Discovery Call Question Bank: 50 questions and what a good answer sounds like
The questions I keep coming back to on B2B SaaS discovery calls, grouped by stage. Each one says why I ask it and what a good answer sounds like. Filter them, copy one, or print the set you need for your next call.
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- 50 questions, why to ask each, what a good answer sounds like
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- 5 minutes to read, a 30-minute call to use
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Showing 50 of 50 questions. Printing prints what's shown.
- 1Situation
“What made you take this call today, and not three months ago?”
- Why I ask it
- The trigger. Something changed: a hire, a lost deal, a board meeting. If nothing changed, nothing will change after this call either.
- A good answer sounds like
- A specific event with a date on it. "Our second sales hire starts in January and there's nothing to onboard her into."
- 2Situation
“Walk me through what happens today, from the moment [the problem] shows up to when it's dealt with.”
- Why I ask it
- I want the real process, the steps and the people, not the org chart version. The gaps are in the steps they skip over.
- A good answer sounds like
- Names, tools and handoffs. "Lisa exports it on Monday, I check it, then it sits in a spreadsheet until someone asks."
- 3Situation
“Who touches this in a normal week?”
- Why I ask it
- Maps the users and the future champion before you ask about decision makers, without sounding like you're hunting for the boss.
- A good answer sounds like
- Several names and roles, ideally including one person who hates the current way of doing it.
- 4Situation
“What are you using for this right now, including the spreadsheet nobody likes to admit to?”
- Why I ask it
- The real competitor is usually a spreadsheet, a habit or an intern. Naming it out loud makes it fine to talk about.
- A good answer sounds like
- Honest and a little embarrassed. "Officially HubSpot. Really, a Google Sheet Mark built in 2022."
- 5Situation
“How did it end up working like this?”
- Why I ask it
- Tells you whether the current setup was a decision or an accident. Accidents are much easier to replace than decisions someone senior made.
- A good answer sounds like
- "It just grew." Be careful with "our CTO designed it": that person needs to be in the conversation, soon.
- 6Situation
“Have you tried to fix this before? What happened?”
- Why I ask it
- A failed attempt is the best information you'll get all call: what they tried, why it died, and what they'll be scared of this time.
- A good answer sounds like
- A story with a reason. "We bought a tool, nobody used it after onboarding, we cancelled at renewal."
- 7Situation
“Where does this sit on your list this quarter, next to everything else?”
- Why I ask it
- Everybody has the problem. I want to know if it's in their top three, because anything below that loses to the next fire.
- A good answer sounds like
- A rank and a reason. "Top two. The board asked about it twice."
- 8Situation
“What does a good month look like for you, in numbers?”
- Why I ask it
- Gives you their scoreboard in their own words, which is the language your proposal should be written in later.
- A good answer sounds like
- A metric they own. "Twenty demos booked and pipeline over €400K."
- 9Pain
“What's the most annoying part of this, honestly?”
- Why I ask it
- "Honestly" gives permission. The first answer people give is the polite one; the annoying part is usually the real one.
- A good answer sounds like
- Emotion plus detail. "Chasing people for updates. I lose every Friday afternoon to it."
- 10Pain
“When did this last go wrong? What happened?”
- Why I ask it
- A recent, specific incident beats any general complaint. If they can't remember one, the pain might be theoretical.
- A good answer sounds like
- A date and a consequence. "Last Tuesday. A demo request sat for four days and they signed with someone else."
- 11Pain
“What do people do to work around it?”
- Why I ask it
- Workarounds are the pain made visible. Every one of them is time somebody spends that your product could give back.
- A good answer sounds like
- A described hack. "We paste every lead into a Slack channel so nobody misses one."
- 12Pain
“Who complains about this the most?”
- Why I ask it
- That person is your likely champion, and the one who'll push for it internally when you're not in the room.
- A good answer sounds like
- A name, said with a smile. "Sales ops. Every single standup."
- 13Pain
“If you could change one thing about how this works by tomorrow, what would it be?”
