Questions to Ask When Evaluating a CRM
For a sales leader, operations manager or small business owner comparing CRM products before signing. The list follows the decision: questions to settle with your own team first, then what to ask the vendor's rep about fit with your sales process, data migration and email, reporting, and getting reps to use it, ending with cost and how to get your data out again.
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The questions
Each question, and why to ask it
Your team
What problem do we expect a CRM to fix that we cannot fix today?
Why ask it
Write the answer as one sentence before the first demo, such as 'deals go quiet because nobody owns the follow-up.' Every feature a rep shows you later gets held against that sentence. If the team cannot agree on one, you are not ready to compare products yet.
What does our sales process look like, stage by stage, from first contact to a closed deal?
Why ask it
Sketch it on one page with the stage names your reps say out loud. A CRM that fits will let you rebuild that page in its pipeline settings. If nobody can draw it, the product's default stages will become your process by accident.
Who will use the CRM every day, and what does each of them need from it?
Why ask it
List the roles: reps, the sales manager, whoever sends invoices, whoever answers customers after the sale. The count is your seat number for every quote, and each role wants a different screen. A list that only spells out what the manager needs is an early warning about adoption.
Which features do we need on day one, and which can wait?
Why ask it
Keep the day-one list to five or six, each written as a task such as 'log a call from a phone', not as a feature name. A long must-have list pushes you up a pricing tier and buries the two things that decide the choice. Hand the same list to every vendor.
What is our budget per user per month, and what can we spend once on setup?
Why ask it
You need two numbers because the monthly price is quoted first, and migration, onboarding and training tend to arrive on a separate line. Give the rep the range early. A good one tells you which plan fits inside it; a worrying one keeps the price back until after the demo.
Do we need a CRM for sales alone, or one that also runs marketing email and customer support?
Why ask it
Some products sell sales, marketing and service as separate parts with separate prices and others bundle them, so ask each vendor how theirs is split. Buying all of it for a team that only tracks deals means paying for screens nobody opens. If newsletters or a support inbox are a year away, it is enough to confirm they can be added later without a second migration.
Where does our customer information live right now?
Why ask it
Count every place: the shared spreadsheet, each inbox, phone contacts, the invoicing system, a notebook. Each one is a separate import with a separate owner. The place nobody lists at first, often a rep's own phone, is worth asking about by name.
What do our reps do today instead of using a CRM, and what do they like about it?
Why ask it
The spreadsheet or notebook they already keep is the product you are really competing with. Find out what makes it quick, then check that the new tool is no slower at that one thing. Reps who were asked now are easier to win over at launch.
Who on our side will own the CRM once it is live?
Why ask it
You want a name and a number of hours a week, for adding users, tidying fields and fixing reports. If the answer is 'everyone', it is nobody. If nobody has the hours, ask each vendor what paid admin help costs and add it to the comparison.
What went wrong with the last system we tried?
Why ask it
Skip this if it is your first CRM. Otherwise the complaints are your test script: ask each vendor to show how their product handles exactly those. If the main complaint was that nobody used it, spend longest on the Adoption questions before blaming the software.
Process fit
Can you set up our pipeline stages in front of us, using our names for them?
Why ask it
A good answer is the rep opening the settings and doing it in a few minutes, with no developer. 'Our implementation team handles that' is not a no, but ask what it costs and how long a change takes after launch, because your stages will change. If renewals or a second product line run differently from new business, ask for a second pipeline as well.
How does a new lead get into the system, and how does it reach the right rep?
Why ask it
Have them show a lead arriving from a web form like yours and landing with an owner. Then ask about the other routes you use: a forwarded email, a list from an event, a phone call. Finish with the lead its owner never opens: you want it to go to someone else after a set time, not to sit there.
What happens in the CRM when a deal sits untouched for two weeks?
Why ask it
You are hoping to see a rule you can set yourself: a reminder to the rep, a flag on the board, a note to the manager. If nothing happens until someone runs a report, stalled deals stay invisible, which is often the problem you set out to fix.
Which fields and record types can we add ourselves, and which need your team or a developer?
Why ask it
If your business tracks something that is not a contact, a company or a deal, such as a property, a policy or a vehicle, name it and watch how they would model it. Custom record types are sometimes kept for higher plans. A workaround with tags can be fine for ten records and painful for ten thousand.
