20 Customer Success Interview Questions to Ask Your Next Candidate

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Sophia Bernazzani Barron
Sophia Bernazzani Barron


A great customer success manager (CSM) needs to be a jack-of-all-trades. That’s why it’s imperative when hiring that your customer success interview questions are ones that allow you to gauge whether or not the candidate is the right fit.

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CSMs specialize in customer service, of course — both providing reactive customer support and proactively offering solutions and strategies for their customers. But in addition to all of those skills, CSMs also need to learn the product or service inside and out to answer questions. They need to be able to write helpful emails and knowledge base content to send to their customers. And on top of all of that, they need to be able to navigate conversations about upselling and cross-selling.

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This level of multi-disciplinary expertise requires a certain set of skills and traits that team leaders should screen for in all CSM interviews. Product details and email best practices can be taught, but emotional intelligence and other character traits are necessary dealbreakers to adding a new CSM to your team. Keep reading to learn the skills all CSMs need, and what interview questions to ask to evaluate your next candidate.

1. Empathy

In order to help customers, day-in and day-out, CSMs absolutely need to be empathetic people — a key aspect of emotional intelligence.

Whether they're answering the same question for what seems like the millionth time, or they're counseling an angry customer through a pricing change, the ability to understand and share the feelings of other people is critical for CSMs to effectively de-escalate tough customer situations, understand a customer's goals and desired outcomes, and advocate for the customer with other teams and departments within the company.

2. Resourcefulness

Effective problem-solving, all day every day, requires a certain level of resourcefulness, too.

CSMs need to quickly answer customer questions — and if they can't answer their question, they need to track down the resource or colleague in a different department that can. This means that prospective CSM candidates must demonstrate a willingness and readiness to collaborate across teams and across departments — and a track record of being able to solve problems no matter how big or small.


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3. Communication Skills

CSMs need to be able to clearly communicate — with customers, with team members, and with other departments within a company — in order to be successful.

CSMs need to answer questions and teach customers — over the phone, on live chat or email, or in a knowledge base article. They also need to share and teach best practices to other team members — as well as identify trends, feedback, and user data to share with other teams within the organization. Excellent oral and presentation skills are important to evaluate in the interview as well.

4. Relationship-Builder

It might seem obvious, but it's worth emphasizing here: A good CSM needs to be able to build rapport with just about anyone in order to get the job done. And this is a hard skill to teach.

Friendly, open, and genuine individuals who can build rapport in a short interview will likely be able to do it over the course of a longer customer relationship, too.

5. Technical Acumen

If they get the job, a new CSM will have to learn how to use a product or service, but a demonstrable level of skill with using — and explaining how to use — technology is valuable during the interview process.

Even once they get to an expert level with the products and technologies a company uses, a CSM will need to break it down from the beginning for new customers, or customers that aren't as technologically savvy — so being able to use and explain different technologies will be key.

6. Self-Motivation

CSMs should be go-getters who don't need to be asked to go the extra mile or put in 110%. Listen for answers that indicate examples of when the candidate went above and beyond to solve problems and get answers for their customers — or examples of when the candidate took extra time and effort to help a fellow CSM or a sales rep to achieve their shared goals.

Now that we've outlined the skills you should be looking for in a candidate, let's review the questions you should ask during an interview.

Customer Success Interview Questions and Answers

Below is a list of the best questions to ask during a customer success interview. We'll explain why you should ask these questions as well as the answers you should look for from candidates.

Screening for Empathy

1. How do you deliver bad news to customers?

Stuff happens. Ask the candidate how they diplomatically share tough news while keeping a customer positive and engaged — or give them a scenario based on a past customer support issue CSMs have had to tackle — to get a sense of their ability to adapt to challenges and bounce back.

Ideal Answer:

"I deliver bad news to customers by getting on a Zoom call, if possible, since it's easier to gauge their response when I can see their body language. If Zoom is not an option, I'll communicate this information through a phone call as I feel it's important to deliver bad news in a real-time setting where you can answer questions and provide support immediately."