- Why I ask it
- Forces a priority. Their one thing is the headline of your proposal.
- A good answer sounds like
- One concrete thing. A list of eight things means nobody has decided what the problem is yet.
- 14Pain
“What have you already decided you won't accept from a fix?”
- Why I ask it
- Gets the deal-breakers out early (the integration, the migration, the price model) before you spend three calls on something they'll reject.
- A good answer sounds like
- Clear constraints. "We're not moving off Salesforce. Anything that needs that is out."
- 15Pain
“How do you know it's a problem? What are you looking at?”
- Why I ask it
- Separates a measured problem from a felt one. Measured problems get budget. Felt ones get "let's revisit in Q3".
- A good answer sounds like
- A number or a report. "Response time is 26 hours, we pulled it last month."
- 16Pain
“Is this a problem for the company, or mostly for you?”
- Why I ask it
- A personal pain with no company cost is a weak deal. A company pain nobody personally feels has no champion. You want both.
- A good answer sounds like
- Both. "It's my headache, and it's also why we missed the target."
- 17Pain
“What happens on the days it works fine?”
- Why I ask it
- Shows what's different on a good day, which is often the real fix, and stops you selling against something that's already solved.
- A good answer sounds like
- A specific condition. "When I'm in the office and catch the leads myself."
- 18Impact
“What does this cost you in a month, roughly? Time, deals or money, whichever is easiest.”
- Why I ask it
- Getting them to put a number on it is the whole game. Let them pick the unit: a number they say themselves beats any number you bring.
- A good answer sounds like
- A rough figure they own. "Probably two lost deals a month. Call it €20K."
- 19Impact
“If nothing changes, where are you in six months?”
- Why I ask it
- The cost of doing nothing, projected forward. Doing nothing is the competitor you lose to most, so make it visible.
- A good answer sounds like
- A worse future, in detail. "We hire two reps who have nothing to sell from and burn their first quarter."
- 20Impact
“What does this stop you from doing that you'd like to be doing?”
- Why I ask it
- The opportunity cost is often bigger than the direct cost, and it's the part founders actually care about.
- A good answer sounds like
- An ambition. "I'd be on customer calls instead of in spreadsheets."
- 21Impact
“Who else feels this, and how?”
- Why I ask it
- Spreads the pain across the org chart, which spreads the reasons to buy.
- A good answer sounds like
- Other teams, with their reason. "Finance hates it, the forecast is wrong every month."
- 22Impact
“Does this show up in the numbers your board or investors look at?”
- Why I ask it
- If it touches a number someone senior watches, it gets priority and budget. If it doesn't, you need another angle.
- A good answer sounds like
- Yes, with the number. "Sales cycle. It went from 40 to 70 days this year."
- 23Impact
“What would fixing this be worth to you?”
- Why I ask it
- Their valuation, not yours. It's also the ceiling on what they'll pay, and they've just told you what it is.
- A good answer sounds like
- A value well above your price. If it comes out below, better to know on call one than on call four.
- 24Impact
“Have you put a number on this before, for anyone else?”
- Why I ask it
- If they've already built a business case, you can use it. If they built one and it got rejected, you need to know why.
- A good answer sounds like
- "Yes, I showed the CFO in September." Then ask if you can see it.
- 25Impact
“What changes for you personally if this gets fixed?”
- Why I ask it
- People buy for the company and decide for themselves. A promotion, fewer weekends, finally hiring: that's the reason they'll fight for it.
- A good answer sounds like
- Something human. "I stop being the bottleneck and get my evenings back."
- 26Impact
“What's the deadline that makes this urgent, if there is one?”
- Why I ask it
- Urgency needs a date. A real event (a hire, a launch, a renewal, an audit) beats "as soon as possible" every time.
- A good answer sounds like
- A date on a calendar. "The new team starts on 6 January."
- 27Decision process
“Besides you, who'll have an opinion on this?”
