5 Strategic Planning Takeaways From 8 Years Of Data

I've been in the strategic planning software business long enough to have seen a lot of plans, good and bad. Until recently, I had no way to separate what works from what just sounds good in a boardroom. That changed when we compiled eight years’ worth of anonymized data from ClearPoint accounts, 31.2 million rows covering:

👉Over 20,000 strategic plans
👉117,547 goals
👉317,809 measures
👉130,324 projects

A dataset this size shows patterns no single organization could see. What emerged wasn't what I expected. Some conventional wisdom held up, some didn't, and a few findings made me rethink assumptions I've held for years. Here are the five takeaways that matter most for how you build and execute your strategic plan.

Takeaway #1: Your Plan Is Probably Too Big

Start with portfolio size. This is where most organizations set themselves up to fail before they begin.

The median strategic plan contains:

• 5 goals
• 9 measures
• 8 projects
• 17 milestones

That's about 39 total elements, which seems reasonable.

Here's what the data shows:

• Plans with fewer than 20 total elements succeed 68% of the time.
• Plans with 60 or more elements succeed 8% of the time.

Look at that ratio. A bigger plan doesn't cost you a little success in exchange for comprehensiveness. It destroys your chances of execution.

It gets worse. From 2017 to 2024, the number of active projects per plan increased 60% by median (from 5 to 8) and 48.8% by average (12.52 to 18.63). Milestones nearly doubled on average, climbing to 56 per plan.

Plans are getting bigger, and bigger plans are harder to finish.

I get it. In the planning process, everything feels important. Every department has legitimate priorities, every stakeholder wants their initiatives included, and the pressure is to add, not subtract.

👉Case in point: Durham, North Carolina

Government leaders in Durham, North Carolina learned this the hard way. They first implemented strategic planning software in 2011 with over 500 performance measures to track, and found that comprehensive did not mean effective. Within a year, most staff had gone back to Excel because the system was too complex to manage.

Their breakthrough came in 2014. Instead of asking "What should we track?" they asked "What can we actually execute?" They rebuilt their performance management structure around focused, manageable portfolios with clear ownership at every level. The result was over 100 actively engaged employees, $1.8 million in budget savings from eliminating non-strategic spending, and a triple-A bond rating maintained through economic challenges.

The uncomfortable truth: If you want to execute your strategy, you need to prioritize ruthlessly. Not everything can be strategic or deserves to be tracked. The organizations that finish what they start are the ones that start with less.

Takeaway #2: Goals Are Shrinking While Projects Are Growing (And That's A Good Thing)

One pattern caught my attention. From 2017 to 2024, the median number of goals dropped slightly from six to five. Meanwhile, projects increased from five to eight, and milestones climbed from 15 to 17.

At first glance, this looks like organizations are just shuffling deck chairs: fewer goals, more projects, little real difference.

The successful organizations are doing something deliberate. They narrow their focus at the top and expand execution capacity below. They do more of what matters instead of simply doing more.

"Goals are shrinking while projects are growing — and that contrast says everything. The best strategy leaders are narrowing their focus at the top while expanding execution capacity below. It's not about doing more. It's about doing more of what matters."
—Ted Jackson, Co-founder of ClearPoint

👉Case in point: Fort Lauderdale, FL

Fort Lauderdale, Florida shows this shift. When the city launched "Press Play Fort Lauderdale" in 2013, it started with 12 goals, 38 objectives, 191 initiatives, and 142 key performance indicators. The plan was comprehensive, community-driven, and overwhelming. Cross-departmental meetings brought together over 100 staff every two months to cover topics most attendees didn't need. People felt busy but not productive, and frustration mounted.

The turning point came when Kristin Tigner, their Structural Innovation Manager, embraced a "simplify, excel, and expand" philosophy. Instead of trying to execute everything at once, they narrowed their strategic focus and built deeper execution capability on fewer priorities.

‍The lesson: Strategic focus means fewer things to think about at the strategic level, not fewer things to do. When your leadership team is focused on five clear goals instead of twelve competing priorities, they can direct resources more effectively. When those five goals cascade into eight well-designed projects instead of 191, teams can finish what they start.

Takeaway #3: Ownership Is The Execution Lever Nobody Talks About

The biggest execution gap in strategic planning is ownership.

Here's what the data revealed:

• Initiatives with a named owner complete at 2.5x the rate (21.5% vs. 8.7%) in ClearPoint data.

For the owners who are assigned, ClearPoint shows who hasn't updated their work in the last 90 days, so teams can follow up before the review. Seeing who is active is the first step to making every owner an active one.