Which steps can we automate on this plan, and is there a limit on how many?
Why ask it
Pick one from your own process, such as creating a follow-up task when a deal changes stage, and ask to watch it being built. Limits on automations are a common line between tiers. Check that what you saw in the demo runs on the plan in your quote.
Which AI features are included in our plan, and what do they do with our customer data?
Why ask it
AI features may be charged per seat, by use or as a separate add-on, so get the price along with the list. One that drafts a follow-up or summarizes a call earns its cost only if that job is on your day-one list. For the data half, a clear answer says whether your records are used to train anything, and says it in writing.
Can it produce quotes and proposals, or does that need another tool?
Why ask it
If you send quotes, have the rep build one from an open deal and send it for signature. When quoting is an add-on or a partner product, its price belongs in your comparison. Teams that sell at one fixed price can leave this out.
Who can see whose deals, and can we limit that by team or territory?
Why ask it
Decide what you want first: some teams sell better with everything open, others need accounts kept apart. Then ask the rep to log in as an ordinary user and show what is hidden. Ask as well whether exporting the whole contact list can be switched off for ordinary users, which matters on the day a rep leaves.
Which kind of sales team was this CRM built for, and which kind struggles with it?
Why ask it
A rep who knows the product can name the poor fit: long deals with many people involved, a field team that is rarely at a desk, a shop with thousands of small orders. Listen for whether the struggling team sounds like yours. 'It works for everyone' tells you nothing.
Data and email
What exactly comes across in a migration: contacts, companies, open deals, notes, email history, attachments?
Why ask it
Go through it item by item and get yes, no or partly for each. Press hardest on notes and old email threads, which are the awkward ones to move. Decide before the call which of them you could not work without.
Who does the migration, and what does it cost?
Why ask it
There are three usual answers: you do it with an import tool, their team does it, or a partner does. Ask what they need from you and in what format. If it is self-serve, import a hundred real records during the trial and see how long the cleanup takes.
How does the import handle duplicates and messy records?
Why ask it
Bring a sample of your worst rows: the same person twice, a company spelled three ways, a missing email. The answer you want is a demonstration with that file, showing what gets merged and what gets flagged. Whatever the tool does, cleaning the list before the move is easier than cleaning it after.
How does it connect to our email, and are messages logged automatically or only when a rep clicks?
Why ask it
Name your email provider, since the connection can differ between them. Automatic logging gives the fullest history; a button or a copied-in address depends on reps remembering. Ask too how a rep keeps a personal thread out of the shared record.
Does the calendar sync run both ways, and how quickly?
Why ask it
Have the rep book one meeting in the calendar and another in the CRM, then watch each appear on the other side. One-way sync means entering meetings twice, and the second entry is the first habit to go.
Which of our other tools does it connect to directly, and which need a connector we would pay for?
Why ask it
Send the list ahead: accounting, email marketing, phone system, help desk, e-signature. For each one ask whether the link is built in, runs through a third-party connector or needs the API, and which fields move in which direction. A paid connector is a second subscription to add to the cost.
Can we call and text customers from inside the CRM, and is each one logged?
Why ask it
Worth asking only if your reps sell by phone. Find out whether the dialer is built in or an add-on, and how minutes and numbers are billed. Rules on recording calls and sending texts vary by place, so ask how the product handles consent and check what applies where you and your customers are.
Where is our customer data stored, and who at your company can see it?
Why ask it
Ask for the security document they give to buyers, whether two-step login can be made compulsory, and how you would delete one person's records on request. Privacy rules depend on where you and your customers are, so ask how the vendor handles yours instead of assuming.
Reporting
Can you build the report our sales meeting runs on, live, right now?
Why ask it
Bring the one you use: open deals by stage and by rep, and what should close this month. Built on screen in a few minutes is the good answer. 'We can send that over after the call' usually means it was harder than it looked.
Which reports and dashboards come with our plan, and which need the next one up?
Why ask it
Building your own reports, and the number of dashboards you can keep, are common places for plans to differ, so ask how it works on the one in your quote. If the report from your sales meeting needs the higher tier, the higher tier is the real price.
How does the forecast work, and can we set our own likelihood for each stage?
Why ask it
A common method multiplies each deal's value by a percentage for its stage. Ask whether you can change those percentages and whether a rep can override a single deal. If you do not forecast yet, it is enough to know the feature is there for later.
