Milestone Mapping Strategies

🏗 How To Tackle Large, Complex Projects. With practical techniques to meet the desired outcome, without being disrupted or derailed along the way ↓ 🤔 99% of large projects don’t finish on budget and on time. 🤔 Projects rarely fail because of poor skills or execution. ✅ They fail because of optimism and insufficient planning. ✅ Also because of poor risk assessment, discovery, politics. 🎯 Best strategy: Think Slow (detailed planning) + Act Fast. ✅ Allocate 20–45% of total project effort for planning. ✅ Riskier and larger projects always require more planning. ✅ Think Right → Left: start from end goal, work backwards. ✅ For each goal, consider immediate previous steps/events. ✅ Set up milestones, prioritize key components for each. ✅ Consider stakeholders, users, risks, constraints, metrics. 🚫 Don’t underestimate unknown domain, blockers, deps. ✅ Compare vs. similar projects (reference class forecasting). ✅ Set up an “execution mode” to defer/minimize disruptions. 🚫 Nothing hurts productivity more than unplanned work. Over the last few years, I've been using the technique called “Event Storming” suggested by Matteo Cavucci to capture user’s experience moments through the lens of business needs. With it, we focus on the desired business outcome, and then use research insights to project events that users will be going through towards that outcome. On that journey, we identify key milestones and break user’s events into 2 main buckets: user’s success moments (which we want to dial up) and user’s pain points or frustrations (which we want to dial down). We then break out into groups of 3–4 people to separately prioritize these events and estimate their impact and effort on Effort vs. Value curves (https://lnkd.in/evrKJUEy). The next step is identifying key stakeholders to engage with, risks to consider (e.g. legacy systems, 3rd-party dependency etc.), resources and tooling. We reserve special timing to identify key blockers and constraints that endanger successful outcome or slow us down. If possible, we also set up UX metrics to track how successful we actually are in improving the current state of UX. When speaking to business, usually I speak about better discovery and scoping as the best way to mitigate risk. We can of course throw ideas into the market and run endless experiments. But not for critical projects that get a lot of visibility — e.g. replacing legacy systems or launching a new product. They require thorough planning to prevent big disasters and urgent rollbacks. If you’d like to learn more, I can only highly recommend "How Big Things Get Done" (https://lnkd.in/erhcBuxE), a wonderful book by Prof. Bent Flyvbjerg and Dan Gardner who have conducted a vast amount of research on when big projects fail and succeed. A wonderful book worth reading! Happy planning, everyone! 🎉🥳

Do you leverage Success Plans for multi-threading and maintaining momentum during holidays and vacations? Maintaining momentum in customer adoption and renewals is critical, but can be difficult during the summer when key contacts may be on vacation. One effective strategy to address this challenge is leveraging Success Plans. Here’s how you can use them to multi-thread across accounts and prevent drop-off in adoption and stalls in renewal conversations: First, lets think of Success Plans as more than just a document that's a repository for action items. They are blueprints for ensuring that we are aligned with our customers on goals, milestones, and responsibilities. They provide a clear path forward, enabling proactive engagement and ensuring no momentum is lost. Here is how I approach multi-threading with Success Plans 1) Identify Key Stakeholders Map out all relevant stakeholders within the customer’s organization. Ensure that you have primary and secondary contacts for each key project/program/milestone. 2) Align Goals and Priorities Detail top business, departmental goals, and individual stakeholder goals, ensuring they are quantified and measurable. I ladder goals down like this: -- Top business goals -- Map business goals to departmental goals -- Map these to department leader goals so now I am at the stakeholder level -- Further map these to program goals -- Map these to champion/admin/main point of contact/individual contributor goals This alignment helps in connecting with various stakeholders and understanding their individual KPIs while ensuring they connect back to top priorities and business level goals (because at the end of the day this is what will make you stay relevant and win renewals). 3) Tactical Milestones Break down the overarching goals into specific, actionable milestones. Assign ownership and set clear due dates. This ensures continuous progress even if key contacts are away. 4) Communication Plan Define a robust communication plan. Schedule regular success calls and regular health checks. Use a mix of synchronous and asynchronous methods to keep everyone informed and engaged. The steps above should be table stakes. But there's more we can do to prevent vacation and summer slow downs: - Proactive Engagement: Before the holidays and vacations starts, identify potential vacation periods for key contacts and plan accordingly. - Secondary Contacts: Ensure secondary contacts are briefed and empowered to make decisions in the absence of primary contacts. - Regular Updates: Keep communication lines open with regular updates, ensuring everyone is in the loop. Be transparent and clear in communications. Be careful to keep everyone in the loop so nobody feels alienated or that we've 'gone around' them. Flexibility: Be prepared to adjust timelines and strategies based on the availability of key stakeholders. This will keep momentum. #customersuccess #sales #gotomarket

Traditional budgets tie spend to time. Milestone-based budgets tie spend to results. That shift matters. Traditional approaches often result in budget overruns, difficulty tracking ROI, and accountability gaps. Milestone-based budgeting flips the model by aligning capital with tangible deliverables. Each milestone completed – whether a product launch, revenue target, or operational achievement – unlocks the next tranche of funding. Biotech offers one of the clearest examples of how this method can be effectively deployed. Clinical development programs have well-defined milestones: → IND/IDE Submission → Phase 1 Completion → Phase 2 Proof of Concept → Phase 3 Enrollment Completion → Regulatory Approval Each stage represents a distinct value inflection point that can be clearly communicated. Aligning budgets to those milestones creates natural accountability, clearer forecasting, and stronger alignment with investors. By tying spend to clear outcomes, milestone-based budgeting drives accountability and keeps resources focused on what works. In the life sciences, where timelines are long and stakes are high, that focus is mission critical.

New year. New goals. But how do you stay focused and execute? My favorite tool is a roadmap. Here's how I use it... First, a roadmap is a strategic plan visually representing the goals and steps/milestones needed to achieve a desired outcome. It is a communication tool to articulate strategic thinking and align stakeholders. I prefer to keep them high-level and not overly prescriptive. I usually create these with a digital whiteboard like Miro, or some tool that is easily accessible to your team. Give yourself/team a few 2-4 hours to complete this. Steps: 1. Set annual goals and limit them to 3.  * You can always add more if you accomplish these. Limiting it to 3 sets the tone for focus and priority. Ex: Increase revenue by 30% YoY from 2023 2. Break annual goals down into smaller goals or milestones.  * These will help determine if you are on track. Limit these to 3-5 smaller goals per yearly goal. Then, determine in which quarter(s) you will evaluate each. Ex: Q1 might see an increase in qualified leads. Q2 might see a 60% increase in qualified customers progressing to the negotiation stage. Q3 might see revenue growth by 20%. And so on... 3. Determine what key actions you need across major components or departments of your business. * This is where it is easy to get overly prescriptive. Try to limit key actions to less than 3 for each department per quarter. Ex: Marketing key actions: 1. Re-define ideal customer profile 2. Launch multi-channel outbound campaign 3. etc... Keeping this high-level and editable enables you to generate a plan quickly and offers the flexibility to adjust the plan as needed throughout the year. It also provides the direction each department needs to return to their teams and do further planning aligned with the company's overall focus. Do you use #roadmaps in your annual #strategicplanning? Anything you would do differently? -- [ Later this week, I'll share thoughts on added structure of meetings and check-ins that can help carry this through the year. Stay tuned…] #operationsmanagement #coo

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!