• What are some things at <company name> that keep you up at night?

• When I have important questions, what is the best way to communicate with you? Could I contact you by email, Slack, or should I just schedule a meeting?

• Can you tell me how your performance is measured, and how I can help you reach your goals?

• Would you like me to provide you with updates about my accounts on a regular basis? If so, how often?

• What do you consider a customer escalation that requires your immediate attention? 

• What skills should I focus on developing over the next few months to make a larger impact in my role?

• How can I best support your leadership and make your job easier?

• What teams do we communicate with the most and how can we improve our collaboration?

• What can I take off your plate?

• What do the top performers at this company do that I can emulate?

• What path did you take to reach your current position?

• Why did you decide to work for this organization?

• In what areas of my work would you like to stay up to date more frequently?

• When you worked with challenging direct reports in the past, what did they do wrong or fail to do right?

• What do I need to achieve over the next x months to make promoting me a no-brainer for you?

• What’s an example of a time a CSM really impressed you at this company? What did they do that stood out to you?

• What’s your vision for my career path at this company?

• If you are only able to promote a few CSMs in the next promotion cycle, would I be considered? If not, what should I improve on to be considered for the next promotion cycle?

• What is something that you want to see more from me on a regular basis?

• Are there any guidelines/templates/job descriptions for the skills/traits you look for so that I can determine if I am suited for a promotion or the next role?

• Is there any career trajectory I could consider? If I want to learn more, who should I contact?

• Are there specific milestones I need to achieve in order to be considered for a promotion?

• What would it take for you to feel confident that I am ready for a promotion?

• If you were in my shoes, what would you do to grow within the company?

• In your opinion, what are my highest priorities for me and my book of business?

• How do you evaluate my performance?

• How will I know that I am meeting my targets and your expectations?

• Do I have ways to pull in my numbers?

  • (If you can’t pull in your own numbers) How am I trending against my goals, KPIs, and OKRs?

• What are some key habits and mindsets that will make someone successful in this role?

• 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?

• Can you describe the typical sales cycle in our organization?

• What methodologies or techniques does our sales team follow?

• How does our sales team track and manage leads throughout the sales funnel?

• What sales tools and software are primarily used?

• How is our sales team structured?

• Can you describe the roles and responsibilities of each member of the Sales team?

• How do different sales roles interact and collaborate with each other?

• What are the primary goals and KPIs for our Sales team?

• How are individual sales targets set and tracked?

• How do these goals tie into our company's larger objectives?

• What is the best way to transition clients from Sales to CS while ensuring they quickly see the value of our software?

• What competitors or alternative solutions were considered by the customer before deciding on us?

• Give me an example of a time when the handoff from Sales to CS went extremely smooth and a tell when it didn’t What were the differences?

• How often should we collaborate after the client has been officially handed off? 

• What information should I update you on after the handoff has taken place? How often do you want this information?

• What are the steps of the sales cycle/process from start to finish?

• How can I best support the customer during the handoff process?

• What are the biggest challenges we face today when handing off a customer from Sales?

• What are things that I can do that will help to maximize the efficiencies during the handoff?

• What are the most critical parts of the handoff that I should be deeply involved with?

• What frustrates you most about this handoff process?

• Have there ever been times in which CS needed to get involved before a customer officially signs their contract? Why were they needed?

• What level of support generally do our customers expect from us after purchasing our product?

• From your experience, why do customers buy our products?

• What is our ideal customer profile?

• What feedback or insights have you received from clients that could help us better understand their needs and provide more value?

• Can you tell me about a time when one of our product offerings/add-ons got cut during negotiations that you felt was a mistake? Why was it a mistake?

• Have any customers expressed a desire to cancel during the trial period? If so, how can we prevent this from happening based on their feedback? 

• Describe how this company makes decisions. Who is the primary decision maker and what where they like during the sales process?

• Who are the main players in the sales process?

• How will the customer measure the success of our solution?

• Did you encounter any significant objections and how did you overcome them?

• What product/service did they use before coming to us?

• What type of need do they have for us, short-term or long-term?

