While everyone else is playing checkers...
They’re playing chess. ♞
Most salespeople think they win by talking.
Explaining more.
Handling every objection.
Listing features.
Trying to prove they’re the best choice.
Elite salespeople know that’s exactly how you lose control of the conversation.
Because in every sales conversation, there’s one person leading...
...and one person following.
The amateur thinks the person doing the talking is in control.
The expert knows it’s the person asking the questions.
♟
It doesn’t.
Persuasion comes from asking the right questions.
The right question uncovers a problem.
The right question creates clarity.
The right question shifts belief.
The right question makes someone sell themselves.
That’s why the highest-paid salespeople rarely dominate the conversation…
They direct it.
Like a chess grandmaster, they’re already thinking five moves ahead.
Every question has a purpose.
Every answer gives them information.
Every conversation moves exactly where they intended it to go.
Over the last decade I’ve sold across retail, technology, B2C services and founder-led B2B businesses. Those conversations have generated millions in revenue.
So I’ve compiled 39 of the highest-leverage sales questions I use to uncover problems, create urgency, challenge assumptions and move conversations forward naturally.
I’ve marked the questions that are particularly useful for B2B selling, but you’ll notice most work in any sales environment.
Because whether you’re selling software, consulting, coaching or candles...You’re never selling to a business. You’re selling to a human being. And human psychology doesn’t change.
Keep this beside you on your next sales call.
One great question can change the entire conversation.
♞
What made you start looking at this in the first place?
On a scale of one to ten, how big of a problem is this for you?
What makes you feel like you don’t have [desired outcome] right now?
What are you doing right now when it comes to [area] that’s causing you to not have the results?
Are you 100% happy with [current situation / current provider]?
What’s this costing you right now if nothing changes?
How long has this been going on for?
What made you decide to look into solving this now, and not six months ago?
How is this issue affecting the wider team or other departments? [B2B]
If we just zoom out a little, where do you want to be in [X months] in terms of your goals?
If you had [desired outcome] already, how would that change things for your business?
What would it mean for you personally if you actually had [desired outcome]?
So let’s say there was a way to help you with [problem]. What would that allow you to do?
What have you already tried to fix this so far, and how did that go for you?
If nothing changes in the next [X months], where does that leave you?
Is it more important for you to keep costs down or to [get a solution to this problem]?
If we fixed this, what would that free up for you and your team? [B2B]
What’s the cost to the business if this stays unsolved through the next [quarter / financial year]? [B2B]
What’s most important to your team when choosing a solution: budget, integration, support, or scalability? [B2B]
On a scale of one to ten, one being not interested at all and ten being 100%, where do you sit right now?
If this were the same price as [the competitor / your current option], would you move ahead with this today?
What would need to be true for this to be an easy yes?
Is there any reason you wouldn’t want to get started today?
How do you feel about everything we’ve covered so far?
Based on everything we’ve covered, do you feel like this could be the answer for you?
On a scale of one to ten, how aligned is the team on moving forward with this? [B2B]
Walk me through how a decision like this normally gets made on your side? [B2B]
Besides yourself, who else needs to be part of this decision? [B2B]
What would need to happen internally for this to get the green light? [B2B]
When you say you want to think about it, help me understand, what specifically do you need to consider?
When you say it’s too expensive, what do you mean exactly?
If money weren’t the issue at all, would this be something you’d want?
What would have to happen for you to feel confident moving forward?
Is it the [investment], the timing, or whether it’ll actually work for you?
When you say you need to check with [other person], what do you think they’ll want to know?
When you say [objection], is that the only thing holding you back, or is there something else?
When you say you need to take this to the team, what do you think they’ll want to know? [B2B]
What concerns do you think [the decision maker / your team] might raise that we haven’t covered? [B2B]
What would you need from me to make the internal case easier? [B2B]
Before your next sales call, ask yourself: “What’s the one question that would change this entire conversation?”
Founder, Empower Sales™
The Empower Sales School of Sales & Influence is where founders, closers and business leaders learn the psychology, positioning and communication skills that make sales feel effortless.
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I work privately with a small number of founders who want to master high-level sales strategy, messaging and influence.
The conversation doesn’t stop here. Find me on Instagram and Tiktok for daily lessons in sales psychology, influence and strategic persuasion.
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