Lead generation questions: what to ask leads, and the ones everyone asks you

    · 7 min read

    "Lead generation questions" can mean two things, and both are worth answering. There are the questions you ask a lead to find out whether they're worth your time. And there are the questions people ask about lead generation itself: what counts as a lead, how many you need, whether any of it works.

    This post does both, in that order. The first set is the one that changes your pipeline, so it gets most of the space.

    Good lead generation questions do one job: they sort

    A question is only useful if the answer changes what you do next. If you'll send the same follow-up whatever they say, you didn't need to ask.

    I used to run discovery like a checklist. Fifteen questions, tick them off, feel thorough. Then I'd look back at the notes and realise I'd collected a lot of facts and no decision. The leads worth chasing were obvious in the first three answers, and I'd spent the other twelve being polite. Definitions for the jargon are in lead generation terms.

    So I now think of every question as one of three kinds: does this person have the problem, can they do something about it, and is now a sensible time. Everything else is colour. If you want the longer argument on why the sorting should start before you've said hello, I wrote it up in prospect and qualify.

    Questions that tell you if they have the problem

    Start here, because nothing else matters if the answer is no.

    • "What made you get in touch now?" For an inbound lead, this is the best opener I know. A real answer is a specific event. A vague one is a browser.
    • "How are you handling this at the moment?" Doing nothing is a different situation from having a half-working process, and you'd sell to each differently.
    • "What have you already tried?" People who've tried and failed are often better leads than people who haven't tried at all. They've already admitted the problem costs them something.
    • "What happens if this stays as it is?" Slightly blunt, but it separates a real pain from an interesting idea. If the honest answer is "not much", you've learned something cheap.

    None of these ask about your product. That's deliberate. A lead who describes their problem in their own words is far easier to help than one who's been asked to react to your pitch.

    Questions that tell you if they can act

    The classic framework here is BANT: budget, authority, need and timeline. HubSpot's guide to BANT gives example questions for each letter, such as asking who else will be involved in the decision, or what they currently spend on the issue. They're decent starting points.

    My view is that most people use them wrong, by asking them as a quiz. "What's your budget?" in the first call gets you a guarded number or a shrug. Asking around it works better.

    • "Who else will want a say in this?" Gets you to the real decision-maker without asking "are you the decision-maker?", which nobody likes answering.
    • "Have you bought something like this before?" Tells you whether there's a process, a budget line and a precedent, or whether you're about to be the first.
    • "How would you normally fund something like this?" A softer way into budget. Listen for whether it sits with them or with someone above.

    The warning sign I've learned to hear is a lead who can describe the problem in vivid detail and can't name a single person who would sign off on fixing it. Lovely conversation. No deal.

    Questions that tell you if the timing is real

    Timing is where optimistic reps fool themselves. "Q1" is not a date.

    • "Is there anything that makes this need sorting by a certain point?" A launch, a renewal, a board meeting. A real deadline is the most reliable timing signal there is.
    • "What would need to happen internally before you could start?" Surfaces the approval steps you'd otherwise discover in week five.
    • "If we got this right, what would you do next?" Oddly good. A lead with a plan has a next step lined up, and a lead without one is still exploring.

    If every answer on timing is "soon" or "when we get round to it", that's an answer. Write it down as one. A related read is how to follow up after sending a proposal, because the follow-up you send should match how real the timing is.

    Questions to ask yourself before you ask the lead anything

    Half of lead generation is upstream of the conversation. Before a lead ever replies, ask these of your own programme:

    • Who is this actually for? If you can't describe your ideal prospect in a sentence, your leads will be a mixed bag, and the mixed bag is why sales stops trusting marketing.
    • What counts as a qualified lead here? Write the rule down. Lead generation vs sales covers why the handoff is where most small teams lose people.
    • What do I do in the first hour after someone raises their hand? Speed matters, and so does having a system. My notes on a lead follow-up system are the practical version.

    What happens to the document you send afterwards

    Here's the beat where I'll mention the thing I built, once. After a good discovery call, you usually send something: a proposal, a one-pager, a deck. That's the point where a qualified lead goes quiet, and you're back to guessing.

    LiveDocument lets you attach a recorded walkthrough to a PDF or image, send it as one link, and see page-level engagement afterwards. It won't tell you who holds the budget, and it isn't a CRM, so it doesn't replace the questions above. What it does is show you what the lead did with your answer, which is often more honest than what they said on the call. Lead engagement is what they do, not what they open, and that's the signal worth qualifying against.

    Frequently asked questions about lead generation

    What are the best lead generation questions to ask a prospect?

    The ones that sort: why now, how they handle it today, who else is involved, and what has to happen before they could start. Pick four or five that fit what you sell. A short set you actually use beats a long one you skim.

    What is lead generation in simple terms?

    It's the work of finding people who might want what you sell and starting a conversation, either because they raise a hand or because you reach out first. The output is a person worth talking to, not traffic or impressions.

    How many leads do I need?

    It depends on your close rate and how many deals you need, which is why I'd work backwards from revenue rather than aim for a lead count. Counting leads without tracking what they turn into is how teams end up busy and broke. If you're deciding whether it's worth the spend, I've answered is lead generation worth it.

    Is lead generation the same as sales?

    No. Lead generation produces the lead, and sales turns it into a decision. They overlap in small teams because the same person does both, but the jobs are different, and keeping them apart in your head helps.

    Where should a small business start with lead generation?

    Pick one channel where your customers already are and do it consistently before adding another. I go into the trade-offs in lead generation for small business.

    I built LiveDocument because I was tired of sending good work into silence. If you know that feeling, it's at livedocument.com.

    About the Author

    Cameron James

    Cameron is the founder of LiveDocument. He writes about sharing documents, PDFs, decks and contracts, and why pairing a video walkthrough with a document beats sending it cold.