Questions to Ask on a Cold Call
For salespeople and sales development reps looking for questions to ask on a cold call, when the prospect was not expecting to hear from you and you have a minute or two to earn a meeting. The list follows the call: permission openers, questions that find out whether there is a problem worth a meeting, a quick check of fit, replies to 'send me an email' and 'not interested', and booking the next step, with a last group for the calls a receptionist or assistant answers. The note under each says what a good or a worrying answer sounds like and what to do with it.
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The questions
Each question, and why to ask it
Opening
Did I catch you at a bad time?
Why ask it
Asked this way around, 'no' is the easy answer and it means keep going. If it is a bad time, do not pitch through it: ask for a specific time to call back, then call at that time and say they asked you to.
This is a cold call. Do you want to hang up, or give me 30 seconds to say why I picked your name?
Why ask it
Honesty about what the call is tends to earn a short laugh and the half minute. Keep to the 30 seconds and end them on a question, because a caller who was given half a minute and takes three has broken the first promise of the relationship.
I am calling about how your team books its deliveries. Are you the right person to talk to about that?
Why ask it
Put your own subject where the deliveries are, and name the task, not your product. 'No, that is Priya' is a good result: ask how to reach her and whether you may say who sent you. A yes opens the way for one question about how it is done today.
I saw you are hiring three more drivers. Does that mean the routes are growing?
Why ask it
A trigger opener needs one fact the prospect can check: a job posting, a new location, a funding announcement. Follow it with a guess about what it means for them and let them correct the guess, because a 'reason' that would fit every company in the directory is worse than none. If they sound surprised that you knew, say where you read it.
Dana in your warehouse suggested I talk to you. Did she mention I would be calling?
Why ask it
Never bend this one. Use a name only when that person really did point you here, and repeat what they said and no more. If the prospect checks and the story is thinner than you made it sound, the call and the account are both gone.
May I take a moment to tell you why I am calling, and then you can decide whether we keep talking?
Why ask it
The formal cousin of the hang-up opener, for a senior or reserved prospect who would not enjoy the joke. Agreeing costs them nothing, because the exit stays in their hands. Have the reason ready in two sentences, one about companies like theirs and one about the problem, and then stop.
I sent you a short email on Monday about your delivery schedule. Did it reach you?
Why ask it
Only when you did send one. 'I don't think so' is a common reply and a perfectly good one: offer the one-sentence version on the spot. Do not ask whether they read it, which sounds like checking homework.
Have you come across our company before?
Why ask it
A no lets you give the one-sentence version without apologizing for it. A yes needs a follow-up before you say anything else: ask what they heard, since an old trial, a former rep or a bad review will color every word that follows.
How is your day going so far?
Why ask it
Small talk at the top of a cold call divides salespeople, and it only helps if you wait for the reply and respond to it like a person. Rushed through as a formality, it tells the prospect a script is coming. If it does not sound like you, leave it out and go straight to why you called.
The problem
People in your role usually tell me about one of two headaches: late deliveries or double-booked docks. Is either one yours?
Why ask it
Swap in two real problems you solve, in the words customers use, and keep each under ten words. 'Neither, our trouble is something else' is the best reply you can get, because the prospect has started describing their own situation without being asked.
What is the hardest part of getting deliveries out on time right now?
Why ask it
Asked in the first ten seconds, this gets 'we are fine' from almost anyone. Ask it once the prospect has agreed the subject is theirs, and tie it to one task, never to 'your business' in general. Whatever they name, ask for an example before you say a word about what you sell.
What are you using for that right now?
Why ask it
Expect a product name, 'a spreadsheet' or 'a person named Dave', and take any of them without comment. Criticizing the current setup on a cold call makes the prospect defend it. Write it down, since it is what you will be compared with.
How long has it been done that way?
Why ask it
A setup chosen last year was probably the prospect's own decision, and they will not undo it for a stranger. One inherited from a predecessor, or nine years old, is easier to question. Ask who picked it if the answer is vague.
If you could change one thing about how that works, what would it be?
Why ask it
It is the gentlest way to ask what is wrong, and one thing is easy to give on a call they did not plan for. 'Nothing, it is fine' said quickly is a brush-off. Said after a pause it may be true, and the honest move is to thank them and go.
On a scale of one to ten, how well is that working for you?
