Your Strategic Plan BEGINS When the Retreat ENDS
Owning an elephant sounds intriguing—until it’s dinnertime. Not to mention after dinner.
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Strategic planning is a large and costly undertaking. It may require thousands of dollars for a consultant, the collective salaries of executives and directors for a two-day retreat, and the time that board members and stakeholders contribute away from their other work. Understandably, leaders want a polished, hefty document, printed in color on very nice paper, to show for the money they spent. But that expensive deliverable often hitches a ride home with the team, only to sit abandoned on a shelf. But, hey, did you see that cool chart on page 17 and the nice cover on the front?
Why do strategic plans so often disappoint?
Let’s be honest: clear and compelling plans have real value. Good graphics, a little showmanship, and memorable themes make strategy easier to communicate by grabbing attention and delivering real content. But the document itself is not the objective—in fact, the strategic plan is not even the objective. The objective is alignment: helping people inside and outside the organization see where they are going so they can make decisions, direct resources, and work toward that destination in a coordinated way.
This creates a telling test for every strategic planning retreat and activity:
Does our plan empower and motivate my team to make decisions that head in the same direction?
Alignment depends on clarity of the destination, not precision of the path.
Long-range strategy clarifies the destination without pretending that leaders can predict the detailed circumstances of the path to the future. A ten-year vision, for example, is indispensable. A ten-year plan is impossible.
A useful progression is:
Ten-year horizon: What are we ultimately trying to become or accomplish?
Three-year horizon: What would meaningful progress look like in concrete terms?
One-year horizon: What has to be true by the end of this year for the multi-year plan to remain credible?
Ninety-day horizon: What are the 5 to 7 most important actions that need to move now?
Weekly horizon: Are those priorities actually moving?
For nonprofits, the three-year horizon should include both impact and financial realities. Revenue is not the mission, but it is the organizational lifeblood that enables the mission to continue and grow. No margin, no mission. Our dreams also become grounded when we confront the revenue required to make our Big Hairy Audacious Goals (BHAGs) a reality. A growth strategy that assumes increasing impact without examining the revenue and capacity needed to sustain it is naive.
I’m borrowing concepts that are well developed in the Entrepreneurial Operating System (EOS). EOS uses the Vision/Traction Organizer and a sequence that moves from long-term vision to a 1-Year Plan and then to 90-day Rocks. It defines Rocks as the three to seven most important priorities to complete during the next 90 days. The real magic is the discipline of aligning the actions directly in front of us with the ultimate goal we are trying to attain. The marketing and structured language are useful, but they are not the main driver.
The next sections move from that ten-year horizon down to the weekly time frame.
Commander’s Intent: Clarify the Goal, Don’t Predict the Future (10- and 3-Year Horizons)
Detailed planning has value because it forces leaders to think through assumptions, dependencies, and possible approaches. It helps make a vague notion of success tangible, concrete, and real. But specificity depends on proximity to the work and to the moment when a decision must be made. The farther the organization is from execution, the more its strategy should emphasize the desired outcome by making the end state as clear as possible and articulating the motiving intent rather than detailed future steps.
Chip and Dan Heath use the U.S. Army concept of Commander’s Intent in Made to Stick to illustrate this balance. Detailed plans may need to change when circumstances change, but a clear statement of the desired end state allows people to adapt without losing alignment. The choice is therefore not planning versus flexibility. The goal is to plan enough to clarify intent, then allow the plan to become more specific as the organization gets closer to the work.
That creates a chain of purpose: today’s action supports the quarterly priority; the quarterly priority supports the one-year plan; the one-year plan supports the three-year target; the three-year target supports the long-range vision; and the vision serves the organization’s mission. That chain provides both freedom and accountability. People can adapt the method, but they cannot simply ignore the intent.
In fact, we can almost hear ourselves answering the childlike question we all ask: “Why?” Like quality improvement professionals trained to find a root cause, we should be able to ask “Why?” five times. Then, as effective leaders, we should be able to answer with a connected chain that leads all the way back to our mission and vision.
