The Strategy-to-Execution Gap
How leaders turn strategic priorities into focused action, stronger execution and measurable results
Woodstock, NY - photo by KPG
As a Vistage member for the past four and a half years, I pay close attention to the issues that keep surfacing among CEOs and business leaders. Vistage, a CEO coaching and peer advisory organization, recently published a statistic that stopped me: 80% of leaders believe their organizations are good at crafting strategy, while only 44% feel confident in their ability to implement it.
That gap feels familiar. Most leadership teams I have worked with are not short on ambition or ideas. They generally know where they want to grow and have identified important markets, customers, capabilities or financial goals. The harder part is figuring out what the organization actually needs to do differently to make the strategy happen.
This is where I have spent much of my career. I tend to move pretty quickly from the strategy to a more practical question: what does this actually mean for the people who have to deliver it? Earlier in my career, I sometimes worried that this instinct was too tactical. Over time, I came to understand that those details are not separate from strategy. They are often how the strategy becomes real.
Increasingly, I think this is an important part of Commercial Excellence.
Strategy has to survive the trip through the organization
A strategic priority can sound perfectly clear at the leadership level: grow existing customers, enter a new vertical, improve profitability, create a more predictable new-business engine or integrate an acquisition. But none of those statements tells the people responsible for execution exactly what needs to change in their work.
If the goal is to grow existing customers, which customers deserve more attention? Which relationships are missing? What should account leaders be doing differently, and what should managers begin looking for and coaching?
If the strategy is to enter a new vertical, the questions change. What does marketing need to activate? What proof will customers need before they trust us? Does the commercial team understand the buying environment? Are operations ready to deliver what we are promising?
The question I return to most often is simple: What has to be true for this strategy to work? It usually exposes the gap(s) pretty quickly.
I learned early that strong execution is rarely the work of one function. Even something as basic as defining an Ideal Customer Profile works better when it is not treated as a sales-and-marketing exercise. Service and operations often know best which customers are most profitable, easiest to retain and best matched to the organization’s strengths. Bringing those perspectives together creates a much more useful answer to the question of where to focus.
Over time, I have started organizing these questions into five areas that help me see where execution is getting stuck.
1. CLARITY: Do we know what we are actually trying to accomplish?
Strategic plans can contain dozens of initiatives, but people cannot focus on dozens of priorities at once. The practical question is which three or four outcomes matter most and where the business really expects growth to come from.
I have sat in meetings where everyone was frustrated by the results, so the answer became “more”: more activity, more reporting, another initiative. It usually made the focus problem worse. Sellers were not necessarily resisting the strategy; they simply were not sure which opportunity mattered most or where they had the best chance of winning.
Clarity means more than being able to repeat the company strategy. People need to know what matters now, what can wait and what may need to stop altogether.
2. FOCUS: Are resources and activity aligned to the strategy?
A company can name something a strategic priority without behaving as though it is one. If you want to know what really matters, look at where people spend their time, where marketing dollars go, what shows up in pipeline and what leadership actually talks about.
In one organization, leadership expanded the growth expectations of a team that had historically focused primarily on serving existing customers. The strategic choice had already been made, but the team had not previously been equipped to work that way.
What they needed was a practical way to deliver against the new expectation. That meant deciding which accounts deserved attention, where meaningful growth potential existed, which relationships needed to be developed and how opportunities could be uncovered. It also meant helping managers make those conversations part of the normal way the team worked.
I have seen this more than once: changing someone’s goal or job description does not mean we have shown them how to succeed at it.
3. ACTIVATION: Do people know what they need to do differently?
This is where the strategy starts to show up in behavior. A useful test is to ask several people across the organization what they personally need to do differently because of a strategic priority. Their answers do not need to sound the same, but they should clearly connect to the same outcome.
Sometimes the opportunity is not to create something new. It is to make better use of something the business already has.
