Best Practices for Training Customer Service Teams

We spend months interviewing to find the “perfect” CSM… and then set them up to fail. Here’s the reality I see too often: ❗ New hires are thrown customers after 1–2 weeks. ❗ Product training is rushed or nonexistent. ❗ SOPs are thin, outdated, or missing. ❗ Leaders don’t invest the time to set expectations or coach. ❗ And then KPIs are handed down that even seasoned CSMs struggle to hit. The issue isn’t the talent, it’s the lack of enablement. But here’s the good news: you don’t need a dedicated L&D team or endless resources to onboard well. You need intention. A simple enablement plan for new CSMs (even with limited resources): 1️⃣ Onboarding Buddy - Pair new hires with an experienced CSM for shadowing, Q&A, and feedback. 2️⃣ 30-60-90 Plan - Outline clear goals and expectations for their first 3 months. (Focus on learning before doing.) 3️⃣ Product Deep Dives - Host weekly “lunch and learns” where Product, CS, or Support walks through one feature in detail. Have them shadow customer onboarding or watch recordings. 4️⃣ Playbook Starter Pack - Even if you don’t have full SOPs, document 3–5 repeatable workflows (renewals, QBR prep, escalation handling). 5️⃣ Mock Meetings – Run practice customer calls internally before they ever face a real customer. 6️⃣ Leader Time - Block weekly 1:1s focused not just on performance but on coaching, context, and confidence-building. These aren’t heavy lifts, they’re discipline and focus. If you want your CSMs to succeed (and your customers to stay), stop spending all your energy on hiring the “perfect” candidate and start spending more on enabling them once they walk through the door.

They say experience is a great teacher. How do you leverage it? I rely heavily on experiential learning as a customer service trainer. Customer service reps have valuable experience from... * Serving customers * Being customers * Interacting with other humans The trick is optimizing what you learn from experiences. David Kolb created a four-step experiential process that anyone can use. 1. Experiencing: doing something. 2. Reflecting: evaluate how it went. 3. Thinking: decide how to adjust. 4. Acting: trying something new. My Customer Service Tip of the Week emails are built around this model. 1. Experience Each tip starts with a relatable story or example. For instance, I went to REI to buy hiking poles for my wife and a knowledgeable sales person used her expertise to help me make the right decision. 2. Reflecting The tip asks you to think about how the tip applies to you. The expertise tip suggested making a list of the top ten product questions customers ask. 3. Thinking Think about how you can use the tip when serving your customers. The expertise tip suggested coming up with extra helpful answers to each of the top ten questions. 4. Acting Apply the tip right away with the customers you serve. This process is self-reinforcing. Trying a new approach leads to a new experience. You can then repeat the steps and continue learning. I bet you already do this! What is one customer service skill you learned from experience?

When your CSM freezes on a tough call, do you blame them? I’ve heard many Customer Success leaders hesitate to use role-playing. Some feel it comes across as awkward. Others believe their teams will learn through exposure to real calls over time. But here’s the truth: observing a tough conversation is very different from being the one responsible for navigating it. Especially when a renewal is at stake or a customer clearly feels frustrated. Most teams struggle less with understanding the product and more with staying composed when a customer pushes back, questions the value, or speaks in a way that throws the team off balance. In those moments, confidence does not appear on its own. It comes from preparation. That’s why we practice regularly. It begins in onboarding and continues as part of our rhythm. We walk through real scenarios that actually show up in the day-to-day. We focus on tone, pacing, phrasing, and staying grounded when conversations get uncomfortable. When a high-pressure call comes up, I join. I stay present without taking over. If the dynamic shifts and the customer starts to dominate, I step in briefly to help reset the tone and bring the focus back to a shared direction. Then I hand the conversation back to my rep. The goal is to build capability, not dependency. After the call, we reflect together. We talk through what worked and where we can fine-tune the approach. That space, where someone can try, miss, and improve, is where real learning happens. If your team struggles when conversations get tough, ask yourself whether they’ve been given the space and structure to train for those moments or if they’ve been left to figure it out while under pressure.