• If they left another provider and chose us instead, what made them leave the previous provider?

• Who is the our product champion, and who is their decision-makers and influencers?

• Who is the economic buyer, the person who has decision-making authority over the budget?

• Can you outline the decision-making process within this company?

• Could you share your experience dealing with the main decision-maker during the sales process?

• What strategies seemed to resonate most with the primary decision-maker?

• How does the decision-making hierarchy function within the organization?

• Are decisions typically made unilaterally, or is there a culture of consensus?

• How did the customer’s decision-making dynamics influence the sales process?

• Are there any particular considerations or factors that greatly influence their decision-making?

• In your experience, what factors or triggers accelerate the decision-making process for them?

• What would you say characterizes their decision-making style: risk-averse, innovative, quick, meticulous?

• 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?

• How has our product evolved over time?

• What do you think are the three most important features of our product?

• What do you wish CSMs on our team knew about your team and working in Product?

• What steps are involved in our product development process?

• How do you prioritize features or improvements for development?

• Can you walk me through how a feature goes from idea to implementation?

• How are release schedules determined and managed?

• What roles are involved in the product development process and what are their responsibilities?

• What is the best way for me to provide product feedback or report bugs?

• How can I stay updated on product changes or upcoming releases?

• How can our teams collaborate more effectively to ensure customer success?

• What is the protocol for urgent product issues or crises?

• How can I contribute to the product development process?

• What is the overarching vision for our product?

• Can you explain our product strategy and how it aligns with our company's goals?

• What are our product's core features and how do they differentiate us in the market?

• How do we plan to evolve our product to stay competitive?

• What major product milestones or goals are we aiming for in the next year?

• What upcoming feature are you most excited about releasing and why?

• How do we incorporate customer feedback into our product development process?

• Can you describe your ideal customer feature request? What are the essential pieces of information that it should include?

• When was the last time customer success influenced a product feature? What made this impactful for your team?

• What process is in place for addressing reported bugs or issues?

• Can you share some examples of customer-driven product improvements we've made recently?

• Can you tell me about a time when uncovered a new use case for the product? How do you discover it?

• How can I help you better understand how our customers use our product?

• What frustrates you about working with CS?

• Which group of customers would you like to interview in order to gain more insights and improve the product?

• How do we ensure that our product remains responsive to customer needs and market trends?

• How do we measure the impact of product improvements on customer satisfaction?

• Is there anything Product looks for when prioritizing feature requests?

  • How can I ensure my feature requests are helpful to your team?

  • How can I best provide input or feedback on product enhancements based on my interactions with customers and their pain points?

• How are new features or product changes communicated to the team?

• What resources are available for me to learn more about our product?

• Is there any form of product training that I can take part in?

• How can I help in sharing product knowledge within our team and with our customers?

• What process is in place for keeping all team members updated on product knowledge?

• 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?

• Could you describe the typical process for a support ticket, from the moment it's received until it's resolved?

• What types of issues do you most commonly handle by our customers?

• How does the Support team handle high-priority or critical issues?

• What systems or tools does your team use to manage and track customer issues?

• Is there additional ticket prioritization in place in addition to ticket criticality? Eg.: ARR, renewal proximity, existing escalation?

• 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

• Could you explain our current marketing strategy?

• What are the main objectives of our ongoing/upcoming marketing campaigns?

• What factors or data points influence the direction of our marketing campaigns?

• How do we measure the success of our marketing efforts?

• Is there a customer advocacy program your team manages?

• What are the customer events /joint activities planned for this quarter/ year?

• What is our current go-to-market strategy?

• How do we determine product-market fit when introducing new product or service offerings?

• How do you currently conduct competitive analysis?

• Who are our biggest competitors?

• What are our competitive advantages?

• Can you explain how our Marketing team is structured?

• What are the roles and responsibilities of each team member in the Marketing department?

• How do the different roles within the Marketing team collaborate with each other and other teams?

• Are there specialized sub-teams within the Marketing team (e.g., content marketing, product marketing, digital marketing)? What are their specific functions?

