3 keys to doing better discovery (and closing more deals).


Closing more deals is NOT about polishing up a slick closing technique, perfecting your pitch, or nailing your demo. In fact, whether a deal closes or not has very little to do with that “closing call” at all. 


Gong found (in an analysis of over 1,000,000 sales calls) that the greater indicator of whether a deal would close or not had to do with the discovery work done on calls before the closing call.


This aligns with my own sales experience… and that of others too:


Successful selling is about peeling back the layers of your buyer’s goals and problems and arriving at a solution together organically.


Here are the 3 keys to doing this better (and positioning your “closers” to close more deals in the process).


Lead with a helpful foot.


When you’re in sales and have quotas looming, the pressure is real. And it can be easy to get wrapped up in that.


However, this is when it’s most critical to set that pressure aside and turn your focus to your buyer.


Forget about your product/service for a second… how can you best help your buyer solve their problem or achieve their goal?


It could be that they’re not sure what solution they need. Or it could be that they’re not sure they need one at all. 


Rather than assume, dig into the details with them!

This mindset is critical, especially at the end of a sales period when everyone is sending discounts and pitch emails:

Again, I know this is not easy with the pressure from looming quotas. So to better enable yourself to lead with the helpful foot, remember – your pipeline trumps all. 


Make sure to fill it with short, near, and long term opportunities because you’re doing the right work with the right people, consistently. This will provide you a little breathing room.


Ask better discovery questions (like these). 


It’s critical to point out that there isn’t a one-size-fits-all approach to discovery (especially in enterprise sales), even though many sales organizations treat it like there is.  


Great questions for inbound leads will differ for outbound leads. And they will also differ depending on the stage of discovery you’re in too (i.e. the first call or further down the road where it’s “rediscovery”).


That’s why the best discovery isn’t about going down a “question checklist” but rather listening to what the customer is saying at every stage of the deal and responding accordingly. And then infusing what they shared with you into the context of what you’re sharing and asking.


You should always shoot to keep it relevant to the conversation while uncovering what’s important to the task at hand. And above all else, always connect it back to “why.”


Here are a few of my favorite discovery questions that help you uncover a prospective buyer’s real needs or goals.


1. What brought you my way?


Understanding why someone is getting in touch with you can help you understand from their perspective what they:


  1. Think you can help with
  2. Feel like they need help with 
  3. Why they’re open to the conversation in the first place. As Simon Sinek would say, ‘it starts with why’.


Since today’s buyers are typically well informed before they reach out, they usually have pretty solid preconceived ideas.


Keep in mind, they’re not always true. So asking this question helps you gauge where they are and what they’re thinking (as well as providing critical feedback to your internal teams as well: Marketing, Product, E-team, etc.).


Think of it as laying a foundation for each question you ask thereafter.


2. How do you currently deal with XYZ?


Once you have your head wrapped around the problem or goal your prospect has, this question will help you understand what they’ve already tried.


As Dennis articulates below, sometimes having the buyer articulate what they’re doing today can help them understand their process (and the gaps in it) better than they did previously:

This sets the deal up for success in 4 ways:


  1. It makes you look helpful – you helped them see something about their process they didn’t realize before.
  2. It helps you better articulate how your solution could help them –  If you know what they’re trying today and why it isn’t working, you’ll be able to better speak to how you could help them.
  3. It makes your solution even more valuable – Think about how this greater understanding will add up in terms of desire for your product/service!
  4. It’s an anchor back to their why – If you make it all about them and why they are speaking to you in the first place, talk about getting a seat at the table and keeping it.


And even in your solution isn’t the right fit, you’ll have left a positive impression for something like a referral or for their business in the future if they move companies.


3. Can you give me a recent example of XYZ?


It’s one thing to ask for them to describe a problem in their own words. But everyone’s perception of a problem is going to be different.


That’s why asking for a real example is so important – it brings real clarity to what’s really going on and leaves no room for making the wrong assumptions.


Troy Cook broke this down really well in his comment on a recent LinkedIn post of mine:

Real-life examples ensure you’re 100% on the same page and set you up to ask better, more impactful follow-up questions!


4. What is your decision criteria?


One of the things that separate truly effective salespeople from those who are just “order-takers” is their ability to understand why a buyer is buying.


That’s why I love this question (which I got from Keenan’s book, Gap Selling). 


The goal should be to know a buyer’s decision criteria to point where “you know before the customer whether or not they will buy or not.”


