Planning is the moment when strategy starts turning into action. But it’s also where many strategic transformation efforts stall—not because of lack of ambition, but because of poor understanding of what real planning entails.

Let me take you to two very different moments in my consulting work. Both clients were in the planning phase of their strategic transformation journey. Both had strong intentions. But both were stuck—in completely different ways.

In the first case, we were mid-journey in a strategic transformation effort. The ambition was clear, the team energized, the direction set. But when it came time to translate it all into strategic projects and initiatives—those that would bring the strategy to life—everything got stuck.

When I asked the executive team to translate ambitions into a portfolio of initiatives, the CEO paused and said, “Well, we need to sell more and better.” That was it. No further breakdown. No projects. No structure. Just a bold declaration.

This wasn’t lack of vision—it was lack of craft. The inability to go from strategic intent to structured action.

On the opposite end, another client proudly called me to help them “refine” their strategic planning process. They had already “done the hard work,” they said, and wanted a final review before implementation. Their main source of pride? A portfolio of 150 initiatives.

I asked to see it.

What I found was a scattered list of tasks, intentions, ideas, and a few actual projects—randomly mixed together. There was no clear distinction between what constituted a strategic initiative, an activity, or a wish. No structure. No prioritization. Just noise.

Why It Happens? Because some leaders fear losing altitude, they think details dilute the vision; others fear missing out, so they include everything, hoping something sticks; and most simply haven’t learned how to define a strategic initiative in project terms.

What Robust Planning Looks Like

Here’s what separates real planning from hopeful guessing:

1. Clarity of Strategic Guidelines You can’t build a portfolio if you don’t know what you’re optimizing for. Define the ambition, and the guiding principles for what qualifies as a strategic project.
2. Rigorous Initiative Definition A strategic initiative is not a goal, nor a task. It’s a structured project with a clear outcome, defined milestones, responsible leaders, and a rough estimate of the resources it needs—capital, operational effort, and internal capabilities.
3. Balanced Portfolio Thinking Not everything is strategic. Not everything needs to happen now. A good portfolio balances urgency and importance, quick wins and long bets.
4. Effort vs. Impact Assessment Each initiative should be evaluated in terms of expected impact and required effort. This doesn’t have to be perfect, but it needs to be good enough to compare and prioritize.
5. Communication of the Plan The plan should make sense to those outside the strategy room. Your portfolio should be a story you can tell: why these initiatives, how they fit together, and how they will move the company forward.

This is hard work. It means translating ambition into a manageable set of short, mid- and long-term initiatives. It means defining projects in terms of outcomes, not just tasks. It means organizing them into milestones, estimating the effort required—not only in terms of capex or opex, but also in capabilities. And it means making sure they don’t just make sense individually, but as a whole.

Planning is not about listing everything you might want to do. It’s about making deliberate choices clearly tied to your goals, each well-characterized and realistically scoped. You don’t need 150 initiatives. You need the right ones. The ones that will move the needle. The ones your team can actually commit to and deliver. The ones you can follow up on meaningfully—not by asking for updates on tasks, but by holding real conversations about progress, learnings, and next steps.

Planning is not a paperwork exercise. It’s not a list. It’s not a backlog. It’s the craft of translating vision into structured action—and if done well, it becomes the engine of execution and the bridge between today’s reality and tomorrow’s goals.

Good planning doesn’t kill strategy. It brings it to life.

Good Luck!

Ximena Jimenez

Founder – Managing Director LITup

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