Reference Calls When Buying an AI Email Tool: What to Ask

A vendor-supplied reference is a reference the vendor believes will not damage them. Take the call anyway — the account is real, the person is real, the invoices are real — but plan the call around the questions the sales rep did not prep them for.

This guide gives you five, a scoring rubric for the answers, a worked example of the call, and a short list of things to also do off the vendor's list. It is written for a buyer running a two-week trial in parallel, because the reference call only pays back if you already know what you are testing yourself.

We build AI Emaily and appear in the verdict at the end as one of the options being weighed — not first, because a reference-call how-to isn't a product page.

The short answer#

The vendor coached the reference on what to say about the product. They did not coach them on the first two weeks, the last support incident, the person on their team who quit using it, or what it would cost them to switch back. Those four questions do the work; everything else is warm-up.

Then, before you decide, find one reference the vendor did not choose — a job title on LinkedIn, a G2 review with an email in the profile, a Reddit thread from six months ago. One unprepped voice next to three prepped ones changes what you hear.

Score the answers on specifics, not sentiment. A reference who says the product is amazing but cannot name a moment it saved them time is telling you the sales rep prepped an adjective, not an account.

The five questions vendors don't prep for#

Ask these in this order. The order matters because each one gets harder to answer with a rehearsed line, and by question four the reference has stopped pattern-matching to the vendor's script.

1. 1

   Walk me through your first two weeks. What surprised you?

   The prepped answer covers the demo and the polished setup. The first two weeks are the part the rep does not see. You are listening for a specific moment — a rule that fired on the wrong thread, a triage bucket that made no sense at first, a setting they had to hunt for. Vague adjectives here mean the reference didn't onboard themselves.

2. 2

   What did you turn off in the first month, and why?

   Every real user turns something off. Auto-labels that were too aggressive, a daily brief that was noise, a smart-reply that used a phrase they'd never say. A reference who says they left everything on either isn't using it heavily or is not going to tell you what didn't work. This one question separates the two.

3. 3

   Tell me about the last time you had to contact support. What happened?

   The prepped line is that support is great. Ask for the incident. You want the shape: how they reached support, how long the reply took, whether the person answering knew the product, and what the resolution was. If they can't name a single ticket in a year of use, they either haven't hit an edge case or they gave up asking.

4. 4

   Who on your team stopped using it, and why?

   In any team rollout, someone rolls back. The interesting question is who — the executive who wanted approval on every send, the assistant whose voice the AI couldn't match, the sales rep who lives in a CRM tab and never opens the inbox. The answer tells you the shape of your own adoption risk.

5. 5

   What would you have to lose to switch back?

   This is the switching-cost question dressed as its opposite. If the answer is nothing, the tool sits lightly on their workflow and it will sit lightly on yours. If the answer is a rules brain, a Context they wrote, or a year of audit history that only exports as vendor JSON — that's what you're really buying, and that's what will keep you when the invoice goes up.

How to score the answers#

Score each answer 0 to 3 the same way you score a trial: specifics count, adjectives don't. Write the evidence next to the number so a second person reading your notes can reach the same conclusion.

Finding a reference the vendor didn't choose#

Two prepped calls plus one unprepped call is a materially better sample than three prepped calls. Off-list references are usually easier to find than buyers expect — the same person the vendor did not offer up posted about the tool on LinkedIn six months ago, or reviewed it on G2, or asked a question on Reddit.

• LinkedIn search: the vendor's product name plus a job title close to yours. Filter to posts from the last year. A one-line DM that names your evaluation and asks for fifteen minutes gets a reply about a third of the time.
• G2, Capterra and Product Hunt reviews with a filled-in profile: the reviewer's email or LinkedIn is often visible. Skip the five-star and one-star extremes; look for a three or four.
• Reddit and Hacker News: search the product name in r/gmail, r/outlook, r/productivity and the general threads. Older comments are more useful than recent ones, because the writer has lived with the product.
• The vendor's own community — Slack, Discord, forum. Someone answering questions there has used it long enough to be worth asking.
• Ask the vendor's supplied reference for one more name. Half of them will give you one, and the one they name is often the person they compare notes with when a problem lands.

Red flags in the call itself#

Some answers end the reference call early — not because the product is bad, but because the reference has been told what to say and can't step outside it. Watch for these on both prepped and off-list calls.

• The reference cannot name a single setting they changed. They are describing the demo, not the product they use.
• Every answer arrives inside twenty seconds. Real answers pause; rehearsed ones don't.
• The pricing question gets deflected to your rep will walk you through it. The reference either doesn't see the invoice or was asked not to say what it looks like now.
• The support question produces a generic praise line. Nobody who has used a product for a year can name zero incidents; the ones who claim to are the ones who stopped filing tickets.
• The reference works at a company that appears in the vendor's case-study page. That is a marketing relationship, not a peer conversation, and the account is coached at a higher level than the individual.
• You cannot get a second name out of them. A reference who is comfortable with the tool will point you at a peer; one who is only comfortable with the script won't.

Building the call sheet you actually run#

The version you take into the call is one page. Print it or keep it on a second screen; do not read from a doc that scrolls, because the reference can hear it.

What we'd pick and why (honest)#

This is the section where an AI email tool would ordinarily rank itself first. On a reference-call how-to that doesn't apply — the reader came to learn a technique, not to pick a product. So the honest version is a shorter one.

We build AI Emaily. If you are running a reference call as part of a wider evaluation and we are on your shortlist, ask us the same five questions and we will connect you to a customer who will answer them without a script. The intake for that is on /book-a-call.

Where a different tool is a better fit for your reference-call outcome: if the shape of your buying process requires three enterprise references with several years of use each, Superhuman and Missive have been shipping longer than we have and can put you on calls with customers who have been paying them since before we existed. If that depth of tenure is a hard requirement rather than a nice-to-have, ask them first. We are newer, and pretending otherwise on a page about verifying vendor claims would be its own red flag.

Where the reference call itself is the deciding artefact: an approval-first email client with a per-account autonomy setting, a full action log with undo, and mail that stays in the mailbox you already own is the thing you can hand to a colleague after the call and have them run the same tests. That is what AI Emaily is built to be. Read the mechanics on /features/ai-email-assistant, the packaging on /pricing (a 7-day free trial on Pro or Autopilot, card required, no charge if cancelled before day seven — we do not have a permanent free tier), or the wider category on /best/best-ai-email-platform.

After the call: what to write down while it's fresh#

The notes are the deliverable, not the call. Anyone on the buying committee who wasn't on the line will decide based on what you write in the next thirty minutes, not what the reference actually said.

1. 1

   Score the five questions inside an hour.

   Use the 0-3 rubric. Write one line of evidence next to each number — the specific moment the reference named, or the specific way they didn't name one. Sentiment fades in a day; specifics don't.

2. 2

   Note the invoice-direction answer separately.

   It is the most volatile fact in the whole call and the one that most affects year-two cost. Whether the reference's bill went up, down or stayed flat since signing is a data point the pricing page cannot give you.

3. 3

   List every artefact the reference named as switching cost.

   Rules, Context, templates, audit history, custom labels, integrations. Cross-reference against the export test you ran in your own trial: what of that list is actually in the export file, and what would you rebuild by hand.

4. 4

   Write the follow-up question you didn't ask.

   There is always one. Send it in a two-line email the same day; you'll get a better answer than a ninety-minute call would have produced, because the reference now knows what you actually care about.