How to Think Like a CSM Before You’re a CSM

How to Think Like a CSM Before You’re a CSM

Over the last few months, we’ve shared tips and tricks around how to break into Customer Success. We’ve talked about where to start in your journey, how to leverage your domain experience, and ways to gain experience without being a CSM.

One other particular way to get into the mindset and understand the work of a CSM is by simply asking questions.

If you’re active on LinkedIn, you probably noticed we CSMs are a talkative bunch. And we love helping people. It’s our job of course.

So as you pursue your first SaaS role, it can be incredibly valuable to set up a few conversations with CSMs to gain insight into their work.

By doing so, you’ll:

  • Form mutually beneficial connections with others in the industry.
  • Learn new things you haven't considered before about Customer Success.
  • Deepen your understanding of the industry and how to talk and think like a CSM.
  • Prepare yourself for interviewing.
  • Better understand if Customer Success is the right career path for you.

This is often called an “Informational Interview” and it's a powerful tool.

The key to Customer Success is asking great questions and getting into the mindset of others so think of this as practice before you land your first CS job.

In this guide, you will find a list of questions that are relevant for any conversation you set up with a CSM.

Some of them are also good questions to ask a hiring manager when you hear the question: “Do you have any questions?”

Spoiler alert - you should always ask questions!

Before the Informational Interview

1. Research & identify

Research and identify the types of companies and CSMs you want to interview (SaaS, Cyber, Fintech, E-learning, etc).

After narrowing down the list - Do your due diligence.

  • Visit the company website to understand their domain and what problem they aim to solve with their product/service.
  • Visit G2 to learn about competitors and read reviews.
  • Visit Crunchbase to understand which stage they are at (seed, scale up, etc.)

🌟 Protip - Coming ready for the interview with an understanding of the company and domain will show you're serious about learning. Doing this research now will also serve you later when prepping for real interviews.

Ideally, you should target CSMs at the company where you want to work.

If this isn't possible, look for CSMs who work in the specific domain you are interested in. as mentioned above.

Either way, every informational interview helps!

2. Connect & engage

Start building relationships with the people you want to interview by engaging with their posts on LinkedIn. Follow them and set alerts on their profile so you’re aware of when they post (see image below).

 LinkedIn notification bell location
LinkedIn notification bell location

Begin to comment, ask questions, and show your curiosity. This will help make your direct outreach to them more personal and recognizable.

The key is to engage thoughtfully and aim to add value to the conversation. Your comments should stand out to the CSM!

3. Ask for the interview

When you’re ready to ask for the informational interview, reach out via LinkedIn or email.

You can use this template for sending a private message on LinkedIn:


Hi [CSM Name],

First I wanted to say thank you for all the great content you provide on LinkedIn. I have learned a lot from you, especially around [Add in personal examples]. Keep up the great work!

I’m on my own journey of transitioning from [Add your background] into Customer Success.

It would be a pleasure to connect with you and learn more about your experience in this field. My goal is to learn as much as I can about Customer Success best practices, but I have some additional questions.

Do you have time to jump on a 30-minute Zoom call with me? I would appreciate the chance to learn from you!


[Your Name]


During the Informational Interview

Tips for the meeting:

  • Find a quiet place with good lighting.
  • Look at the camera, and don’t forget to smile - be natural.
  • Use a computer if possible and not your smartphone.
  • Be on time.
  • If you wish to record the meeting - ask for permission in advance.

When you start the meeting - thank the CSM for making the time to meet you. Articulate again the reason for the meeting and ask if it's ok for you to go over the questions you prepared in advance.

Here are some examples of questions you can ask during the interview. Choose the ones that will most help you in your journey to becoming the next top CSM!

🌟 Protip: Start off with a question that's designed to break the ice. Don't go too deep, too fast!


  • How did you get involved in Customer Success?
  • Why did you choose the company you work at now?

Company Structure:

  • What’s your company's product/service?
  • What’s your company’s business model?

Team Structure:

  • How many CSMs do you have on your team?
  • What does the hierarchy structure look like in your department?
  • Do your CSMs own renewals?
  • Do your CSMs have additional responsibilities or specializations (Onboarding, Support, etc.)
  • What does the hiring process look like in your company for CSMs?
  • What are your goals as a CSM for the upcoming year?
  • What are your team goals for the upcoming year?
  • Do you have Customer Success playbooks in place? If so, which ones have been most helpful for you and why?
  • Do you have a daily/weekly check-in with the larger CS team? What does that look like?

Tech stack

  • How do you keep track of your day-to-day tasks?
  • What tools do you use to plan and evaluate your short and long-term projects?
  • What channels do you use for customer communication (Slack, MS Teams, Sykpe, Drift, etc.)?
  • Do you use any Customer Success tools (Catalyst, Gainsight, Churnzero) and how do they contribute to your work?
  • How do you track and report on customer usage?

Internal Stakeholders

  • How do you work with Support to ensure customer tickets get resolved in a timely manner?
  • How do you collaborate with Product to ensure the right features get built?
  • How do you collaborate with Sales to ensure the customer has the right expectations of the product and a smooth handoff?
  • How do you collaborate with Marketing to capture the right study cases, reviews, and other assets?

External Stakeholders

  • How often do you meet with your customers?
  • How do you help your customers be more successful using your product/service?
  • What does your onboarding process look like?
  • What do you do when a customer is unresponsive?
  • How do you segment your customers?
  • Do you have a low or high-touch model with customers?
  • Do you automate any of your work processes? Which ones?

Personal Experience and Knowledge:

  • What are some vital steps someone should take to prepare for a role in Customer Success?
  • What is the most exciting project you are working on at the moment?
  • What skills have you developed since starting your role?
  • What does a typical day look like for you?
  • What most surprised you about working in Customer Success?
  • What is something you wish you knew earlier in your career as a CSM?
  • What do you like most about your role?
  • What do you wish was different about your role?
  • What advice would you give me as I transition into CS?
  • How do you see Customer Success evolving in five years?

After the Informational Interview

After the call, reach out and thank them for their time. Often just a simple thank you is enough. If you can however, offer something in return.

Here is a template you can use:


Hi [CSM Name],

Thank you so much for meeting with me today. It was a pleasure to learn more about your role as a Customer Success Manager - I learned a lot!

What was most helpful to me when learning about...[Give an example here and how it will help you transition to CS].

Let me know if there is anything I can offer in return. It would be my pleasure to write a LinkedIn recommendation for you, post about our conversation and tag you, and/or endorse your skills. Let me know what you think is acceptable.

Thanks again!
[Your Name]


🌟 Protip: Keep records of your informational interviews, key takeaways, and trends in a centralized location like Google Docs or Notion.

There you have it. A simple way to gather inside knowledge of the Customer Success industry. If possible, try to set up one or two meetings a week.

The more you connect and learn from those who have done it, the more confident you will be about your decision to explore this exciting career path and your ability to rock your next interview.

Good luck!

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