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About This Resource

As a Customer Success Manager (CSM), you are on the front lines of driving customer relationships and fostering loyalty. Navigating through this multifaceted role, with its unique challenges and dynamic landscapes, requires a keen understanding of both your customers and your organization. 

One indispensable tool for unlocking this understanding is the effective use of questions – whether directed towards others or self. Inquiring, probing, and reflective questions not only help clarify and navigate complex situations, but also stimulate learning, foster deeper relationships, and spark growth. 

Harnessing the power of questions can significantly enhance your CSM role, enabling you to better respond to evolving customer needs, adapt to organizational changes, and progress in your career.

We hope this toolbox of questions helps you! 

How to Use This Resource 🤔

(This recourse was obtained from https://www.csinsider.co/)

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Your Manager 🧭

Building a healthy, open, and effective relationship with your manager is essential to succeeding in your role. This section provides an extensive list of questions designed to help you better understand your manager's work preferences, objectives, and key performance indicators (KPIs). The aim is to facilitate improved communication, align expectations, enhance your professional development, and foster a collaborative environment that aligns with the company's goals and values.

...

  • How is knowledge captured, maintained, and distributed from within the team?

  • If I ask customers about the strengths of our product/solution - what would they say?

  • If I asked the customers about the areas we need to improve - what would they say?

  • I'm looking to collaborate with other departments to streamline our processes. Can you suggest any teams and stakeholders that might be a good place to start and capture a few early wins?

  • Are there cross-team knowledge initiatives with support/pre-sales/professional services that I can assist with?

  • What are some projects or initiatives within the company to which I can contribute?

Your Sales Team 💰

Collaboration with your sales team is essential to ensure seamless customer experiences, productive handoffs, and effective upselling strategies. This section offers a compendium of questions aimed at streamlining the interface between Customer Success (CS) and Sales, gleaning critical customer insights from the sales process, and enhancing the coordination of upsell and cross-sell opportunities. The inquiries are clustered into these specific categories for easy reference:

...

  • Are there any verticals that you need references for?

  • What is your commission structure like and how can I help you hit your targets? 

  • What is the best way for me to provide you with customers that are near renewal, or are ready to be upsold?

  • When I identify an upsell or cross-sell opportunity, how would you like to be notified?

    • How can we tag-team this opportunity?

Your Product Team 🤖

Building strong alliances with your Product team is instrumental in bridging the gap between customer needs, business objectives, and the actual product offerings. This section presents a comprehensive set of questions designed to facilitate a better understanding of the product development process, foster effective collaboration, and align customer success initiatives with product strategy and vision. The questions have been categorized into six specific areas for easy navigation:

...

  • What are the key metrics for measuring our product's success?

  • How do these metrics influence our product development decisions?

  • What is our current performance against these key product KPIs?

  • How are these product performance metrics tracked and shared with the team?

  • How can I contribute to improving these product performance metrics?

Your Support Team 🆘

The Support team is an indispensable ally in driving customer satisfaction and promoting customer loyalty. Familiarizing yourself with their processes, and the way they communicate, not only helps improve your collaboration but also enhances your ability to deliver unified and excellent customer service. This section is dedicated to fostering this understanding, and it 

...

  • How can we better align our communication between the Support and Customer Success teams?

  • How can we collaboratively work on complex cases that need the input of both Customer Success and Support?

  • How does the Support team communicate updates or changes to policies/procedures?

  • How can we improve our coordination so that customer issues don’t fall through the cracks?

  • Are there any recurring challenges or patterns you're observing in customer inquiries that we should proactively address?

  • What steps or criteria do you fulfill before escalating an issue from Support to Customer Success?

  • Is there a process to tag specific tickets so that a CSM has visibility into the issue?

  • What is your preferred way to escalate a ticket?

  • What is the best way for me to share common issues or feedback from the Customer Success team to Support?

  • How to make sure I do my due diligence before asking a customer to submit a ticket?

  • What do you wish CSMs did more of that would make your team’s job easier?

  • How can I help with following up on bad CSAT?

  • Are there scheduled meetings between the teams to discuss product malfunctions/ issues and share insights from customers?

    • If not, how we can schedule this together?

  • Are there current training opportunities for CSMs to better understand common support-related issues?

    • If not, how we can schedule this together?

📌 Read 6 Ways Support & CS Can Become a Powerhouse

Your Marketing Team 📈

Understanding the Marketing team's goals, strategies, and challenges can significantly enhance your efforts to align with their initiatives and contribute to the business's overall success. This section provides a series of thought-provoking questions structured around key areas designed to help you better comprehend the workings of the Marketing team and strengthen your collaboration with them.

