Dear Insider: How much should you guide Your CS team?

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Q: I'm a CS leader and I'm struggling with how to empower my team to do their best work. Do I get into the nitty-gritty and provide tasks and to-dos, or do I give them high level objective and KPIs and let them figure out their own way to work? How do other CS leaders manage and track their team's workload?

‍As a CS leader, striking the right balance between empowering your team and providing them with clear direction is key to building an effective, motivated team.

Here’s how I’d approach it:

1. Start with the “why” and set clear expectations: Give your team a high-level objective that’s closely aligned with business goals. Define KPIs and outcomes that clarify what success looks like but leave the how open. This approach keeps them focused on driving impact rather than just checking boxes.
2. Define guardrails, not roadmaps: Offer frameworks, best practices, and guardrails that help them understand boundaries without limiting their creativity or autonomy. Instead of handing them a task list, guide them with examples or “best practice playbooks” they can adapt as they see fit.
3. Use regular check-ins for guidance, not micromanagement: Weekly one-on-ones are great for assessing workload and identifying roadblocks. Instead of focusing on every task, focus on where they might be stuck, what’s holding them back, or what support they need from you or others to achieve their goals.
4. Leverage tools to track workload and performance: Tools like a capacity plan or a dashboard of core KPIs can help you and your team track workload and manage priorities in real time. This way, you’re able to see how well they’re managing their responsibilities and coach them on balancing high-impact work. I’d also have to shamelessly plug ClientSuccess.

Ultimately, empowering your team is about giving them trust, a clear sense of purpose, and the resources they need to be successful. When they’re challenged to solve problems on their own, they’ll grow more confident, and you’ll end up with a team that’s highly engaged and capable of delivering real business impact.

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Q: When taking a CS course, how do I know which one to choose? Do you think that taking a CS course gives someone who is trying to break into customer success an edge? How do you speak about it in an interview without exposing that you don't actually have any CS experience?

‍I see a lot of value in Certification Programs and courses but let’s align on how to find the right one and where and how it adds value.

Start with finding the right course. Look for courses that:

• Focus on practical skills: A course that emphasizes key frameworks, best practices, and tools used in CS (like customer journey mapping, health scoring, or QBRs) will give you a solid foundation.
• Include real-world examples and case studies: This helps you understand the real challenges and scenarios CSMs face, giving you relevant insights to bring into interviews.
• Provide certifications: Certifications from well-known platforms or organizations
• Offer networking opportunities: Some courses include access to CS communities or mentorship, which can be invaluable for breaking into the field and understanding what companies expect from CS professionals.

I highly recommend SuccessHACKER for CS courses and ongoing education.

When interviewing, you’re not going to talk about the certification. Here is how you’ll use it to support you in the interview process:

1. It will help you speak the language of Customer Success; you’ll understand what’s being asked of you and how to think about best practices
2. It will show your commitment to education and growth; ongoing learning and mastery are very important for CSMs
3. It will support you in thinking about your stories and how they demonstrate transferable skills which is what you’ll highlight during the interview process

No one will hire you because you have a certification or completed a course; and it won’t be the thing that brings you to the top of the pile. But you can use it to ensure you master the right storytelling, highlight the right skills and speak confidently to the hiring manager.

Q: What are the top three interview questions asked of a CS leader candidate, and how do you go about searching for jobs in specific industries, such as tech, for the CS leader roles?

‍When interviewing for a CS leadership role, there are a few core questions that almost always come up. Here’s how I’d approach these questions, as well as some strategies for finding CS leader roles in specific industries like tech:

Top three interview questions for a CS leader candidate:

1. "How do you measure the success of your Customer Success team?"
   • What they’re looking for: They want to see if you’re metrics-driven, understand CS impact, and can align your team’s success with business outcomes.
   • How to answer: Talk about key performance indicators (KPIs) like Net Revenue Retention (NRR), Gross Retention, Customer Health Scores, and Customer Satisfaction (CSAT) scores. Describe how you use these metrics to gauge success, assess team performance, and drive decisions. I’d also touch on how I align the team’s goals with the company’s strategic objectives to ensure Customer Success has a clear impact on growth.
2. "How would you approach building a Customer Success strategy from scratch?"
   • What they’re looking for: They want to understand your strategic thinking, ability to design scalable processes, and how you prioritize initiatives.
   • How to answer: Walk through a high-level plan. Start with understanding the customer journey and identifying key touchpoints for proactive engagement. Then, outline how you’d establish essential processes like onboarding, health monitoring, and renewal workflows. Finally, talk about collaborating cross-functionally to ensure a unified customer experience. I’d emphasize the importance of listening to customers and internal stakeholders when building out the strategy.
3. "How do you handle a situation where a customer wants to churn?"
   • What they’re looking for: They want to know if you’re able to approach challenging situations with empathy and strategic thinking and how you lead the team in handling difficult conversations.
   • How to answer: I’d describe how I’d assess the root cause, listen to the customer’s concerns, and work to address their issues while finding a solution that aligns with their goals. I’d explain my approach to empowering my team with frameworks for retention, but also how I’d step in for executive involvement when necessary to demonstrate the company’s commitment to the relationship. In my experience, having a structured playbook for risk mitigation is essential, as it keeps the team aligned and focused on preserving customer value.

Searching for CS leader roles in specific industries:

1. Focus on industry-specific job boards and sites: Websites like LinkedIn, Built In, and AngelList have industry filters and are great for tech roles. LinkedIn also lets you create job alerts based on specific titles, industries, and companies, which helps you stay on top of new opportunities.
2. Network with industry leaders and join CS communities: The CS community is very active. Engaging in Customer Success groups on LinkedIn, Slack communities, and networking events often uncovers opportunities in tech and other specialized industries. Many roles are shared in these communities before they’re posted publicly, so it’s a great way to get an “in.”
3. Target specific companies and make connections: Identify tech companies that interest you and research their Customer Success teams on LinkedIn. Reach out to current or former employees, ideally in CS or adjacent roles, to learn more about the company culture and their approach to CS. Building connections can sometimes lead to a referral, or at least better insights when you apply.

Overall, when you’re a CS leader targeting a specific industry, aligning your experience and network with the needs of that industry is essential.