Best Practices for Renewing Client Contracts

Too many renewals go like this: Rep: “Here’s the renewal quote.” District: “We’ll let you know.” Status: Ghosted. But a renewal isn’t a contract. It’s a decision to keep partnering. And that means you need to re-sell value, not just ask for the next check. The best reps and CSMs treat renewal as a strategy moment: They come in with impact metrics. They share what’s worked. They ask what’s changing next year and how they can evolve with it. They say: “We saw a 38% increase in student usage this spring. What else are you planning that we can support next?” Or: “You mentioned earlier this year that Tier 2 support was going to be a bigger focus. Should we talk about how this could be part of that strategy?” Even better, get ahead of the ask: “Would it help if we built a proposal that addresses both renewal and expansion, with phased options?” The renewal isn’t just about retention. It’s your best shot at deepening the partnership, if you show up ready.

Customer success managers shouldn't own renewals. Renewal managers should... A couple of CCO jobs ago I had CSM team responsible for renewals and few things were happening: 1/ finance systems complexity - because our systems were messy, the CSMs often "messed up" the renewals in our systems. Unfortunately, if you didn't do things in the exact correct order (and hold your tongue a certain way), it was easy to create issues between CPQ, Salesforce, and our Intacct. (Should we have fixed the systems issues? Of course.. But it was a lower priority than other projects at the time.) 2/ negotiation - Our CSM wasn't filled with negotiators. And that was okay. Most CSMs are product and services experts, and know how to help customers use the product and ascribe value to it. Unless the CSM team is really focused on account management, they likely don't have the sales skillset, and besides, wanted them consulting with customers on how to get better leverage out of our products. Not negotiating renewals. 3/ everything was custom - to make matters even worse, all of the renewals were custom. We lacked defined parameters for one-year vs. multi-year renewals, annual vs. more frequent payment terms, etc... And price increases were arbitrary. So what did we do? First, we centralized renewals to a small team of Renewal Managers. Most of our contracts auto-renewed, but there were many that required negotiation around price increases, new packaging, expansion, etc. We created structured renewal offers that gave the customer options, but weren't custom. They could "choose their own adventure." i.e., if you wanted a one-year renewal, price increase was X% and payment terms were Y. If you were willing to do a 2- or 3-year agreement, then there were options for that as well. We also restructured our pricing plans to include additional value that we offered at renewal time to get customers on standardized plans with annual payments (if they weren't already). Did the CSMs play a role? You bet they did. They had relationships we could lean on, and helped articulate the value prop for the executive buyers, especially in the larger, high touch account segments. In the low-touch accounts, renewal managers mostly handled everything (most of the adoption was 1:many and community-led in that tier anyway). Aside from all of that, we began to treat the renewal program as a commercial program instead of a "customer success" program. We developed forecasting methodology, operating rhythms, and used MEDDICC to validate our enterprise renewal opportunities. This approach proved extremely successful for us. One thing I preach constantly about customer success is that specialization is key as you scale a subscription business, and this is one of the many specializations that you'll likely need as you grow. Have you specialized renewals? If not, what are the reasons, and do you think this approach will work in your company? 🤘

An Auto-Renewal Clause is NOT a Retention Strategy. Let’s be real—if your renewal strategy is “trap them with an auto-renewal,” you’re not running a Customer Success org. You’re running a glorified contracts department. Stop weaponizing auto-renewals. Stop hiding behind fine print. Stop thinking a trapped customer is a retained customer. Because here’s what actually happens: That “surprised” customer you locked in? 🚫 They’re now actively shopping for alternatives. 🚫 They’re venting in their community. 🚫 They’re roasting your company in group chats. Congrats—you didn’t just kick the churn can down the road. You lit it on fire. 🔥 I’ve been there. Back in the day, the playbook was: "Shh, don’t wake the dormant customer before auto-renewal." Let the clause do its thing—then re-engage. Spoiler: It was a disaster. No trust. No partnership. Just resentment. Look, I’m not here to cancel auto-renewals entirely. They can serve a purpose: ✅ Ease of execution: Customers do appreciate less paperwork. ✅ Prompt decision-making: Forces a conversation when needed. ✅ Cash flow consistency: Revenue predictability matters. But here’s the deal—auto-renewals only work if you have good practices in place: 📅 Proactive Communication: Remind your customers well before the renewal window. Transparency builds trust. 💻 Flexible Opt-Outs: Allow opt-outs without immediate cancellation. Give them breathing room to decide. 🤝 Collaborative Approach: Be the partner who earns renewal, not the one who enforces it. Design solutions together. If your strategy is “let the contract auto-renew and hope they stay,” you’re not in Customer Success. You’re just avoiding churn today at the cost of tomorrow’s reputation. Customers should want to stay with you. You should earn that right. So, tell me—are you Team Trap Em or Team Talk To Em? ___________________ 📣 If you liked my post, you’ll love my newsletter. Every week I share learnings, advice and strategies from my experience going from CSM to CCO. Join 12k+ subscribers of The Journey and turn insights into action. Sign up on my profile.

