9 Questions to Think Like a Client and Win Big Deals

We talk a lot about empathy in business, but we don’t make the idea practical and tactical for salespeople, making it easy to execute. Thinking like a client can help you discover what they might need from you and how you can best help them.

Here are nine questions that are worth answering, either individually or with a small team dedicated to improving their sales results.

What Would Cause You to Change?

When you are prospecting and scheduling meetings with your dream clients, you are doing so to create a new opportunity that will move you towards your goal and target. There is nothing wrong with working to meet your goal. But your prospective client may—or may not—be considering some significant change.

The way you serve your prospective client is by helping them explore the reasons they might change. Whether you use a more traditional approach, asking questions that allow your contacts to share the areas in which they believe they need improvement or a modern approach that helps your client learn something about themselves and their company, understanding what should cause them to change improves this part of the sales conversation.

What Results Would You Find Challenging?

While you can occasionally be surprised by a client with some unique challenge, one you have never before seen, most of the time, you know what results your clients and prospective clients struggle to produce. Thinking like your client lets you recognize the results they struggle with, why they have trouble in these areas, and the root cause of their problems.

Your experience with your existing clients provides you with the knowledge you need to know what results your prospective clients will need help improving. You might still need to identify the prospect’s “hot button,” but you should know the common hot buttons that are universal enough to be true in most places.

In What Area Would You Need to Know More?

Those who work in consultative sales and aspire to be considered a trusted advisor have always taught their clients how to think about their business and the decisions they make. They’ve always provided context for a conversation that helps the client make sense of their world and the dissonance that often precedes real change.

Were you in your client’s shoes, what would you need to know to have a higher resolution view of your challenge or your opportunities? Answering this question gives you a running start on building the insights you need to provide a clearer lens and compel your client to change.

What Would Change Mean for You?

Not you, the salesperson. You, the client. What would change mean for you if you were the client? Would it mean a major initiative that would take time, money, and board approval? Would it mean displacing a partner who has, up until this time, done excellent work, even if they are now complacent? Would it mean restructuring their business or a loss or increase of headcount?

Recognizing the real implications of the change you are trying to enable can help your client know what they need to consider, how to manage the conversation, and prepare the rest of the organization to engage in the conversation.

Who Would You Need on Your Team?

Placing yourself as the head of this initiative, who would you expect to need to bring into the conversation to develop the right solution, build consensus, and gain support from the executive leadership team, or some senior leadership representative?

Thinking this through, including going back over the common roles and titles that attended meetings with your clients and the prospective clients who moved forward with you gives you the ability to offer advice as to how to build consensus inside your client’s company, controlling the process, and helping them to have the conversations and make the necessary commitments.

What Might Work for You?

We don’t always pay enough attention to how powerful developing a solution can be when it allows you to collaborate with your client. But you can start that conversation by taking all the information and data you have collected through the process to develop a theory about what might work for you if you were the client and not the salesperson.

Discovery and solution design is almost always a nonlinear, iterative process in a complex sale. Serving your client means coming up with a starting point that engages your client, allowing them to make adjustments and customizing the solution to make sure it is going to produce the better outcomes you are selling.

How Do You Justify the Expense?

If you were the one sitting behind your contact’s desk, you would expect someone from your team to ask you what you are doing, why you are doing it, and what it is going to cost. It’s important to remember that your client is going to be asked about the investment you are asking them to make.

You help your client and make selling easier if you do the work to make a business case that proves the return on investment makes sense to the client and all the people who are going to vet it.

What Concerns Do You Have?

What would you be concerned about if you were making the buying decision you are asking your client to make? What would stop you from moving forward, and what would you need to be assured to agree to move forward? Your answers here are more than likely to be very close to the ones your contacts have when you ask them to commit and sign a contract.

Whether you forestall these concerns by working to address them throughout the process or ask to address them as you come to the end of the sales conversation, knowing what your clients are going to be worried about and being prepared to resolve their concerns will improve your approach—and your win rate.

What Will It Take to Execute?

As the client, what do you believe you need to execute the new solution you are buying? What help are you going to need from your potential partner, and what kind of support is your team going to need? What sense of dread would you feel if you agreed to a new solution without knowing what to do to capture the promised value?

The more clearly you outline precisely what your client is going to need to do to succeed with what you sell them, the better the guidance you can provide them. You will also reduce the time it takes them to produce the better results you owe them.

If you want to improve your effectiveness in the sales conversation, you could do worse than spending a little time putting yourself in your client’s chair and considering what you would need from a consultative salesperson who is a professional b2b salesperson.

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