If I asked you “What’s the most important skill to master to uncover buyer objectives ?”, what would you say ? Qualifying ? Needs analysis ?

You’d be wrong.

All of the above are important, but they’re not the most important. What is ?

Asking great questions.

Whenever I’m in front of my clients, I like saying “The quality of your sales depends on the quality of your conversations. The quality of your conversations depends on the quality of your questions”. 

Great questions elicit insights. Build rapport. Forge a strong, emotional connection with your prospect. Position you as a trusted advisor. Help you uncover the real, underlying buyer objectives.

Great questions do the selling for you. Click To Tweet

By the way, if you want to know more about which questions I LOVE asking my clients, check out these three posts:

But back to questions. Great questions sell. But it’s not just about asking questions (after all, if it were just about asking questions, you could ask whatever you want and “automagically” close more sales. And things don’t quite work that way, do they ?).

In addition to knowing which questions to ask (see above), you’ll also need a strategy for asking questions. Specifically, I want you to start thinking about questions in four categories.

Open Questions

Open questions are questions designed to get a prospect to talk. Again, don’t just use any questions (and please don’t use “What keeps you up at night”), but make sure that each question you ask serves a specific purpose.

Some of my favourite open questions are:

  • Why are we speaking ? Why did you decide to invest the time ?
  • Can you briefly tell me what you’re looking to accomplish ?
  • What is your #1 priority right now, and why ? (asking “why” is key)
  • Ideally, what would you like to see happen as a result of our work together 6–9 months down the road ?
  • How would you know this has been successful ? What would you see ?

Open questions are great to start conversations, and help uncover buyer objectives. But they’re not so great when you’re trying to validate options, work towards a decision or seal the deal. That’s when closed questions are a much better fit.

Closed Questions

Closed questions are questions that are designed to present a choice, and get a clear answer from your prospects (and by the way, the answer doesn’t always have to be yes/no, see below).

Some of my favourite closed questions are:

  • Are you looking to make a decision right now, or at some point in the future ?
  • How urgent is this for you: very, somewhat or not at all ?
  • (After I’ve walked them through 2–3 scenarios on how to work together): which option would you prefer ?
  • Are you ready to move forward, or is there anything else you need from my side ?

Closed questions are deceptively simple, but they’re a very powerful tool in any sellers’ arsenal of strategies. When used well, they can be used to convince buyers, create a sense of urgency and help close sales more quickly and effectively.

Asking open and closed questions are must-have skills for any seller, and mastering them is key to sales success. But, if you’re just using questions in this way, you’re missing out. There’s another, important secondary dimension to asking question.


Watch “4 Must-Ask Questions To Uncover Buyer Objectives” on YouTube 

Macro-level Questions

Macro level questions are designed to bring the conversation up to a higher level – to get your prospect to talk about their strategy, vision, long-term outlook and legacy.

If you want to get prospects excited and talking about their dream, or vision for changing their world (organisation, life, career, …), there’s nothing like asking a series of carefully crafted macro-level questions.

Some of my favourite macro-level questions are:

  • What are your priorities for the next 2–3 years ?
  • Let’s imagine this goes well: what would you like people to remember you for ?
  • At some level, we all work for more than money. What’s your primary motivation (for doing this) ?
  • Let’s step away from the short term for a second: what do you think the long-term impact of this will be ?

Micro-level Questions

Some prospects love to talk about the big picture stuff. And many prospects (especially in large organisations), love to talk in broad terms, using words like “enablement”, “overarching objectives” and “alignig stakeholders”.

And that’s fine, but all of those are very vague descriptions, and can carry a lot of meanings. For fear of being “found out”, or seen as not all that competent, many sellers are afraid to stop and ask them what they mean by those terms.

Big mistake.

Unless you know exactly what your prospect means by certain terms, you’ll always stay selling at a vague, conceptual level. You’ll never uncover the real details, the nitty gritty, the minute aspects of what they’re really trying to achieve.

Take a statement like “we need to align the main stakeholders”, for example. Whenever I’m coaching salespeople, I notice they have a tendency to leave things like this slide. Just nod, and keep the conversation going.

But the very best sellers do something very different. They dig, and they dig deep.

To start, they might say something like “Excuse me. ”Aligning stakeholders“ is a flag that can cover many loads. Would you mind expanding on that a little ?”.

Then, they use some of the questions below:

  • What exactly do you mean by _______ ?
  • Who should be involved ?
  • Why does that matter so much ?
  • In reality, what would that look like ?
  • What would be the most important/first step we’ll need to take ?

If you’ve ever been in sales training, you’ve probably been told to “ask questions”. And then left to your own devices, or given a few “sample” questions like I included in this post. Problem is: that’s either too broad, or too rigid.

Simply asking questions isn’t going to get you anywhere. And just having a carefully defined list of questions will often mean you’re not uncovering as much information as you could, or you keep turning in circles.

What you need is a framework – something that allows you to be systematic and strategic about asking questions. Scaling up and down as needed. Mixing it up as you move through the sales conversation. Asking questions that both clarify and define.

Try This: A Simple Tool To Uncover Buyer Objectives

Using the framework below, draft 4–5 questions for each category. Try to mix it up, and cover different topics, areas, angles, … The first few times, you might want to take this with you when you go to a prospect or client meeting. Then, as time develops, you’ll start memorizing certain questions, and develop your own set of go-to questions.

Question Categories