Coaching CSMs to become trusted advisors

In Customer Success, being the hero can backfire. As a CSM, it’s tempting to jump in and fix things for your customer. It feels good to solve a problem quickly. But when we do this for the customer (instead of with them), we’re actually hurting them in the long run. There’s a principle in psychology: “𝘋𝘰𝘯’𝘵 𝘴𝘵𝘦𝘢𝘭 𝘺𝘰𝘶𝘳 𝘱𝘢𝘵𝘪𝘦𝘯𝘵’𝘴 𝘱𝘳𝘰𝘣𝘭𝘦𝘮𝘴.” If you give someone the answer without their participation, you’ve only solved one issue — not made them more capable for the next one. In CS, we can fall into this same trap. And the consequences are real:    ❌ Endless “quick asks”  ❌ Unpaid services  ❌ A customer who’s reliant — but not successful So how do you build a real partnership instead? 𝟭. 𝗔𝗹𝗶𝗴𝗻 𝗼𝗻 𝘁𝗵𝗲𝗶𝗿 𝗴𝗼𝗮𝗹𝘀 𝗲𝗮𝗿𝗹𝘆 If you don’t know the customer’s “why,” you can’t lead. Once you do, you have a North Star to guide every conversation and expectation. 𝟮. 𝗔𝘀𝘀𝗶𝗴𝗻 𝘁𝗵𝗲 𝗿𝗶𝗴𝗵𝘁 𝗮𝗰𝘁𝗶𝗼𝗻 𝗶𝘁𝗲𝗺𝘀 Your customer has homework — not just you. Your role is to clearly explain what must be done, why, and who owns each piece. 𝟯. 𝗦𝘂𝗽𝗽𝗼𝗿𝘁 𝘄𝗶𝘁𝗵 𝘀𝗰𝗮𝗹𝗮𝗯𝗹𝗲 𝗿𝗲𝘀𝗼𝘂𝗿𝗰𝗲𝘀  Make it easier for them to succeed. Templates, guides, short videos — anything that helps them help themselves. 𝟰. 𝗙𝗼𝗹𝗹𝗼𝘄 𝘂𝗽 (𝗮𝗻𝗱 𝗱𝗼𝗻’𝘁 𝗹𝗲𝘁 𝗴𝗼) Circle back. Confirm completion. If they’re stuck, offer help. But never let them off the hook. Your follow-up proves you take their success seriously. When you do this right, you create a real partnership — one that delivers results and preserves your boundaries as a CSM. Don’t be the hero. Be the partner that makes them better. #customersuccess #CSM

LinkedIn is flooded with terrible advice for CSMs. Every day, I see posts telling CSMs to: ❌ "Push back on customers!" ❌ "Be more strategic!" ❌ "Own the renewal!" Sounds great (until you realise nobody tells you *how*). Here’s the real problem: Too many CSMs operate like order-takers because they: ⚠️ Lack the confidence to challenge customer assumptions. ⚠️ Don’t have the data or insights to back up their recommendations. ⚠️ Feel like they’re just relationship managers, not business consultants. 💡 How do you fix it? CSMs who operate with first principles thinking and focus on the customer vs. the process get better outcomes. 1️⃣ Know your customer’s business like an insider. → How do they make money? → What are their goals for the year? → Where are they investing vs. cutting back? → Who are the decision-makers and influencers? Use a Success Plan to build a clear picture of the present and design the future. ⭐ Bonus points to leaders who give the team the tools and data to execute on this 2️⃣ Understand what drives your product’s value. If a customer asks, “How does this impact revenue?”, can you answer? → Do you know the metrics they report to their business? → Are you tracking the right indicators of success? Set a baseline (where they started), track month-over-month progress, and tie it back to their business goals. ⭐ Bonus points to leaders who build value metrics for their products. 3️⃣ Act like an advisor, not an order-taker. → Don’t just relay information—interpret it. → Don’t just agree—challenge bad strategies with facts. → Don’t just talk about risks—proactively solve them. This requires preparation. Collect call agendas ahead of time, analyze customer usage patterns, and come up with insights. ⭐ Bonus points to leaders who implement AI to help CSMs uncover insights. And here's a piece advice for CSMs... Stop consuming vague, one-size-fits-all advice and start building strong opinions about how your customers can get value from your product at every stage of their journey. 💬 Want to sharpen your Swiss Army knife and build the skills to succeed in the future? Join 15K CS professionals in Unconventional Growth [link in comments]. #CustomerSuccess #CSM #CustomerRetention #RevOps #CX