What to Look For:

Look for a candidate who can put themselves in the customer’s shoes — anticipating any concerns or questions they may have prior to calling them. Pay close attention to their problem-solving skills and ability to read customers.

Red Flags:

Be on the lookout for candidates who deliver bad news through an impersonal email or phone script and don’t make themselves available for explanation.

2. How do you communicate with customers if you can't resolve a problem right away?

CSMs can't answer every question right away — and they can't always promise the customer a solution. Ask candidates their strategies for managing long-term requests and following up with customers — and how they handle letting a customer know if their feedback or request won't be taken into account by the product team.

Ideal Answer:

"I would be proactive with my communication. If a customer requested a product feature that didn't exist, I'd let them know why this feature isn't available and what their alternatives were instead. If the customer was insistent on having that feature, I'd meet with our product team to share this feedback.

If the product could make the feature, great! I'll share the timeline for when the feature will be created. If not, I'd communicate the reason why to the customer, re-emphasize the alternatives provided earlier, then share some channels they can use to pitch this idea formally to my company."

What to Look For:

Someone who can proactively set customer expectations is a good sign. If they can’t fulfill a certain request, they should be able to communicate to the customer why they can’t, then provide alternative solutions. If you can’t provide a solution, you should at least demonstrate to the customer that you are trying to solve their issue.

Red Flags:

A candidate that provides a terse “no” without providing an explanation or context is most likely not a good fit. If they don't mention providing an alternative solution when available, that's also a bad sign.

Screening for Resourcefulness

3. What's the toughest case you've ever handled?

The candidate's experience and strategies will demonstrate their problem-solving abilities — as well as their communication and conflict resolution skills.

Ideal Answer:

"One customer called me demanding a refund for their purchase. They were clearly upset because they felt they had purchased the wrong product and that the sales rep they worked with only wanted to close a deal. Thing is, the product they had was exactly what they needed, they just needed to learn how it could help them achieve their goals.

I apologized for the frustration they must have felt and asked them to walk me through the problems they had with the product. Once they shared all of their feedback, I aligned myself by telling them that their concerns were fair and that what they wanted the product to do, it wasn't designed to do it. But, I told them if they used the product slightly differently, they might see different results. I then offered to walk them through how I'd recommend using the product, and it became clear to them that they misunderstood how to properly use our software.

Once this was cleared up, the customer was excited about using the product moving forward. They decided not to cancel their subscription and we agreed to follow up in a couple of weeks to make sure everything was still going well."

What to Look For:

While no one likes being yelled at, candidates should be able to keep a level head when dealing with an upset customer. Additionally, they will have mastered the art of delivering a sincere apology and work to remedy the situation.

Red Flags:

If you have a frustrated customer, you definitely do not want a service rep that matches their energy. Being curt or flippant with an already upset customer can just make the situation worse. If the candidate can't come up with an example of a difficult call or interaction with a customer, they may not be a seasoned CSM.

4. How do you collaborate with sales and product teams in your current role?

Customer success professionals have to communicate and collaborate with other people across the company in order to get the job done. Whether it's sharing product feedback or collaborating on an upsell, the candidate should share their workflows and best practices for cross-team communication that suggest speed, diligence, and a collaborative mindset.

Ideal Answer:

"I will often refer customers to sales reps if it's clear that there is a product that they need but do not currently have. I will only do that, however, if I truly feel that product will help the customer achieve their short- or long-term goals.

If a customer requests a product or feature we don't currently offer, I'll report this to our product team. They might have a workaround the customer can use, or they might be working on this new product or feature already. If that's the case, I'll share this timeline with my customer to let them know when they can expect to see that product, service, or feature. "

What to Look For:

Look for CSMs that can get to the heart of the customer’s pain points and evaluate what products would work best, rather than simply trying to upsell them. These reps should also be able to demonstrate how well they function across teams and highlight any method's for successful collaboration that they've used.

