We Asked, They Answered - What Top Customer Success Leaders Ask During Interviews

We asked Customer Success leaders across North America to share one key question they would ask if they were hiring to replace themselves. The answers might just surprise you: 

Question: I would like to know how the candidate would prioritize their starting weeks in order to come up to speed. This would tell me whether the candidate actually understands the job.  

Reasoning: I would expect that they would want to assess how clear the solution value proposition is to define and measure (likely meeting with Sales and Product Mgmt). Also, that they would want to meet with CS staff to assess churn rates and client health scores. If they have health scores, determine whether they are representative (this would include support tickets). 

If they own Services (now commonly part of a CX portfolio vs pure CS), they should review past engagements and understand whether time to value is consistent and predictable. Growth is also important but the items above are the priority. If the candidate jumps right to growth before these items, it tells me that they don’t understand the fundamentals and have never developed a CS program.

Jamie Cappelli - Partner, Customer Experience Practice - King Tide Inc.


Question: I love this question as it brings up numerous different avenues to go down. If I had to boil this down to a single question, it would be this:  'Why do you do what you do?' 

Reasoning: As background, having interviewed and been interviewed hundreds of times over the years, I was recently asked this question by a very senior leader and for me, it was an eye opener. This question really cuts to the core and given it can be interpreted broadly the response should ideally be both an indication of the candidate's thought process and their perspective and outlook on customer experience and engagement.  

To me a suitable response shows that a candidate truly understands themselves, their strengths, and how it applies to the often challenging Customer Success space. Being able to share an overarching narrative of your background, experiences, and learnings through the context of a long term, client first approach is not easy so I view this as a conversation starter and less about the exact answer. It's about the thought process behind the response.

More specifically, for an ideal candidate to lead Customer Success, I'd want to hear about their dedication to and focus on developing people, their 'built to serve' mentality, and how they can connect a people focused approach to solving client challenges. Ideally, there are real world stories peppered in to provide context and confirmation that they have done this before, learned hard lessons, and adjusted their approach over time. It should demonstrate a growth mindset and confirm that they strive to improve, adjust, and learn given we can never truly be at the end of a job from a skills perspective.

Rob Birring - VP, Client Success -Sensibill

Question: How would you resolve the often conflicting priorities of hitting corporate revenue targets whilst preserving the customer experience?

Reasoning: In SaaS companies, customer renewals are the outcome of many parts of the business working in harmony together. As a VP of CX (in a SaaS company), it is important to understand how a potential hire would ensure alignment and accountability toward driving a unified customer experience across all departments.  

Chris Petko - VP Revenue - Sureshot.io

Question: The question I would ask my replacement self is: give an example of how you were able to build a loyal customer following that was able to advocate for your product/brand. What did you do? How long did it take? How did you ensure your team followed your vision? 

Reasoning: I guess that's three questions, but I think this is at the core of customer success and how invested a leader is in their customer's success. These answers also show their planning and strategic thinking, and ability to push that belief down to the rest of the team so it's scalable. 

Michael Li - Vice President, Operations & Customer Success - BookJane



Question: My favorite question to ask during an interview might seem common (which it is) but is a bit deeper. I ask the candidate to describe where they see themselves in 3-5 years and more importantly, what they are doing to get there. 

Reasoning: This type of question can show if a candidate is willing to put in the work, take the initiative, and that they have thought it through from a planning/ strategic perspective.

The easiest answer I hear is that the role they are interviewing for is the step or that they are looking to get into leadership, both of which are fair answers. But the better answers are when a candidate is able to tie in their past experience to the path they are trying to create. This tells you that the candidate is on a good path and is willing to leverage their opportunities in their previous roles to learn, develop and hone their skills.

Most of us want to hire driven professionals who understand where they are going, are actively involved in their development and willing to do the work. We want committed individuals who are not only going to excel but also elevate the overall success of your organization and themselves creating a mutual win-win relationship. 

Petrisa Pecnik - SVP of Customer Experience - BlueCat



Questions & Reasoning: There are two questions that I'd ask that are really the flip side of each other as a senior people leader and as functional leader of Customer Success/CX. 

  1. How do you create customer raving fans of your products, solutions, and services? 
  2. How do you find, grow, and retain your people?

Anusha Srijeyanathan - Executive Vice President, Client Success - Benevity


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