The day I finally understood how trust really works, everything changed for me as a CSM. In my first Customer Success role, our leader had us read a book before our team offsite: The Trusted Advisor. Short. Simple. Game-changing. Inside was something that flipped a switch for me, the Trust Equation: Credibility + Reliability + Intimacy / Self-Orientation For the first time, trust wasn’t a feeling, it was something I could build intentionally. So I made a move, and this changed how I worked with customers: I wrote each element of the equation into their account. And every engagement became a chance, an opportunity to build on trust with purpose. Here’s what that looked like in real life ✅ Credibility Know your stuff. Speak with clarity. Bring insights, not just product updates. → When a customer asks how to achieve a specific outcome in your product and you clearly walk them through 2-3 workflows that get them there. → When they ask, “What are other customers like us doing?” and you give just the right amount of relevant context and detail. ✅ Reliability Do what you say you’ll do. No surprises. No dropped balls. → You follow through after every meeting. → You send the recap. → You make the intro. → You deliver on that one thing they asked for, even if it seemed minor. ✅ Intimacy Be human. Build connection. Care about what matters to them. → You remember their kid’s name. → You know they’re prepping for a board meeting next week and ask how it’s going. → You lead with empathy, not agendas. 🚫 Self-Orientation Don’t make it about you. Ever. → You don’t flex your product knowledge to sound smart, you share what helps them win. → You don’t push your goals, you stay focused on theirs. Every CSM wants trusted relationships. Not every CSM builds them on purpose. This equation gave me a new level of intention. What’s one small way you can build more trust? ________________________ 📩 If you liked this post, you'll love The Journey. Head over to my profile and join the thousands of CS professionals who are along for the ride as I share stories and learnings going from CSM to CCO.

As CS leaders, we can’t ask CSMs to be more strategic and leave them to figure it out alone. That responsibility sits with us. Amy Edmondson, the Harvard Business School professor who coined “team psychological safety,” defined it as a shared belief that a team is safe for interpersonal risk-taking. In simple words, people can ask questions, raise concerns, admit mistakes, and try new approaches without fear of punishment or humiliation. That applies directly to CS leadership. Because today’s CSM is already carrying a heavy role. They are expected to manage relationships, protect retention, understand product usage, find expansion signals, speak to executives, handle escalations, and stay calm when the customer is unhappy. So when we say, “be more strategic,” we have to be honest. Have we created the environment where they can actually try? A safe environment does not mean a soft environment. It does not mean lower targets, less accountability, or no pressure. It means a CSM can test a better way of working without fearing that one imperfect attempt will be held against them. They should be able to say: “This account looks green, but I don’t trust it.” “This customer conversation needs to move from adoption to commercial value.” “I want to try a different executive review format.” “I may be wrong, but I think there is expansion here.” That is how strategic judgment develops. Not by repeating the same routine forever. And definitely not by hearing “work smarter” in a team meeting. The routine work will always exist in CS. Follow-ups need to happen. Tickets need visibility. Customers need answers. Renewals need attention. But strong CS teams are built when CSMs have enough confidence to improve how the work gets done. Sometimes that redesigning a QBR because the old format has become theatre, calling out risk when everyone else still sees the account as healthy or may be admitting that a customer relationship is friendly, but commercially weak. That takes courage and courage does not grow where every experiment feels like job risk. CSMs do not become strategic because we raise expectations. They become strategic when we give them room to think, test, learn, and come back sharper. That is the environment we owe them.

