Creating a Client Retention Checklist

Everyone talks about onboarding new customers. Nobody talks about reonboarding your old ones. If you're lucky enough to have customers who’ve been with you for 2+ years, it’s time to hit pause and audit. Because while your product evolved, many of them didn’t. They're still operating with old workflows, outdated training, and missed opportunities for impact. Who should you prioritize? Start with customers who: ➡️ Haven’t expanded in the last 12+ months ➡️ Haven’t logged into new features ➡️ Show signs of stagnant adoption ➡️ Have new stakeholders who weren’t around at onboarding ➡️ Were onboarded before your CS org/process matured Here’s what I've done to kick this off: 1️⃣ Run a deployment audit Identify feature usage gaps and map against current best practices. 2️⃣ Re-engage stakeholders Confirm if the original champions are still involved and who needs a reset. 3️⃣ Tailor updated training Highlight new features, improved workflows, and relevant use cases. 4️⃣ Reset goals + KPIs Align on where they’re going next, not where they’ve been. 5️⃣ Rebuild your success plan Give them a “Day 1” experience, grounded in today’s strategy. Use this as a guide but adjust based on your business. This isn’t just retention, it’s renewal insurance. This is expansion through enablement. This is Customer Success in motion. Are you giving your oldest customers your newest thinking?

Sales tracks pipeline by stakeholder. CS tracks churn by account. That’s the disconnect. Because your logo didn’t churn…your champion did. You’re forecasting retention based entirely on the wrong variable. Accounts don’t buy. People do. And when the person who bought is gone - or sidelined - you’re no longer in a renewal motion. You’re in a brand new sales cycle WITHOUT the benefit of discovery. Most churn isn’t a usage problem. It’s a power gap, and most CS teams don’t know it exists until it’s too late. Here’s how to fix that: 1. Build stakeholder maps post-sale and update them quarterly. - Don’t stop mapping power after the deal closes. - CS should treat every renewal like sales treats a deal: - Identify the buyer, the influencer, the blocker, and the champion. Know who owns budget. Know who owns outcomes. 2. Create internal alerts for political turnover. - Champion leaves? Trigger exec outreach within 48 hours. - New CFO? Revalidate success criteria and prior commitments. - Department shake up? Reposition the product around new metrics. If someone internally has a tracker for PTO, you can build one for political risk. 3. Don’t just serve the champion. Build the bench. - Run QBRs with multiple execs, not just your original buyer. - Build renewal messaging that survives turnover. Don’t just rely on “happy users.” Make them internal advocates. At the end of the day, you didn’t lose the account. You lost the relationship. Churn is rarely about dissatisfaction, rather it tends to be about disconnection. Maybe the budget moved, or maybe the stakeholder changed. Regardless, no one rebuilt the bridge. Retention isn’t just about keeping the customer happy. It’s about staying connected to power. Because when that connection breaks, so does your forecast.

One thing I've noticed when working with clients and doing discovery calls is that a lot of companies are not using customer signals to be proactive instead of reactive. Being proactive rather than reactive is the key to ensuring customer satisfaction and retention. One effective strategy to stay ahead of potential issues is by documenting and understanding "customer signals" – subtle behaviors and indicators that can serve as red flags. Recognizing these signals across the organization allows businesses to engage with customers at the right moment, preventing issues from escalating and ultimately fostering a more positive customer experience. Teams should not just try to save the account once there is a request to cancel or an escalation. You need to pay attention to the signs before you hit this point. Ensuring the entire team knows what to look for means that everyone is empowered to care and improve the customer experience. Here's a list of customer behaviors that could be potential red flags, gradually increasing as they check out or consider leaving: 🔷 Reduced Engagement: Decreased interactions with your product or service. Limited participation in surveys, webinars, or other engagement opportunities. 🔷 Decreased Usage Patterns: A decline in frequency or duration of product usage. Reduced utilization of features or services. 🔷 Unresolved Support Tickets: Multiple open support tickets that remain unresolved. Frequent escalations or dissatisfaction with support responses. 🔷 Negative Feedback or Reviews: Public expression of dissatisfaction on review platforms or social media. Consistently low scores in customer feedback surveys. 🔷 Inactive Account Behavior: Extended periods of inactivity in their account. No logins or interactions over an extended timeframe. 🔷 Communication Breakdown: Ignoring or not responding to communication attempts. Lack of response to personalized outreach or engagement efforts. 🔷 Changes in Buying Patterns: Drastic reduction in purchase frequency or order size. Shifting to lower-tier plans or downgrading services. 🔷 Exploration of Alternatives: Visiting competitor websites or exploring alternative solutions. Engaging in product comparisons and evaluations. 🔷 Billing and Payment Issues: Frequent delays or issues with payments. Unusual changes in billing patterns.

We onboarded 7 Amazon accounts in June & July. 6 are now long term clients.. Here are some top lessons that I've learned over the last 5 years about nailing client retention: 1. Get going with THE work ASAP ⏲️ - First two months is when the client trust is 0 - Slow/shaky performance in this period can hurt - DON'T delay real work for only 'digging out insights' - Start with the most immediate biggest opportunities of improvement - The client needs to see a lot of little positive hints in first two months ↳ Remember, you're buying yourself time & trust to do the bigger time-taking improvement. 2. Draw CLEAR projections early on 📄 - When clients don't know what to expect, they expect too much - They can't know which week/month will be slow if you don't tell them - Underpromise only enough so that the client is still satisfied with it - Set up tougher projections internally and try to overdeliver all the time - Monthly or 10-day breakdowns work the best (add notes) ↳ For example, if the client is told TACOS will go up in July and reset in August, he won't panic when it goes up in July. 3. Be proactive NOT reactive with communication ☢️ - When clients see a decline, they don't investigate external factors - They assume it's because of you - Or they panic that they were not informed - Clients can't be patient with challenges they're kept unaware of - Proactively informing clients > Reactively responding to panic texts ↳ Nothing builds trust stronger than knowing this team is on top of my account. 4. Know the small details better than the client 🔢 - Clients expect you to give their account the attention they can't give - I have seen our clients fire agencies over this EXACTLY - 1 person in the team has to know the account's stats really really well - If the client sees repeatedly he knows more, you're getting replaced 💩 ↳ Question, why would at least 1 person in the team not know the macro & micro details really, really well anyway? 5. Meet the client once every week or two weeks 💻 - You want to know how the client is feeling about recent progress - Address any objections or confusions built out of overthinking - Get them on the same page about any challenging strategies to execute ↳ Clients are much quicker to notice declines vs improvements. Weekly meetings allow you to show what you've been doing for them. A lot of the other stuff is a waste of time. Just aim to make them more money and nail these 5 lessons. That will get you 90% of the results.