The Greatest Discovery Questions

Great discovery doesn’t come naturally… it is learned. When prospects get on the phone with you there is a chess game that begins. You want to gain a deep understanding of their problems and make sure your solution can fix their problems. The hard part is getting them to open up.

You have to remember that buyers don’t fully trust you on the first call. They don’t know you, it might be their first time buying a solution or they’ve been handed a task which they have no context. You need to build rapport and trust.. This provides insight on how they might be evaluating and buying.

Once you are there you don’t want to get into “feature” questions. Something like “what automations do you want in place?” Or closed ended questions that result in a yes or no. “Is this an important project?” You don’t really gain anything when you ask these types of questions.

Imagine in your 1:1 if you get asked about the deal and you can only tell them “Yes. They need automations and want it ASAP. That’s why they want to buy it.” Your reporting manager will probably have a stroke if they are not already doing some deep breathing.

So how do we “un-gray” more of the map so we can see the terrain? Great, open ended questions that get people talking. They feel more comfortable and you establish credibility in the eyes of the buyer. After I set up my upfront contract with an agenda here is one that I loved to ask…

What compelled you to reach out to us?

You can get insight into how they have heard about you as well as problems they are having. Knowing if that got referred your way by a current customer or they are friends with a board member who recommended us… those are pretty important to know.

Also, they may walk you through problems they are having and how they want to solve them. We have too many support requests dropping out and customers are leaving. I can immediately start to understand how many times this is happening and what the average customer contract size is.

This allows me to do some fast mental math to justify the spend of the purchase. If 100 tickets are dropping per month from a lack of notification then I can reduce that 100%. If an average customer contract is $75k X 3 saves per month = $225k in savings per month. ROI established, quantifiable pain achieved… Now I need to understand all the people involved in the process.

How have you evaluated and bought software in the past?

There are so many great things that come out of this. You can understand how they buy solutions, who is involved in the decision making process as well as a timeline on how to do it. You can also get some insight on the level of success they’ve had in solving this problem. This allows you to ask…

How many times have you tried to solve this in the past and what was the result?

If you wanted to get a sense of whether or not this is a deal worth pursuing then there is nothing that beats this one. This allows you to understand how good your champion is at pulling projects across the finish line.

Additionally, you can get a sense of potential obstacles in the deal and get in front of them. “We tried last year but couldn’t get the spend approved…” That’s concrete intel and allows you to uncover who owns the budget and how to get to them. Which opens up another great question…

Which executive is sponsoring this project and how do they like to get involved?

If you hear a “they don’t like to get involved at all” then that’s a major red flag. They should answer if they want to see a final demo and/or a final presentation of a potential solution. That is pretty typical of an executive buyer.

In some VERY rare cases you will get an exec on every call but those are few and far between. You have a better chance of winning the lottery than having that happen.

But this does allow you to start to establish a timeline. You’ll need to understand the compelling event that’s driving this.

What other projects is the team working on and when will this one need to go live?

I actually heard an SDR ask this when I was a VP. It blew me away at how good it was and it was a little embarrassing that I didn’t think to ask this in 20+ yrs of sales. We constantly make the mistake that we are the center of the universe and they are not working on any other projects. This is a good reality check on how important this is to them.

If they are deploying an ERP and that is tying up all the resources then you know it'll be 10-16 months. Deal is dead.

On the other hand, they are wrapping up a project now and this is the next one slotted to begin in 8 weeks using the Q3 budget. Great! We have a timeline, compelling event and budget confirmation.

What happens if this doesn’t get completed?

This gives a sense of urgency depending on the answer. “This is tied to a budget and other projects cannot commence until this is completed.” Fantastic, that’s a pretty strong compelling event.

“This is tied to one of our 2025 initiatives set by our CEO.” Also a great compelling event and I feel pretty good about this one.

“We’ll just tackle it in Q4 if we miss the deadline.” This one is definitely NOT GOOD. This has all the tell-tale signs of a deal kicking forever because the champion or organization is not highly motivated to get it done.

Asking good questions helps the prospect understand their needs as well. If you have a coherent process of questioning that builds it is very valuable for them. It forces them to organize their thoughts, make sure they understand their true needs and how many people they need to partner with internally. Also the consequence if it doesn’t get done on time and on budget.

I am a big believer in great discovery questions and how much it can help in your deal. Asking them not only gives you insight initially on the deal but when it stalls out you can understand what moves need to be made.

99.9% of deals are won or lost on the first call. Knowing what questions to ask is very valuable in the process. Getting the right information lines up everyone for success on the opportunity. Try asking these questions in a row and tell me about the results.