You can't have a strong SaaS org without a strong team. And in order to build a strong team, you've gotta set those expectations high. At Future of SaaS, we know that starts with the interview questions you prepare for your customer success manager.

Customer success is an exciting, burgeoning field. Across the industry, SaaS leaders are experiencing the benefits of a solid customer success strategy firsthand. Though it’s still a relatively new field, the top customer success specialists have refined it through the years, and we now have a clearer picture than ever of the kind of candidates you should be looking for.

How SaaS and customer success fit hand-in hand?

According to Stewart Butterfield, CEO of Slack, in a company-wide memo in 2013: “Even the best slogans, ads, landing pages, PR campaigns, etc, will fall down if they are not supported by the experience people have when they hit our site, when they sign up for an account, when they first begin using the product and when they start using it day in, day out.”

With a subscription-based model, the power is well and truly in the hands of the customer, and if you want to stop customers from churning, you need to arm your org with an army of empathy experts.

And more than anything else, it’s about building those long term relationships that foster customer retention and cut customer churn down to size. Of course, the kind of folks who can deliver on this are often a rare breed. Before we dive into the questions, let’s outline the key qualities you should be looking for when hiring a customer success manager.

Key qualities in a customer success manager candidate


We put this one front and center because it really is the most pivotal and the one that’s probably the most difficult to teach. It’s also really difficult to define it; it’s the kind of thing you just know when you see it. When you interview the candidate, ask yourself these questions:

  1. Did this person make me feel good about myself, did they brighten my day, did I feel a natural warmth from them?
  2. Did they seem generally interested in me and the company I represent?
  3. Were their main goals centered around helping others as well as themselves?
  4. Did they display insight and perspective on consumer behaviors?

If the answer to all of these questions is yes, chances are you’re dealing with a naturally empathetic person. With a customer success hire you’re looking for someone who’s going to make it their mission to proactively reach out to customers.

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A person who’s lacking in empathy simply isn’t going to be capable of this, and you might find that the customer churn rate starts to grow. Emotional intelligence is the cornerstone of customer success and it should be an important factor in your decision making.


This is a term we really don’t need to define, but when assessing it for an interview, you want to see in-depth examples of the various ways the candidate has solved customer problems, how they’ve overcome obstacles and how they’ve improvised at pivotal moments.

The fact is, a CM is going to be dealing with a whole plethora of personality types and there’s an unpredictable element that goes hand in hand with that. With this in mind, you need someone who’s going to be have a lot of tricks up their sleeve and isn’t simply reliant on a company playbook or script to solve customer problems.

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Communication skills

And when we say communication we’re not just talking about someone who appears to be very chatty (although it can be a good indication) we’re talking about someone who understands the nuances of customer communication.

This also doesn’t mean giving customers exactly what they want, but communicating what you think would best suit their needs, giving them what they really need as opposed to what they say want. This is a tricky tightrope to walk that requires a lot of nuance. But this is exactly the kind of sophisticated communication abilities you should be gunning for in your candidate.

Rapport builder

Ever been on the consumer end of a sales call or entered a store, and felt a pang of guilt that you didn’t make a purchase? The reason for this is likely because the salesperson was successful in building a rapport with you, and as a result you feel like you’re rejecting a real person as opposed to an organization.

This really highlights how a good communicator can be absolutely indispensable to your growth efforts. Trust is the foundation of a good relationship, and a good relationship is the foundation of conversion, retention – and the gold standard– customer advocacy.

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Technical acumen

So they don’t exactly have to be a technical wiz (although again, it’s certainly a bonus) But it’s going to be impossible for the customer to really feel like the CM is actually addressing their concerns unless it's apparent they understand how the software can help customers with their problems. On top of this, customers have to feel like the CM is really hearing them and understanding their pain points.

So now that you’ve assessed the qualities of your candidates, it’s time to see how they perform during interview, but this is tricky. You want to ensure that you'r4 asking the question that are really going to reveal qualities about the candidate. Luckily, we’re here to guide you a long the way with our top interview questions for your customer success manager.

Let’s dive in!

How do deliver bad news to your customers?