• How do marketing projects and campaigns typically get assigned within the team?

• Who are the key contacts for specific marketing-related questions or collaboration efforts?

• How does our Marketing team segment our target market?

• What are our primary customer personas and how are they used in our marketing efforts?

• How does the Marketing team stay updated on customer preferences, needs, and industry trends?

• How does the Marketing team decide what type of content to produce?

• Which channels does our Marketing team utilize to distribute content?

• What is the process for updating or revising marketing materials?

• 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?

• Could you describe your role and responsibilities within our CS team?

• What's a typical day (or week) look like in your shoes?

• How do you typically structure your day or week?

• What are your top priorities at the moment?

• Got any big to-dos on your plate right now?

• What are the kinds of customer issues you usually take care of with your book of business?

• How do you measure the satisfaction of your customers?

• How do you measure the engagement of your customers?

• Got any recent customer wins to brag about? What's the magic behind it?

• What's the craziest customer situation you've wrestled with lately? How'd you tackle it?

• Any epic fail that turned into a great learning moment?

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

• When was a time when you upsold one of your customers? How did you know it was the right time? How did you approach this opportunity?

• When was a time you managed to turn a negative customer experience into a positive one?

• Can you remember a time when you had to manage a customer crisis? How did you restore their confidence in our product or service?

• When was a time you had to collaborate with other teams (like sales, product, or marketing) to help a customer? How did that go?

1. What strategies or techniques have you found most effective in ensuring your customers are successful?

2. In your experience, what has helped your customers be the most successful using our product?

3. In your experience, what’s the most common reason our customers churn? How we can prevent this from happening with other clients?

4. How do you approach difficult conversations with customers? Do you have any recent examples of this? What was the issue and how did you approach it?

5. What's your magic formula for juggling tasks and prioritizing your workload?

6. What resources would help us be more productive? How can we build it together?

7. How can we better share our wins and lessons learned so we avoid making repetitive mistakes?

8. What resources or tools do you think would benefit our team's efficiency and effectiveness, and how can we work together to implement them?

9. What are the best ways to reduce admin work to free our time to add more value?

10. Which customer journey do you find most challenging and we can collaborate to help each other?

• 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?

• Can you summarize the role and objectives of our CS Operations team?

• What key responsibilities does the CS Operations team hold?

• How does CS Operations support the work of the Customer Success team?

• What are our biggest data challenges?

• What are your priorities for the next quarter that will impact my job?

• What customer surveys are we distributing and how frequently are those being distributed out and reviewed?

• What projects are the CS Ops team working on now and what is on the roadmap for the year?

• What systems and tools does our CS Operations team manage?

• How do these tools support the broader CS team and our customers?

• Can you explain some of the key processes managed by CS Operations?

• What are the key metrics that the CS Operations team tracks?

• How are these metrics used to gauge the performance of the CS team?

• What type of reports does the CS Operations team generate and who are the main recipients?

• What metrics go into our health scores today and how are they calculated?

• What’s the most valuable customer data I should be using today?

• How are you reviewing and analyzing customer churn and retention metrics?

• 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?

• Could you outline the main purpose and objectives of our Digital CS/Scale Team?

• What are the primary responsibilities of the Digital CS/Scale Team?

• How does the Digital CS/Scale Team interact with other teams within the CS function?

• Which client segments are supported by the digital-led CS model?

• How is the digital-led approach different from the human-led CS approach?

• What digital tools or platforms does our team use to provide personalized support to customers?

• How do we use automation today? What tasks or processes in the future would you love to automate as well?

• What are the key channels you’re using to reach customers?

• How do these strategies help us deliver a personalized yet scalable customer success experiences?

• Are there reports indicating usage and/or deviation from a certain usage baseline?

• Could you share a case study of a successful digital engagement campaign that we have run recently?

• What playbooks and 1:many/scaled initiatives are you using today? Can I leverage any of them with my clients?

• What are the key metrics that the Digital CS/Scale team uses to track success?

• How do these targets impact your strategies and actions?

• What defines successful digital customer engagement in the context of these metrics?

• 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?

