Your CRM is the nervous system of your sales operation. Pick the wrong one and you’ll spend the next two years fighting the software instead of closing deals. I’ve personally migrated a business off a bad CRM, and I can tell you it cost more in lost productivity and data headaches than the original software ever cost in subscription fees. These crm questions to ask will save you from that pain.
The CRM market is bloated with options, from free tools to platforms that charge $300 per user per month. This checklist gives you 14 questions that cut through the marketing fluff and help you find the CRM that actually fits your business, your team, and your budget.
Before You Start Evaluating CRMs
Do these five things before you schedule a single demo. Skipping this prep is how businesses end up with a CRM that looks great in a presentation but falls apart in daily use.
- Map your current sales process from first contact to closed deal. Write down every step, every handoff, every touchpoint. Your CRM needs to support this process, not force you into someone else’s workflow.
- Count your contacts and estimate growth. Know how many contacts, deals, and companies you’re managing today, and project where you’ll be in 12 to 24 months. This directly affects pricing and which tier you need.
- List every tool your team uses daily. Email platform, calendar, accounting software, project management tool, phone system. Your CRM needs to connect to all of them or you’ll end up with data silos that defeat the whole purpose.
- Identify who will use the CRM and how. Sales reps need different features than managers who need different features than customer support. Get input from actual users, not just the person signing the check. A quality headset makes CRM demo calls and sales calls much more productive.
- Set a budget that includes hidden costs. The subscription is just the beginning. Factor in data migration, training, customization, and the productivity dip during the transition. A realistic total budget is 2 to 3x the annual subscription cost in year one.
Scalability and Growth
1. What happens to my pricing as my team and contact list grow?
This is where CRM sticker shock lives. A tool that costs $25/user/month for 5 users might jump to $75/user/month once you need the features that come with scaling. And contact limits are sneaky. Some platforms charge extra once you pass 1,000, 5,000, or 10,000 contacts. Get the pricing table for every tier, plug in your projected numbers for year one and year three, and calculate the real cost. That $25/month CRM might cost $15,000/year once you actually run the math.
2. Can the CRM handle multiple pipelines, teams, or business units?
If you sell multiple products, serve different markets, or have separate sales and account management teams, you need a CRM that supports multiple pipelines without everything collapsing into one messy view. Some CRMs handle this natively. Others require you to buy their enterprise tier (often 3 to 5x the base price) to unlock multi-pipeline functionality. Ask before you’re locked in at a tier that doesn’t support your actual business structure.
3. Is there a limit on custom fields, automations, or workflows?
Custom fields are how you make a CRM actually useful for your specific business. Automations are how you stop doing repetitive tasks manually. If the CRM caps these at the tier you’re buying, you’ll hit a wall fast. Some platforms limit you to 5 automations on their starter plan and charge $50+/month more for unlimited. Know the limits before you build your workflows around them.
Integrations and Data
4. Does this CRM integrate natively with the tools I already use?
Native integrations are reliable and maintained by the vendor. Third-party integrations through Zapier or Make work but add cost ($20 to $70/month for Zapier alone), introduce another point of failure, and can break without warning. Make a list of your must-have integrations (email, calendar, accounting, phone) and verify each one. “We have an open API” is the vendor’s way of saying “you’ll need a developer to make it work.”
5. How easy is it to import my existing data, and what formats do you support?
Data migration is where CRM switches go sideways. Ask whether they support CSV import, direct migration from your current platform, and how they handle field mapping. Good CRMs have dedicated migration tools or will assign someone to help. Bad ones hand you a CSV template and wish you luck. Also ask about data deduplication during import, because importing 5,000 contacts with 800 duplicates creates a mess from day one.
6. Can I export all my data if I decide to leave?
This matters more than most people realize until it’s too late. You need full export capability for contacts, deals, activities, notes, emails, and custom fields. Ask about the export format (CSV, API access, native backup) and whether there are any restrictions. Some CRMs let you export contacts but not activity history. That’s not a full export, that’s a hostage negotiation.
