6 Questions to Help You Win Your Biggest Deal Ever

By Tom Searcy

Between two competing companies, whichever sales team has the most information wins. This is called reconnaissance. In this buyer-driven economy, if you want to make big sales, you must solve big problems for high-level executives – the kind of systemic, organizational problems that affect the overall output of your customer’s business. If you’re going to solve big problems, your reconnaissance must entail understanding what is going on in your customers’ industries as well as, if not better than, they do.

Public information is easy to find, but it is not particularly insightful and won’t give you much of an advantage – especially when you are going after large, complex sales. To land that much-larger account, you have to evaluate not just the selling process, but also any supporting technologies and all of the subject matter experts who participate in the overall process. The information you need to land your biggest deal comes only from inside the prospect company. You will get this information from the questions you ask early, but it is not just about asking questions. It is about how you word the questions and to whom you ask them.

Below are six questions to help you land your biggest deal ever – with insight into when and how to ask them.

1) What has changed in the past six months in your business – and what changes have happened because of it?

Of course, instead of “in your business,” you will phrase the question to be specific to the area or department you are investigating, but you get the idea. “Change” is the operative term. You need to understand the environment. If things are in flux, often that is an opening for solutions – not just a price fight.

2) What is the threshold of performance you need in a proposal to change what you are doing now?

By using the term “threshold,” you are setting a number to achieve, and the customer is establishing a performance floor for getting the business. Too often, we provide a guesstimate of performance and hope it will entice the prospect to change.

3) Who is involved in the evaluation process for selecting partners like us for new or additional work?

If you ask someone at the prospect company who the decision maker is, he or she will often answer, “I am.” Then, of course, when it is time to sign an agreement, you find out that the person is not. By asking a process question, you are not challenging the person’s power or authority. Instead, you are asking about process – which is less threatening and will get you more information.

4) For companies who do business with you on projects like this, what do you always expect and what will you never tolerate?

You might think the answers would be formulaic. However, my experience is that, after the prospect has given the usual responses, he or she will give you particular issues that reflect a past experience with a vendor. That experience has now set the absolutes for all go-forward selections.

5) How was the last provider on-boarded and how did that process go?

This question tells you a lot. First, it tells whether your prospect has made any changes in providers lately. If they have not, they may not know how or they may have a culture that is unwilling to change. The answer may tell you if they have a good process, or if you may have to provide the majority of the effort to on-board yourself.

6) Under what conditions will your company change to a new provider?

Often we are told that a company is not interested at this time. This question moves the conversation away from “yes” or “no” and moves it to the consideration of the elements that will change – possibly opening a door for future opportunity.

These six questions help you understand motivation, required performance, decision makers, and influencers. They will give you an edge when considering your strategy and approach and even help you decide if the business is worth pursuing.

Tom Searcy is CEO and founder of Hunt Big Sales – a sales strategy company that helps CEOs double the size of their company – and author of Life After the Death of Selling: How to Thrive in the New Era of Sales. Follow @tomsearcy.