Execution Reality: Why Only 30% Of Your Roadmap Work Matches The Plan

I keep having the same conversation with product and strategy leaders. The strategy from the top is clear, the priorities are named, and there is even a list of ten projects leadership has committed to for the year. On paper, it all makes sense.

Then I ask a simple question: how much of your team's actual work is aligned to that plan, and what impact is it having on your top goals? That is where things start to get uncomfortable.

Measuring impact is already tough when you are shipping features, fixing issues, and reacting to the business. It gets even harder when the ideas in the plan were never validated, the impact was never modeled, and we have no shared view of what six months of work and ten million dollars of software investment are supposed to deliver. If you want a deeper dive into that challenge, I unpack it in more detail in Are We Really Tracking Outcomes.

This article is about something even more basic: I call it execution reality - getting an honest, quantified view of what you are actually executing, and whether it looks anything like the strategy you signed up for.

The strategy looks clear, the execution does not

Most mid market and enterprise teams I work with are not suffering from a lack of strategy. The C suite has articulated a few big bets. There is usually a roadmap or initiative plan that says, in effect, these are the ten things we are going to build or fix this year.

On a slide, it looks aligned and disciplined. In your work tracking system, it looks like two hundred Jira tickets, dozens of side tasks, and a calendar full of meetings.

When I ask leaders what percentage of their team's work today is actually tied to those ten initiatives, the answer is almost always unclear. You can not easily tell which tickets roll up to which strategy. You can not see, in one place, what portion of capacity is going to the plan versus everything else.

And when we do the hard work of connecting the dots, the picture is usually mind blowing.

Where the work really goes: 30 percent on the plan, 70 percent on everything else

Across teams, a consistent pattern shows up once you map work to strategy:

• Roughly 20 to 30 percent of the work is clearly aligned to the agreed initiatives.
• The remaining 70 percent is a mix of unplanned requests, operational noise, internal favors, and legacy commitments that no one wants to own.
• On top of that, there is a huge layer of meetings, coordination, and status reporting that adds significant overhead to the cost of every unit of work.

If only 30 percent of your team's time is going to the plan, and 70 percent is going elsewhere, you are not really investing what you think you are. The ten million dollar product budget you believe is aimed at your top strategies might effectively be more like three million, once you account for misaligned work and the operational drag around it.

This is why so many leadership teams feel like they are doing everything right at the top and still not seeing the expected movement in revenue, retention, or efficiency. The gap lives in the messy middle, where strategy is supposed to turn into execution.

Before you chase outcomes, make sure you have a plan you are actually executing

A lot of organizations try to jump straight to outcome measurement. They ask for dashboards, KPIs, and OKRs. All of that is useful, but if the underlying work is random, your outcome reporting is just a prettier view of the noise.

Before you obsess over impact, you need absolute clarity on three foundations:

• Outcomes: What are the specific business outcomes we are trying to drive this year and this quarter.
• The plan: What are the concrete initiatives or opportunities we believe will move those outcomes.
• The roadmap: How have we translated those initiatives into a sequence of work the team can actually execute.

Only then does the key question make sense: are we actually doing what we said we would do.

If you want to see how this connects across the full product lifecycle, I broke that down in Navigating the Product Life Cycle. The short version here: if your day to day work does not map cleanly to the outcomes, the plan, and the roadmap, any attempt to measure impact will feel disconnected and frustrating.

Execution reality: turning on the GPS for your product organization

Execution reality is about building a constant reality check into how you run product and strategy. Think of it like a GPS for your roadmap.

When you are driving with a GPS, it tells you where you are, which direction you are heading, and how far you have drifted from the route you planned. If you make a wrong turn, you see the impact on your arrival time right away.

Too many product teams are effectively driving in the middle of the ocean. They have drifted so far from the original route that the map and the terrain have almost nothing to do with each other.

To avoid that, you need a simple but disciplined version of a GPS for your execution:

• Map every initiative to one or more strategic goals so you can see why it exists.
• Tag every work item to an initiative, or mark it explicitly as unplanned work.
• Regularly measure what percentage of effort is going to the plan versus everything else.
• For each initiative, agree on a projected outcome up front, even if the model is rough.
• Track early leading indicators so you can tell if the work is on track to deliver its promised impact.

Once you have this in place, the conversations with stakeholders start to change. Instead of arguing about individual features or tickets, you can talk about tradeoffs at the level of initiatives, capacity, and outcomes. You are managing a portfolio of bets, not a grab bag of tasks.

If you are moving your organization from output to true value, that shift is critical. I wrote more about that transition in From Velocity To Value.

What great product leaders do differently

The best product and strategy leaders I work with treat execution reality as a core part of their operating system, not a one off exercise. They tend to do a few things consistently well:

• They obsess over alignment of work, not just alignment of slides. They can tell you, at any point, what portion of current effort is tied to the plan and what portion is not.
• They limit the creep of unplanned work. When something important appears mid quarter, they do not simply pile it on. They make conscious tradeoffs against the existing plan.
• They treat meetings and operational overhead as real costs. Standing meetings that do not move the plan forward get redesigned or removed.
• They tell the story of the work. They are constantly connecting day to day execution back to strategy in clear, human language. If you want to build that muscle inside your own leadership style, I shared some ideas in Moving Beyond Execution: How Storytelling Elevates Product Leaders.

All of this creates a culture where people understand not just what they are doing, but why it matters, and how it contributes to the larger bets the company is making.

Connecting execution reality to measurement and strategy

Once you have a clean view of execution reality, measurement starts to work in your favor instead of against you. You can finally answer questions like:

• How much capacity are we really investing in each strategic goal.
• Which initiatives are consuming significant effort without clear outcomes.
• Where are we consistently under investing relative to what we say is important.

At that point, more advanced measurement approaches become powerful instead of distracting. For example, resources like MarTech's guidance on improving marketing measurement or The KPI Institute's strategy planning resources are far easier to apply when you already know how your work maps to strategy. The same is true if you are leaning into AI and analytics, as firms like PwC explore in their AI predictions - those tools only drive value when they are pointed at the right work.

This is also how we think about product strategy and execution at Iteright. The goal is not more dashboards for their own sake. The goal is clearer bets, cleaner execution, and a tighter feedback loop between what you say you will do and what actually happens on the ground.

A closing question for your next leadership meeting

Before you ask your teams for better impact metrics, ask this instead: how confident are we that the majority of our time, money, and attention are going to the plan we already agreed on.

If you can not answer that with data, your first job is not another tool or another report. Your first job is to build your version of execution reality and turn on the GPS for your product organization.

Once you are actually doing what you said you would do, then all the work you put into measurement, AI, and strategy will finally have a chance to pay off. And that is when product teams move from busy to truly effective. If you want help thinking through how to make that shift in your own context, you can explore how we approach it at Iteright Solutions.