Red Flags:

Avoid those CSMs who indicate they may be unwilling to work across teams to solve for the customer.

Screening for Communication Skills

5. Explain to me how [Product Feature] works.

The answer to this question will tell you two things: if the candidate did their research about your product or service before arriving, and how well they can break down complicated concepts and demonstrate value.

Ideal Answer:

"HubSpot's Workflow tool automates tasks for your business. Workflows begin with a trigger or an action that the customer must complete. Once completed, that launches a series of actions that are executed chronologically. You can also set up branches within the workflow that act as secondary triggers. If a customer completes that action — or doesn't — the next step in the workflow changes based on the customer's behaviors."

What to Look For:

Look for a CSM that can simply and succinctly connect the dots for your customers. The best way to understand a concept or product is to explain it to someone else. This will help you evaluate whether or not the researched your product.

Red Flags:

Avoid reps that use jargon and can’t clearly explain what your product or service does.

6. How would you explain Twitter to your grandparents?

This question is along the same lines as the previous one, but it will reveal how skilled the candidate is at breaking down a tool they might use every day to an absolute beginner — which is a key skill needed for new customer onboarding calls.

Ideal Answer:

"Twitter is a platform where you can share brief ideas and comments with peers, strangers, and businesses. Once you create an account, you can customize your profile and start engaging with other accounts on Twitter. The messages you share are called 'Tweets' and these messages have a set character limit. You can't go past that limit, unless you write a follow-up tweet.

You can also engage with other people's tweets by commenting on them, liking them, or "retweeting" them, which essentially means you're reposting their tweet to your account to show support. Who you can engage with depends on which accounts you're following. You can also use hashtags, too, but we'll get to that later on once you've mastered the basics."

What to Look For:

Look for a rep that demonstrates patience and empathy. They will most likely be onboarding customers that are completely new to the product and the company — some may not be tech-savvy at all.

Red Flags:

Candidates who demonstrate impatience or give a brief answer. For example, responding with "Twitter is a social media company that allows users to communicate with each other” doesn't really explain how a person would use it.

Screening for Relationship-Building

7. How do you demonstrate value in the first phone call or email?

The first phone call with a new customer is a critical building block of the future of the relationship — and it's often a predictor of if the customer will churn or be retained.

During the first phone call, CSMs have to set up new customers to start using the product or service, but need to show the value of working with them so the relationship will continue to grow. Ideally, the CSM will show the customer a way to save time or achieve their desired outcome using the product or service, and then open a conversation for the next steps working together.

Ideal Answer:

"I demonstrate value by immediately aligning myself with the customer and their goals. I show that I understand what they're trying to achieve as well as the roadblocks they're facing, and that I have the resources they need to be successful. I let them know I'm on their team and I'm available for support in whatever way is needed. This helps build rapport and establishes my value early on in the relationship."

What to Look For:

Find candidates who are good listeners. It’s easy to get caught up in making the pitch, but listening will help you truly understand the customer’s pain points.

Red Flags:

Candidates who deliver a canned response that focuses on getting the customer off the phone rather than addressing their issue should be filtered out.

8. Pitch me on an upsell of our product's next tier-level.

Cross-selling and upselling is a delicate balancing act for any good CSM. Making a suggestion that's not in line with the customer's goals or that seems pushy could endanger the customer relationship — and even make the customer switch to a competitor.

Asking the candidate to demonstrate how they start that conversation will tell you if they understand best practices — and the role of a CSM in the sales process — or not.

Ideal Answer:

"I see that you're using this product to attract new leads to your business. How do you feel that's going? From my standpoint, it looks like it's going well and I'm excited to see this growth.

With that in mind, one concern that you shared with me early on in our relationship is scalability. You're getting close to achieving your goals, but you don't want to plateau once you reach the finish line. We want to keep that growth going so you can continue to scale.