Usability and Adoption
7. What does mobile access look like, and can my team work from their phones?
If your sales team is on the road, mobile functionality isn’t optional. But “we have a mobile app” doesn’t mean it’s actually usable. Ask for a demo of the mobile app specifically. Can reps log calls, update deal stages, and view contact history from their phones? Can they work offline and sync later? A desktop-first CRM with a stripped-down mobile afterthought will kill adoption with field teams.
8. How long does it take for a new team member to become productive?
The best CRM in the world is worthless if your team hates using it. Ask about the average onboarding time for new users, not the “our product is intuitive” marketing line, but actual data. Salesforce is powerful but has a famously steep learning curve (4 to 8 weeks for most users). HubSpot is easier to learn (1 to 2 weeks) but less customizable. Know the tradeoff before you commit.
9. What training and support resources are included in my plan?
“Support” varies wildly between CRM vendors. Some include live chat, phone support, and a dedicated account manager. Others give you a help center and an email address that takes 48 hours to respond. Ask specifically about response times, whether support is available during your business hours, and whether onboarding assistance is included or costs extra. Enterprise-level support packages can add $200 to $500/month.
Reporting and Analytics
10. What reports come built in, and how customizable is the reporting?
You need at minimum: pipeline value by stage, win/loss rates, activity metrics per rep, and revenue forecasting. Most CRMs include basic reports, but the useful ones (custom dashboards, multi-touch attribution, cohort analysis) are often locked behind premium tiers. Ask to see the actual reporting interface, not screenshots. Build a sample report during the demo using your real metrics. That tells you more than any feature list.
11. Can I track the full customer journey from first touch to closed deal?
Attribution matters. You need to know which marketing channels, campaigns, and touchpoints are actually driving revenue. Some CRMs only track from the point of lead creation forward, which misses everything that happened before someone entered your pipeline. Ask whether the CRM tracks website visits, email opens, ad clicks, and form submissions as part of the contact timeline.
Security and Compliance
12. What security certifications do you hold, and where is my data stored?
At minimum, look for SOC 2 Type II certification. If you handle healthcare data, you need HIPAA compliance. EU customers mean GDPR compliance. Ask where data is physically stored (US, EU, other) and whether you can choose your data region. Also ask about encryption: data should be encrypted both in transit (TLS 1.2+) and at rest (AES-256). These aren’t nice-to-haves, they’re baseline requirements.
13. What are your uptime guarantees and disaster recovery procedures?
Your CRM goes down, your sales team sits idle. Ask for the SLA (99.9% uptime means roughly 8.7 hours of downtime per year, which is the industry standard minimum). Check their status page history for actual uptime over the past 12 months. Also ask about backup frequency and recovery time. If their server catches fire, how quickly can they restore your data?
Contract and Migration
14. What does the cancellation process look like, and are there any penalties?
Read the fine print before you sign. Some CRMs lock you into annual contracts with hefty early termination fees (sometimes the remaining balance of the contract). Others offer month-to-month with no penalty. Ask about the cancellation notice period (30, 60, or 90 days is common), what happens to your data after cancellation, and how long you have to export everything before it’s deleted.
What to Prepare Before CRM Demos
Bring these to every evaluation meeting:
- Your current sales process mapped out step by step, including deal stages, handoff points, and approval workflows
- A list of every software tool your team uses daily, noting which ones absolutely must integrate with the CRM
- Your current contact database size and 24-month growth projection, so the vendor can recommend (and price) the right tier
- Three to five specific reports you need to generate regularly, so you can test the reporting engine during the demo
- Questions from your actual end users, because the person buying the CRM and the person using it daily often have very different priorities
- A sample dataset (50 to 100 contacts with all your custom fields) to test the import process during evaluation
Typical Cost Range and Factors
CRM pricing in 2026 breaks down roughly like this:
- Free CRMs (HubSpot Free, Zoho Free): $0/month, limited features, good for solopreneurs or very small teams under 5 people
- Starter/Basic tiers: $15 to $30/user/month, covers core CRM with basic automation and reporting
- Professional tiers: $50 to $100/user/month, adds advanced automation, custom reporting, and more integrations
- Enterprise tiers: $100 to $300/user/month, includes everything plus advanced security, unlimited customization, and dedicated support
- Data migration services: $500 to $5,000 (one-time), depending on complexity and data volume
- Custom implementation and training: $1,000 to $15,000 (one-time), often essential for teams over 10 people
What drives the price up: Per-user pricing with large teams, premium support packages, advanced automation limits, multi-currency or multi-language needs, and custom API integrations.
