Running a CRM evaluation without a structured checklist is like buying a house without a home inspection. The vendor demo always looks good. The sales rep is always helpful. Problems surface three months after you've migrated 40,000 contacts. This CRM evaluation checklist gives you 30 specific questions -- organized by category -- so you interrogate the platform, not just the pitch.
How to Use This Checklist
Don't treat these as a questionnaire to email. Go through them live, during the demo, and watch the vendor's reaction as much as their answer. A confident, specific answer is a good sign. Vague deflection, sudden topic-changing, or promises to "check with the product team" on a basic question -- those are the signals that matter.
Before the demo, assign roles. Your sales manager owns the pipeline and workflow questions. Your IT lead owns security and integrations. Your finance contact owns pricing. Each person should be present for their category and should feel free to push back on unsatisfying answers.
The table below shows which roles to include, approximate time needed, and how much risk you carry if you skip the category entirely.
| Category | Who Should Attend | Time Required | Risk If Skipped |
|---|---|---|---|
| Data | Sales manager, ops lead | 20-30 min | High -- data loss, poor migration, no export |
| Integrations | IT lead, ops lead | 20-30 min | High -- broken workflows, manual workarounds |
| Security | IT lead, legal/compliance | 15-20 min | Critical -- regulatory exposure, breach liability |
| Pricing | Finance, decision-maker | 15-20 min | High -- hidden fees, budget overruns at renewal |
| Support | Sales manager, team lead | 10-15 min | Medium -- slow issue resolution, training gaps |
Print the checklist. Take notes. And give each vendor a score out of 30 -- or just count how many red flags appeared.
Category 1: Data
Your CRM is only as useful as the data inside it. These six questions probe how the platform handles data ownership, migration, quality, and exit.
Can we export all our data -- including custom fields, attachments, and activity history -- in a standard format like CSV or JSON, at any time, without extra cost? Red flag: "Export is available in our enterprise tier." Any platform that locks your own data behind a paywall is not a partner. It's a hostage situation.
What does the migration process look like, and do you provide migration support or is it self-serve? Red flag: "We have documentation for that." If a vendor has never migrated a company of your size from your specific legacy system, that documentation is going to hit a wall fast.
How do you handle duplicate detection and data deduplication after import? Red flag: No automatic deduplication, or deduplication is a paid add-on. Importing 8,000 contacts and spending two weeks cleaning them manually is a real cost.
What is your data retention policy after we cancel our subscription? Red flag: "Your data is deleted after 30 days." Some vendors give you 90 days, some give you a final export window, some delete immediately. Know this before you sign.
Can we set custom fields, custom objects, or custom data models without writing code? Red flag: "Our standard fields cover most use cases." That phrase means no. Your sales process is not standard.
Is there a limit on records, contacts, deals, or storage -- and what happens when we exceed it? Red flag: Pricing tiers that throttle your record count without being upfront about it. One company we spoke with discovered their "unlimited contacts" plan had a 25,000-record hard cap buried in the terms.
Category 2: Integrations
A CRM that doesn't talk to your other tools creates more work than it saves. Six questions to pressure-test the integration story.
Which of our current tools does your CRM integrate with natively -- not via Zapier, not via a third-party connector, natively? Red flag: Everything is "available via Zapier." Native integrations are maintained by the vendor. Zapier integrations are maintained by the market -- and frequently break without notice.
Do you have a public API, and is it included in our plan or a separate purchase? Red flag: API access is enterprise-only. If your ops team ever wants to build anything custom, you don't want to discover a paywall mid-project.
How do you handle bi-directional sync between the CRM and our email or marketing platform? Red flag: Sync is one-directional or needs a manual trigger. That's the top cause of duplicate records.
What is your rate limit on API calls, and does it scale with our subscription? Red flag: A fixed rate limit that doesn't scale. For teams sending bulk emails or pulling daily reports, 1,000 API calls per hour is a bottleneck that arrives fast.
How do you handle integration failures -- alert, log, or silent drop? Red flag: "The integration just retries." Silent dropped data stays invisible until something breaks.
Do you support webhooks for real-time event triggers? Red flag: Polling-only. Instant lead routing and triggered follow-ups need webhooks; polling adds lag.
Category 3: Security
This section is non-negotiable for any team handling customer PII, payment information, or operating under GDPR or similar frameworks. Bring your IT lead.
Are you SOC 2 Type II certified, and can you provide the audit report? Red flag: "We're working toward SOC 2." Working toward is not the same as certified. The audit report is the evidence.
Where is our data stored geographically, and can we specify a region? Red flag: "Our servers are in the US." For teams with EU customers, this creates a GDPR problem. Region selection is a basic feature of any serious SaaS platform.