...

  • How can the Customer Success team contribute to the Marketing team's initiatives?

  • How can we better communicate customer feedback and insights to the Marketing team?

  • How can we align our customer success stories, testimonials, and case studies with marketing’s efforts?

  • Can you tell me about any upcoming plans that may affect what customers think or want? How can I help with those plans?

  • How can we be of help to you in gathering advocacy content?

  • G2 Crowd reviews - Yes/No and why?

  • Which type of case studies could improve our marketing process?

  • Which pages and FAQ questions are most frequently viewed and how can I use customer stories to make them more engaging? How can I be of assistance in this process?

  • Is there a way for us to see how much our customers are engaging with our email campaigns?

  • Can you provide me with the key benefits of <X> feature so that I can effectively communicate them to our customers?

Your CS Team 🤝

On a Customer Success team, the whole is greater than the sum of its parts. We're a unit, a tribe, and the more we understand each other's work styles, tactics, challenges, and victories, the better we can support one another. This section is designed to keep the conversations flowing, spark deeper insights, and strengthen our team dynamics. Check out these areas to chat about:

...

  • How can we level up our teamwork and support for each other?

  • What kind of updates or info from me would make your day a little easier?

  • What's your favorite way to keep in touch about ongoing tasks or issues?

  • What does our team need from leadership and how can we communicate this?

Your CS Operations Team 📊

A highly functioning Customer Success (CS) Operations team is a key ally in driving customer success and value realization. The CS Operations team ensures that systems, processes, and metrics are in place to support the team's work and measure outcomes. To facilitate effective collaboration and understand their work better, this section contains a set of questions distributed across significant areas.

...

  • How can we, as the CS team, best collaborate with CS Operations?

  • What common challenges arise in collaborating with CS Operations, and how can we mitigate them?

  • How can we provide feedback or suggestions to CS Operations to improve tools, processes, or metrics?

  • How can I ensure that I am, in my capacity as a CSM, that I am routinely keeping our CRM records clean and up-to-date?

Your Digital CS/Scale Team 💻

In today's digital age, providing personalized experiences to customers at scale is paramount to success. The Digital CS/Scale Team stands at the forefront of this initiative, leveraging cutting-edge tools and data-driven strategies to deliver bespoke customer experiences on a large scale. They navigate the intersection of technology and customer success, making personalization and engagement achievable for your diverse and expansive customer base. To better comprehend their pivotal role and foster effective collaboration, this section offers a curated set of questions divided across key areas of their function. The categories are as follows:

...

  • How can the broader CS team contribute to the Digital CS/Scale Team's efforts?

  • What hurdles should we be mindful of in our collaboration with the Digital CS/Scale Team?

  • How can we share valuable customer insights or feedback with the Digital CS/Scale Team to enrich our digital engagement strategies?

Your Senior Leadership 🗻

Senior leadership sets the strategic compass for the organization, leading the charge in our mission to deliver unrivaled customer success. Their vision, decisions, and feedback have the potential to elevate your contributions as a Customer Success Manager (CSM) and align your work with the larger goals of the organization. This section provides a curated list of questions, designed to help you understand their perspectives, gather insights about their priorities, and define your role in the grand scheme of the company's success journey.

...

  • How should I communicate important updates or challenges related to my customers with the leadership team?

  • What's the best way to bring new ideas or constructive feedback to the leadership's attention?

  • How does the leadership team prefer to provide feedback to the Customer Success team?

Your Peers 🤝

As a Customer Success Manager (CSM), the relationships you build with your peers across the company are instrumental in fostering a collaborative, supportive, and efficient work environment. Your peers can offer valuable insights into their experiences, best practices, and unique perspectives that can enhance your understanding and approach to customer success. To help you facilitate meaningful discussions with your peers, we've grouped a set of questions under relevant categories.

...

  • If you could go back in time and give yourself advice, what would it be?

  • What's something new you've learned recently about our customers or our product that changed your perspective?

  • How do you keep up with industry trends, customer needs, and our evolving product features?

  • Can you share a feedback or learning moment that led you to change your approach to customer success?

  • What is your favorite Customer Success Book? Tell us about lessons learned that you were able to implement. 

  • What other CS resources have you found particularly valuable in your career?

Your Customers 😍

As a CSM, your role revolves around understanding, assisting, and fostering relationships with customers. Their needs, wants, challenges, and objectives are at the heart of your job, making it important to thoroughly understand them. This section is tailored to assist you in gaining critical insights into your customers' motivations, their business goals, how your product is assisting them in meeting those objectives, and ways you can help them further. The questions are divided into multiple categories to ensure a comprehensive understanding of your customers.