• Could you share your vision for the company in the next 3-5 years?

• How has the vision of this company changed over the last x years?

• How do you see the role of Customer Success evolving in our company?

• What strategic initiatives are we planning in the Customer Success space this year?

• How can the Customer Success team contribute towards achieving these strategic goals?

• What is the goal of the CS department in your own words?

• How do we forecast churn, retention, and expansion metrics at our organization and is that visualized for teams to leverage?

• Does the C-Level team visit/meet customers? 

• Is there a CS update taking place as part of the board meeting?

• What are the CS KPIs presented during the board meeting?

• Does the CS leadership team participate in board presentations?

• What are the key performance indicators that you use to evaluate the success of our Customer Success team?

• How does the leadership team monitor and assess these KPIs?

• How is the performance of individual CSMs considered at the leadership level?

• What is the North Star metric for our CS department?

• 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?

• Can you share a bit about your background and journey into customer success? What drew you to this field?

• Do you have any interests or hobbies outside of work that you're passionate about?

• Who do you look up to, professionally or personally, and why?

• Do you participate in any professional or industry groups related to customer success? If so, can you share your experiences?

• How do you handle work-life balance, and do you have any tips for maintaining it effectively?

• What are some of the books, podcasts, or resources that have influenced your approach to customer success?

• How do you manage stress or overcome work-related challenges? Any mindfulness or resilience strategies you could share?

• Do you have a mentor or a coach? If so, how has that relationship influenced your career?

• What's the most exciting part of your role as a CSM? What motivates you every day?

• If you could switch roles with anyone in the company for a day, who would it be and why?

• If you weren’t in CS, what would you be doing instead?

• Which type of company do you prefer working in - a startup, scale-up, or corporate? Why?

• What excites you about Customer Success? Which part of CS inspires you the most?

• What has been your most challenging experience with a customer, and how did you handle it?

• Do you have any go-to strategies or techniques when dealing with difficult situations or customers?

• Can you share a customer success story that you're particularly proud of?

• How do you prioritize your day-to-day activities?

• What does a busy day look like to you?

• What is something you think CSMs often get wrong?

• Can you tell me about a situation where you had to advocate for a customer within the company? How did you handle it?

• Tell me about a time when you had to collaborate with another department to resolve a customer issue. How did you navigate it?

• What's the most memorable feedback you've received from a customer, and how did it influence your approach to customer success?

• What is one valuable lesson you've learned in your career that you would like to share with others?

• What are some key skills or experiences you bring to the team that you feel could benefit others?

• If you could solve one problem or improve one aspect of our organization, what would it be and why?

• 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?

• Could you share some ways our product has brought tangible benefits to your business?

• Could you help me understand how our product impacts your company's revenue?

• What level of friction do you experience adding new employees/users to the platform?

• If you were sitting next to a leading expert in your field, what would you ask them?

• What are you concerned about during your next board meeting?

• Why did you decide to upgrade from <competitor> to <our product>?

• What’s one initiative on your whiteboard that wasn’t there 30 days ago?

• Can you provide an overview of your company's structure and how different teams interact?

• What metrics are you held accountable to in your specific role?

• What are the key business challenges you face currently and how is our product helping you address them?

• How is your industry changing and how might those changes impact the way you use our product?

• Who are the people stakeholders in your organization who are impacted the most by our product?

• What are the main tasks you use our product for? Are there tasks you wish you could use our product for?

• Could you walk me through your workflow with our product? Where does our product fit in your day-to-day operations?

• What strategic initiatives or goals is your company focused on right now?

• What are some of the key performance indicators (KPIs) that your team is measured on? How our product assists in achieving those KPIs?

• How has your use of our product evolved since you first started using it?

• How do you see your company’s needs evolving in the future, and how can our product adapt to meet those needs?

• Are there aspects of our product that you feel you are not fully utilizing yet?

• How would your business be affected if you could no longer use our product?

• Can you share a recent success story related to the use of our product in your business?

• How does your team stay up to date with our product’s updates and new features?

• Are there any aspects of our product that you find to be particularly beneficial to your industry or line of business?