- Why I ask it
- Softer than "who's the decision maker", and you hear about the influencers too: the ones who kill deals quietly.
- A good answer sounds like
- Names and roles, including at least one person who isn't senior.
- 28Decision process
“How did you buy the last tool of about this size?”
- Why I ask it
- The last purchase is the map: who was involved, how long it took, where it got stuck. Far more reliable than how they think this one will go.
- A good answer sounds like
- A story with steps. "I found it, IT did a security review, the CFO signed. Six weeks."
- 29Decision process
“Who signs, and who can say no?”
- Why I ask it
- Often two different people. Legal, IT, procurement: anyone with a veto needs a plan of their own.
- A good answer sounds like
- Two names and an honest answer about the vetoes.
- 30Decision process
“What does IT or security need to see before something like this goes live?”
- Why I ask it
- In B2B SaaS this is where deals go to wait. Ask it on the first call, not when the contract is ready.
- A good answer sounds like
- A known list. "Our standard questionnaire, a DPA and SSO."
- 31Decision process
“Is anyone else in the company looking at this from a different angle?”
- Why I ask it
- Another team might be evaluating a competitor or building it themselves. Better to hear it now than at procurement.
- A good answer sounds like
- "Not that I know of," or an honest "Marketing looked at something similar last year."
- 32Decision process
“What would make you pick someone else?”
- Why I ask it
- Invites the objection while you can still answer it. Their answer is your competitor's pitch.
- A good answer sounds like
- A concrete criterion. "If you can't do Dutch and German."
- 33Decision process
“How will you decide: a trial, references, a business case?”
- Why I ask it
- Tells you what the evaluation looks like, so you can prepare for it instead of reacting to it.
- A good answer sounds like
- A clear format. "Two-week trial with three reps, then we decide."
- 34Decision process
“Who on your side would run this day to day?”
- Why I ask it
- The owner after the sale decides whether it gets used, renewed and expanded. Get them on the next call.
- A good answer sounds like
- A name that isn't the person you're talking to, said with some enthusiasm.
- 35Decision process
“If you were me, who else would you talk to before sending a proposal?”
- Why I ask it
- The best question in this section. They know the politics, so ask them to coach you.
- A good answer sounds like
- Names, plus a warning. "Talk to Anna first. She killed the last one."
- 36Budget and timing
“Is there a budget for this already, or does it need to be found?”
- Why I ask it
- Found budget takes a business case and a quarter. Existing budget takes a decision. Those are very different deals.
- A good answer sounds like
- Either, as long as it's clear. "There's a line for sales tooling, about €20K left this year."
- 37Budget and timing
“What have you spent on this problem so far, people's time included?”
- Why I ask it
- Anchors your price against what the problem already costs, and shows whether they've been willing to pay before.
- A good answer sounds like
- A rough figure. "A contractor for two months, so maybe €15K."
- 38Budget and timing
“When does your budget year start, and when is it decided?”
- Why I ask it
- Miss the planning window and a yes turns into next year.
- A good answer sounds like
- Dates. "The year starts in January, budgets lock in November."
- 39Budget and timing
“What range would this need to be in to make sense?”
- Why I ask it
- Asking for a range instead of a number gets an honest answer far more often. If their range and your price are far apart, say so on this call.
- A good answer sounds like
- A range with a rule. "Under €1,000 a month I sign myself. Above that it goes to the board."
- 40Budget and timing
“What else is competing for that same money?”
- Why I ask it
- Your competitor might not be another vendor. It might be a hire, a campaign or the laptop budget.
- A good answer sounds like
- An honest list. "We were going to hire an SDR with it."
- 41Budget and timing
“When would you want this working, and what's driving that date?”
- Why I ask it
- The go-live date, worked backwards, gives you the real decision date. If nothing drives it, it'll slip.
- A good answer sounds like
- A date with a reason. "Before the new reps start in January."
- 42Budget and timing
“What could push this to next quarter?”
- Why I ask it
- Asks them to name the risk while there's time to deal with it. The deals that slip had a risk nobody said out loud.