This product that we offer should help you do just that. It's intended for a customer who's facing the same challenges you are and I feel it would be exactly what you need to continue growing your business. If you're interested, I'd like to set up a demo for you with our sales team to see if this tool would be useful. If so, great! If not, no worries at all. I just wanted to keep your best interests in mind."

What to Look For:

Candidates that have the ability to make a genuine case why a customer may want to upgrade based on their specific business needs and goals. Solving for the customer should always be the end goal when upselling.

Red Flags:

Avoid candidates who suggest new products or upgrades when they don’t necessarily make sense for the customer.

Screening for Technical Acumen

9. How would you explain our product or service in a single sentence?

This question tests the candidate's preparation for the interview, but it also gives them the chance to flex their communication skills and technological muscles to accurately explain what they're proposing to help customers within the prospective role.

Ideal Answer:

"HubSpot's products help businesses grow better and scale faster without having to hire as many employees."

What to Look For:

Candidates should be able to put together what your company does at the macro level without making it complicated. This could be with information pulled from your company’s mission statement or “About” section that shows they actually researched your company beforehand.

Red Flags:

A vague statement that doesn’t get to the heart of what your company does could indicate that the candidate didn’t do their research.

10. How would you change our product or service?

This is another question that tests the candidate's understanding of the company — but takes it a step further by evaluating how well they understand customers and users, too.

CSMs have to interpret Voice of the Customer (VoC) and share it with the broader organization, and answering this question will give you an idea of how they'd do that in the role.

Ideal Answer:

"One piece of feedback that I've noticed from online reviews is that customers are struggling with understanding how to use some of your tools. I notice your company doesn't offer a knowledge base and that might be useful to customers who need support, but don't want to spend time reaching out to your service team for help."

What to Look For:

CSMs are often the bridge between customers and the broader organization. Look for someone that can find patterns in customer feedback about what’s working and what’s not — plus figure out what's causing the friction.

Red Flags:

Short-sighted candidates don’t go beyond initial customer complaints. They won't examine the cause or how the issue might be remedied.

Screening for Self-Motivation

Ideal Answer:

"I really like to help people. I've always been a team player and I always feel a sense of accomplishment whenever I help others achieve their goals."

What to Look For:

Look for a candidate that indicates they will solve for the customer and have a vested interest in helping them succeed.

Red Flags:

A candidate that can’t articulate why they want to work as a CSM or provide service at all is a red flag.

12. How do you handle rejection?

People working in customer success might face as much rejection as salespeople. And it might even be tougher to bear after building a relationship with your customers, only for them to churn and leave for a competing product or service.

By asking this question, you'll learn how the candidate is intrinsically motivated, as well as how adaptable they are. There could be months when customers churn due to outages or a competitor dropping their price, and you need to make sure the candidate will be motivated enough to keep creatively problem-solving to keep things going.

Ideal Answer:

"I always take failure as an opportunity to learn and improve myself for next time. If possible, I'll ask for feedback or advice on where I can stand to improve. Then I apply that learning moving forward and move on to the next case."

What to Look For:

Customer success candidates should take rejection in stride and use the experience as a learning opportunity to improve for next time. They may have a routine or other method that doesn't allow customer rejection to derail their entire day.

Red Flags:

A candidate who internalizes customer churn or rejection may not last long in a customer success role.

13. What skills are you hoping to develop in this role?

As with any position at your company, applicants should consider how they'll develop in their role over time. They should be familiar with the skills needed to be a successful CSM and create a roadmap that will outline how they'll acquire those abilities. During their response, pay attention to the skills they describe, as this will outline some of the candidate's weaknesses.

Ideal Answer:

"I would really like to fine-tune my ability to problem solve and think creatively while on my feet. Working with customers in a face-to-face setting should help me develop these skills which will help me become more proficient in this role."

What to Look For:

Look for candidates that are proactive and seem eager to learn new skills. We’re always learning and there are always areas to improve.

Red Flags:

Avoid candidates that indicate there isn’t any room for improvement.