• What’s the biggest blocker preventing your team using our product more?

• What data is most valuable to your executive leadership team?

• What is one thing that still confuses you about our product?

• What feature of ours do you find yourself using most often and why?

• What’s the biggest value our partnership has brought over the last x years?

• In your opinion, what’s the biggest challenge our partnership faces right now?

• How comfortable would you be if you were asked to train your staff on our product next week?

• If you could change one thing about our product, what would it be?

• What can I do in the future to help you achieve more success using our product?

• Is there anything you wish vendors understood better about your role or your needs?

• Are there any projects or initiatives you're currently excited about?

• What was the best customer experience you've ever had and what made it great?

• Are there specific events or times in your business cycle when you particularly need our support?

• Can you share a time over the last <time> when I did something that really helped your team or organization? 

• What types of content or insights are most valuable to you (industry trends, product updates, case studies, etc.)?

• What should I keep doing as your CSM that you find particularly valuable? 

• What should I start doing as your CSM that would make your job easier? 

• What should I keep doing as your CSM that you stops you from making progress in your role? 

• What are some professional development goals you have and is there a way our product can support them?

• What type of reports/updates are required to demonstrate successful outcomes?

• Are there major changes expected in your own competitive markets which we should plan for?

• How will you measure the success of our product?

• How did you go about evaluating a new solution?

• If you had the power to change one thing about our product right away, what would that be and why?

• Are there any aspects of our product that you find puzzling or tricky to navigate?

• Imagine you had to train your team on our product next week; how comfortable would you feel doing that?

• What is your leadership focused on accomplishing over the next few years?

• What metrics are you held accountable to in your specific role?

• What are our largest risks right now if we maintain the status quo and don’t change what we are currently doing?

• What is one thing you hated about another service provider that you used before us?

• What is something we can do to make you consider using us for the long term?

• What are the measurable KPIs that you define our value based on?

• What feature if released tomorrow by one of our competitors would make you consider leaving us as a client?

• In one year from now, what would make you look back at our partnership and think it was successful?

• As we approach your renewal date, I'm interested to know how you're feeling about continuing our partnership. Do you plan to renew? 

• Which features would you like to see next in our product?

• If your CFO said your budget was cut and you needed to make some tough decisions, how strongly would you advocate keeping our software?

• 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?

• What does my ideal workday look like, and how can I structure my time to make this a reality?

• What tasks give me energy or inspiration, and which ones drain me?

• Where do I see myself in three years, and what do I hope to have achieved professionally?

• What are the additional skills I need to develop to progress in my career?

• Which career path am I interested in pursuing—management or senior expertise? Why this path?

• Do I have a personal development plan (PDP), and am I discussing it with my manager regularly? If not, how can I start this process? What is holding me back?

• What is the opportunity cost of staying in my current role or company versus exploring other opportunities?

• What's a personal growth goal that scares me, but I know it's necessary for my advancement?

• If fear was not a factor, what would I attempt in my career?

• What do I want to be known for in my career?

• What has been my most impactful contribution to my team or to a customer?

• What comes to mind when my co-workers think of me, and how does this align with how I want to be perceived?

• What motivates me most in my job, and how can I leverage this motivation?

• When do I feel most fulfilled in my role, and what contributes to this fulfillment?

• How do I handle stress and challenges in my role, and how can I improve my responses?

• When was the last time I stepped out of my comfort zone professionally, and what did I learn from that experience?

• What are my core values, and how do they align with my current role as a CSM?

• What elements of my work do you find the most meaningful? Why?

• How does my role allow you to make a positive impact?

• How do my personal values influence my interactions with customers and colleagues?

• How do I stay motivated when facing challenging situations or difficult customers?

• How do I balance my personal life with the demands of my job? What strategies work best for me?

• How do I manage stress and prevent burnout?

• What activities do I engage in outside of work that helps maintain my physical and mental well-being?

• How do I manage my energy levels throughout the day to ensure peak productivity?

• How does my organization support my wellness and work-life balance?

• 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?

• 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).