Renewals don’t fall apart in Q4. They fall apart six months earlier...when nobody’s looking for the cracks. Most post-sales teams are trained to manage accounts. That's not the right way to think about it. You should think about it as managing risk. If the past 2 years have proven anything, it's that renewals aren’t won with check in emails. They’re won by spotting friction early and acting fast. And that requires one thing above all else: Structured, proactive risk discovery. Not “How are things going?” Not “Let us know if you need anything.” Real questions. Real signal. Real action. Here's some ideas on how to do this: 1. Treat check ins like investigations, not pleasantries. - “What’s changed internally since we last spoke?” - “Anything new on the roadmap we should be aligning to?” - “Who’s under pressure to show impact from this investment?” 2. Surface disconnection before it becomes dissatisfaction. - “Has this become easier or harder to use since onboarding?” - “What’s something you thought this would solve, but hasn’t yet?” - “Where are you still using workarounds?” 3. Don’t wait for risk signals. Manufacture them. You should know stakeholder turnover, shifting priorities, or usage dips don’t always come with a calendar invite. CSMs should: - Monitor usage like pipeline - Map power like a rep - Treat every renewal like a forecastable event...not a hope and see CSMs are notorious people-pleasers. That's why we ❤️ them. But customer success isn’t about being liked. It’s about being aligned. And alignment doesn’t happen by accident. It happens by asking better questions. And asking them earlier. In CS, the best way to secure the renewal is to surface the risk no one else is talking about.

You are starting your renewal process too late. Are you starting to think about renewals 3 months before the deal end date? Too late. Starting to think about the renewal mid-contract? Too late. Starting to think about renewal during onboarding? Too late. Yes, that’s right, it’s too late. That doesn’t mean customers won’t see success and won’t renew if you start at the times above. It just means that you can do better. The best time to start the renewal process? During the sales cycle. Here’s what that looks like: 1) The sales process isn’t rushed - You take your time to do proper discovery and fully understand the use case for the prospect. One-call closes aren’t always something to be proud of. 2) Multiple parties are involved - You bring in ALL the right people to make this decision. Every owner, stakeholder, and influencer is engaged and understands how your tool helps them and their teams achieve success. 3) You have a clear plan - Your business case is put together with the help of the prospect, and you both agree on how this will be implemented. You also have clear ROI data points that tie back to business objectives. 4) Bring in CS pre-sale - CS/Implementation shouldn’t just show up out of the blue when a deal is closed and drop 25 to-do tasks on the client’s plate. Instead, introduce them early to walk the prospect through what onboarding will look like and what resources are needed from their end. If you do these things, you’re setting yourself up for renewal even before the deal is closed. The first 60 days of any customer engagement are generally the best predictor of retention, so getting out of the gate fast is imperative. Start your renewal process early—before your relationship legally begins.

Never wait until a "renewal call" to ask a customer to extend or renew their contract. By then it's too late. Instead, have a "step-back" convo 4 - 6 months into the relationship to uncover hidden risks and insights to ensure the renewal and inoculate against surprise churn. What is a step-back convo? 👉 Uses truth-sparking questions about THEM to drive engagement and trust, and uncover actionable insights. 👉 Occurs sometime during the first half of the relationship (like 4 - 6 months into a one-year contract). 👉 Either a standalone meeting or a 10-minute agenda item during a regularly scheduled meeting. Here's your mini-playbook for step-back convos: ❓ "We'd love to take a step back and get your perspective on a few topics above the day-to-day. I'm wondering, what's the biggest thing that surprised you since you started working with us?" In my experience, about half the time it's a positive surprise. This is great because you can pursue why it was so positive and how working with your company has led to their desired business outcomes. This info comes in handy when you do ask them to renew their contract. And of course a negative surprise means you should dig in to understand how it is impacting their world and offer potential solutions. Here's the second question to ask during the step-back convo: ❓ "If you got an outreach from our competitor tomorrow, how would you react on a scale of 1 - 5 where 1 = ignore and 5 = you'd pretty quickly get back to them to learn more?" No matter what number they give, instead of assuming what they mean by it, ask this follow-up question: ❓ "Is there something a competitor might mention that would definitely get your attention and cause you to get back to them?" Their response will help you identify gaps in your product or service that may be important to their decision. Once again, this keeps you ahead of the game because you can address their perceptions and concerns either on the spot or in subsequent meetings in advance of the renewal conversation. Lastly, make sure to say this: "Thanks for being so candid. That's exactly the type of info we are looking for." This rewards the behaviors you want from them - transparency, candor, and authenticity. -------- Having a step-back convo gives: 👉 The customer a chance to open up in a non-sales context where they tend to be more relaxed and transparent. 👉 You an opportunity to course correct if their perceptions are not where they should be. 👉 You the insight into the benefits they're getting from your solution, so you can double down on those leading up to the contract renewal date. --------- Hey #customersuccess and #accountmanagement professionals: Want ALL 25 questions, tips and techniques for having more strategic and revealing step-back convos? Take my Radically Authentic Discovery Online Course. Just visit my profile and click the “upskill” link.

Our first 3 customers all just renewed for their 3rd year - some moving to multi-year agreements. Here’s our 7-step playbook for renewing (and expanding) key customers: 1. Proven, documented value with real metrics → fluffy ROI and “time savings” don’t cut it today 2. Consistent monitoring of adoption and success metrics – then taking action as early as possible with warning signs – run toward negative trends, not away 3. Multiple stakeholders – our CSMs are the quarterbacks, but having multiple lines of communication is key (exec, eng, product, etc) 4. Handle support issues and customer questions as quickly as possible – every one is an opportunity to over deliver and WOW the customer 5. Ask the hard, direct question early when there are doubts and address the doubts in a timely manner 6. Periodic exec updates – you are fighting for attention with 100s of other apps and workflows – making sure the right people within the account know about the success, progress, and active projects is critical 7. Find natural touchpoints with customers to foster feedback - speaking at events, giving product feedback, collaborating on content, etc – increasing touch points increases the chance of you learning important account intel TAKEAWAY As a first-time founder, watching the team close new logos is just as exciting as it was when I was starting as a rep 10+ years ago Now, renewals get me 10x more excited Simple, not easy