Questions to Ask Customer Success Manager (CSM) Candidates

14. How do you measure success in your current role?

The answer to this question will tell you two things: It will tell you how the candidate was evaluated in the past, and what concepts and metrics they're familiar with. It will also demonstrate the candidate's views on individual vs. team success, and how the team's success contributes to business success. You want a CSM who's highly motivated to achieve goals, but is also looking toward making a bigger impact for the team, and for the business as a whole.

Ideal Answer:

"In my current role, I measure success by analyzing customer feedback and quantitative performance data. I always ask customers for feedback because I'm eager to hear their thoughts about working with me and with my company. For a more objective viewpoint, I'll look at how many cases I take each week, how often I'm on the phone, and how many emails I send to each customer. This gives me real-time data that I can track over time to ensure I'm meeting my customers' and my team's goals."

What to Look For:

Look for someone who demonstrates they care about customer feedback as well as feedback from their team.

Red Flags:

If a candidate hasn’t measured their success at all, whether qualitative or quantitative, it could be a sign that they don’t have a handle on what constitutes success in their role.

15. What would you add to our culture, or what would you change about it?

When you're hiring for a managerial position, you're bringing on someone who will influence your company's culture. They're in charge of leading employees and ensuring your team meets short- and long-term goals. You'll want to make sure their philosophy and methods align with your business's corporate culture. If not, it will be difficult to motivate team members and maintain employee satisfaction.

Ideal Answer:

"I would love to add a diversity and inclusion program to your company's culture. This would make everyone feel more involved and appreciated while working on our team. It would also show that we're paying as much attention to our employees' needs as we do with our customers'."

What to Look For:

If a candidate can find a gap in your company’s culture code or overall employee satisfaction, and propose a solution for it, it shows they can anticipate needs and provide employees with support when needed.

Red Flags:

Avoid candidates that provide answers indicating they’re not concerned with employee needs. You want people who will add to your company’s culture, not alienate the rest of team.

16. How would you prevent customer churn?

As a CSM, your job is to prevent customer churn. So, you need a candidate who's passionate about customer retention and willing to go above and beyond to retain a user. Consider laying out a mock scenario for your candidate, then ask this question to see what they'd do to ensure the customer reaches their goals.

Ideal Answer:

"I would prevent customer churn by proactively communicating with the customer. If I noticed a potential roadblock that might impede a customer from achieving a goal, I would reach out immediately to provide a solution. I would also follow up afterwards to make sure the customer is still happy and that our workaround solution is still effective."

What to Look For:

Hiring a candidate that can anticipate customer needs and roadblocks is key. It’s much better to be proactive in communicating roadblocks rather than waiting for the fallout after. Your customers will appreciate your honesty and attention. This is also why it's important your CSMs have excellent relationship-building skills.

Red Flags:

Avoid candidates that lack patience or the foresight to anticipate potential problems and communicate them to customers.

17. How would you de-escalate a frustrated customer?

Not all customers are good at receiving bad news. Some will be rightfully upset that your company can't help them achieve their goals. In these situations, you need a CSM who can diffuse an angry user and salvage their customer experience. While your company should always strive for perfection, what matters most is how your success team responds to your organization's mistakes.

Ideal Answer:

"De-escalation starts with aligning yourself with the customer. You need to show that you truly understand why they're upset and what they want to change. If possible, physically align yourself by sitting on the same side of the table as the customer. This symbolically shows that you are on the same side of the issue as they are — not on the opposite side, where the friction is being created.

Once aligned, summarize the situation for the customer. Talk about what they want to accomplish, the roadblock that's preventing them, and their options moving forward. This will show that you understand their case and will make it clear what the potential solutions are. You can recommend one solution over another, but only if you can tie that solution back to the customer's needs.

Once a solution is settled upon, always follow up with the customer. Make sure the solution is still effective, and offer follow-up support if needed. This continued effort will prove to the customer that you are committed to their needs."