Can we see where deals are lost, by stage and by reason?
Why ask it
This only works if closing a deal as lost makes the rep choose a reason, so ask to see both the field and the report. Without it you can count lost deals but not learn from them. Keep the list of reasons short enough that 'Other' does not come out on top.
Can we report on activity, such as calls, emails and meetings, as well as on deals?
Why ask it
Activity numbers are only as good as the logging behind them, which takes you back to how the email and calendar sync work. The useful version sets activity beside results, such as meetings held against deals opened, for one rep over a month. Be careful what you reward: a team measured on call counts will log calls.
Can reports go out by email on a schedule, and do they export to a spreadsheet?
Why ask it
This is for the owner or finance lead who will never log in. Check whether a recipient needs a paid seat, and open an exported file to see that the columns survive. If the only way to share is a screenshot, expect someone to rebuild the numbers by hand each week.
Will our managers run pipeline meetings from the CRM screen and nothing else?
Why ask it
This one is for your own side. When the weekly meeting is run from the live board, a deal that is not in the CRM does not get discussed, and reps update it. If managers still ask for a spreadsheet on the side, reps keep two records and one of them goes stale.
Adoption
How long from signing until every rep is working in it, and what do you need from us to hit that date?
Why ask it
A real answer comes as steps in order with a rough length for each: setup, import, connecting inboxes, training. The step that slips is often one of yours, such as cleaning the contact list or agreeing the stage names, so ask which of them holds teams up. A date with no steps behind it is a guess.
How many clicks does it take a rep to log a call and set the next step?
Why ask it
Count them aloud during the demo. A rep does this many times a day, so one screen with the next step on it is the good answer. Several pages with a save button on each is how records end up being filled in from memory on Friday afternoon.
Can a rep update a deal from a phone between meetings?
Why ask it
Ask to see the app on a real phone, not on a slide. In the trial, have a rep add a note, move a deal and look up a number while out of the office. Field teams should also ask how it behaves with no signal.
Can our reps try it with real deals before we sign, and for how long?
Why ask it
Find out which plan the trial runs on. If it is the top one, features can disappear the day you buy a lower one, so ask to try the plan in your quote. Put your most skeptical rep in the trial; their list of complaints is the useful one.
What does a rep get from it that a spreadsheet does not give them?
Why ask it
Put this to the vendor, then to your own reps after the trial. Good answers are things that save the rep effort: reminders, email templates, a view of their own numbers, fewer status questions from the manager. If the only winner is the manager's report, expect half-filled records.
What training comes with our plan, and what do we use when someone new joins in six months?
Why ask it
The first half gets you the kickoff: live sessions, a named contact, a help center. The second half is about what lasts. Short recorded lessons and prompts inside the product will still be there for the next hire; a launch webinar will not.
Which fields can we make required, and at which stage?
Why ask it
Required fields keep the data clean and also give reps a reason to put off creating the deal. Ask whether a field can be required only once a deal reaches a certain stage, which spreads the typing out. Start with as few as you can stand and add later.
Who do our reps contact when they are stuck, and how fast is the reply on our plan?
Why ask it
Chat, email and phone support can each belong to a different plan, so ask what yours includes. Then test it: send a real question during the trial and time the answer. A rep who waits two days for help goes back to the spreadsheet.
What do teams that fail to get their reps using it have in common?
Why ask it
Someone who has watched rollouts will name something concrete, such as too many fields at launch or a manager who never opens the product. That is free advice, so write it down. 'We do not really see that' is the worrying answer.
Can we speak to a customer with a team our size who moved from what we use now?
Why ask it
Ask that customer two things: how long it took before reps stopped keeping their own lists, and what did not survive the migration. A vendor who offers only much larger companies may not have many customers like you, which is worth knowing too.
Cost and exit
What is the price per seat on the plan that includes everything we saw in the demo?
Why ask it
Demos tend to run on the fullest version. Go down your day-one list and have the rep name the plan each item needs, then price that plan for your seat count. If one feature drags you up a tier, ask what it costs as an add-on.
Is there a minimum number of seats, and does someone who only reads reports need a paid one?
Why ask it
Some plans are sold in blocks of users and some offer free or cheaper view-only seats; ask how it works with this vendor. Count the owner, the bookkeeper and anyone who just looks things up. The answer can move your total more than a discount does.