Why ask it
Hardly anyone says ten. Whatever number comes back, ask what keeps it from being higher: the gap they describe is the reason for the meeting. A flat eight with no detail usually means there is no pain worth a calendar slot yet.
When was the last time that held something up?
Why ask it
A date and a story, such as 'last month, during the audit', mean the problem is alive. 'I can't remember' means it is your problem and not theirs. Do not supply an example for them: wait.
Roughly how much of your week goes to it?
Why ask it
You want a rough figure in their words, such as 'a day a month' or 'most of Monday'. Repeat it back when you ask for the meeting. Do not multiply it into an annual cost on this call: that sum belongs to the discovery conversation.
Is fixing that on your list this year, or something you have learned to live with?
Why ask it
Offering 'learned to live with' as a respectable answer gets you the truth. If it is on the list, ask where. If they are living with it, ask what would have to happen to move it up, and keep the answer for a later call.
Have you looked at other ways of doing it before?
Why ask it
If they looked two years ago and gave up, ask what stalled it: price, effort, a manager who said no. That reason will come up again, so you may as well hear it now. A prospect who has never looked needs a different first meeting, one that starts with why the question matters at all.
Fit
How many people would a change like this touch?
Why ask it
A size check in plain clothes. Know before you dial what number is too small or too large for you to serve well. If the answer falls outside it, say so and end the call kindly, which saves two calendars.
Is that handled the same way at every location, or only at yours?
Why ask it
One answer gives you the size of the account and how far this person's say reaches. A branch manager can often agree to a meeting but cannot speak for headquarters, so ask who sets the standard for the other locations. Skip it when you already know the business has one address.
If this turned out to be worth a closer look, who else would want to hear it?
Why ask it
Softer than asking who the decision maker is, which can sound like a demotion in the first minute. Asked as a hypothetical, it commits them to nothing. If five names come back, expect a slow purchase and aim the first meeting at whoever can gather the others.
When does your current agreement come up for renewal?
Why ask it
Prospects will often give the month even to a stranger. If it is far off, ask when they would start looking and offer to call then. If it has just been renewed, a meeting now is probably a courtesy, and you should both know that.
What would have to be true for this to be worth twenty minutes of your time?
Why ask it
Useful when the prospect is lukewarm and you cannot tell why. They may name a proof you can bring, such as a customer in their industry or a price range. If they cannot think of anything, there is no meeting here, and pressing for one earns a no-show.
So the booking is done by phone, and Fridays are where it falls apart. Do I have that right?
Why ask it
Put their two facts where these are: what they use and what bothers them about it, in their words. A correction is welcome, since it shows they are listening. The summary makes the request for a meeting follow from what they said and not from what you wanted when you dialed.
Brush-offs
Happy to send an email. What would you want it to cover, so it is worth opening?
Why ask it
This sorts the real request from the polite goodbye. A prospect who answers with a topic has told you what they care about, and you are back in the conversation. 'Just the general information' is probably a no.
When someone asks me for an email, it is sometimes a kind way of saying no. Is that the case here?
Why ask it
Say it with a smile in your voice and no edge. Plenty of prospects admit it, which frees you both. Others insist they do want the email, and that small commitment makes your follow-up call an expected one.
Once it is in your inbox, when would be a fair time for me to call and hear what you thought?
Why ask it
An email with no agreed follow-up is where a cold call tends to end quietly. Get a day and a rough time, put it in the subject line of the email, and open the next call with 'you suggested Thursday'.
That is fair, you have heard almost nothing yet. Is it the timing, or is this not a problem you have?
Why ask it
For the 'not interested' that arrives in the first ten seconds, which is a reflex and not a judgment. Give the two options and accept either: 'timing' earns a question about when, and 'no problem' earns a thank-you and a clean exit.
Before I let you go, what would I have needed to say for this to be relevant?
Why ask it
Ask once, lightly, after a firm no, and then really let them go. A few prospects answer with the thing they do care about. Most give a short reply you can use to fix your opener before the next call.
What do you like best about the company you use now?
Why ask it
When the prospect says 'we already have someone', agree that they are probably well served, then ask this. It takes the fight out of the call. Listen for what is missing from the praise: a buyer who mentions price and says nothing about service has shown you where to look.
Do you keep a backup supplier for when they are stretched thin or let you down?
Why ask it
A backup role is a much smaller ask than replacing someone the prospect likes. Few buyers switch on the strength of a phone call, but a meeting about a plan B is easy to agree to. If they already have one, ask how often it gets used.
