How to Use Milestones for Client Communication

We once built an entire email strategy around a client's product launch date, only for them to delay by 3 months. That miscommunication cost us $200K in projected revenue. Here's the system we now follow to prevent it from happening again. 1. Document everything in writing No more verbal only agreements or assumptions. Every key date, deliverable, and dependency gets documented and shared with all stakeholders. This creates accountability and gives everyone a single source of truth to reference. 2. Implement regular check-ins Schedule brief status meetings to confirm timelines are still on track. These quick touchpoints help catch potential delays early before significant resources are invested. 3. Build buffer time into all schedules Add extra time to every major milestone (just in case). This padding accounts for the inevitable hiccups that occur in any project without derailing the entire strategy. 4. Create contingency plans For every campaign, develop Plan B scenarios: - What if key elements are delayed? - What if resources are limited? - What if priorities change? Having these alternatives ready means you can pivot quickly without starting from scratch. 5. Leverage dependency roadmapping Implement a visual system that shows how each part of your strategy connects to deliverables. This makes it immediately clear to everyone what happens if one piece gets delayed. The biggest lesson? Communication breakdowns are expensive, but they're also preventable. By implementing these systems, we've reduced timeline-related issues dramatically and saved countless hours of rework. What systems have you built to prevent costly miscommunications?

🔁 Closing the loop Before They Ask 🔁 I work a lot with deployment strategists and customers nowadays, and I've noticed something: the difference between good partnerships and great ones often comes down to a single habit—closing the loop proactively. Most people wait until someone asks for an update. But by then, trust is already starting to erode. The customer is wondering if you forgot about them, if the project is stuck, or if they should be worried. That mental uncertainty creates friction, even when everything is actually going well. Last month, I was working with a deployment strategist on a complex integration. Three weeks in, I realized I hadn't updated them in four days. Nothing was wrong—I was just heads-down solving a tricky problem. But when I finally reached out, their first response was relief: "I was starting to wonder if we hit a roadblock." That's when it clicked for me. 𝐏𝐞𝐨𝐩𝐥𝐞 𝐡𝐚𝐭𝐞 𝐮𝐧𝐜𝐞𝐫𝐭𝐚𝐢𝐧𝐭𝐲 𝐦𝐨𝐫𝐞 𝐭𝐡𝐚𝐧 𝐛𝐚𝐝 𝐧𝐞𝐰𝐬. The most effective people I work with don't just communicate when there's news—they communicate to eliminate that uncertainty entirely. Here's the framework that's transformed how I handle this: 1. 𝐒𝐞𝐭 𝐜𝐨𝐦𝐦𝐮𝐧𝐢𝐜𝐚𝐭𝐢𝐨𝐧 𝐞𝐱𝐩𝐞𝐜𝐭𝐚𝐭𝐢𝐨𝐧𝐬 𝐮𝐩𝐟𝐫𝐨𝐧𝐭. "I'll update you every Tuesday and Friday, even if it's just to say 'still on track.'" 2. 𝐆𝐞𝐭 𝐚𝐡𝐞𝐚𝐝 𝐨𝐟 𝐩𝐫𝐨𝐛𝐥𝐞𝐦𝐬. When you see a potential issue brewing, mention it before it becomes a problem—your stakeholders can often help unblock you. 3. 𝐂𝐥𝐨𝐬𝐞 𝐭𝐡𝐞 𝐥𝐨𝐨𝐩 𝐨𝐧 𝐞𝐯𝐞𝐫𝐲 𝐝𝐞𝐥𝐢𝐯𝐞𝐫𝐲. When you complete work, update all relevant stakeholders—sponsors, collaborators, customers. They're all eager to learn what you accomplished. 4. 𝐂𝐞𝐥𝐞𝐛𝐫𝐚𝐭𝐞 𝐭𝐡𝐞 𝐰𝐢𝐧𝐬. Every milestone completion is a chance to demonstrate progress and build trust. Don't let these moments pass in silence. 5. 𝐀𝐥𝐰𝐚𝐲𝐬 𝐥𝐞𝐚𝐯𝐞 𝐭𝐡𝐞𝐦 𝐰𝐢𝐭𝐡 𝐜𝐥𝐚𝐫𝐢𝐭𝐲 𝐨𝐧 𝐧𝐞𝐱𝐭 𝐬𝐭𝐞𝐩𝐬. End with what you're doing next and when they'll hear from you again. Think of it like GPS navigation. You don't want to wonder if you're still on route—you want constant confirmation that you're heading in the right direction, with clear visibility into any upcoming turns or delays. The magic isn't in having perfect execution. It's in making sure people never have to wonder where they stand with you. What's your approach to keeping stakeholders informed without overwhelming them? #StakeholderManagement #Communication #ProjectManagement #TrustBuilding

The Promise of Milestone Conversations While Reconnaissance, Pathway and Enrollment conversations all happen in the context of the larger vision for transformation and how to achieve it, mapping out the smaller steps helps your customers make progress little by little, ALONG their journey. We use Milestone Conversations as a tool to set up an accountability structure with our customers to ensure they achieve specific goals and make progress over time. The posture of Milestone conversations requires you to show up as a COACH to your customers. At this stage in your relationship, your trust bank account should be overflowing, which grants you the ability to challenge and support your customers in equal measure with the goal of holding them accountable to create their desired future. The promise of leading Milestone Conversations is that: ➡️ You will help your customers push pause and evaluate progress made. ➡️ Get feedback and look ahead. ➡️ Decide if any adjustments need to be made and create a plan of action for what comes next. Milestone Conversations happen in 4 parts: 1️⃣ Look Back & Progress: Reflect on lessons learned and shared with your customer so far. See how to influence next steps in the process-based lessons learned. 2️⃣ Check the Campaign: - Are each of the parts of the campaign clear and understood? - Where has the customer made detours/had to change their approach? - Were there any missing resources or stakeholders that presented issues? - Are they on track to reach the next milestone on time? - Are they running behind, on time or ahead of schedule? - What adjustments can be made to support progress? 3️⃣ Horizon & Adjustments: - Are there possible challenges that could come up that need to be considered? - What is the next milestone? - Which actions are critical to take next? - Are the priorities clear? - Does everyone know what they’re responsible for? 4️⃣ New Promises: Recap the conversation with a special focus on checking the horizon and making adjustments. Clarify, prioritize and assign action items to be completed outside of the conversation. Milestone Conversations are your opportunity to continue adding value to your customer's experience. Once you get to the end of your engagement, it's time to go back to Reconnaissance!