timeline?"
  3. "What would you need to become a champion for this internally?"
  4. "Are you willing to invest the time to properly evaluate this?"
  5. "Can we schedule our next meeting now?"

Discovery Call Best Practices

Before the Call

  • Research the company and person
  • Prepare 20-25 relevant questions
  • Send agenda in advance
  • Test your technology
  • Review previous interactions

During the Call

  • Follow 70/30 rule (them talking 70%)
  • Take detailed notes
  • Ask follow-up questions
  • Validate understanding
  • Get specific examples

Question Techniques

  • Start broad, get specific
  • Use open-ended questions
  • Ask "why" and "how"
  • Quantify whenever possible
  • Confirm and summarize

Active Listening

  • "Tell me more about that..."
  • "Help me understand..."
  • "What do you mean by..."
  • "Can you give me an example?"
  • "Why is that important?"

After the Call

  • Send summary within 24 hours
  • Include key points and next steps
  • Share relevant resources
  • Connect with other stakeholders
  • Update CRM immediately

Question Flow Templates

30-Minute Discovery Flow

  1. Context Setting (3 min)
  2. Company Overview (5 min)
  3. Current State (7 min)
  4. Pain Points (7 min)
  5. Decision Process (5 min)
  6. Next Steps (3 min)

60-Minute Deep Discovery

  1. Rapport & Context (5 min)
  2. Business Strategy (10 min)
  3. Current State Analysis (15 min)
  4. Pain Quantification (10 min)
  5. Future State Vision (10 min)
  6. Decision Process (7 min)
  7. Next Steps (3 min)

Executive Discovery (45 min)

  1. Strategic Priorities (10 min)
  2. Business Impact (10 min)
  3. Success Metrics (10 min)
  4. Investment Criteria (10 min)
  5. Partnership Approach (5 min)

Red Flags to Listen For

Buying Signals

  • "We need to solve this quickly"
  • "Our current system can't do that"
  • "That would save us hours"
  • "When could we start?"
  • "What would that cost?"

Warning Signs

  • "We're pretty happy with current state"
  • "This isn't a priority right now"
  • "We don't have budget"
  • "I need to think about it"
  • "We're looking at lots of options"

Objection Triggers

  • "We tried that before"
  • "That sounds complicated"
  • "We're too small/large for that"
  • "IT makes those decisions"
  • "The team won't adopt it"

Last Updated: 2025-01-09
Version: 2.0
Owner: Sales Enablement Team
Usage: Select relevant questions based on persona, industry, and stage