What keeps costs down: Choosing flat-rate plans over per-user pricing when available, starting on a lower tier and upgrading as needed, annual billing for 10 to 20% savings, and doing your own data migration with CSV imports.
Red Flags vs. Green Flags
| Red Flag | Green Flag |
|---|---|
| Per-user price jumps dramatically between tiers with no clear added value | Transparent pricing with a clear feature comparison chart for every tier |
| No free trial or the trial requires a credit card and auto-enrolls you | 14 to 30 day free trial, no credit card required, full feature access |
| ”Our CRM does everything” with no focused use case | Clearly defines what it does best and who it’s built for |
| Mobile app has terrible reviews or hasn’t been updated in months | Mobile app is regularly updated with high ratings and full functionality |
| Data export is limited or requires contacting support | Self-serve data export in standard formats at any time |
| Can’t provide uptime statistics or dodges SLA questions | Publishes a public status page with historical uptime data |
| Requires expensive professional services just to set up basic features | Self-serve setup with good documentation, professional services optional |
| Sales rep pushes a multi-year contract before you’ve finished the trial | Flexible contract options including month-to-month |
Money-Saving Tips
- Start with the free tier if one exists. HubSpot’s free CRM is legitimately useful for small teams. Use it for 60 to 90 days before deciding whether you need paid features. Most businesses can run on a free CRM longer than they think.
- Negotiate at end of quarter. CRM vendors have sales quotas too. If you’re evaluating in March, June, September, or December, you have more negotiating leverage. Ask for a discount, extra users, or free onboarding.
- Skip the premium support tier in year one. Most teams can get by with standard support and community forums during initial setup. Upgrade to premium support later if you actually need it.
- Do your own data migration. If your data is clean and straightforward, a CSV import is free and takes an afternoon. Only pay for professional migration services if your data is complex or massive.
- Audit user licenses quarterly. Teams accumulate ghost licenses for people who left, changed roles, or just stopped using the CRM. Each unused seat is money wasted. Clean up every quarter.
- Choose annual billing only after you’ve validated the tool. The 15 to 20% savings on annual billing is real, but it’s meaningless if you realize three months in that the CRM doesn’t fit. Pay monthly for the first quarter, then switch to annual once you’re confident.
- Consolidate tools. Many CRMs now include email marketing, live chat, and basic project management. If your CRM can replace a $50/month email tool and a $30/month chat tool, the math gets very favorable.
Quick Reference Checklist
Use this during every CRM evaluation:
- What happens to pricing as my team and contact list grow?
- Can the CRM handle multiple pipelines, teams, or business units?
- Is there a limit on custom fields, automations, or workflows?
- Does this integrate natively with my existing tools?
- How easy is data import, and what formats are supported?
- Can I export all my data if I decide to leave?
- What does mobile access look like?
- How long until a new team member is productive?
- What training and support are included?
- What reports come built in, and how customizable are they?
- Can I track the full customer journey from first touch?
- What security certifications and data storage practices?
- What are uptime guarantees and disaster recovery procedures?
- What does cancellation look like, and are there penalties?
Glossary
Pipeline: A visual representation of your sales process, showing deals moving through stages (like “Lead,” “Qualified,” “Proposal Sent,” “Closed Won”). Think of it as a funnel that shows where every potential deal currently sits.