The gap is a culture problem that looks like a planning problem, not a software or process problem. Organizations treat ownership as an administrative detail, something you fill in on a spreadsheet so the plan looks complete. But ownership is the fulcrum of execution. Without it, even a brilliant strategy is an expensive wish list.

👉Case in point: Carilion Clinic

Carilion Clinic in Virginia figured this out early. When they began building their performance management system in 2007, they did more than assign owners. They made ownership mean something. They created scorecards for individual physicians, departments, and sections, then linked compensation to patient-centered care outcomes.

Darren Eversole, the Director of Finance, explains the impact: "Everyone is rowing in the same direction, physicians and providers have control of their results as an individual, which contributes to the overall performance of the scorecard." When people own their metrics, behavior changes. Carilion eventually managed around 300 scorecards through ClearPoint. The system worked because of real accountability at every level, not sophisticated technology.

"Stop naming committees. Name a person. One champion with 3-4 helpers beat crowds every time."
—Robin Champ, VP, LBL Strategies

The fix isn't complicated: Every goal, measure, project, and milestone needs one accountable person, not a team or a department. If that person hasn't updated in 90 days, reassign or remove them. Put owners on page one of your strategic plan where everyone can see them.

Make ownership real, or don't bother planning at all.

Takeaway #4: The Calendar Reveals More Than You Think

When I first looked at the seasonal patterns in our data, I expected some clustering around fiscal year boundaries. What I didn't expect was how much the calendar shapes execution, and how predictably organizations repeat the same patterns year after year.

• February records the most updates at 2,045,105.
• January launches 1.8 times more projects than all of Q4 combined.
• November records the most logins to ClearPoint. That's when leaders are building next year's strategic plan, aligning goals, and ensuring a smooth transition.
• December sees 29% of project completions; no other month exceeds 10%.

Organizations have settled into a "launch in January, close in December" cadence, and that cadence creates predictable bottlenecks.

When 29% of your projects are due in December, you get more than a busy month. Quality suffers, resources get stretched thin, and projects get delayed because everyone is buried in year-end work.

👉Case in point: JEA

JEA, one of the nation's largest utilities serving 2,200 employees, recognized this problem and spreads work deliberately throughout the year. Each quarter, they produce strategy reports with "more visuals and fewer tables" to tell the story quickly. That cadence keeps momentum going year-round instead of piling pressure on year-end.

The elite performers in our dataset do something similar. They set a guardrail that no single month should contain more than 15% of planned finishes. They pull work forward from December and June into Q2 and Q3, creating mid-quarter finish windows that smooth out the workload.

The goal is steadier work, not faster work. When you spread execution across the calendar, you keep momentum without burning out your team.

The calendar also revealed something about project timelines. During COVID in 2020, median project duration dropped to 163 days, nearly half of 2017's 303 days. Organizations proved they could move fast when they had to.

By 2023-2024, project timelines had settled back at 364 days. That reads less like a regression than a recognition that strategic transformation takes sustained, deliberate effort.

The lesson: Your calendar tells you something about your execution capacity. If 47% of your projects finish in just two months, you have a scheduling problem, not an execution problem. Fix the calendar, and you'll fix a lot of execution issues you thought were about capability.

Takeaway #5: Industry Matters Less Than You Think

This one surprised me.

When we segmented the data by industry, we saw predictable differences in portfolio size:

• Manufacturing, Non-Profits, and Professional Services set twice as many goals (median of 10) as Governments and Financial Services (5).
• Education tracks the most measures (a median of 16).
• Energy & Utilities show the highest milestone intensity (median of 20).

These differences make sense. A utility managing physical infrastructure needs more milestones than a financial services firm. A nonprofit juggling multiple funding sources needs more goals than a government agency with a clear mandate.

But completion rates, the metric that matters, varied less than I expected.

Energy & Utilities leads at 25.81% completion. Financial Services (17.48%), Government (17.38%) and Manufacturing (16.95%) follow close behind.

Every industry has the same basic challenge: finishing what it starts.

The organizations in the top 5.7%, the ones completing 93% of their projects, come from every sector. Durham and Fort Lauderdale are in local government. Carilion Clinic is in healthcare. JEA is in utilities.

Their industries, contexts, and constraints differ. What they share is a commitment to execution fundamentals.

👉Case in point: JEA

JEA runs a complex operation as a major utility, but Kendra Cash explains their approach simply: "Our day-to-day metrics live in internal systems, but anything related to our strategy lives in ClearPoint. It keeps things clean and eliminates confusion."

