100 Key Questions to Ask During CRM Evaluation

Make the right CRM choice by asking smarter questions.

Choosing the right Customer Relationship Management (CRM) system is a strategic decision that can significantly impact your company’s ability to generate leads, close deals, and deliver excellent customer service. But with so many platforms offering overlapping features, how do you choose the right one?

The answer: ask better questions during your evaluation process.

This article covers 100 key questions across categories like functionality, integrations, scalability, pricing, compliance, and support — helping you assess CRM solutions from every angle.

Why Asking the Right CRM Questions Matters

CRM software is not one-size-fits-all. A system that works for a SaaS startup might fall short for a large manufacturing company. By asking pointed questions, you uncover how well a solution aligns with your processes, goals, and long-term vision — while avoiding common pitfalls like under-adoption, cost creep, or integration chaos.

General Business Fit

1. What is the primary business problem this CRM will solve for us?

2. Does this CRM align with our current sales, marketing, and service processes?

3. Is it built for our company size and industry?

4. Does the vendor understand our use case?

5. Is the platform scalable as we grow?

6. How easy is it to customize workflows without developer help?

7. Can it handle multi-language and multi-currency setups?

Sales and Pipeline Management

1. How does the CRM support different sales processes (e.g., B2B vs. B2C)?

2. Can we define custom sales stages and pipelines?

3. Does it support multiple sales teams with different processes?

4. Are quotas and targets trackable per rep or team?

5. Does it allow real-time sales forecasting?

6. Can it automate tasks like follow-ups and reminders?

7. How well does it integrate with email and calendar tools (e.g., Gmail, Outlook)?

8. Is lead scoring configurable?

9. Can sales managers track activity across the funnel?

10. Does it support guided selling or playbooks?

Marketing Automation

1. Is marketing automation native or via integration?

2. Can we build lead nurturing workflows?

3. How are contacts segmented for campaigns?

4. Does it offer A/B testing for email campaigns?

5. Can we score leads based on behavior?

6. Does it integrate with paid media platforms?

7. Is web tracking included?

8. Can landing pages and forms be built in the platform?

Customer Service and Support

1. Does the CRM include a service module or helpdesk?

2. Can we manage support tickets within the CRM?

3. Does it support chat, email, and phone interactions?

4. Are SLAs trackable?

5. Can we build a customer portal?

6. Does it support knowledge base creation?

7. Is it easy to escalate and route tickets?

8. Can agents view full customer history during service interactions?

Reporting and Dashboards

1. What types of reports are pre-built?

2. Can reports be customized without code?

3. Are dashboards interactive and real-time?

4. Can we set up automatic report delivery?

5. Is forecasting visual and easy to share?

6. Does it support cohort and funnel reporting?

7. Can we compare team or rep performance easily?

User Experience and Adoption

1. How easy is it for new users to learn?

2. Is the UI intuitive and modern?

3. Can we personalize the home dashboard?

4. Is mobile usage fully supported?

5. Are user roles and permissions customizable?

6. Is it cluttered or streamlined for our users’ day-to-day needs?

7. What’s the average time to onboard a new user?

Integration and API

1. What integrations are native (plug-and-play)?

2. Is there an open API?

3. Can it integrate with our ERP, accounting, or data warehouse?

4. Does it work with our marketing stack?

5. Is data syncing bidirectional and real-time?

6. Can we automate workflows across tools using webhooks or third-party tools (e.g., Zapier, Make)?

7. Is there a middleware or iPaaS layer included or recommended?

Implementation

1. What’s the average time to implement?

2. Is a CRM implementation partner required or optional?

3. What support do we get during onboarding?

4. Will we receive data migration assistance?

5. Are best practices and templates included?

6. How much of the implementation can we manage internally?

7. Are there sandbox environments for testing?

Pricing and Cost Transparency

1. What’s the pricing model (user-based, feature-based, flat rate)?

2. Are there any hidden costs (setup, integrations, support)?

3. Is there a minimum contract or seat number?

4. Can we scale pricing as we grow?

5. Are different modules priced separately?

6. Is pricing different for sales, service, and marketing users?

7. How does the renewal process work?

Compliance and Security

1. Is the platform GDPR compliant?

2. Is data stored in our region or country?

3. Does it support role-based access control?

4. Is audit logging included?

5. Are regular penetration tests performed?

6. Can we easily manage user access when someone leaves?

7. Is the vendor SOC2, ISO27001, or HIPAA certified?

Data and Customization

1. How flexible is the data model (custom fields, objects)?

2. Can we build calculated fields and conditional logic?

3. Can we enforce data validation rules?

4. Is deduplication automatic or manual?

5. Can we import/export data easily?

6. Is offline access available?

7. Does it support multilingual data entry or translation?

AI and Automation

1. Is there native AI functionality (e.g., predictive scoring, sentiment analysis)?

2. Does the CRM support sales or support bots?

3. Can it recommend next-best actions or upsell opportunities?

4. How customizable are automations and workflows?

5. Does it support auto-data capture from emails, calls, and meetings?

6. Can we use AI to summarize interactions?

Mobile and Remote Sales

1. Is there a mobile app?

2. Does mobile support offline use and syncing?

3. Can field sales reps log meetings, calls, and notes easily?

4. Is GPS/location tracking available for reps?

5. Are voice notes and speech-to-text supported?

6. Can managers access dashboards on mobile?

Vendor Reputation and Roadmap

1. How long has the vendor been in business?

2. What do other customers in our industry say?

3. Is the CRM updated frequently?

4. Is there a transparent product roadmap?

5. Can we influence roadmap features as a customer?

6. What does customer success and account management look like post-sale?

Final Thoughts

CRM software should fit your business like a glove — not force you to bend your processes to its limitations. Whether you’re comparing Salesforce vs HubSpot, Microsoft Dynamics 365, Zoho, or another platform, the questions above will help you probe deeper and choose with confidence.

Looking for a faster way to evaluate your top CRM choices?
📥 Download our free CRM RFP Template to streamline your selection process and ask all the right questions.