Effective Questioning for Customer Success Managers — Part 2

Artem Gurnov
6 min readApr 8, 2022


Every customer success manager (CSM) is focused on maximizing the value the customer is getting from each interaction with them. As a result, the value of the company’s product or service is also going to be maximized, and the decision to renew the subscription will come naturally. Regardless of how experienced CSMs are, they can never know the customer’s challenges and expectations without asking questions.

The ability to ask effective questions is one of the critical skills for any customer success manager, and improving it can make a tangible impact on their results. If CSMs build the conversation with the client based on certain assumptions about their situation, they may get lucky sometimes and hit the spot. But in most situations, some of the topics discussed do not resonate with the customer, and time is wasted discussing them.

In this article, we’ll explore the best practices for effective questioning based on our experience here at Wrike. It expands the ideas presented in my 2018 article “Effective Questioning for CSMs” written in collaboration with Peter Lyon, and provides additional recommendations on the topic.

Opening questions need to be as general as possible

At the beginning of the conversation, when the CSM is gathering information on the customer’s goals for the product, it’s important not to limit the client with specific boundaries. At this point, just like the customer doesn’t know much about your product or service, you don’t know much about their challenges and objectives.

Opening questions need to be as general as possible to get the customer started. We usually ask something like, “Can you please tell me a bit about your team and what you expect to get from Wrike in the next three to six months?” We then have the opportunity to build on top of the client’s answer and tailor the conversation to their needs. Starting with very specific questions would lead to very specific answers. As a result, you risk missing some points that are important to the client but that do not fall into the scope of the questions asked.

Ask open questions

The goal of a customer success manager is to gather as much information as possible so that all the solutions offered are relevant to the client’s needs. For that to happen, it’s important to ask “open” questions that can not be answered with a simple yes or no. For example, when we’re interested in finding out what level of visibility into the business processes the client requires, we don’t ask “Do you need to have any reports on your projects?” Instead, we ask “What kind of reports do you need on your projects, and what insights do you expect to get from such reports?” Asking open questions gets the clients to talk, and that’s exactly what you need as a CSM.

Prepare questions in advance

The chances for CSMs to make the most of a customer call are increased when they take time to prepare. This includes reviewing the notes from previous interactions with the customer (if any), visiting their website and checking the company information, and reviewing the cases of clients from the same industry. Additionally, CSMs can prepare the questions they’re going to ask during the call.

As I highlighted in the article “Owning the Conversation With the Customer” it’s always a good idea to ask the client to provide a list of questions and topics to discuss in advance. Our experience tells us that many customers are supportive of this because they also want to make the most of the time with you.

When finishing the basic preparation for the call, brainstorm on what elements may be missing and prepare the questions to cover them. For example, on a previous call, a client told us that one of their Wrike-related goals is to streamline internal communication. Between the calls, the CSM learned from the company’s website that their organization has merged with another. A logical question to prepare for the next call would be: “How does the sister company manage internal communication, and what plan do the two companies have to streamline global communication after the merger?”

Keep the desired outcome in mind when asking questions

Choosing the right wording when asking questions is critical if you want to control the flow of conversation and steer it in the right direction. Most of the questions you ask (except the initial ones we discussed previously) need to be formulated so the customer’s answer could potentially lead to the outcome you desire — increased product usage, upgrade to a higher subscription tier, etc. So, in a nutshell, the scheme of asking the question would be as follows:

Ask the question that will most probably lead to an answer you need -> get the confirmation from the client -> offer the prepared solution

Again, an example from our experience here at Wrike: Instead of asking general questions about clients’ business processes with the hope of getting lucky and hitting the right spot, we ask questions with certain Wrike solutions in mind. For example, “Are you working on any projects that you would describe as repetitive?” followed by offering the blueprints functionality, or “Would it be fair to say that the approval process sometimes significantly delays project closeout dates?” followed by showcasing the proofing and approvals features. This approach to asking questions makes conversations with the customers more positive since more solutions are offered and, as a result, the chances for the client to get value from the product are increased.

Ask confirmation questions during the call

Even when you do an awesome job asking discovery questions to clarify the client’s situation and business challenges, it is still critical to pause every now and then and ask whether the features that you just presented resonate with the customer.

These pauses do not need to be long — say something like, “I would like to pause here and ask whether this would be useful to you and your team members.” If you get a clear yes, that’s great. Maybe it would be worth taking a deep dive into that area. If the customer is unsure, ask follow-up questions to confirm that you explained everything clearly and discern if you should switch to a different topic.

Ask follow up questions on follow up calls

One of the key components of the relationships CSMs build with their customers is the continuity of conversations. It means that they need to pick up from where they left off last time and not cause any frustration for the clients by asking the same questions repeatedly.

For that to happen, it’s important to document all the critical items discussed so you can review the notes before the next call and continue the conversation. When a CSM jumps on a call with a customer they have spoken to previously, it would be good to circle back to the topics discussed last time and ask about progress on that front. For example, say on the previous call our CSM discovered that reporting on deadlines is very important for the client and shared the best practices on how to do that. A good question for the start of the next call would be, “Last time we discussed reports since you highlighted that they’re important for you. Did you have the time to build any reports and if so, how have they been working for you so far?” Executing this approach also contributes to the CSM’s reputation as a professional, since it’s clear to the customers that they take the time to prepare and maximize the output of the call.

Put some common questions in front of you

This one is probably more applicable to those just starting in their role as customer success manager. The first several dozens of calls can be pretty stressful, and it’s easy to forget certain critical items. As we previously discussed, asking the right questions in the right way is essential to bring the most value during the call. I recommend printing out a list of the most important questions you’re planning to ask and having it in front of you. I’m most definitely not recommending that you read from the paper the whole time — the conversation flow needs to be natural. But having these clearly formulated questions in front of them enables CSMs to stay on track and build a foundation for a great customer call. Approach experienced CSMs and ask them to help formulate these questions. Not only will they be able to recommend what to ask, but they will also advise on specific wording that has worked for them.

Constant practice with effective questioning and experimenting with new approaches to asking them enables customer success managers to make the most out of their calls with clients. There’s always room for improvement, but the more they do it, the more natural and elegant the questions sound, and the easier it is to come up with the right question at the right time.



Artem Gurnov

Director, Account Development WW at Wrike