Creating Meaningful Connections in Customer Success

You’re missing one of your customer’s most important goals. You know to capture the company goals: reduce costs, drive revenue, increase efficiency. That’s good. That’s essential. But the company isn’t the one you work with every week. A person is.  • Your executive sponsor.  • Your admin champion.  • Your day-to-day point of contact. And guess what? They have goals too.  • They want to look good.  • They want a win they can put on their resume.  • They want to move up, or over, or out, and your project is a vehicle for that. If you help them 𝘱𝘦𝘳𝘴𝘰𝘯𝘢𝘭𝘭𝘺 win, you won’t just retain the account — you’ll gain a true champion. Here’s how: 𝟭. 𝗔𝘀𝗸 𝘁𝗵𝗲𝗺 𝗮𝗯𝗼𝘂𝘁 𝙩𝙝𝙚𝙞𝙧 𝗰𝗮𝗿𝗲𝗲𝗿 𝗴𝗼𝗮𝗹𝘀. “What are you personally trying to accomplish long term? Where are you trying to get at [company]?” 𝟮. 𝗠𝗮𝗸𝗲 𝘁𝗵𝗲𝗺 𝘁𝗵𝗲 𝗵𝗲𝗿𝗼 𝗶𝗻 𝗶𝗻𝘁𝗲𝗿𝗻𝗮𝗹 𝗰𝗼𝗺𝗺𝘂𝗻𝗶𝗰𝗮𝘁𝗶𝗼𝗻. “Here’s the success we saw because of Sarah’s leadership with ___, ____, and ____.” 𝟯. 𝗖𝗼𝗮𝗰𝗵 𝘁𝗵𝗲𝗺 𝗼𝗻 𝗵𝗼𝘄 𝘁𝗼 𝘀𝗵𝗮𝗿𝗲 𝘄𝗶𝗻𝘀. Use your QBR slides to help them present results to their execs, offer to help role play their presentation to their internal team an provide feedback. If you make your customer contact the star, your solution becomes the secret weapon behind their success. And when they win, you win too. How do you help your customer contacts advance their careers? #customersuccess

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.

One of the best ways to create authentic relationships with your customers, get honest feedback on your product and surface game changing ideas is to create a Customer Advisory Board (CAB). Here are the lessons I’ve learned about how to create and run a successful CAB. Your personal involvement as CEO is critical. If you lead it yourself, customers will engage at a deeper level. They’ll be more honest, more vulnerable, and more likely to become evangelists for your company. No one else can unlock this dynamic the way a CEO can. Be clear on the persona. Is your CAB for buyers, users, or budget holders? At BetterCloud, our sweet spot was Directors of IT. Not the CIO, not the IT admin. Know exactly whose voice you want in the room and tailor everything to them. Skip the compensation, give them “status”. Don’t pay CAB members—it gets messy. Instead, make them feel like insiders. Give them a title, early access to roadmaps, VIP treatment at events, and public recognition. People want to feel valued and influential, not bought. Set a cadence you can maintain. I tried monthly meetings once. That was a mistake. Quarterly is the sweet spot. One in-person gathering per year—ideally tied to an industry event—goes a long way in deepening relationships. Structure matters. CABs aren’t just roundtables. They’re curated experiences. Keep meetings tight (90-120 minutes), show real products that are still in the development process (even rough wireframes or high level ideas), and create space for interaction. Done right, they become the ultimate feedback engine. Build real relationships. Your CAB shouldn’t just exist in meetings. Build one-on-one connections. Text, email, check in at events. Keep it small enough that people feel seen and valued. When they have a direct line to the CEO, they stay engaged—and they speak the truth. Done right, your CAB becomes more than just a feedback mechanism. It becomes a strategic asset. It can shape your roadmap, sharpen your positioning, and strengthen your customer relationships in ways no survey ever could. For a deeper dive and detailed tactics behind each of these, check out the full writeup on the Not Another CEO Substack.