Most companies do not have a problem coming up with ambitious targets or running strategic offsites. The real breakdown happens on Monday morning, when teams have to translate high-level ideas into real daily work. Windy Elstermeier spent 17 years at Walmart helping lead operations and launching more than 800 store formats across the United States. Today, through Pivotal Solutions, she works with chief executive officers (CEOs) and executive teams to bridge that gap between growth strategy and practical execution.
Starting with Where the Business Stands Today
When leadership teams sit down to plan for the coming year, their first instinct is normally to look ahead. They focus on new revenue targets, entering fresh markets, and deciding where they want the business to be down the road. Windy finds that this forward-looking habit often sets companies up for frustration before the work even begins. “One of the biggest mistakes I see companies make is starting their growth plan with where they want to go,” she explains.
Instead of jumping straight to the end goal, she believes leaders must start with a direct, honest look at their current operations. “I actually start with: Where are you right now?” Windy says. “What is working? What isn’t? Where are you making money? Where are you losing opportunities? What’s slowing the business down? Where is the CEO spending time that they shouldn’t be? What can your current team and systems realistically support?” Answering those questions gives executives a clear baseline so they do not build ambitious goals on top of operational blind spots.
Defining Specific Targets and Clear Roadmaps
Once an executive team knows its true starting point, mapping out the next stage of growth becomes much more straightforward. Vague statements about wanting to scale or expand market share rarely give teams the direction they need to make decisions. “Then we get very clear about where we’re going,” Windy points out. “Not: We want to grow. Instead: How much? By when? What does that growth look like? What has to be true in the business for us to get there?” From there, leadership can build a structured operating plan that connects today’s reality to those future milestones. “Then we build the roadmap between those two points,” she says. “What are the priorities? Who owns each one? What are we measuring? What happens in the first 30 days? The next 60? The next 90?” Assigning specific names and clear timelines to each priority ensures that important projects do not get lost between departments.
The main reason strategic plans fail is not a lack of effort during planning sessions, but what happens after the meeting wraps up. “Then comes the part I think most strategic plans are missing: execution,” Windy notes. “A strategy shouldn’t disappear into a folder after the planning meeting.” If a plan is going to drive real results, leadership has to keep it active in the daily rhythm of the company. That means reviewing progress on a weekly basis instead of waiting for quarterly board meetings or end-of-year reviews. “You should be looking at it every week,” Windy advises. “What did we say we were going to do? Did we do it? Are the numbers moving? What’s getting in our way? What decision needs to be made? What needs to change?” Looking at these questions every week allows managers to spot friction early and make adjustments before small delays turn into major missed targets.
Staying Focused on Outcomes Over Rules
Maintaining a regular weekly check-in does not mean treating the original strategy document like an unchangeable set of rules. Market conditions change, unexpected bottlenecks show up, and practical leadership requires adjusting day-to-day tactics along the way. “The plan is allowed to change,” Windy emphasizes. “The goal is not to perfectly follow the plan. The goal is to get the result.”
Building a company that can consistently hit its growth targets comes down to closing the distance between long-term ambition and weekly accountability. “That’s the difference between setting goals and building a business that can actually achieve them,” Windy says. When leadership teams start with an honest view of where they are today and review their priorities every week, growth becomes a steady operational habit rather than an unpredictable hope.
Follow Windy Elstermeier on LinkedIn for more insights on growth strategy, operational leadership, and bridging the gap between planning and execution.