- A good answer sounds like
- A specific risk. "If the funding round drags on."
- 43Budget and timing
“If this goes well, how far does it grow: more seats, more teams?”
- Why I ask it
- Tells you the size of the account, not just the first deal, and whether the first deal should be priced to land.
- A good answer sounds like
- A path. "Sales first, then customer success if it works."
- 44Next step
“Based on what you've heard so far, is this worth another conversation?”
- Why I ask it
- A direct question gets a direct answer. A maybe now is cheaper than three weeks of follow-ups.
- A good answer sounds like
- Yes, and why. "Yes, if you can show us the Salesforce part."
- 45Next step
“What would you need to see next to move forward?”
- Why I ask it
- Lets them design the next meeting. Whatever they ask for tells you what they still doubt.
- A good answer sounds like
- Something specific. "A demo on our own data, with Mark there."
- 46Next step
“Who should be in the next meeting?”
- Why I ask it
- Every next step should widen the circle. The same two people in the same meeting three times is a deal stalling politely.
- A good answer sounds like
- New names. "Bring it to Anna and our ops lead."
- 47Next step
“Can we put it in the calendar now?”
- Why I ask it
- A next step without a date isn't a next step. Book it while you're both still on the call.
- A good answer sounds like
- A date and an invite, before anyone hangs up.
- 48Next step
“What would you tell your colleagues about this call?”
- Why I ask it
- Their summary shows what landed and what didn't, and gives them the words to sell it internally.
- A good answer sounds like
- Your value in their words. If they repeat a feature and not their problem, the call didn't land.
- 49Next step
“Is there anything that would make you say no that we haven't talked about?”
- Why I ask it
- The last chance to hear the hidden objection. People answer it more often than you'd expect.
- A good answer sounds like
- "No, it's really the price." That's at least an honest problem you can work on.
- 50Next step
“What's the best way to reach you if something comes up before then?”
- Why I ask it
- Practical, and the answer tells you how they work: email, WhatsApp, an assistant. Follow up through that channel.
- A good answer sounds like
- A channel and a time. "WhatsApp, mornings."
My first-call sheet: the ten I'd ask in 30 minutes
Leave your email and you'll see, right here, which ten of these I'd use on a first call, in order, with rough timings.
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A bank, not a script.
Fifty questions is a bank, not a script. On a real call I ask eight to twelve of them, and most of the call is follow-ups on the answers. They're grouped in the order a call usually runs: situation, pain, impact, decision process, budget and timing, next step.
Every question says why I ask it, because a question you don't understand comes out sounding like a form. And every one says what a good answer sounds like, because the answer is the point. A vague answer to a good question is information too. It usually means the pain isn't there yet.
The section founders skip is impact. They find the pain and start the demo. Without a number on what the problem costs, the proposal competes on price, and doing nothing is always the cheapest option on the table.
What to do once the call is over, so the answers don't die in your notes, is in the discovery to demo handoff.
Questions people ask
How many questions should I ask on a discovery call?
Eight to twelve. More than that and it turns into an interview, and prospects can tell. Pick the ones that fit the deal, ask them in roughly the order of this bank, and spend the rest of the call on follow-ups to what they said.
What is the most important discovery question?
The impact one: what does this cost you, roughly? A prospect who puts a number on their own problem has written your business case for you. One who can't usually isn't buying this quarter, however friendly the call was.
Can I use these questions in my own sales playbook?
Yes. Copy them, print them, put them in your playbook or your onboarding doc. A link back to this page is appreciated, not required.
Do I need to give my email?
No. All 50 questions, with why I ask each one and what a good answer sounds like, are free on this page, and so is printing them. The email only shows my first-call sheet: the ten I'd ask in 30 minutes, in order.
Calls go well and deals still stall?
Then it's usually what happens after the call. Send me your website and I'll record a 10-minute video going through it, your positioning and your sales process, with the three leaks I'd fix first. Free, in your inbox within 48 hours.