When is a better time: later today, or a set day next week?
Why ask it
Take 'I am in the middle of something' at its word and ask for the slot, not for one more minute. A named time is an appointment. 'Whenever' is not, so offer a day and an hour yourself and see whether they take it.
Leaving the cost aside for a moment, is the problem itself one you would want solved?
Why ask it
'We have no budget', said before any price has been mentioned, is often not about money. If they do want the problem solved, cost is a later question and the meeting is still worth having. A shrug tells you budget was the polite reason and something else is the real one.
Is there someone else in the business this would matter more to?
Why ask it
Save it for the prospect who said 'not for me' and stayed civil. A name given freely is a referral, and it becomes the first line of your next call. Check that they are comfortable with you saying who pointed you there.
Would it be all right if I checked in again in a few months, and what would need to have changed by then?
Why ask it
The useful part comes after the comma. 'When the new warehouse opens' or 'after the contract ends' gives the next call a reason and a date. Without it you are only asking permission to interrupt them again.
Would you prefer that I not call again?
Why ask it
Ask it plainly when the answer has been no twice. If they say yes, mark the record and keep to it. Your employer, and the rules where you are calling, may also set out what you must do with that request, so ask how it works there.
Next step
Does it make sense to set aside twenty minutes later this week to go through this in detail?
Why ask it
Ask as soon as the prospect has named a problem in their own words, and not one question later. Say what the twenty minutes are for in terms of that problem. A meeting 'to learn more about us' is the kind that gets canceled.
Do you have your calendar in front of you?
Why ask it
It moves the call from whether to when without any pressure. If they do not, offer to hold while they open it. 'Just send me some times' is how a meeting that was agreed thirty seconds ago slips away.
Would Tuesday morning or Thursday after lunch work better for you?
Why ask it
Two real slots are easier to answer than 'when are you free?'. Have them open in your own calendar before you dial. If neither works, ask the prospect to name one and take it, even if it is awkward for you.
What should I bring so the meeting is about your situation and not a general presentation?
Why ask it
The prospect writes the agenda and so has a stake in turning up. Put their answer in the invitation, word for word. If they say 'just the overview', choose the one thing they complained about on this call and lead with that.
What is the best email address for the calendar invitation?
Why ask it
Read the address back letter by letter, because a typo here undoes the whole call. Send the invitation while you are still on the line and ask them to accept it before you hang up, so you know it arrived.
Is anything coming up that might push this off your calendar?
Why ask it
Better to hear about the trade show or the quarter-end crunch now than to sit in an empty meeting. If something is looming, move the date yourself. A meeting set further out and kept is worth more than an early one that is missed.
Is there anything you would like to ask me before we hang up?
Why ask it
Their question is often 'what does it cost?' or 'who else uses you?'. Answer in a sentence and save the rest for the meeting. A prospect who asks something has started to picture the next conversation, and one who asks nothing may need a reminder the day before.
Gatekeeper
Could you help me find the person who schedules your deliveries?
Why ask it
A request for help, with the task named in place of a job title, is one most receptionists can answer in a sentence. Put your own subject in. Write down the name and the exact title they use, since titles differ from company to company.
May I ask who I am speaking with?
Why ask it
Ask early, use the name, then write it on the record. Whoever answers the main line talks to your prospect every day and remembers who was courteous. On the next call, 'Hello Maria, it is Tom again' gets a different reception from a stranger's voice.
Is the operations manager the right person for this, or would you point me somewhere else?
Why ask it
Reception often knows who really handles a thing, whatever the website says. If they redirect you, ask whether you may mention that they did. Being sent by the front desk is a small introduction, and it has the merit of being true.
When is the best time of day to catch Priya at her desk?
Why ask it
Assistants will often tell you: before the morning meeting, or after five when the office has emptied. Call at that time. If they would rather not say, do not push, and ask for the best way to leave word.
Does Priya prefer a call or an email for something like this?
Why ask it
Some people never return a voicemail and answer every email within the hour, and the person at the front desk knows which kind this is. Follow the advice, and mention in your first line that reception suggested it.
Could you put me through, or would you prefer to take a message?
Why ask it
When asked what the call is about, answer plainly: your name, your company and the subject in a few words. Vague or evasive replies are exactly what a gatekeeper is there to stop. Offering the message yourself shows you are not trying to slip past.
Is there a direct line or extension I should ask for next time?