The closer you are to the work, the more specific the decision should become. The board should own the long-range destination and help form the multi-year direction. The CEO should carry primary responsibility for translating that direction into the multi-year and annual agenda. Executive leaders turn annual goals into near-term priorities, while directors, managers, and frontline teams make increasingly specific decisions closer to execution. The boundaries will never be perfect, but the logic is that intent travels down the organization while decision authority moves closer to the work.
Flipping this logic exposes the foolishness of how we sometimes operate. Should a board really spend time deciding whether a patient gets an appointment at 8:15 a.m. or 10:30 a.m. two years from today? Of course not. We do well to leave decisions with people. We do even better to leave the right decisions with the right people.
In other words, “Push Decisions Down, Push Intent Up.” See how far down you can reliably push a decision to make it as close to the work as possible. Then push intent (“What are we trying to do here?”) up to the highest levels in the organization if they are not clear.
Use the Annual Budget to Clarify Annual Goals (1-Year Horizon)
Annual priorities precede the budget because the budget codifies the decisions that have been made.
This collaboration between the board and management demonstrates the principle of pushing decisions down. The board sets the ten- and three-year intent and direction; management then decides how best to advance that direction during the coming year and presents those decisions back to the board in the structured form of a budget.
The number-one error I see is treating strategic planning and budgeting as unrelated—or, at best, parallel—processes. Too often, leaders view the budget as a necessary evil and a laborious exercise. They rely on past materials or begin only from where the organization is today. Then, when the 90-day strategic plan update arrives, they realize they have made little progress and created no budget capacity to turn their ambitions into reality.
Instead, strategic planning should account for financial management, and financial planning should make this year’s priorities concrete by showing how they can be accomplished. That is what makes the budget the real plan rather than something at odds with what the organization wants to do.
The best budget processes:
Revisit the multi-year destination.
Determine what must happen during the coming year to remain on track.
Define the annual priorities and required outcomes.
Build a budget that provides the people, capacity, and resources needed to accomplish them.
Set revenue assumptions within the range of historical performance, then evaluate the tradeoffs required to pursue new initiatives with existing resources and identify any known new resources that can support them.
If the budget cannot support the annual priorities, resolve the conflict now rather than discovering the strategic miss a year or two later.
The question is not, “How do we balance this year’s budget?” It is, “Does this budget describe the strategy that will move us toward our three-year goal?”
The EOS model calls for a two-day annual planning session to create the 1-Year Plan (and to reset each year) to align the organization around those objectives. Connecting that process to the actual budget is a practical extension drawn from experience.
Motivate Change by Bringing the Year Down to Quarters (90 Days)
Annual goals are helpful, but they are too distant to manage effectively from week to week. If they are ambitious enough, they are also too large to accomplish all at once. A bad week can leave a team feeling that the goals are unreachable and tempt people to abandon them altogether.
Instead, the leadership team should have the discipline to ask every 90 days: What must happen during the next 90 days for us to remain on track toward the annual target?
When I worked with a health center to introduce morning huddles, I heard a familiar objection: “We don’t have time to do that! It sounds like a great idea, but I already have too many things to do to prepare for the day ahead.” Many of us feel the same way about setting aside a full day each quarter to stop and decide what matters most for the next 90 days.
But that exercise can help us regain control of the daily experience. Consider the analogy illustrated below. In the jar on the left, the sand goes in first, followed by the pebbles, stones, and rocks. It does not fit. If the rocks represent the most important things we need to do, the conclusion seems obvious: there is simply not enough room in the jar—or enough time in the day—for the work that matters most.
But if we approach the jar on the right by placing the rocks first, then adding the pebbles, gravel, and sand, everything fits—with room to spare.
The discipline of quarterly planning is subtraction. The hard work is to list everything the team must do this quarter to stay on track with its annual goals, then whittle that list down to five—and no more than seven—truly important Rocks. I have adopted the EOS term because of the clarity it brings to the team.
The leadership team does this so everyone in the organization can think, “If I am starting my day and choosing between two things that have landed on my desk, I know how to prioritize them because one is a Rock and the other is not.” That does not mean the other task never gets done. It means people know which one to do first.