In a customer-facing role like CS, it's essential that you hire a person with the finesse to be able to deliver bad news in a way that sounds like good news. The answer should rarely be an outright "no," the CM should assess the needs of the customer and find an alternative solution.

The most important quality to stress here is honesty. Lying to customers or promising things that aren't deliverable can lead to massive problems down the line and even damage to your brand.

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How do you communicate with customers if you can’t solve a problem right away?

An essential part of good CS practice is managing expectations.It’s all about laying the foundation for a relationship of long-term trust over time. If you’re continuously promising customers solutions and then failing to deliver on them, you might please customers in the short term, but you’re going to shatter that foundation of trust that leads to a long-term relationship between the customer and your org.

At the SaaS Metrics Summit 2021, Rebecca Nerad, Vice President of Customer Success at E2open, stressed the importance of honesty in customer success.

“There are times where we have to push back on the customer. We have to push back internally. It's one of the challenging and amazing things about this role. I like to say sometimes, it's good cop, bad cop. But that role changes toward one direction or the other. It all starts with understanding customers' expectations in the first place. Also, it’s about being able to fairly represent what we think would be the right final result for them”

What’s the toughest case you’ve ever handled?

With customer success, there’s always a significant element of unpredictability to the role. Each customer is different, after all, and there are always going to be surprise challenges, keeping you on your toes.

The thing you want to be looking for: is an adaptable, agile individual who can think on their feet. Customer success is a field in which the practice has to be continuously re-fashioned around the needs of the client. Customer success is all about problem solving, and there's no one solution for all problems.

According to Paula Mendes at Hubspot:

"We quickly realized it was not possible to help customers achieve their goals if we had a one size fits all onboarding. Our onboarding and professional services needed to be tailored to our customer's most important priorities. You want to hear stories, not where the onboarding has gone smoothly and you’ve really wowed the client, but where the CSM has had to constantly negotiate a barrage of curveballs hurtling their way."

This is the ultimate evidence that the candidate is constantly adapting their practices to the customer's needs. Anybody working in a customer-facing role knows how unpredictable it is, how all the careful planning in the world can be shattered by one tricky request. Those that thrive best are those that can not only dodge the blows but effectively roll with the punches as well.

How do you collaborate with sales and product teams?

Customer Success only works when it’s successfully aligned with the org as a whole. After all, as a CSM, what is the essential service that you’re providing to your org?

One is that you’re both utilizing essential customer data from your sales teams and translating them into really great customer service, the second is that you’re then feeding invaluable data back into the org from your experiences with customers.

In their 2016 book, Customer Success: How Innovative Companies Are Reducing Churn and Growing Recurring Revenue, Nick Mehta, Dan Steinman, and Lincoln Murphy emphasized this:

"CS is a philosophy, and it must pervade the entire company. No organization or job role can function in a vacuum, it requires a top-down company-wide commitment."
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In order for any SaaS org to effectively compete, it’s crucial that they’re always adapting to the changing demands of the market. You can achieve this through collecting, monitoring and analyzing customer data.

With the CSM being up close and personal with the customer, CS is an invaluable tool for this function. Patrick Kelly, Senior Director of Customer Care Enablement & Operations at Brainshark, describes how data can be the foundation for improving practice in customer success.

“We review for trends first and then for details on an individual basis. We make training and enablement decisions based on gaps that we might identify, and we use the data to influence product development.”

Explain to me how [product feature] works

Now, it’s pretty much a no-brainer that this is the kind of question you would be expecting in the interview for any SaaS org. You want the candidate to demonstrate diligence and conscientiousness, and this is shown in how much the candidate knows about the product prior to taking on the position.

But for a CSM, this is even more essential. The CSM is the guiding hand for the customer along the way. And that goes way beyond a generic, broad knowledge of the product, it encompasses the minutiae of issues that a customer might encounter when interacting with your product.

No two clients are going to interact with your product in exactly the same way. To effectively catch and run with those curveballs along the way, CSMs must have an intimate knowledge of your product’s features and how they may be handled or mishandled.

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

A crucial aspect of a CSM’s job is not only what information they deliver to the customer, but how they deliver it. As a CSM, you might have all the knowledge in the world, but it’s important not to overwhelm the customer with a dense wall of technical know-how.