They use Power BI for operational data, embed it live into ClearPoint for strategic visibility, and track hundreds of tasks while keeping leadership focused on what matters. The collaborator field lets them break down silos. "Now you can see Technology is working with Customer, and HR has a piece in that same objective."

That visibility works whether you run a utility, a hospital, or a city government.

The uncomfortable truth: if your organization isn't executing well, you can't blame your industry. Healthcare is complex, governments have constraints, and utilities have regulatory burdens. But organizations in your industry are executing at elite levels.

The data shows it's possible. What matters is whether you're willing to implement the disciplines that make it possible.

A "challenging" industry isn't an excuse for strategic failure. It's a chance to outperform competitors who use industry as an excuse.

What The Data Doesn't Tell You (But You Need To Know Anyway)

After all this analysis, I've learned that numbers tell only part of the story.

For example, the data shows that Durham, Fort Lauderdale, and Carilion Clinic all succeeded in their strategic endeavors. What it doesn’t show is:

• The years of refinement and failed first implementations.
• The difficult conversations with leadership about what a data-driven organization should look like.
• The frustration of early meetings.
• The courage of strategy leaders in advocating for focus over comprehensiveness.
• The careful studying of and learning about frameworks like the Balanced Scorecard.
• The incremental expansion of strategy, from leadership scorecards to provider scorecards to department scorecards.
• The work that goes into structuring focus areas and building quarterly reporting processes that executives actually use.

Data can tell you what works, but not how hard it is to implement. Every organization in the top 1% of execution faced setbacks, had to unlearn old habits, and had to make uncomfortable changes.

Shari Metcalfe, Durham's Strategy and Performance Manager, puts it this way:

"A big turning point for our performance management was getting a system that we could use to manage all that data. It's just easier. Less time putting numbers in a system and more time actually looking at the numbers and making decisions based on them."

The shift from data entry to data-driven decision-making sounds simple. It took three years of organizational learning, a complete redesign of their governance structure, and leadership commitment to change how the city operated.

The data tells you what to do. Experience tells you that doing it is hard. Both are true.

Start With What You Can Control

If you've read this far, here is what to do with these insights.

Start by auditing your current state against the five takeaways:

1. Rightsize Your Portfolio

• Count your total elements (goals + measures + projects + milestones)
• Calculate where you sit: under 20 (68% success rate), 20–60 (declining success), or over 60 (8% success rate)
• If you're over 40 total elements, start cutting.

2. Narrow Your Strategic Focus & Build Execution Capability

• Count your strategic goals.
• Count your projects.
• Ask: Are we narrowing focus at the top while building execution capacity below?
• If you have more than nine goals, consolidate.

3. Build In Accountability

• Calculate what percentage of your elements have no owner.
• Pull a report of all owners who haven't updated in 90 days.
• Decide: Will you reassign or remove them?
• Track "% unowned elements" and "% active owners" on page one.

4. Optimize Your Calendar

• Map when your projects are due throughout the year.
• Calculate what percentage finishes in December and June.
• If any month exceeds 15%, start moving projects.
• Create mid-quarter finish windows in Q2 and Q3.

5. Check Your Reality

• Stop comparing yourself to industry averages.
• Start comparing yourself to execution fundamentals.
• Ask: are we implementing the disciplines that work across all sectors?

This is tuning, not transformation. The organizations that excel at execution didn't revolutionize their approach. They implemented basic disciplines consistently.

Disciplines compound. Durham didn't see results in year one. Fort Lauderdale didn't simplify overnight. Carilion didn't build 300 scorecards in a month. JEA didn't break down silos with a memo.

They built execution capacity incrementally, learning from each cycle and refining their approach based on what worked. The data shows this is possible. Your job is to make it happen.

The 5.7% Question

I'll leave you with this: 5.7% of organizations average 93% completion.

The interesting part is that they make strategic plans like everyone else. They hold planning sessions. They create goals and measures and projects. They assign owners and track progress.

The difference is in how they do it, not what they do.

After analyzing eight years of data, I can tell you what separates the 5.7% from everyone else:

Organizations that struggle treat strategic planning as an event. The successful 5.7% treat it as a system.

Organizations that struggle confuse comprehensiveness with effectiveness. The 5.7% associate focus with impact.

Organizations that struggle assign owners administratively. The 5.7% create real accountability.

Organizations that struggle let the calendar happen to them. The 5.7% design their execution flow.

Organizations that struggle blame their industry for execution challenges. The 5.7% implement disciplines that work regardless of sector.

The data says which side of that gap you land on is your choice. Unlike most strategic challenges, this one has a clear path forward. You just have to start walking.