By Brian S. Smith, PhD | IA Business Advisors | The I in Team Series®
I often find that annual strategic planning lives on the periphery of most business owners’ realities.
Our clients are not in the business of building strategic plans. They are plumbers, contractors, doctors, lawyers, restaurateurs, and entrepreneurs, people whose primary influence is applied daily in their craft, their clients, and their teams. Strategic planning, while critically important, often becomes something they know they should do, but rarely feel equipped, or resourced, to do well.
And that’s not because business owners lack discipline or ambition.
It’s because most strategic plans fail at the point of translation.
The challenge isn’t deciding what you want to achieve. The challenge is developing a strategic plan that is contextual, realistic, and capable of evolving into meaningful tactical engagement. This is the same reason New Year’s resolutions, and many individual or organizational plans, fail at a rate exceeding 85%. Goals are declared, but the pathway to achievement is unclear, unrealistic, or unsupported.
The Problem Isn’t the Goal—It’s the Structure
At IA Business Advisors, our answer to this challenge is S.M.A.R.T. (Specific, Measurable, Attainable, Relevant, Timely)
But I want to be very clear:
I am not just talking about S.M.A.R.T. goals.
I am talking about applying S.M.A.R.T. thinking to the entire system:
- Goal
- Objective
- Milestone
- Task
- Feedback loops that keep the cycle alive and responsive
When S.M.A.R.T. is only applied at the goal level, failure is almost guaranteed. S.M.A.R.T. must become a discipline, not a declaration.
Why Milestones Matter More Than Most People Realize
The most critical, and most misunderstood, component of the S.M.A.R.T. cycle is the milestone.
A milestone is not a task, and it is not a date.
A milestone is a measurable checkpoint of progress that confirms you are moving toward the objective in a meaningful and responsible way.
This is where attainability lives or dies.
- If milestones are unattainable, we fail.
- If milestones are not specific and measurable, we fail.
- If milestones are not relevant to the goal or timely in sequence, we fail.
Milestones are what turn intention into execution.
They provide clarity for teams, context for leaders, and early warning signals when something needs to change, before failure becomes inevitable.
Start With the Goal – But Build Through Milestones
One of the most effective shifts in strategic planning is this:
Set the S.M.A.R.T. goal first, then immediately identify the milestones required to reach it.
Only after milestones are identified should we begin filling in the gaps between them.
Why?
Because assigning timelines too early often creates artificial pressure that leads to poor assumptions, rushed execution, and missed accountability. When we first define what must be true at each milestone, before defining when it must happen, we dramatically improve the quality of planning.
As those gaps are filled, each milestone becomes supported by:
- Objectives that define intent
- Tasks that define action
- Measurements that define success
- Feedback loops that allow adjustment
Only then do timelines become meaningful and responsible.
The S.M.A.R.T. Question That Changes Everything
As the plan comes together, one question must always be asked:
Is this truly attainable in a timeline that is healthy for the team and responsible for the organization?
S.M.A.R.T. planning is not about stretching people until they break. It is about aligning ambition with reality in a way that sustains performance, trust, and progress.
Why Most Strategic Plans Still Fail
Very few businesses intentionally plan for the work required to build a S.M.A.R.T. goal.
As a result, goal setting is rushed, objectives are fragmented, tactics are reactive, and accountability is vague or nonexistent. When structure is missing, even the most capable teams struggle, and failure becomes the default outcome, not the exception.
Bringing It All Together
S.M.A.R.T. is not a tool.
It is not a worksheet.
And it is not a once-a-year exercise.
S.M.A.R.T. is a way of thinking that creates clarity, alignment, and momentum.
Milestones are the connective tissue between vision and execution. They turn strategy into something teams can see, measure, and believe in. When goals are supported by properly sequenced milestones, and those milestones are supported by clear objectives and tasks, achievement becomes far more than possible. It becomes predictable.
When businesses learn to build S.M.A.R.T. goals through milestones, they stop hoping for results and start managing toward them.
And that is where strategic planning finally becomes what it was always meant to be: a responsible, attainable, and empowering path forward, for the individual, the team, and the organization.