• Diana De Jesus

Preparing For Customer Success Interviews: Part 3, Questions To Ask Your Interviewers (37 Examples)

Updated: Sep 28

My first job in Customer Success wasn’t exclusively “Customer Success.”


It was a combination of many things. I was doing Onboarding, Sales, Support (lots of Support), and some elements of Customer Success (like renewal conversations and check-in calls).



Yes, “Customer Success” is broad. It could very well be that Customer Success also includes Implementation and Renewals. I know several CSMs that do Customer Support as part of their role. CS is different from company to company.


The Interview process is the perfect opportunity to uncover the true nature of the CS role you’re applying to and, more importantly, get to know the company. I was listening to a podcast the other day with Amy Volas, and she said something that aligns with what we’re covering in this post.


“It is your responsibility, it is your career, to peel back as many layers as you can to understand what you’re getting into”


That’s the energy we’re going to approach this part of the interview with 💪


Part 2 of the Customer Success mini-series was all about questions the interviewer(s) will ask you. In this post, we’re going to dig into Part 3, the questions you should ask them.


I’m outlining 37 questions for you, and I’m breaking it down between the role, personal development, and cross-collaboration & the company. These questions aren’t your stale questions from HubSpot (shots fired); these are a bit deeper.

The role


If you have an interview with a CSM, this is the perfect opportunity to learn about the role in a way no one else can explain. But if you don’t, asking this to anyone, especially the CS leader, can give you true insight into what the role entails and all the moving parts around it. Here are some questions to lead with:

  1. What’s a typical day for a CSM (great to ask a CSM)?

  2. What are your current OKRs, how’s your progress on that?

  3. How many customers do you manage?

  4. Are customers segmented? How?

  5. What’s the biggest focus for the CS team right now?

  6. What does your growth path look like here?

  7. What’s the biggest challenge the CS team has right now?

  8. Where do you see the CS team headed in a year?

  9. What’s your vision for the CS team?

  10. If you had to break down your role based on your responsibilities, how would that look?

  11. Do you have a process for sharing customer feedback? If Yes, can you explain?

  12. Can you tell me about a challenging customer? Why is it difficult?

  13. How do you stay on top of product changes?

Red flags to look out for:

  • The Customer Success role is a catch-all for everything else: Support, Sales, Marketing.

  • The CSMs are managing too many high-touch customers. If a CSM is responsible for bi-weekly syncs, QBRs, strategic calls, etc., and has 50 accounts in their book of business… that’s A LOT of work.

  • The CSM doesn’t share any insights around growth path and vision. This can mean that the CS team is too reactive (not a huge red flag but one you should keep in mind depending on your goals.)


Personal development


If I could go back and start all over again, I would focus on finding a great leader. To me, a great leader is someone who invests in your progress. They give you constructive feedback often, get to know your personal development goals, and puts in place the path to help you grow.

It’s easy to skip over questions related to growth and personal development, but they are critical. Back to Amy’s quote at the top, it’s really up to you here to peel back the layers and understand what you’re getting into.


Here are some questions to help you gather some insights on personal development:

  1. Where do you want to be in X years, and how do you feel X company is helping you get there?

  2. What are your 1:1s like?

  3. How often do you have 1:1s?

  4. Do you have skip levels?

  5. Do you use a performance management tool like Lattice, TinyPulse, or 15five?

  6. Do you have performance reviews? How did your last one go?

  7. What skills do you feel you want to develop? How does X company help you with that?


Red flags to look out for:

  • There are no 1:1s 😱. This is the BIGGEST of all red flags here. If you have no 1:1s, you don’t have a mentor, a point of escalation, someone to discuss strategy and growth with… so many things.

  • Performance reviews are essential, especially if you’re concerned about personal development. Of course, joining a scrappy small startup may not have the luxury of formally having performance management in place so keep that in mind.


The company/cross-collaboration


I really can’t stress this enough…


Customer Success ≠ the Customer Success team


You need the entire company on board to make “Customer Success” actually successful. We can think of Customer Success as roles at a restaurant –– I’ve written a bit about this on LinkedIn if you’re curious ––The waiter isn’t responsible for making the food and drinks; they are the communicator. The person who lets the rest of the restaurant know what the customer needs and then delivers those things in a timely fashion.

It’s a true team effort! Get to know how the team communicates, operates, and the setbacks with these questions:

  1. How do you communicate with Product today?

  2. Why did the last 5 customers churn?

  3. What team do you work with the most outside of CS?

  4. How would you rate your Sales <> CS handoff?

  5. What internal calls do you have?

  6. How does someone go about giving feedback at X company?

  7. Are you guys on track with your product roadmap?

  8. What are the top features your customers are requesting, are those in the roadmap today?

  9. What does a successful customer look like at X company?

  10. Which team would you like to improve your relationship with and why?

  11. What is the vision of X company, and how does CS fit into that vision?

  12. How do you stay on top of product changes?

  13. What’s employee onboarding like?

  14. What made you join X company?

  15. What’s the biggest challenge of X company?

  16. How would you describe the leadership team at X company?

  17. How does the CS team contribute to the roadmap?

Red flags to look out for:

  • If the last 5 customers churned because of frustrations with the Product. This one you’ll need to dig into and judge accordingly, but it’s tough to be a good CSM if the Product is 💩

  • A lot of friction with other teams. Again, Customer Success isn’t just your department, and you need to align with other teams so that the customer experience isn’t negatively impacted. You’re going to lean on other teams A LOT.

  • CS isn’t a priority at the company. If CS barely contributes to the roadmap, customer feedback isn’t really welcomed if it sounds like they could do without CS… All of these things are red flags.



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