Having them articulate exactly what is going to go into their purchasing decision helps you understand what their “current state” is from their perspective and frame what the “gap” you’re trying to cover is.


5. What will happen if you don’t make a change?


In a crowded marketplace, salespeople can often lose sight of the fact that they have a “hidden” competitor – the option to do nothing.


This is especially true with enterprise buyers where many times the better business option is to maintain the status quo due to scale.


But by having your buyer articulate what they think about changing nothing, this will help you both better frame the problem or goal.


That, and it will help you better understand whether there is an opportunity there at all in the first place!


6. Many of our clients are facing challenges with A, B, and C. How are these areas affecting you?


This question is particularly helpful if your prospect hasn’t mentioned anything about pain points that you know are common with other buyers.


It makes you look helpful, yes. But more importantly, it ensures you’re covering all the angles on the deal (which is very important in big, complex deals you find in the enterprise world).


The more pain points you can solve, the higher the value your solution becomes. Simple as that!


7. What does success look like for you?


One of the biggest reasons deals fail to close is because you get through the demo and the buyer still feels like the solutions won’t be the best fit for their needs.


This question, when asked early on in the process, is like a shortcut to figuring that out.


If you can come to an agreement early as to what success would look like (in terms of desired results), it makes it obvious what you need to show them in order to earn their business. 


It also will shed light on whether you can actually help or not.


The last thing you want to do is get to the close and have them feel like “that was a was a waste of time.” But remember – if you can’t really help them, it’s a waste of yours too!


8. How do you think the Board would evaluate the success of this project?


The reality we face today in the dynamic world of startups is that many of our buyers will have a VC funding them. And with that, comes a board that will need to offer its input into deals of consequence.


By asking this, you’ll gain a greater understanding of how the board would view the outcomes of the deal.


This also helps you evaluate how much of a role the board will play in the final purchasing decision as well… something that is very important to ensure you don’t waste your time (or theirs).


9. When evaluating a new partner, what’s most important to you?


Many salespeople assume their only goal is to qualify to ‘yes.’ But the truth is, it’s just as important to qualify to a ‘no.’


Bad business hurts you in the short term and long term. You typically spend more energy getting a mediocre client across the line than one that’s a perfect fit. And one that’s not right for you will typically provide less LTV.


Why waste your time on something that was never made to be?


Asking this helps you understand what’s important and to confirm/deny if you align. It’s a much better use of both of your time to have an open, honest, and collaborative discussion. 


(Note: this is also a great anchor for later in the process to tie back to if you need it)


10. What’s missing from your current approach/process/tech stack/etc?


Buyers will contact you for any number of reasons that may or may not include the intent to buy.


Maybe they’re just curious. Maybe they want to learn more about potential opportunities they weren’t previously aware of. Maybe they were told to do a demo (yes, this happens). 


Whatever the case, you never want to assume. And that’s why I ask this question –  to avoid making an ill-founded assumption.


Always ask the questions to understand what their problems are (and most importantly why)!


11. Who else have you included internally to solve this problem?


There is rarely just a single buyer in any sales process these days. This is especially true in enterprise sales where the average is 6.8 people and climbing.


So you don’t want to be single-threaded with a single contact in the buyer’s journey. You’ll just end up having to start over with each person late in the process.


When you ask this question early, it helps you understand who is involved and pull them in right away.


Keep your discovery hat on all the way to the close.


One of the biggest misconceptions about discovery is that it’s something you only do at the beginning of the deal. 


Nothing could be further from the truth.


From the book Gap Selling, as Keenan puts it: 


“Your goal is not to ask specific questions… it’s to get specific information.” 


And since the conditions around deals often shift and morph over time (for example, when your customer brings others into the ‘mix’) you’ll have to embrace this process all over again. 

Never assume you know what your buyers are experiencing and what they want to achieve. Stay in discovery mode all the way through the close… and beyond.  


Wait… discovery AFTER the close?


New clients are 5x more expensive to acquire than keeping existing clients. Not only that, the additional profit potential from retaining existing clients is big:


Courtesy of invesp.


That’s why one of the most important things you’ll ever do as a sales organization is to keep your discovery hat on even after the close.


By staying in discovery mode well after the ink is dry, you’ll be on top of new issues or opportunities that may arise even after the deal is done, ensuring you’ll keep them delighted and engaged.


You’ve worked so hard to bring them on board, why let them go?


(Note: this is why so many sales organizations have a Customer Success team. But if yours doesn’t, this is still very important!)


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