...

📌 Bonus: Access additional customer questions by Anita Toth.

Your Partners/Vendors (coming soon) 🔗

Partnerships often represent an opportunity to expand the value you can deliver to your customers, but they also bring along an added layer of complexity in managing customer success. Establishing a clear understanding of how you can best work with partners is crucial for providing seamless, unified support to your shared customers. In this section, you'll find questions designed to help you gain a thorough understanding of your relationship with third-party vendors or partner entities, spanning topics such as shared objectives, role definitions, communication strategies, risk management, customer satisfaction, and performance measurement.

...

  • What are our shared objectives with delivering the project or service to our joint customer?

  • How do both parties envision a successful outcome for the project or service?

  • Are there any specific business goals or metrics that both parties are aiming to achieve together?

  • How does the joint project or service align with the overall business strategies and goals of both of us?

  • Are there any specific milestones or key deliverables that need to be achieved throughout the project or service duration?

  • What are the expected timelines or deadlines for different phases of the project or service?

Yourself 🫵

Welcome to the most unique and personal section of this comprehensive guide: Yourself. This is the space dedicated entirely to introspection, self-understanding, and personal development. As a Customer Success Manager (CSM), your journey toward growth is constant and often challenging. The following categories of questions are designed to stimulate critical thinking about your personal and professional trajectory, as well as identify opportunities for development and improvement.

...

  • How comfortable am I with receiving feedback? Do I actively seek it out?

  • How do I incorporate feedback into my performance and growth?

  • What is my preferred learning style, and how do I leverage it in my role?

  • What was a recent learning or piece of feedback that had a significant impact on my work?

  • How do I stay up-to-date with new developments and best practices in the CS field?

Anyone 🪣

Ask these general icebreaker questions to anyone you want to connect with!

  • What does the perfect weekend look like for you?

  • What do people tend to ask you for help with?

  • What’s a household item that holds significant meaning for you?

  • What is your biggest non-academic, non-work-related accomplishment?

  • What is something you’ve done/felt/seen/etc. that you wish you could experience again for the first time?

  • If you had the chance to time travel, what part of the history would you like to explore?

  • Which 3 books have had the most profound impact on your life/career?

📌 Read this list of other icebreaker questions (Source: Reddit).

Meet the Resource Creators 👋

  • Brandon Cestrone – Co-Founder of CS Insider  

  • Guy Galon –  Guy is passionate about customer management and driving people (customers, direct reports, friends, and colleagues) to success. Guy is also a mentor, lecturer, and novelist.

  • Katrina Kugelmeier –  Philly ex-pat happily living in Berlin, breaking into the CS scene & ready to sweat in the sauna any day of the week. I love connecting with and learning from fellow CSMs! 

  • Kenneth Sinensky – Enterprise CSM, Editor at CS Insider, and full-time Children Success Manager. I love talking CS Ops or breaking into customer success and how to make a splash once you’re in! 

  • Sumitra Narayanan– CS leader at Braze and passionate about health, writing, and of course… CS.

  • Dan Ennis – CS Leader with a decade of experience in CS and scaling/leading teams. Passionate about seeing others grow and succeed.

  • Anita Toth – Churn Crusher & Customer Success Leader

  • Ashna Patel – Certified Customer Success Leader & Leadership & Growth Coach. Co-Founder of CS Insider 

  • Guy Rahamim – Enterprise CSM at LinearB, passionate about helping others.

  • Fouad Adel – CSM enthusiast that is trying to make CS job hunting easier.

  • Angelika Marek – Digital CSM at Bazaarvoice. Love all things CS, in particular Digital/Scale CS. CS mentor, money educator and avid learner of Italian language. 

  • Kevin Leonor – Customer Success Coach, trainer.

  • Jared Orr – CSM at Totango and Founder of the Customer Success Whisperer Blog 

  • Noah Little – Enterprise CSM at Recharge Payments and CSM Coach 

  • Vinny Conti– Sr. CSM at RevenueWell. Breaking into CS Advocate. 

  • Jan Young – CS Leader Coach, Consultant, and Trainer

  • Amber Monroe – Head of Enterprise Strategy at Paradigm Senior Services & Founder of Monroe Concierge, a Customer Success Consulting Firm for healthcare organizations. 

Dana Alvarenga– VP of Customer Experience at SlapFive. Customer Voice Coach who has conducted hundreds of customer interviews extracting key insights, feedback and results from B2B execs across the globe.