Do you support SSO (Single Sign-On) and MFA (Multi-Factor Authentication) at our plan level? Red flag: SSO is enterprise-only. Forcing smaller teams onto password-only authentication to save on plan cost is a genuine security gap.
What is your data encryption standard -- in transit and at rest? Red flag: "We use HTTPS." TLS in transit is table stakes. Ask specifically about AES-256 at rest and whether encryption keys are managed by the vendor or can be customer-managed.
How do you handle security incidents -- breach notification timeline, communication process, remediation steps? Red flag: Vague or entirely scripted answer that mentions "we take security seriously" more than once. Ask for the specific SLA on breach notification.
What role-based access controls exist, and can we restrict data visibility by team, region, or individual user? Red flag: Binary permissions only (admin vs. user). If your sales reps in two different regions can see each other's accounts, that's both a CRM selection criteria failure and a potential compliance issue.
Category 4: Pricing
Pricing conversations are where the most expensive surprises hide. These questions pull the real number out.
What is the total cost if we add 10 users, double our contact count, and turn on the email marketing module in 12 months? Red flag: "We'd need to put together a custom quote." That answer tells you the pricing is complex enough that they don't want you to calculate it yourself.
Are there setup fees, onboarding fees, or mandatory training packages? Red flag: Yes to any of these, without them being disclosed up front. A $2,000 onboarding fee on a $200/month plan is a 10-month cost hit before you've sent your first email.
What does the contract look like -- month-to-month, annual, multi-year? What are the cancellation terms? Red flag: Automatic annual renewal with a 30-day cancellation window that starts 90 days before renewal. These clauses are common and catch teams off guard.
Will the price increase at renewal, and is the cap written into the contract? Red flag: "Pricing is subject to change." Without a cap, your $400 plan becomes $700 in 18 months.
Which features are add-ons versus included -- can you show us a feature matrix? Red flag: No published matrix. The more opaque the pricing, the bigger the eventual surprise.
Do you charge per seat or per usage, and how is "active user" defined? Red flag: An "active user" definition that includes anyone who logged in that month, even once -- meaning a manager who checks one report in March counts as a full seat for March.
Category 5: Support
Support quality separates tools that actually get adopted from ones that sit unused six months after purchase.
What is your guaranteed response time for support tickets at our plan level? Red flag: "We have a dedicated support team." That's not a SLA. Ask for the written response time. Eight hours? Forty-eight hours? The answer matters when something breaks at 4pm on a Friday.
Is phone support available, or is it email and chat only? Red flag: Email-only support with a 24-48 hour window. For complex migration or configuration issues, async email support extends simple problems into week-long ordeals.
Do you assign a dedicated customer success manager at our tier? Red flag: CSM access is reserved for enterprise contracts above a threshold your company doesn't hit. Onboarding without a human point of contact is a recognized adoption risk.
What training resources exist and are they kept current with feature changes? Red flag: Docs last updated 14 months ago, or help articles referencing UI that no longer exists.
Can we talk to two or three customers of similar size and industry who have been on the platform for at least a year? Red flag: References provided are curated, all enterprise-tier, or the vendor takes more than a week to arrange a call. A confident vendor produces references quickly. An insecure one stalls.
What is your process when a feature we depend on is deprecated or significantly changed? Red flag: "We communicate changes in our release notes." Release notes nobody reads are not a communication strategy. Ask whether they notify affected customers directly and what lead time they give.
The Absolute Dealbreakers
Most red flags above signal friction. These five are different — they should end the CRM evaluation checklist exercise immediately.
- Dealbreaker: No data export without a paid upgrade. Your data is not a feature the vendor owns.
- Dealbreaker: No SOC 2 Type II and no credible timeline. Security certifications are not optional for any team handling customer PII.
- Dealbreaker: Auto-renewal with a cancellation window shorter than 60 days. Contract terms this aggressive predict how disputes will be handled.
- Dealbreaker: API access is enterprise-only. Any operations team that touches automation will eventually need API access. Building without it is building on a ceiling.
- Dealbreaker: References unavailable or only provided after contract signing. This has never ended well. If they won't let you verify their claims, the claims are probably wrong.
Making the Final Call
A CRM evaluation is not a feature comparison -- it's a risk assessment. The 30 questions above are designed to reveal how a vendor behaves when things go slightly off-script.
After running three or four vendors through this process, you'll notice a pattern. The platforms that answer cleanly, produce documentation immediately, and connect you with real customers without hesitation -- those are the ones worth shortlisting. The ones that pivot, promise, or deflect on questions 1, 13, and 21 will do the same thing when you have a data crisis six months post-launch.
Before you sign anything, check what each vendor actually includes in their standard plan against a side-by-side CRM tools comparison. The feature list rarely lies. The demo often does.
One final question to ask yourself: would you rather spend two extra weeks running this CRM evaluation checklist now, or spend the next two years working around a platform you can't leave?
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