A lot of Customer Success leaders are frustrated because their teams are treated like glorified customer support or a “white glove” concierge service. If you want to change that, take control of the narrative. Define the purpose. Clearly document the role of CS, including what your team does and what it does not do. Once you’ve documented, you have to socialize those expectations with other teams (especially sales.). Create a few slides that explain what role CS will play with customers and have it added to the sales deck. You need to set expectations early and repeat them often. Make the business case. Explain why CS needs to focus on strategic, revenue-generating activities—not cleaning up service issues. That’s not where their value lies. Solve for support. If your company treats CS like Support, it’s probably because there’s no alternative. But here’s the thing: CSMs cost more than support agents. The math doesn’t math for CS to own support. So build support into your product and/or stand up a proper support team. Protect strategic time. Create space for your team to do strategic work. Create a framework to help them build strategic plans, and give them a quarterly day to focus solely on this work. Let the company know—this is protected time. In team meetings, let them share their strategy plans and collaborate to refine. Build the muscle. Hire accordingly. If you want strategic thinkers and revenue-minded operators, don’t hire reactive, order takers. Control internal access. Giving every department in the company permission to send Ad hoc requests to CS will bury your CSMs. Build a process for internal teams to route requests, and assign an "air traffic controller" to keep the flow manageable. You want to be a team player, but it requires structure and process. Build revenue muscle. Even if your CSMs don’t own a quota, they’re perfectly positioned to surface upsell and expansion opportunities. Train them. Equip them. Let them contribute. Customer Success can be a strategic growth engine—but only if we design it that way. Take control of the function. Tell the story. Then build the system to match.

In Customer Success we love to talk about ROI, value, “trusted advisor.” Here’s the problem, most of the time we expect customers to just tell us what success looks like. Reality check, many don’t know. Sometimes they inherited the tool. Sometimes someone else bought it for them. Sometimes “success” is just a vague idea in their head. That’s where high touch CS earns its stripes. You don’t just wait for answers, you coach them to find clarity. Here’s a simple framework I use: 1. Current problem – What are you actually struggling with (in your solution domain - Break down your domain for them. They might not realize where you can help). 2. Desired outcome - No fluff. *What would success mean to you, your team, and your company?" In that order. You want them invested. 3. Timeframe & measurement – "By when, and how will you know you’ve hit the mark?" Let them seriously resonate on it, don't speed it up, this is where accountability builds up. 4. Partnership – "How can I help you get there? And how can I make sure you succeed and become the hero?" You are in the trenches to with them to ensure *They* succeed. It takes time. It’s uncomfortable. Sometimes they won’t have the answers. But that’s the work. That’s where relationships are built and real outcomes are shaped. Stop chasing buzzwords. Start coaching clarity. That’s where value lives.

