An old manager of mine at Dell once asked me, in the middle of a deal review, "Have you asked the hard questions here?"
It felt like going up a level in my sales education. I wasn't sure exactly what he meant, so I asked him.
We were competing with CrowdStrike on the deal. I felt like we were favourites to win it, but I could not quite articulate why I felt that way. And he blew my mind a little bit. He said, "Have you asked them directly: why would you not just buy this from CrowdStrike?"
Initially, that felt counterintuitive. Wouldn't I just be pointing them towards the competition? They might not even have been thinking about CrowdStrike until I said the name.
He told me, "Get your champion to articulate to you exactly why they can't just buy this from the competition. That reason is why you win. Get them to rehearse it to you. So when they meet with the economic buyer, it's like a song they have sung a thousand times."
This mindset really resonated with me. So I went away and built a document: "Potential Hard Questions to ask a prospect." I have been adding to it ever since. The best of that document is below.
what a hard question actually is
A hard question is not a rude question. These are the questions that are not easy to ask. Part of you will feel a bit uncomfortable asking them. However, these are the questions which you really need to ask, and you really need the answers to, if you want to win deals.
Most sellers spend entire meetings asking easy questions. Tell me about your environment. What tools are you using today?
A hard question is different. Why would you not just buy this from CrowdStrike? What is stopping this from happening? The answer that comes back might be a result of DEAL OVER. That might hurt. That is exactly why it is worth asking.
Because here is what my manager understood. The feeling I had, that we were favourites but I could not say why, is not knowledge. It is hope. His question exposed that in one sentence. I had a feeling. He wanted a reason, in the customer's own words, that we could bet a forecast on.
why we avoid them
Everyone knows they should ask about budget, competition, and who actually signs. Almost nobody does it, and I do not think the reason is a lack of training.
The reason is fear of the answer. You've already forecasted the deal, part of you has already planned what you are spending the commission on, it would be an about face to suddenly get told you have no chance of winning this deal.
If you ask why they would not just buy from the big name, they might not have a reason. If you ask what is stopping this from happening, they might tell you, and it might be something you cannot fix. The dream dies today. Whereas if you never ask, the dream gets to live for another quarter, sitting in your pipeline, quietly costing you the deals you did not work while you were nursing it.
Hard questions kill deals faster, and that is their job. A deal that dies in the first meeting cost you an hour. A deal that dies in month four cost you a quarter.
the song sung a thousand times
The deeper lesson in my manager's advice took me longer to see. The hard question is not really for you.
You will not be in the room when the decision gets made. Your champion will. And at some point an economic buyer, or a finance director, or a board, is going to ask them some version of the same hard question: why this, and why not the obvious alternative?
If the first time your champion hears that question is in front of their CFO, you lose. They will improvise, badly, the way everyone improvises under pressure.
But if they have already answered it, out loud, to you, in their own words, and you have sharpened it together over two or three conversations, then when the moment comes it is like a song they have sung a thousand times. That is what asking the hard question actually does. It is not an interrogation. It is a rehearsal.
This is also why the answer has to be theirs, not yours. A champion reciting your battlecard is obvious and weightless. A champion giving their own reason, one they arrived at because you asked and then shut up, will defend that reason like they built it. Because they did.
the seven questions
From the document. None of them are clever. All of them are slightly uncomfortable, which is how you know they are doing something.
- Why would you not just buy this from [the obvious alternative]? The original. If the answer is strong, you have found your win theme and your champion has rehearsed it once. If the answer is weak, you found out in week two instead of at the loss review.
- What is stopping this from happening? The question behind every stalled deal. It surfaces the real blockers, the budget that is not signed, the stakeholder who is not convinced, the project competing for the same money, while there is still time to work them.
- What happens if you do nothing? Most deals are not lost to a competitor. They are lost to the status quo. If the honest answer is "probably nothing for a year or two", better to hear it now.
- Is there money set aside for this, or would we need to build the case together? You are not demanding a number. You are finding out whether you are selling to a buyer or recruiting an ally. Both are fine. They are different jobs.
- Last time you bought something like this, how did it actually get signed off? Not "who is the decision maker". People flatter themselves about that. Ask what happened last time and you get the real process: the CFO who appears at the end, the security review that takes six weeks.
- Who is going to argue against this, and what will they say? Every deal has an opponent. If your champion cannot name one, they have not thought about it yet, and you have just prompted them to start before it costs you the deal.
- It sounds like this might not be a priority right now. Have I got that right? The scariest one and the most useful. Half the time you are wrong, and the buyer talks you back into the deal with more conviction than you could have generated yourself. The other half, you just got your time back.
There are plenty more. You should think about your company, the normal sales conversations you have and think about the questions that might make your stomach a little bit uncomfortable when you hear the answers. Those are the questions you should be asking more of.
the data, briefly
If you want numbers: Gong analysed 519,000 B2B sales calls and found the highest win rates among sellers asking 11 to 14 targeted questions, spread through the whole conversation rather than front-loaded like a checklist. And the questions that correlated with winning were about the buyer's problems and business, not their tech stack. The data says what my manager said, with more syllables.
the test
Take your biggest live deal, the one you feel good about. Now answer this, in one sentence, in your customer's words, not yours: why can't they just buy this from the obvious alternative?
If you can, you have probably earned your optimism. If you cannot, you have a feeling, not a forecast. And you know exactly which question to ask this week, and who needs to rehearse the answer.
If your champion has never answered the hard question to you, they will fail it in front of the person who signs.
The seven questions on this page are rehearsed live in our cybersecurity sales training, drilled until your team asks them without flinching.
James Irving is the founder of Emotive JLI, a sales consultancy for technical founders. He learnt to sell the old school way: 50 cold calls per day in a Manchester boiler room, then enterprise cybersecurity, then ThreatSpike, where he joined as the first commercial person and left with a £10M sales engine. Tell him what you've built or watch the stories.