CSM from the Trenches – Asking the Right Questions to Challenge Customers

Sam Feil

Customer Success Manager

Being on the CSM frontline allows us to directly influence the success of our clients. I love that; as our clients are successful, we’re successful. We’re lucky to have this weeks CSM from the Trenches post from Priscilla Zorrilla of 15Five. Priscilla has been a Customer Success Manager for 15Five since January 2015, with a background as both an Account Executive and National Sales.

Let’s move forward with this week’s blog post!

CSM from the Trenches Best Practice – Open and Transparent Communication – Opening the Kimono
Company: 15Five
Location: San Francisco, California
From: Priscilla Zorrilla, Customer Success Manager

Best Practice: Open and Transparent Communication (Opening the Kimono)

One of the key things I love to do with customers takes inspiration from Patrick Lencioni’s Getting Naked: A Business Fable About Shedding The Three Fears That Sabotage Client Loyalty: not being afraid to be vulnerable with and challenge customers. I refer to this best practice as “opening the kimono”. For those unfamiliar with the phrase, it essentially means open and transparent communication.

Don’t Be Afraid to Ask to the Hard and Right Questions

This form of communication comes down to the way one interacts with their customers and challenges them, not being afraid to ask the hard questions. By society’s standards we try to avoid risks and not make people uncomfortable or angry, but I’ve found that challenging customers in what might be an uncomfortable situation empowers them to become more successful in the end. I believe this practice can help you stand out as a CSM if you ask the right questions beyond the standard business objectives or success criteria because it establishes a relationship based on trust.

Example of Being Open and Transparent – The Hard Questions

There was a situation where I challenged a customer to think about why they don’t require managers to have regular 1:1’s with each person on their team. He processed the question for 1-2 minutes. Reflecting. Radio-silence on the call (which is important…. let there be silence!). After he had time to process, he told me he didn’t know why they don’t require it. In fact, he admitted that he was scared to mandate anything – scared that the team wouldn’t receive a “mandate” in the best light.


After this question, the switch flipped in his mind. He realized providing managers with resources and training for great 1:1’s and making it required would have a positive impact on employee engagement (which they wanted to improve). So the question made him think about what he was doing and why, and when he realized something wasn’t right, it compelled him to take action. He figured it out on his own right before my eyes. All I did was listen without judgement.

Key Takeaways

1. Ask the right questions. I’ve found that challenging the status quo with thoughtful questions for customers builds “CSM-cred”; my contact began to think outside-the-box and solved the problem on their own and I became a trusted advisor.

2. Ask customers why, how, and for more context regularly

3. Be curious. There’s usually something deeper to understand which will enable you to truly make them successful.

15Five is a complete performance management solution that delivers a full suite of integrated tools – including continuous employee feedback, Objectives (OKRs), pulse surveys, peer recognition, and one-on-one meeting agendas.

Join the CSM from the Trenches Community

You can become involved in two ways:

1. Guest blog posts: Have a frontline CSM best practice you’d like to share? I want to hear from you! This is a great way to share your unique perspective and thought-leadership. Example – this post is a good example

2. CSM shout-outs: Do you know a CSM who goes above and beyond the call of duty? Have a team member you’d like to give a special shout-out? This is what CSM from the Trenches is all about – celebrating the frontline CSM. Example here

Here are other customer success resources that will help you excel in your role:

Customer Success eBooks:

Customer Success as a Culture: Customer Success Leaders Edition

Ultimate Guide to SaaS Customer Success Metrics

Other CSM from the Trenches Posts:

SoapBox Team Shout-Out

4 Segmentation Strategies for Frontline CSMs

Why Product Usage Isn’t Always King & 3 Lessons Worth Learning Early

2 Techniques to Avoid the ‘Overpromise and Underdeliver’ Temptation

My Purpose as a Customer Success Manager

Learn more about how ClientSuccess can help your company develop a strong Customer Success methodology and strategy with easy-to-use customer success software by requesting a 30-minute demo.

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