I have often seen teams leave a quarterly meeting with immediate energy because they invested the effort to decide collectively what matters most. The very next day, people are eager to collaborate on those priorities and get to work. It is like a team coming out of a timeout with clarity about the play and who will take the shot.
That stands in sharp contrast to the countless leadership meetings in which someone spends significant time reminding the staff that an issue is important, yet nothing changes from week to week. The team returns, and the work still has not happened. Quarterly planning creates momentum by giving everyone clarity about what matters most.
The point of the quarterly meeting is not necessarily to force every detailed milestone into the executive discussion. The leadership team's first responsibility is to agree that these are genuinely the most important priorities and assign one accountable owner to each.
Name the Owner and Let Them Work (90 Days)
Once a quarterly Rock is defined and makes the cut, it is assigned to one accountable leader. That person then needs room to translate the priority into an executable project.
Instead of belaboring every detail of the Rock in the group meeting, I assign the accountable leader a first task: define what completion means and turn the quarterly Rock into a SMART goal.
After watching several teams adopt and improve this process, I have found a useful litmus test for a well-defined Rock:
Could someone who was not in the planning meeting look at the result at quarter-end and determine whether it was completed?
The group does not need to wordsmith every detail of a Rock, but it should establish the Rock’s “acceptance criteria.” In other words, what must be true at the end of the quarter for the group to agree that the Rock is complete?
Once that question is answered, the owner’s assignment is to:
Identify the team and resources needed to complete the Rock.
Develop key milestones, often at roughly monthly intervals.
State the immediate next step.
Share any known barriers or dependencies.
Once these elements are defined, they become standing topics in the weekly conversation. After all, if these are the organization’s most important priorities, what else should its leaders be discussing?
At the end of the quarter, the team reviews which Rocks were completed, studies which were missed, and sets the Rocks for the next quarter.
Review Weekly With a Structured Evaluation (1 Week)
The beautiful strategic plan mentioned at the beginning often becomes a dusty artifact because, once it is created, the team returns to doing what it did before. People vaguely hope they will find time to advance the objectives, but there is no guarantee—and, honestly, no accountability to do anything differently.
Instead, the weekly leadership meeting becomes the natural place to discuss the organization’s most important Rocks and check their progress. A quick on-track/off-track review is more useful than a lengthy explanation, color-coding scheme, or progress meter because it keeps the most important quarterly work visible without consuming the entire meeting.
EOS uses this pattern in the Level 10 Meeting: Rock owners report on-track or off-track, and off-track Rocks move to the Issues List.
Although this remains a judgment call for the Rock owner, I have found it helpful to define several conditions that must be in place for a Rock to qualify as “on track.”
A Rock is on track when:
The Rock’s outcome is stated clearly enough that any team member will know when it is complete.
The owner has a credible project or milestone plan.
The next action is known.
The work is progressing at the rate needed to complete the rock’s stated outcome on time.
There are no unresolved barriers that materially threaten completion.
If one of those conditions is missing, the Rock should generally be considered off track even if the owner believes it might eventually recover.
“Off Track” Is Not a Status Update; It Is a Trigger for a Leadership Decision
Let’s get more granular: What happens in the meeting when someone says, “Off track”?
First, the team leader must normalize the decision to mark a Rock as off track. When the facts are ambiguous, people naturally tend to call the work on track. The conditions above provide a more disciplined way to determine its status.
Second, the leader must maintain accountability for progress on these key objectives. The team does not need to discuss the Rock the moment its status is reported. Instead, the Rock moves to the top of the agenda when the team addresses issues. That creates time to decide how to get it back on track before the next week. The discussion may be simple, but it signals that the team meant what it said when it designated this work as one of the most important priorities for the next 90 days.
As teams learn this model, I sometimes see a Rock marked “off track” for two or three consecutive weeks while the meeting simply moves on. The team used the definition and reported the status, but it did not honor the priority assigned to the Rock. It allowed sand to displace the Rock. Less important work took the place of more important work in the name of busyness or a quick sense of accomplishment.
