When Should You Ask Questions on a Cold Call?

Image of a question mark symbolising when to ask questions on a cold call

Short Answer

Questions come after you’ve earned the right to ask them, when you’re gathering information and qualifying, or with inbound leads when the prospect contacted you first. Ask at the wrong moment, and you turn your prospect off and trigger hard objections. Ask at the right moment, and prospects engage in meaningful conversations.

Key Takeaways

  • Never open a cold call with a question. Opening questions hand control to a stranger with no context or reason to answer your question.
  • Open with who you are, why you’re calling, and a relevant reason for them to meet with you or give you qualifying information.
  • The primary objective of a cold call is to set an appointment, NOT engage in a discovery conversation.
  • Questions on cold calls are most appropriate when the objective is to gather information and qualify.
  • When calling inbound leads, since the prospect made first contact, leading with a qualifying or engagement question is appropriate.

Why You Should Never Open a Cold Call With a Question

You’ve heard the bad advice, probably from a so-called cold calling “expert” with a course or book to sell: Open cold calls by hooking your prospect with a question. And you’ve heard the questions:

  • “How are you today?”
  • “Did I catch you at a bad time?”
  • “Could I have 30 seconds to tell you why I called?”
  • “Mind if I steal 30 seconds to explain why this caught my attention?”
  • “How are you doing today?”
  • “How’s your day going?”
  • “Did I catch you at a bad time?”
  • “I don’t suppose I caught you at the worst possible time, did I?”
  • “Are you free for a quick chat?”
  • “Is now a bad time for a two-minute conversation?”
  • “Do you have a minute for me to explain why I’m calling?”
  • “Can I share why I’m calling, and then you can decide whether it’s worth continuing?”
  • “Have you heard our name tossed around?”
  • “Could I get your opinion on something?”
  • “Are you the right person to speak with about ______?”
  • “What are you doing to address ____________?”
  • “Would you be open to hearing an idea that might help you with _______?”
  • “Is improving _ a priority right now, or is your attention somewhere else?”

Why do they suggest that you open with a question? It’s always about avoiding rejection. But the irony is that opening a cold call with a question creates more rejection, more awkward moments, more hangups, and more objections.

All of these questions fail for the same reason. A cold call is an interruption and you are interrupting a stranger. That stranger owes you nothing, knows nothing about you, and has answered a thousand cold calls that opened exactly this way.

An opening question put them on the spot. It forces them to do work for someone they have no reason to help, and it flags you as just another sales rep running a cheesy script before you’ve said one relevant thing.

Opening questions overcomplicate cold calls and they don’t work. The people who tell you to use them are just dead wrong.

What to Do Instead

Think about your reaction if you were interrupted by a caller. What would you want? If you’re honest, you’d want them to quickly get to the point by telling you who they are, what they want, and relevant reason why you should care. That’s it and it is that simple.

No tricks, no fake rapport, no permission-seeking, and no stupid opening questions. When you primary objective is to set an appointment, just get to the point, be relevant, and ask for the meeting. Relevance is the heart of a proven cold calling approach.

When you do this, you’ll get a response in about 30-seconds: They might say yes, they might say no and hang-up, or they might hit you with a question or an objection (a maybe). It is at that inflection point that you’ve earned the right to engage and ask questions because your prospect, through their objection, is telling you to give them a better reason to say yes to you.

When Questions Belong on a Cold Call

When you primary objective is to gather information and qualify you’ll need to ask questions to get the information you need. In these situations you simply want to tell them who you are, how you help, and gain their permission to ask your questions. It sounds like this:

“Hi Jamal, my name is Jeb Blount and I’m with a company called Sales Gravy, we deliver cold calling training for sales teams in your industry. I’m looking for little information about your sales team. May I ask you a couple of questions please?’

Most people will give you a hesitant yes to this request as long as you get to the point and sound confident. Once they do, you must remember that your job to gathering information, not there to pitch.

Two rules govern qualifying questions:

  1. Ask one question at a time, then SHUT UP and let the silence work. You’ll typically get two questions in before they push you off the phone (though some people will engage in a much longer conversation). Just remember that you can call back and ask more questions later.
  2. Stop qualifying the moment you’ve uncovered enough information to justify asking for a meeting. When you have what you need, ask confidently for it: “Sounds like it’s worth thirty minutes to explore this further. How’s Thursday at 2?”

Prioritize your questions from three main qualifying zones.

Current State Qualifiers. Find out what they’re doing today. “How are you handling X right now?” “Who are you using for that today?” “What does that process look like on your team?”

Technical Qualifiers: Learn how many, how much, tech stack, size, specs, requirements, decision makers and process etc.

Buying Window Qualifiers. Find out when they can act. “When does your current contract come up?” “When do you typically budget for this?” “Is this a this-quarter problem or a next-year problem?” Even a prospect with zero interest today will usually tell you when the window opens, and that answer is the entire value of the call. You now know exactly when to be back.

Inbound Leads Flip the Rules

Everything above assumes you interrupted your prospect with a cold call. The script flips with inbound leads.

When the prospect calls you, engages at a tradeshow, downloads your guide, or fills out your form it is completely appropriate to open your follow up call with a question designed to engage them in a conversation.

They initiated the contact and the first job is to find our why: “Thanks for reaching out. I’m just curious, what prompted you to contact us?”

Sadly, salespeople get this backwards constantly and make big mistakes when following up. They pitch inbound leads and turn off prospect’s who were ready to talk, and they interrogate cold prospects who weren’t.

Match the mode to who started the conversation and both types of cold calls get easier and stop feeling like combat.

For the exact words that turn a qualified conversation into a booked appointment, download the free Cold Calling Guide with 25 word-for-word ways to ask for the appointment. Run it for two weeks of call blocks and watch how many more real conversations you have. And if your whole team needs the full system, that’s exactly what we build in The Cold Calling Edge training.

What Salespeople are Asking About Cold Call Questions

When should you ask questions on a cold call?

After the prospect engages, not at the open. Open with a because statement that gives them a relevant reason to keep listening, then use questions to learn their current state, find the pain, and identify the buying window before asking for the appointment.

Should you open a cold call with a question?

No. Openers like “How are you today?” and “Did I catch you at a bad time?” force a stranger to do work for someone they have no reason to help, and they mark you as a scripted rep. Open with who you are, why you’re calling, and a relevant reason why they should care.

What are the best qualifying questions to ask on a cold call?

Work three zones: current state (“How are you handling this today?”), technical (“How many of those are you using right now?”), and the buying window (“When does your current contract come up?”). Ask one at a time, listen, and stop when you have enough qualifying information to justify a meeting.

How many qualifyinf questions should you ask on a cold call?

You’ll typically get two questions in before they push you off the phone (though some people will engage in a much longer conversation). Just remember that you can call back and ask more questions later.

Are questions different when following up on inbound leads?

Yes, completely. The buyer initiated, so questions lead from the beginning: “What prompted you to reach out?” Ask questions to learn about your prospect before you pitch the next step.

How should you prepare before making a cold call?

Prepare enough to be relevant and no more: build your target list in a separate time block, research each prospect for a couple of minutes, and craft one because statement that connects your call to their world. Know your ask before you dial. If preparation routinely eats your call block, it has stopped being preparation and started being avoidance.


Related article: Why Cold Calling Will Never Die

Related e-learning: Qualify Better and Win More

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