Here, the candidate demonstrates that they can master concision: often a cornerstone of effective communication. Equally, the candidate will demonstrate an ability to adapt to the expertise and knowledge-field of the customer. Not all customers are going to be able to grasp long, intricate scrolls of technical information.

You might be dealing with a client from a non-tech background, for example, or someone from a less tech-savvy generation. Being able to cut down your spiel to its most fundamental aspects ( i.e what does the product/feature do and how can it help me in my day-to-day?) shows an aptitude for inclusivity on the part of the candidate. In short, it’s not about what you, the CSM, knows, it’s about how it can improve the life of the client.

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How would you change our product or service?

The benefit of this question is two-pronged. Candidates show the potential not merely to unquestioningly go along with a business-as-usual approach, but to be continuously thinking about innovating and improving your product as they continue with their careers. What’s the point in hiring fresh talent if they’re not going to provide fresh solutions for your org going forward?

The second benefit is the nerve and courage to question your org’s mission and/or strategy. CSM’s have to be able to keep a close ear to the ground, listening to customer needs and demands. Sometimes those needs might be at odds with your company’s strategy.

A courageous CSM can help an org headed in the wrong direction to effectively pivot in the right direction. If you’re hiring a ‘yes -man’ in a field like customer success it’s a pretty poor indication of how they’re going to fare when having to deal with ‘difficult’ customers.

According to Rebecca Fenlon, Head of Customer Success at Cognassist.

"Attempting to be a ‘yes-man’ will ultimately leave you with poor product-market fit and you'll end up trying to service customers who shouldn't really be your customers in the first place. You waste time, you waste money; that’s not what good CS is about, and it’s not what good customer centricity is at all."

What was the most recent investment you made in your professional development?

You really want someone who in committed to upskilling all the time. Your SaaS product is going to be evolving in order to keep pace with the evolving needs of your customers. Simply put: you don’t want someone who’s going to be content to just rest on their laurels.

A good attitude is demonstrated by someone who doesn’t feel like they know everything, but feels like they always got more to learn. This is will also reveal whether the candidate is going to be easy to work with. Are they going take change in their stride and the necessary retraining that comes along with that, or are they going to feel like they already have enough to know?

The former demonstrates good qualities in any kind of candidate, while the former, well, it goes without saying…

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Describe your approach to prioritizing tasks when managing multiple customer projects.

It might seem from this question that you want someone who can handle a heavy workload, and though that might be partly true, you also want to avoid someone who’s likely to let themselves get overloaded. Are they able to keep cool under pressure and calmly prioritize tasks?

This also encompasses the various customer issues that they’re going to be dealing with. You want your CM to be a people pleaser, but some customers are going to be more high priority than others, and some issues are going to need more attention than others. The CM who isn’t able to sort through these is someone who’s going to burn out quickly.

What cost-effective strategies would you consider implementing in this role to ensure customer success?

When a SaaS company is looking to become profitable, some people are tempted to simply throw money at it, however, if your goal is sustainable growth – and it should be – you want to be hiring those who can make the most with a modest budget.

Although a certain amount of spend is obviously necessary, it can never be a substitute for real innovation. Hire talent for their ingenuity and though you might not be able to spin gold out of straw, you’d be surprised at how far ingenuity and creativity can get you.

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How would you upsell products to our customers?

Upselling is a big part of the SaaS game. Acquiring customers can be seriously expensive, and one of the major problems for SaaS companies is that the value their users bring doesn’t make up or exceed CAC.

So it’s imperative that you try to get the most value out of your customers. This starts with building a foundation of trust, of course, but once customers have gotten comfortable and trust that your org isn’t simply out to rinse them for all their worth, you can start directing them towards additional features.

Patience is essential here because the CM needs to have time to know a little more about the customer and what their individual needs are. So there are three skills that your candidate must demonstrate:

  • The ability to identify the appropriate upsell for the customer's needs.
  • The ability to communicate upsells without sounding overly mercenary.
  • The ability to accurately assess a customer profile.

How frequently do you believe it's necessary to visit and follow up with your customers?

