The Strongest Sales Questions You Can Ask

This is the blog transcript of our video “The Strongest Sales Questions You Can Ask”. If you’d like to see more of our videos, you can subscribe to our YouTube channel here.

We all search for that one question or statement that will help us close the sale.

The truth is that there is no single question to help you actually make a deal happen. It’s a series of questions that you need to be asking your prospect, and yourself, to bring the deal to a natural conclusion.

So what are those questions? 

Hey everyone, I’m Ian Campbell, CEO of Mission Suite. Before we jump into today’s video, do me a favor and hit the subscribe button and ring the bell so that you’re notified whenever we post new videos.

Questions are everything in sales.

They’re what give us the information that we need to qualify our prospects. They tell us exactly what the issue is that the prospect is trying to resolve. They tell us what we need to know to build a solution for that prospect.

Questions tell us everything that we need to know to grow our business.

That is, if we know what questions to ask. And, of course, if we shut up and listen to the answers.

Questions in sales need to be open ended and probe for the right information. We all know that questions all boil down to some variation of who, what, when, where, and how.

So what are the right questions to focus on in the sales process?

Let’s take a look at my favorites.


The question of “why” is such a powerful question. 

Understanding someone’s motivation for making a change or implementing something new will help you quite a bit when it comes time to discuss your offering.

There’s a great video of a TED talk by Simon Sinek about the question of why people do anything. His talk primarily focuses on getting to the core of why you’re doing what you’re doing before talking about how or what you actually do, but there’s a lot of value in coming at that same question as a sales person to a prospect as well.

In his talk, Sinek essentially makes the case that if you can get someone on board with what you do, or what you’re offering then you can get them to stay with you until they can find something better. 

If you can get them on board with HOW you do something, you can get them to stay with you until they can find someONE better. 

But if you can get them on board with WHY you do something, they’ll walk barefoot through Hell and back with you.

Of course, I’m paraphrasing, but the idea holds true that because everyone has their “why”, if you can align your offering with that why, you’ll be coming at your sales conversation from a significantly stronger position.

Now don’t get me wrong, I’m not telling you to be inauthentic or to try to be manipulative here. People will be able to see through you if you’re blowing smoke.

But if it fits that your offer is in perfect alignment with their “why” then you can make sure to dial into that as you discuss that offering.

But you’ll only find out if you ask.

Next is your “How” question.

We’re kind of working our way through Sinek’s Golden Circle concept as we go through our questions, aren’t we?

How is a really important question because it helps to uncover the real impact that you might be able to make for this prospect. It’s one of my favorite questions because it can really dive into the heart of what they’re trying to accomplish in a very practical way.

I’ll use myself as an example here. Let’s say I’m working with a business owner and I find out that their “why” for talking to me about automating their sales processes is that they need to work less on generating new revenue and focus more on building out the next level of their service offering.

Well that’s a perfect “why” in my world, and we fit really well into that.

Now let’s dive into “How”. 

I need to know how this business owner expects that to happen to make sure that we’re still well aligned.

For example, if he says that he’s planning on building a series of funnels to manage the lead flow and make sure that he’s only talking to prospects who are ready to roll and make a deal, then that’s perfect for me.

On the other hand, if he says that he needs to automate the lead generation aspect of the sales process through LinkedIn and Facebook ads because he doesn’t have any way to get leads in the first place, well I’m not as clear of a fit there.

Sure, I can still implement a system to make sure that the leads that he does generate are managed well and all, but I’d be better off making an introduction to one of my social advertising partners because they’re a better fit for the part of the solution that he wants to work on right now.

That way I still get to provide value to this person, and I set myself up for a good relationship when he gets that part of his process dialed in.

What’s your favorite sales question to help you get the deal closed? Let us know down in the comments and, while you’re there, give this video a like so that we know that you’re getting something out of it.

On to “What”

Continuing out the Golden Circle, “what” is still a necessary question to ask as you’re qualifying your prospect. This should be pretty obvious, but I find it’s helpful to make a point to say so just the same.

You need to know what the prospect is interested in buying to solve their problem. Continuing down our example, if I find that this business owner that I’ve been talking to about automating their sales process is a perfect fit for me when it comes to why they want to do it and how they want to do it, I still need to know what they want to implement to make it happen.

Yes, Mission Suite is a CRM and sales automation software platform, and I think it’s perfect for everyone, but maybe it’s not what they’re looking for. Maybe they have their heart set on one of my high priced competitors. 

Maybe they don’t really want a CRM, but just want a system to automatically send these leads down an email path but doesn’t really need to track any other interactions with those leads.

If I know what they’re intentions are when it comes to the systems that they want to work with, I can make a decision for myself to try to keep the conversation going and see if I might be able to show enough value for them to consider Mission Suite or simply move on because they’re clearly not going to budge.

On the flip side, if I find out that the business owner I’m talking to doesn’t know what she wants to implement and is open to exploring her options, now I have a perfect opportunity to discuss why Mission Suite is a good fit.

And I’m not fighting an uphill battle to do so.

Both scenarios can land me a new client. But which one sounds more appealing to you?

And, finally, the question of “When”

This question is less about qualifying a prospect and more about setting your own expectations.

When you’re selling, timelines are important. By the time you get to this question, you already know that they’re ready to do something, and it’s easy to let excitement carry you away and try to rush the deal.

We all want things to happen on OUR timeline.But what about their timeline? When will they be ready to move forward?

More often than not, making a deal happen is going to require time on both sides to implement. It’s your job to implement, so you’re always ready to roll! But remember that this is most likely just ONE part of their job, if it’s even a part of their job at all.

You have to figure out how to fit in THEIR calendar, not how to make them fit in yours.

I know that, in the past, the goal was always to get the deal to happen as soon as possible. I’m as much to blame as any other sales person for using fear, uncertainty, and doubt to create a sense of urgency and make something work faster than I should have.

What did that lead to, though? 

Well, every now and then it led to successful customer relationships, I have to admit that. But more often than not, it led to a client who was frustrated at having their arm twisted, reluctant to really do the work that needed to get done, and never really trusted me as the sales person.

What’s more, it often led to projects never actually getting off the ground, which led to more frustration, which led to an angry client and a much shorter than average client lifespan.

On the flip side, when I was able to hold off on the pressure tactics and let the deal flow naturally, I gained the trust and goodwill of the client, we were able to work together to implement our solutions, and the longevity of my relationship with that client increased significantly.

There are plenty of people who need to act on a solution like yours now. You’re much better off going to find them and leaving the people who aren’t ready to move forward on your follow up list.

As long as you know their timeline, and it’s not unrealistic on your end, they’re probably still a good opportunity. 

All you need to do is ask them when they want to move forward. And then give them the time that they need to get there.

Hey I hope you got something out of this video. And if you did, go ahead and give it a thumbs up and maybe a share so that others can see it too. Also, don’t forget to subscribe to our channel and ring the bell so that you’re notified whenever we post new videos and while you’re at it, check out these videos too!

We’ll see you next time around!

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