So, the items above become a diagnostic as well.
Is the rock clearly assigned to one person? Is that still the right person?
Is the rock well defined? Does everyone in the room understand it?
Is there a credible plan to accomplish the rock? What will it take to get a plan together?
What needs to happen next? Are there other insights from the team to clarify what should happen?
Is progress proceeding at a sufficient pace? Are additional resources needed to accelerate it?
Are there blockers or barriers? How can those be moved?
Rallying the team around these questions reinforces the importance of the Rock and creates shared ownership of the outcome. In rare cases, a goal will prove unattainable. Even then, the leader should resist the temptation to adjust the Rock mid-quarter or quietly remove it. Reviewing results at quarter-end is like studying a sports team’s win-loss record: it gives the team useful evidence to consider when drafting the next quarter’s Rocks.
In the EOS model, off-track Rocks move to the Issues List, where the team uses IDS—Identify, Discuss, Solve—to address the problem and get the work back on track.
Recap
📄 Poor execution Don’t fall into the pretty-report, poor-execution trap.
The strategic plan is not the objective; alignment is.
🧭 Alignment Depends on Clarity of the Destination, Not Precision of the Path
A ten-year vision is indispensable; a ten-year plan is impossible.
🚩 Commander’s Intent: Empower Decisions with Clear Intentions
Push Decisions Down. Push Intent Up.
💰 Use the Annual Budget to Clarify Annual Goals
The budget should describe the strategy, not compete with it.
🪨 Motivate Change by Drilling the Year Down into Manageable Quarters
The discipline of quarterly planning is subtraction: decide what matters enough to go first.
👤✅ Name the Owner and Let Them Work
Name one accountable owner, define what done means, and give them room to work.
📋 Review Your Rocks Weekly with a Simple Evaluation
If these are truly the organization’s most important priorities, they deserve a few minutes every week.
⚠️ “Off Track” Is Not a Status Update; It Is a Trigger for a Leadership Decision
Off track should trigger action, not become a label you repeat for three weeks.
The leader must measure the success of the retreat by the decisions people make afterward, not by the report they carry home.
The value of a strategic plan is measured by the daily and weekly choices that move the organization in the right direction. A clear vision of the destination helps people navigate the valleys, twists, and turns along the way.
Measure the success of your leadership retreats not by the graphics in the report, but by the decisions your staff make afterward to move the organization toward its destination.
Contact dp3solutions today for help in implementing a process that turns strategy into action.
Source notes
Books and foundational concepts
Collins, J. C., & Porras, J. I. (1994). Built to last: Successful habits of visionary companies. HarperBusiness.
Supports: BHAG (Big Hairy Audacious Goal) as a clear, compelling, long-range focal point that stimulates progress and unifies effort.
Heath, C., & Heath, D. (2007). Made to stick: Why some ideas survive and others die. Random House.
Supports: Commander’s Intent as a simple statement of the desired end state that preserves alignment when detailed plans must change.
Wickman, G. (2012). Traction: Get a grip on your business. BenBella Books.
Supports: the EOS sequence from long-range vision to the 1-Year Plan, 90-day Rocks, and weekly execution.
EOS implementation sources
EOS Worldwide. (n.d.). What are EOS Rocks? The 90-day priority system.
Supports: three-to-seven priorities, a 90-day horizon, one owner, weekly Rock Review, and the connection between the annual plan, Rocks, and To-Dos.
EOS Worldwide. (n.d.). What is a Level 10 Meeting?
Supports: weekly Rock review, on-track/off-track status, movement of off-track items to the Issues List, weekly To-Dos, and IDS.
EOS Worldwide. (n.d.). What is IDS? Identify, Discuss, Solve.
Supports: Identify–Discuss–Solve as EOS’s structured approach to moving issues toward decisions and To-Dos.
EOS Worldwide. (n.d.). Quarterly business planning: Why annual goals fail and how 90-day priorities actually get done.
Supports: clear, measurable, owned Rocks and the principle that completion should be objectively determinable at quarter-end.