Customer success is a tricky art to master for many reasons. Customers today like a certain amount of freedom to get their hand on your product and experiment. An overly attentive CM can be suffocating, but a neglectful CM can also lead to churn.

Let’s say, for example, you have a customer who simply hasn’t reached the value moment yet. There’s an aspect to your product that would make a meaningful difference to their lives but they simply haven’t discovered it. The job of your CM is to unlock the real value of your product for customers, and that means having the instincts to know when a customer needs a little more guidance vs when they're best left to their own devices.

What do you believe sets your customer relationship skills apart?

This is the kind of question you should be asking precisely because it tends to make candidates squirm. Although you don’t want to create the impression that you’re a toxic environment, you want to see how the candidate is going to respond to stressful situations.

After all, being on the front line of handling customer concerns demands a certain level of resilience. But another major thing that you’re assessing here is that the candidate is aware of the common pitfalls in the profession. It’s only by showing that they’re aware of these mistakes that they’re going to be able to convince you they can avoid them.

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Illustrate a challenging relationship you've encountered with a colleague previously and detail your approach to resolving it

A good customer success manager is able to take a holistic view, meaning that they are aware of how their work impacts other parts of the business. Communication is key here and a willingness to learn.

And for that you need a team player. Here, you’re looking for the kind of response that demonstrates the ability to compromise and see things from other perspectives. How can you expect your CM to adapt to customer needs if they don’t demonstrate this quality in their working life? Having said that, you’re also looking for someone who has confidence in their convictions and is able to persuasively communicate their own point of view.

I know nothing about [X software.] Explain it to me in the simplest terms possible

In any customer service role, it’s essential that you don’t make a customer feel overwhelmed, patronized, or out of their depth. Your idea customer will be able to explain something relatively complex in the simplest terms previously.

The main objective is to get the user to see the value in the product and you have to hire someone who can not only describe what it is, but how exactly it’s going to help the user. Pay attention to whether they’re using ‘ they’ or ’you’ in the answer. The latter will indicate that they are putting the user at the center of their explanation.

This question is different from the one where you ask them to describe your software. You're testing their versatility and quick thinking skills by putting them on the spot and also testing their industry knowledge.

Illustrate a highly positive and a notably negative experience you've encountered while collaborating as part of a team.

You want to see that the candidate is aware of what good and bad working paractises look like. You want to hire a team player, but you also want to hire someone who isn’t going to come in and muddy up the good work culture that you have going. Another more direct way of asking this would be: ‘What does a good work culture look like?’

Will this candidate fit into the work culture you’ve established, will they enhance it? You can hire the most talented person in the world but if they can’t play well with others, it’s unlikely they’re going to succeed in any company.

Describe a time when you were a team leader. How did you handle it and how did you go about it?

Ultimately, you want someone who is going to have the ability to take charge when needed. Look for evidence of initiative and the ability to lead in their previous experience, all of this conveyed in a respectful manner of course. Although a SaaS company is made up of many moving parts in sync, without the ingenuity of individuals, you end up in a creatively stagnant place.

Which skills do you aim to enhance or acquire through this position?

A mature candidate will be aware that your company will be looking to expand and grow and with that comes the opportunity for personal growth. Somebody who does not demonstrate maturity, drive and ambition is not going to be able to take you very far. The skills they say they want to acquire will also give you an insight into their previous experience with customers.

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What feedback would you give me on how this interview has gone?

If your candidate is attentive to those they are talking to – and a good CM is – they should have an answer for this question. The only potential hurdle is the fear of upsetting a potential employer, but the best candidates will know how to give constructive feedback that doesn’t demean or patronize. It’s another hot seat question that really tests the mettle of your candidate.

Final thoughts

Customer success might sound like a frilly position, but the individuals you’ll be looking for to spearhead a solid CS initiative, will be anything but that. CS managers can ask tough questions, and more importantly, answer them.

A good CSM can be the ambassador for your company’s principles and play a pivotal role and delivering a first class customer experience.During this SaaS revolution, we have a unique opportunity to continuously customize the product to the customer’s needs. That’s why SaaS and CS, when it’s done right, is a match made in heaven. The CSM can be the linchpin of any good SaaS strategy.

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