4 Strategic Questions a CSM Should Ask That Might Just Save a Renewal
Four strategic questions every CSM should ask customers to deepen relationships, surface the value you deliver, and protect renewals before they're at risk.

TL;DR
- Strategic conversations are big-picture discussions with customers that build trust and move them toward their goals, separating senior CSMs from those just starting out.
- Four questions can save a renewal: Why did you choose to partner with us? What's one thing we do better than others? What could we do to create a better experience? Do you refer us to others?
- Use "what" follow-up questions instead of "why" questions, which can feel interrogative and put customers on the defensive.
At a high level, strategic conversations are discussions with customers about big-picture items. They might take the form of a Quarterly Business Review, onboarding, or even a quick check-in call, but no matter what the context is, theyâre completely different from the âin the weedsâ day-to-day conversations. They focus on the long-term instead of the tactical.
From Weeds to Strategy and Conversations that Matter
For customer success managers (CSMs), itâs imperative to have strategic conversations with customers on a regular basis. These strategic conversations are your best opportunity to build trust with customers â which is a cornerstone trait of any CSM. Learn more about the power of building trust with your clients in this webinar. The ability to have a strategic conversation also separates senior-level CSMs from those just starting out. When you show that you truly care about your customersâ day-to-day pains, as well as their future goals, youâll gradually level up from a âresourceâ to a true âpartnerâ.
According to a recent article on Glide Consulting, a good strategic conversation between a CSM and a customer:
- Always puts the customer first, not the company
- Moves the customer closer to the end goal of where they want to be with your product
- Builds trust by asking powerful questions
- Shows that youâre genuinely curious about how the customerâs world works
Dig Deeper to Find the Real Impact
As a CSM, itâs also good practice to listen for the keywords where you can open up the conversation a bit more. The article goes on to suggest that, âWhenever a customer uses a generic word like âhelpful,â or âusefulâ, try to take the conversation deeper. What does that specifically mean to the customer? Another helpful tip to consider is when you ask a customer a follow-up question, use âwhat?â questions instead of âwhy?â questions. A âwhyâ question, like âWhy was that helpful?â can feel interrogative and question the customerâs judgment. A âwhatâ question, like âwhat about that was helpful?â demonstrates curiosity that comes across as genuine.â
4 Strategic Questions that Might Just Save a Customer Renewal
Below are several strategic questions that CSMs should ask customers that might just save a renewal â or at the very least, open up a deeper conversation:
1. What Made You Decide to Partner With Us?
Asking customers why they chose to partner with your company is an eye-opening question, and an important one to ask across the entire customer organization. One userâs response may be very different from an executiveâs response, so asking multiple stakeholders is key.
Understanding why your customers initially decided to move forward with your product or service rather than your competitorsâ (or doing nothing at all) is incredibly important to understand so you know what value props or differentiators were key in their decision process. And when renewal time approaches, itâs helpful to do a gut check and ensure they would still select your product or service again if given the choice. If their response is anything less than a resounding âYesâ, then thatâs a red flag and something to work hard to remedy and identify the cause(s) before the renewal.
2. Whatâs One Thing We Do Better Than Others You Partner With?
By asking this question, you can discover true differentiators that you may not even realize are important to your customers. When asking this question, be prepared to follow up to their response with âwhatâ instead of âwhyâ questions so you can dig deeper and get at the true value they see from what your company, product, or service provides them. Be on the lookout for words and phrases and actual experiences that keep coming up over and over again, no matter how insignificant they may seem to you.
Do other customers answer the question in the same way? If responses from multiple customers are similar, then perhaps the reasons they like partnering with your company are true value propositions and differentiators that should be built upon.
3. What is One Thing We Could Do to Create a Better Experience For You?
On the surface, this question could be viewed as a customer support question rather than a strategic customer success question. But the gold in this question is when your customers can identify an innovation or a new concept for your company to consider. Often times we get stuck in a rut of doing things the way theyâve always been done⊠just âbecauseâ theyâve always been done that way. However, customers have a fresh view from an outside perspective into other opportunities or potential innovations that would be valuable to them. When asking this question of customers, push them to describe the perfect experience with your product or service, from start to finish.
4. Do You Refer Our Company to Others?
This is the ultimate question of customer satisfaction. A truthful answer means your customer likes the product or service they have purchased. In todayâs tech world, many companies use whatâs called a Net Promoter Score (NPS), which is an index ranging from -100 to 100 that measures the willingness of customers to recommend a companyâs products or services to others. While the score certainly has flaws, NPS is used as a proxy for gauging the customerâs overall satisfaction with a companyâs product or service and loyalty to the brand.
The answer to the question of whether or not your customers refer your product or service to others is a good indicator of how happy they are â and how likely they are (or not) to renew. But more important is the follow-up question of what it is about your company, product, or service that makes them refer others â or not refer others.
What Strategic Questions Do You Ask Your Customers?
Asking strategic questions opens the door to having meaningful conversations and relationships with customers. But knowing what questions to ask and when is vitally important. What questions do you ask your customers, and how do you follow up to learn more? How do you take what youâve learned and put that information to use?
Frequently Asked Questions
What questions should a CSM ask to save a renewal?
What is a strategic conversation in customer success?
Should CSMs ask "why" or "what" follow-up questions?
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