What will we pay beyond the seats: onboarding, migration, support, add-ons, contact or storage limits?
Why ask it
Ask for one written quote with every line for the first year. Limits on contacts, stored files or emails sent are the ones that surface months later, so ask what happens when you pass each. A quote that is only a seat price is not finished.
How much less is annual billing than monthly, and can we start monthly?
Why ask it
The annual discount commits you before your reps have really used the product. Where a monthly option exists it usually costs more per seat, and what the extra buys is the right to walk away after a few months. Ask whether you can switch to annual later at the rate being offered today.
Can we add and remove seats during the term, and what happens to the price at renewal?
Why ask it
Adding seats is rarely a problem. Removing them may only be possible at renewal, so ask how it works in this contract. Ask too whether the contract renews on its own, how much notice it takes to stop that, and whether an increase can be capped in writing.
What would push us onto the next plan up, and what does that plan cost?
Why ask it
The trigger might be a number of contacts, a number of users, or one feature such as custom reports. Find the one nearest to where you are now. A product that is cheap today and doubles when you hire two more reps should be compared at the higher price.
How do we export everything, and what does the export leave out?
Why ask it
Do it during the trial: run the export, open the files, and check that a deal still shows its contact and company. Notes, email history and attachments are the places to look for gaps. The good answer is an admin button on your plan; a support ticket, a fee or 'through the API' is worth pausing on.
After we cancel, how long can we still log in and download our data?
Why ask it
Ask for a number of days and where the terms state it. Whatever the answer, plan to take a full export before you give notice, not after. A rep who does not know should be able to find out within a day.
How to run a CRM evaluation
Practical guidance for the conversation itself
Before the first demo
Hold your own meeting first
The first group on this page, Your team, is for your own side, and it takes one meeting. Come out of it with three things on paper: the sentence that says what the CRM is for, the stages of your sales process, and a day-one list of five or six tasks. Without them, each demo is judged on whichever feature looked best that afternoon.
Keep the shortlist to three
Every extra product adds a demo, a trial and a quote to compare. Two or three is enough to see real differences. If a fourth keeps coming up, swap it in for the weakest instead of adding it.
Send your list ahead
Email the rep your stages, your day-one list and the other tools you use a few days before the call. A rep who has read it will show your process instead of the standard tour. One who has not has told you something about how the account would be handled.
Bring your own data
Take a small file of real records, messy ones included, and the report your sales meeting runs on. The questions under Data and email and Reporting get much better answers when they are asked about your file than about the sample company in the demo account.
In the demo and the trial
Ask to see it, not to hear about it
'Can it do that?' nearly always gets a yes. 'Can you do that now, with our stages?' gets either a demonstration or an honest account of what it would take. Most questions under Process fit work best asked this way.
Ask which plan, every time
Many of the answers on this page change with the plan: automations, custom reports, permissions, support. Each time the rep shows something you want, ask which plan it is on and keep a running list. That list is what turns the demo into a price.
Use the trial for the dull jobs
A trial is for the tasks nobody demos: importing a hundred contacts, connecting one inbox and one calendar, logging a call from a phone, running an export. Give two or three reps real deals to work in it for a week, then ask what annoyed them.
Put the same questions to every vendor
Use one sheet with the same questions for each product and write the answers down during the call. A week later, memory favors whoever presented best, and the notes are what let you compare the products.
Comparing the answers
Score against your day-one list
For each product, mark every day-one task as shown working, possible with setup, or not available. A product that does all six plainly is usually a better buy than one that does four brilliantly and has forty other features.
Compare the same price
Put each quote on the same footing: the plan that covers your day-one list, your real seat count, one year, with onboarding, migration and any add-ons or connectors included. The lowest seat price is often not the lowest first-year cost.
Let the reps have a vote
The people who will type into it every day decide whether it works. If the reps in the trial clearly preferred one product, that preference is worth more than a feature the manager liked. A tool the team uses with gaps is better than a complete one they avoid.
Check the way out before you sign
Run an export in the trial and open it. Read the cancellation and renewal terms yourself instead of relying on the call. Plans, limits and contract terms differ by vendor and change over time, so where an answer matters, ask how it works on your plan today and have it written into the quote or the order form.