Custom Fields: Data fields you create beyond the CRM’s default options. For example, adding “Industry,” “Budget Range,” or “Preferred Contact Method” to contact records. The more custom fields your CRM supports, the more you can tailor it to your business.
Automation/Workflow: A rule that triggers actions automatically based on conditions you set. Example: “When a deal moves to ‘Proposal Sent,’ automatically send an email template and create a follow-up task for 3 days later.” Saves hours of manual work every week.
SLA (Service Level Agreement): A contractual promise about service quality, usually focused on uptime (the percentage of time the software is available) and support response times. A 99.9% uptime SLA means the vendor commits to no more than about 8.7 hours of downtime per year.
Data Migration: The process of moving your contacts, deals, and activity history from one CRM to another. It’s almost always harder than the new vendor claims, especially with custom fields and historical data.
Helpful Tools and Resources
The best CRM in the world won't fix a broken sales process. A good sales strategy book helps you define the workflow your CRM needs to support.
A clean workspace helps you focus during CRM evaluations, demos, and data migration. A simple desk organizer keeps your notes, comparison charts, and login credentials accessible.
If your team spends time on sales calls (the whole point of a CRM), a quality headset with noise cancellation improves call quality and reduces fatigue during long demo sessions.
- G2 CRM Comparison - Side-by-side comparisons of every major CRM with real user reviews, pricing details, and feature breakdowns. Filter by company size for the most relevant results.
- HubSpot’s CRM Comparison Tool - Yes, it’s biased toward HubSpot, but the feature comparison tables are genuinely useful for understanding what different CRMs include at each tier.
- CRM.org - Independent CRM reviews and guides that cover pricing, features, and use cases across dozens of platforms. Good for initial research before scheduling demos.
Frequently Asked Questions
Do I really need a CRM if my team is small?
Yes, but you don’t need an expensive one. Even a two-person sales team benefits from having all contacts, conversations, and deal history in one place instead of scattered across email inboxes and spreadsheets. Start with a free CRM like HubSpot Free or Zoho Free. If it saves you from losing even one deal because you forgot to follow up, it’s already paid for itself.
How long does a typical CRM migration take?
For a small business (under 5,000 contacts, simple pipeline), expect 2 to 4 weeks including data cleanup, import, configuration, and basic training. For mid-size companies with complex data and multiple integrations, plan for 6 to 12 weeks. The biggest time sink is always data cleanup, not the actual migration. Budget extra time for that.
Should I choose the CRM my industry commonly uses?
It’s a good starting point but not the only factor. Industry-specific CRMs (real estate, healthcare, financial services) often have built-in features that general CRMs lack, but they can also be more expensive and less flexible. If a general CRM with customization covers 90% of your needs at half the price, that might be the better call.
What’s the biggest mistake companies make when choosing a CRM?
Buying based on features they’ll never use. The most common pattern is this: a team gets dazzled by an enterprise-tier demo full of advanced analytics and AI predictions, signs up, and then uses it as a glorified contact list. Start with the problem you’re solving today. You can always upgrade. Downgrading from an overbuilt CRM that you’ve customized is much harder.
Can I switch CRMs later if I pick the wrong one?
You can, but it’s painful and expensive. Budget 20 to 40 hours of staff time for a basic migration and expect some data loss (activity logs and email history are the hardest to move). The cost of switching is exactly why asking these questions upfront matters so much. Getting it right the first time saves you thousands in migration costs and months of disruption.
Next Steps
You’ve got 14 questions that will expose every weakness in a CRM before you sign a contract. Schedule demos with your top three options, run each one through this checklist, and compare the answers in a simple spreadsheet.
The right CRM will feel like it was built for your sales process. The wrong one will constantly fight you. Let these questions help you tell the difference before it costs you money.
For more technology decision guides, check out our Questions to Ask Before Using AI Tools for Business and Questions to Ask Before Choosing a Website Builder. Browse all our checklists in the Technology category.