Asking Questions to Uncover Opportunities

By Kristen Hayer

The regular meetings and calls that a Customer Success Manager has offer a terrific chance to uncover opportunities to retain and expand customer relationships. In addition to learning about selling opportunities (upgrades, professional services, new products), a CSM can also uncover needs related to retention (improved or broader utilization) and engagement (training, user groups, conferences). Unfortunately, most CSMs don’t have a background in consultative selling to provide a framework for discovering opportunities.

A simple approach to uncovering client needs is asking a systematic series of open-ended questions. This technique is a sales tactic, but in the loosest possible sense of the word. In the context of customer success, sales can mean anything from getting a customer to sign a renewal agreement to simply persuading a client to take a free class that will improve their experience with your product. Follow these 3 steps to learn more about your clients and uncover opportunities for selling, retention and engagement.

Step 1: Understand the Company

Do your homework, both behind the scenes and in conversations with your customer. Start by doing some online research. If you’re lucky and have a research tool like or InsideView, use that to learn about any company news, initiatives, or funding that could create opportunities to use your solution in different ways. A quick Google search or run through the customer’s website can also turn up great information. From there, ask your contacts if there are any new initiatives they are focused on this quarter. Even if those projects seem unrelated to your solution, they can impact timelines and priorities so it is important for you to be aware of them. Finally, get a broad view of your client by speaking with several different people at the company. Each of your contacts will have a unique perspective on the organization’s priorities.

Step 2: Ask about Problems

As a Customer Success professional, it can be very tempting to focus solely on positive interactions and outcomes. However, digging into problems is the only way to uncover opportunities. Ask questions when a customer expresses an issue; when they they complain about something that is bugging them or share challenges they are running into. If your customer isn’t bringing up problems on their own, you can spur the conversation by inquiring about the initiatives you uncovered in Step 1. Do you suspect they might be running into a problem some of your other customers have experienced? Ask about it. What is happening? How are they dealing with it now? What other concerns is it causing? Ask questions until you have solid understanding of the problem your customer is facing.

Step 3: Dig into Value

Once you understand the customer’s issue, it’s time to go one layer deeper. Ask about the impact the problem is having on their business. Is the problem costing them money? If so, how much? Is an issue taking up way too much time? How much time are they spending on it each week? Digging into the quantifiable impact of a problem will help you understand the value of a solution. When you can present your solution in terms of value, you are in a much better position to persuade your client to renew the agreement, upgrade, or take that free class. It can feel awkward and invasive the first few times you try asking these kinds of questions, so start with an easy one like, “Wow, how much do you think that is that costing you?” or “That seems like it’s taking up a lot of your time, how much of your week do you have to spend on that?” You’ll be surprised by how much customers are willing to share.

Once you’ve uncovered an opportunity and the value your solution can offer the customer, the next steps will depend on how your customer success team is set up. If you hand off selling opportunities to a sales team, set the expectation with the customer that you’ll have a rep follow up, and pass along all the great information you uncovered. If you’re the one working on the opportunity, set up any next steps with your client and go from there.

There are various methodologies for this type of approach, and if you’re interested in learning more about consultative selling, I would recommend reading SPIN Selling (a classic, research-based book) or The Challenger Sale (the current darling of consultative selling).

Want deeper training on how to ask questions to uncover opportunities? The Success League is a customer success consulting firm that works with executives who are ready to build and develop a top performing team. We offer online classes and workshops on selling as a CSM. Visit our Training page to learn more.