The difference between a good and great CSM if often how they frame an issue Real examples below, how to shift conversations from reactive to advisory 1️⃣ 𝗪𝗵𝗲𝗻 𝗮𝗻 𝗶𝗻𝘁𝗲𝗿𝗻𝗮𝗹 𝘁𝗲𝗮𝗺 𝗺𝗲𝘀𝘀𝗲𝗱 𝘀𝗼𝗺𝗲𝘁𝗵𝗶𝗻𝗴 𝘂𝗽 ❌ “I’m so sorry, our internal team really dropped the ball on this.” ✅ “I can see how that caused frustration. Here’s what we’re doing to make it right - and how we’ll prevent it next time.” 💡 Finger pointing may feel good in the moment, but it erodes all your credibility. Shows you're not in control 2️⃣ 𝗪𝗵𝗲𝗻 𝘁𝗵𝗲 𝗰𝘂𝘀𝘁𝗼𝗺𝗲𝗿 𝗿𝗲𝘀𝗰𝗵𝗲𝗱𝘂𝗹𝗲𝘀 𝗮𝗻 𝗶𝗺𝗽𝗼𝗿𝘁𝗮𝗻𝘁 𝗺𝗲𝗲𝘁𝗶𝗻𝗴 ❌ “No problem, just let me know when works again.” ✅ “Totally understand, this is important to knock out - let’s get a new time locked in this week so we keep momentum on your goals.” 💡 You stay in control and show their success is still your priority. You also don't let your time or work be devalued 3️⃣ 𝗪𝗵𝗲𝗻 𝘆𝗼𝘂 𝗺𝗮𝗱𝗲 𝗮𝗻 𝗲𝗿𝗿𝗼𝗿 ❌ “Sorry about that, I’ll try not to let it happen again.” ✅ “That was my miss. Here’s what happened, and here’s what I’ve already done to fix it.” 💡 Customers forgive mistakes when they see accountability. 4️⃣ 𝗪𝗵𝗲𝗻 𝘁𝗵𝗲 𝗰𝘂𝘀𝘁𝗼𝗺𝗲𝗿 𝗶𝘀𝗻’𝘁 𝘂𝘀𝗶𝗻𝗴 𝘁𝗵𝗲 𝗽𝗿𝗼𝗱𝘂𝗰𝘁 𝗲𝗳𝗳𝗲𝗰𝘁𝗶𝘃𝗲𝗹𝘆 ❌ “You’re not using the product the right way.” ✅ “I noticed a few areas where you could get more value. Can I show you how others have driven better results?” 💡 Move from critic to coach. That’s where credibility lives. 5️⃣ 𝗪𝗵𝗲𝗻 𝘁𝗵𝗲 𝗽𝗿𝗼𝗱𝘂𝗰𝘁 𝗲𝘅𝗽𝗲𝗿𝗶𝗲𝗻𝗰𝗲 𝗰𝗮𝘂𝘀𝗲𝗱 𝗳𝗿𝘂𝘀𝘁𝗿𝗮𝘁𝗶𝗼𝗻 ❌ “I’m so sorry the tool caused issues.” ✅ “That would definitely be frustrating. Let me show you how other customers approached this and got better results.” 💡 Empathy without apology keeps the focus on progress, not problems. 6️⃣ 𝗪𝗵𝗲𝗻 𝘁𝗵𝗲 𝗰𝘂𝘀𝘁𝗼𝗺𝗲𝗿 𝗶𝘀 𝗳𝗿𝘂𝘀𝘁𝗿𝗮𝘁𝗲𝗱, 𝗯𝘂𝘁 𝘁𝗵𝗲𝗶𝗿 𝗼𝘄𝗻 𝗽𝗿𝗼𝗰𝗲𝘀𝘀 𝗼𝗿 𝗲𝗿𝗿𝗼𝗿 𝗰𝗮𝘂𝘀𝗲𝗱 𝘁𝗵𝗲 𝗶𝘀𝘀𝘂𝗲 ❌ “Actually, this happened because your team didn’t follow the steps.” ✅ “I can see where this went off track. Here’s what likely caused it, and here’s how we can prevent it next time.” 💡 Acknowledge emotion, guide toward insight. Never blame, educate through partnership. 𝗕𝗼𝘁𝘁𝗼𝗺 𝗹𝗶𝗻𝗲: Accountability reigns supreme. Selling out your team hurts you in the long run. When a customer is frustrated, show empathy + ownership and drive to solutions. What other “say this, not that” examples do you see in CS every day? 👇 Drop one in the comments — I’ll feature the best ones in a follow-up post.

We hand CSMs a won deal and a pat on the back: "Go make them happy." "Here’s a ticketing system, training script & NPS score": everything but a way to be strategic. Then we act surprised when ARR bleeds. We didn’t build CS to drive revenue—we built it to babysit. And it comes down to one word...Post-Sale It’s like saying: "Here, take this SOLD customer and watch over them, okay? Watch over them. Read them something educational. Check in once in a while. Oh - and make sure they don’t fall or break something. They’re very delicate." There is no POST-Sale phase. Not in SaaS. There’s only the NEXT Sale. We are in the ARR business. Recurring Revenue = Recurring SALE. So why do we treat the deal like it’s done? It’s not. It just changed phases. And it’s sure as hell not the babysitting phase. Your CSM is a coach. A guide. A business partner. A seller. YES. CSMs sell: - They don’t train users. They sell them on why to use. - They don’t set up accounts. They lead projects to value. - They don’t "check in." They drive strategic next steps. When that happens, customers buy again. They renew. They expand. If that’s not selling, I don’t know what is. To win, your CSMs must: - Run discovery - Multithread - Find problems - Navigate politics - Build business cases - Coach champions Is this all completely new to you - and yet nothing’s breaking? Cool. Maybe your product really is that good. But you’re probably not seeing explosive NRR. No deep case studies execs care about. No word-of-mouth that builds hypergrowth. Build CS right and you’ll have all of that. Just because we got used to something doesn’t make it right. And when you fall out of product-market-fit, face a downturn, or internal chaos, that’s when you learn the hard way: You didn’t build a revenue team. You built Sales… with some help. Your CS org is just a glorified support center. That’s when your ARR is in a free fall. But your CSMs aren’t "the help." They’re a growth engine. Just like sales. Treat them like it. Shut down "Post-Sale." Build a Next Sale team.