What to Look For:

Having empathy is key. Hiring someone who can keep their cool under pressure is equally important. Remaining calm will help you figure out a solution to your customer's issue or at least provide an alternative.

Red Flags:

Beware of hot heads. The last thing you want when dealing with a flustered customer is a flustered CSM. CSMs should focus on solving for the customer and not get distracted by anger.

18. Let's say you have to complete multiple tasks; how would you determine their priority?

This question will help you understand the candidate's ability to manage time. Customer success managers need to be adaptive and capable of changing their routines on the fly. Sometimes they'll provide proactive customer service, while other times they'll handle inbound service requests. Your CSM should be able to account for all of their daily tasks and consistently complete them on time.

Ideal Answer:

"I would first look at how long I have to complete each task. Tasks that have a more immediate deadline would be prioritized first, then followed by simple, easy-to-complete tasks that I can do in a matter of minutes. I would save the most complex tasks for when I have more time to dedicate to them."

What to Look For:

CSMs should be able to create a plan for themselves to tackle each task. You’re not looking necessarily for a “right” answer as everyone will solve problems differently. However, they should be able to put together a game plan and execute it.

Red Flags:

A candidate that can’t articulate how they would prioritize tasks or gives clues that show a lack of organization may not be a good fit. For example, if they don't take into account deadlines or how long certain tasks take to complete, that could prove to be a pain point later on.

19. If you saw a customer using more seats than they're paying for, how would you handle it?

This one is a bit of a trick question because there really isn't a right or wrong answer. Instead, this question demonstrates the candidate's ability to think critically about a complicated customer situation.

They not only have to consider the possible actions they can take but also the potential repercussions that will occur when they take those steps. The best candidates will provide a comprehensive breakdown of how they'd approach the situation as well as how they'd handle any roadblocks that may arise.

Ideal Answer:

"The first step I would take is to analyze their account details. I would look at how long they've been a customer, when their subscription will be renewed, what their monthly recurring revenue (MRR) is, if they've opened previous support cases, etc. This should give me an idea of how valuable they are to our company and how I should best proceed.

If the customer's subscription is close to renewal, I would let them know about the situation, but assure them that their rates won't increase until the upcoming renewal. If this felt like a problem, I would talk to the customer about their options at this point — either paying for more seats, or brainstorming ways to use the product the same way with fewer seats.

If the customer's subscription isn't close to renewal, I would touch base with my team. Since we made the clerical error, it doesn't feel right that the customer has to suffer. I would see if we could continue with their rate until the next renewal. If not, I would be proactive and immediately reach out to the customer to brainstorm solutions."

What to Look For:

Like the previous question, this is more about observing the candidate’s thought process rather than getting the answer right. Look for someone who takes into account the customer’s history with the company and their willingness to discuss options with the team before diving in and charging the customer more.

Red Flags:

A CSM that moves immediately to charge the customer without communicating why could indicate that they make hasty decisions without evaluating the scope of the issue.

20. What feedback would give the interviewer?

This is another interview question that doesn't necessarily have a right answer. Rather, this question shows the candidate’s ability to pay attention and think on their feet. You want a candidate who's actively listening and taking note of important details. By having them provide feedback, you can get a feel for their ability to read and react to customers.

Ideal Answer:

"I would love to see a little more transparency with the interview process. While I feel confident enough to speak to anyone, it would be nice to know how many interviews I can expect to participate in during this process and who those conversations will be with."

What to Look For:

Look for signs they were actively listening. Can they reference a particular question or have feedback regarding how the interview is formatted?

Red Flags:

Not having any feedback to give at all could be a sign that the candidate wasn’t really invested in the interview or simply lacks the ability to think on the fly.

Hiring the Right Customer Success Manager

The best customer success managers are customer-centric, empathetic, and creative problem solvers. Use the list of questions above during your interview process to effectively evaluate candidates and find the right person for your company.

This article was originally published in August 2021 and has been updated for comprehensiveness.

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