I have seen several companies sit on incredibly strong customer proof without fully using it. In one case, the business had an unusually strong Net Promoter Score, but that strength had not really become part of the way the company talked about its value with customers.
The opportunity was to help people understand what that proof meant, where it could strengthen trust and how the field could use it naturally. That required more than communicating a number. It meant helping people understand why it mattered and turning it into something they could actually use consistently.
Training may be part of the answer, but it is not where I would start. First, figure out what people need to do differently and why.
4. OPERATIONALIZATION: Does the system reinforce what we are asking people to do?
People can know exactly what they are supposed to do and still struggle if everything around them reinforces the old way of working.
If leaders want better qualification but managers still inspect activity volume, activity volume will probably win. If account leaders are expected to build stronger executive relationships but account reviews never examine relationship depth, that expectation is easy to ignore.
This is where the surrounding system matters. Pipeline stages, qualification criteria, account planning, management reviews, CRM expectations, coaching, onboarding and marketing priorities all influence whether new behaviors stick.
I saw this at much greater scale earlier in my career while working inside a rapidly growing, distributed organization. As the business expanded, growth could not be treated simply as a sales or marketing issue. Field operations, service, customer support, HR, IT, shared services and communications all had a role in where the company was trying to go.
The work was helping those functions understand how their priorities connected and creating enough consistency that the organization could scale without every team developing its own version of the strategy.
That experience changed the way I think about organizational change. You cannot expect materially different outcomes while leaving every process, expectation and management habit exactly as it was before.
5. PROOF: Can we tell whether execution is improving?
This may be the hardest part of strategy-to-execution work because the financial outcomes leaders care about most are usually lagging indicators. Revenue, margin, retention, account growth and win rates matter, but by the time they tell us something is off, we may have already lost valuable time.
Most businesses already have plenty of metrics. The harder job is choosing the few that tell you whether the change is actually taking hold.
If account growth is the goal, that might mean looking at stakeholder depth, executive access, opportunities per priority account or qualified expansion pipeline. If the goal is new-market penetration, target-account engagement and movement through the funnel may tell us more early on than revenue alone.
The point is to build a short chain of evidence between what people are doing differently and the result the business ultimately wants.
A simple Strategy-to-Execution Diagnostic
I think leaders can evaluate execution by asking five questions:
CLARITY
Can our people clearly explain our most important growth priorities, and do they understand what those priorities mean for their work?
FOCUS
Are our time, resources and investments actually concentrated around those priorities, or are we spreading effort across too many competing initiatives?
ACTIVATION
Do people know the specific actions and behaviors that need to change in order to deliver the strategy?
OPERATIONALIZATION
Do our processes, tools, managers and measures reinforce those behaviors consistently?
PROOF
Have we identified the few indicators that will tell us whether execution is improving before the final financial results arrive?
I have worked with some exceptional leadership teams, and even in strong organizations people can usually recite the company goals more easily than they can explain how their own work contributes to delivering them. That is where senior leaders and mid-level managers matter so much. They help turn broad goals into choices and expectations that make sense closer to the work.
Most execution problems I have seen do not sit neatly in one box. Sometimes the strategy is clear but the organization is chasing too many things. Sometimes people understand the priority but do not know what to change. And sometimes the team is doing the right work, but the management system has not caught up.
This is why I increasingly think of Commercial Excellence as something broader than sales effectiveness, enablement or marketing alignment. To me, it is the work of getting an organization aligned around what it needs to do differently and making sure the surrounding systems support it.
The opportunity may not always be to develop another strategy. Sometimes the more useful question is whether the organization has translated the strategy clearly enough for people to act on it and built the systems to support them when they do.
This is the work I find most satisfying. I love the point when a complicated growth goal starts to become practical, when teams understand where they fit, people know what to focus on and you begin to see evidence that the plan is moving.
If your team has a clear strategy but is struggling to translate it into consistent results, a strategy-to-execution diagnostic can be a useful place to begin the conversation.