Developing A Clear Roadmap For Strategy Execution

A roadmap is not a strategy! Yet, most strategy docs are roadmaps + frameworks. This isn't because teams are dumb. It's because they lack predictable steps to follow. This is where I refer them to Ed Biden's 7-step process: — 1. Objective → What problem are we solving? Your objective sets the foundation. If you can’t define this clearly, nothing else matters. A real strategy starts with: → What challenge are we responding to? → Why does this problem matter? → What happens if we don’t solve it? — 2. Users → Who are we serving? Not all users are created equal. A strong strategy answers: · What do they need most? · Who exactly are we solving for? · What problems are they already solving on their own? A strategy without sharp user focus leads to feature bloat. — 3. Superpowers → What makes us different? If you’re competing on the same playing field as everyone else, you’ve already lost. Your strategy must define: · What can we do 10x better than anyone else? · Where can we persistently win? · What should we not do? This is where strategy meets competitive advantage. — 4. Vision → Where are we going? A roadmap tells you what’s next. A vision tells you why it matters. Most PMs confuse vision with strategy. But a vision is long-term. It’s a north star. Your strategy answers: How do we get there? — 5. Pillars → What are our focus areas? If everything is a priority, nothing really is. In my 15 years of experience, great strategy always come with a trade-offs: → What are our big bets? → What do we need to execute to move towards our vision? → What are we intentionally not doing? — 6. Impact → How do we measure success? Most teams obsess over vanity metrics. A great strategy tracks what actually drives business success. What outcomes matter? → How will we track progress? → What signals tell us we’re on the right path? — 7. Roadmap → How do we execute? A roadmap should never be a list of everything you could do. It should be a focus list of what truly matters. Problems and outcomes are the currency here. Not dates and timelines. — For personal examples of how I do this, check out my post: https://lnkd.in/e5F2J6pB — Hate to break it to you, but you might be operating without a strategy. You might have a nicely formatted strategy doc in front of you, but it’s just a… A roadmap? a feature list? a wishlist? If it doesn’t connect vision to execution, prioritize trade-offs, and define competitive edge… It’s not strategy. It’s just noise.

Scaling an agentic AI business to $10s of millions in ARR and $100M+ in funding has taught me a hard lesson: Most leaders get planning wrong. Especially OKRs. I see it all the time—especially with ops teams and customer support orgs trying to align across functions. And I’ve made these same mistakes myself as a founder. OKRs (Objectives and Key Results), made famous by Intel Corporation's Andy Grove, are supposed to bring clarity and focus. ➤ The Objective is the mission: clear, ambitious, human-readable. ➤ The Key Results are how you measure success: tangible outcomes that prove it’s working. The problem is: OKRs are outputs. OKRs are "strategy". They’re the result of consistent execution—but they aren't a roadmap for how to get there. One of the most important leadership lessons I’ve learned (reading Amp It Up! by Frank Slootman and convos with leaders like Sami Ghoche and Manny Medina) is this: 🎯 Execution eats strategy for breakfast. So we started thinking differently about how we lead. Rather than just defining the “what” and “how we’ll measure it,” we became more intentional about how we’ll do the work—and how we’ll stay on top of it. That’s what led me to start calling the framework OKRIMs: ✅ Objectives – What we’re trying to accomplish ✅ Key Results – How we’ll measure success ✅ Initiatives – The plan. The actual work. Sprints, launches, experiments. ✅ Mechanisms for Inspection – How we’ll check in. The rituals and systems that keep us honest and aligned. This last piece—mechanisms of inspection—has been a game-changer. Sometimes it’s a simple daily standup. Other times it’s a shared Google Doc where we document next steps and action items. Or just a Slack message every Friday to check in. No fancy tech required—just clear expectations and a regular rhythm. It’s not micromanagement. It’s not being hands-off either. It’s just... managing. We never formally “rolled this out” at Forethought, but over time, we got a lot more intentional about the I’s and M’s. My co-founder Sami Ghoche is especially masterful at this—turning strategy into action, week after week. If you’re a support or operations leader (or a founder/CEO), this shift in mindset might be one of the most valuable things you do. Would love to hear from others—What frameworks or habits have helped you execute better? #leadership #entrepreneurship #customerexperience #ai #agents

As a CIO, this mistake might end up costing you... Don't start an integration project without a true north to guide you. 🧭 Recently, I was speaking with an ex-colleague who was working on a complicated integration spanning multiple business units and regions. 💬 He asked me: "How can I get to results quickly?" 🗣 My response: "Slow down. In this case, taking a little extra time... equals fast." When you're running an integration project, make sure you take the time to properly understand the current state environment at the outset while also getting crystal clear clarity on where you're going – your target state. Too often, the assumption is that you know everything and the temptation is to run off fast to show that you're starting to act. But, believe me, this will end up costing you more time, money, and energy – right at the time when the business might be short on all of these things. Don't get me wrong. I understand why you just want to run off and start executing. There is pressure. And there is pressure to deliver fast. But that's precisely the time to step back. You don't want to run off in one direction just to find out that you need to run all the way back to the start again. So, after that discussion, here's what I told them: 📌 Take the time to really understand where you are right now. In almost every integration I've led, I've ended up finding something out that was known at the management level but not at the technical team level, or vice-versa. Conduct a current state assessment. 📌 Define your target state. It's not possible to pull together a proper plan of action if you don't know what success really looks like. Start with the high-level definitions, and then get detailed. 📌 Get senior management buy-in for that target state. And buy-in means more than just the tools and tech – you need the right mix of resources and their time as well. 📌 Translate this into a strategic roadmap to get from A to B efficiently and effectively. 📌 Finally, communicate up, down, and across the business throughout. Now that you have your integration roadmap, connect the company's mission with your own IT story. If you don't invest time at the beginning, an integration project can end up costing you time and money down the road. More time upfront in planning means faster execution. In this case, taking a little extra time = fast. #CTO #CIO #digitaltransformation #integration #leadership