Why ask it
Ask after a helpful exchange, never as the first request. Some companies do not give out direct numbers, and a polite 'I can't share that' is the end of the matter. If you do get the extension, it is still worth calling at the time reception suggested.
How to use these questions on a cold call
Practical guidance for the conversation itself
Before you dial
Have one true reason for calling this person
Every opener on this page works better with a reason behind it: a job they posted, a location they opened, a role that usually owns the problem you solve. Two minutes of looking is enough. If you cannot find a reason, use one of the plain permission openers and say honestly that it is a cold call.
Know what the call is for
A cold call sells a meeting, not the product. The questions under The problem and Fit are there to find out whether a meeting is worth both people's time, and two or three of them are plenty. The long version, with costs, budgets and the buying process, belongs to the discovery call you are trying to book.
Write the first two sentences and nothing else
The examples on this page are written for someone selling to a delivery operation, so swap in your own subject, names and facts. Write out your opener and the two problems you will name, and say them aloud until they sound like you. Past that point a script gets in the way, because the prospect's reply decides what comes next.
Choose a handful per call
Nobody asks a stranger every question on a list. A working call uses one opener, two questions about the problem, one check of fit and one request for the meeting. Have a reply ready for each of the common brush-offs: send me an email, not interested, we already have someone, call me later, no budget.
Check the rules where you are calling
Who you may call, at what hours, what you must say about who you are, whether a call may be recorded and what a request not to be called again obliges you to do all depend on the country, the state and your employer's own policy. Ask your manager or compliance team how it works there before you start dialing, and again when you begin calling a new region.
During the call
Ask, then stop talking
The silence after a question feels longer to the caller than to the person thinking. Count to three before you say anything. Filling the gap with a second question, or with the answer you hoped for, gives the prospect nothing to do but agree and hang up.
Ask for the meeting as soon as the problem is named
Once the prospect has described something that bothers them, in their own words, go to Next step. Each extra question after that is a chance for the call to be interrupted or for the prospect to decide they have heard enough.
Answer a brush-off once
Each question under Brush-offs is one calm reply, not the first move in an argument. If the prospect says no again, thank them, ask whether you may try another time and end the call. A caller who takes a no well is remembered more kindly than one who had three rebuttals ready.
Treat the person who answers as a colleague of your prospect
Receptionists and assistants are doing their job when they ask what the call is about. Give your name, your company and the subject without being asked twice, ask for their help, and thank them by name. The Gatekeeper questions only work when they are meant.
If you reach voicemail
Give your name and company, one sentence on why you called this person, and your number said slowly, twice. One question from The problem makes a better message than a description of your product. Say when you will try again, then try again at that time.
Reading the answers
A reflex is not a decision
The first 'not interested' usually comes before the prospect knows what the call is about. It is a reply to being interrupted. One gentle question tells you whether there is a real no behind it. The second no is the real one.
Detail means the problem is real
A prospect who names the tool, the month it went wrong or the colleague who complains has a problem worth a meeting. Short agreeable answers such as 'yes, that can be an issue' tell you very little. Ask for the last time it happened before you offer a time to meet.
A quick yes can be a way off the phone
Some people accept a meeting because it is the fastest way to end the call. The calendar questions test it: someone who opens their calendar, picks a slot and says what they want covered means to be there. Someone who says 'send me an invite for whenever' may not be.
No is a useful result
A clear no from the wrong company, the wrong size or the wrong year lets you spend the next call on someone else. Record why, in a few words. Looked at after a week of calls, those reasons show whether the list or the opener is the thing to change.
Mistakes to avoid
Running discovery on a call nobody agreed to
Ten questions about budget, process and timelines, put to someone who picked up the phone expecting a colleague, feel like an interrogation. Find one problem, confirm it matters, and book the time to go into it.
Hiding that it is a sales call
Pretending to return a call, implying you know the prospect or telling the front desk it is personal may get you put through once. The meeting that follows starts from a lie, and the prospect knows it. Say your name and company before any opener on this page, and let the opener say why you called.
Pitching straight after the opener
Permission to continue is permission for a sentence or two, not for the presentation. Say why you called, ask one question about the problem and let the answer decide whether there is anything to describe.
Booking a meeting that will not happen
A slot with no agenda, no accepted invitation and no named problem is a likely no-show. Before you hang up, the prospect should know what the meeting is for, have the invitation in their inbox and have told you who else ought to be there.