When Planning Almost Works (But Doesn’t Stick): The Real Experience of a Builder-Stage Business
There’s a stage many companies hit where they aren’t new to planning anymore — they’ve tried it, maybe multiple times — but they still haven’t been able to make it stick. This is the Builder stage.
Builders don’t struggle because they “don’t believe in planning.” They struggle because they’ve had just enough experience with it to feel discouraged by it. They’ve seen the plan fade. They’ve seen a strong start lose momentum. They’ve seen energy turn into fatigue somewhere around mid-quarter.
And after a few repetitions of that pattern, a kind of scar tissue starts to form — not dramatic, just subtle doubt:
Are we just not good at this? Is planning one of those things that “other companies” can sustain, but we can’t?
That’s a very real sentiment we hear from Builder-stage teams.
The first kind of frustration: “We made a plan… and then it fell apart.”
Most Builders already understand the value of planning. They don’t need convincing. They’ve held planning sessions. They’ve set goals. They’ve had good intentions.
But when goals aren’t met — or when the plan gets buried under the day-to-day — trust in the process erodes. Teams internalize the feeling: “What’s the point of making a plan if we never finish it?”
That’s when the doubt creeps in:
Maybe planning doesn’t work for our kind of business.
Maybe we’re not “disciplined” enough.
Maybe our industry is too reactive.
Maybe our people just can’t keep up.
The belief becomes the obstacle — not the plan itself.
And then a second story starts to develop
Once a team has tried planning and watched it fade a few times, something important shifts internally. The next planning cycle doesn’t begin fresh — it begins from skepticism.
The CEO may be trying to gear up the team again, but they feel resistance.
The team may want planning, but they feel wary — “we’ve done this before.”
Some CEOs have the scars.
Some leadership teams have the scars.
And often, both do.
But the real issue usually isn’t “follow-through” — it’s conditions
When we start working with Builders, we don’t ask, “Why didn’t you try harder?” That’s the wrong question.
We ask:
“Did the business actually have the conditions required for the plan to succeed?”
More often than not, the answer is no.
Sometimes the issue is:
The team was simply too busy to give priorities attention
The company didn’t have enough people for the level of ambition in the plan
Or the wrong people were in the seats, resisting accountability
Sometimes it’s structural:
There wasn’t a rhythm for checking in on progress
The metrics weren’t the right ones
The priorities (“rocks”) weren’t specific or measurable
Sometimes the barrier is leadership pace:
The CEO is moving at 400 mph in six different directions
The team can’t match that velocity, so they eventually give up on the plan
Builders often think they have a planning problem.
In reality, they have a capacity/clarity problem.
So the work at this stage isn’t “try harder” — it’s “set it up to actually work”
When we help Builder-stage companies, we begin by honoring the fact that they have tried. Builders don’t need to go back to square one — they need to go back and look at why their earlier plans were hard to execute.
That usually includes:
Reviewing past quarters to see what actually blocked momentum
Asking whether the metrics and targets were realistic
Determining whether the team had the bandwidth to focus on the work
Looking at whether roles, accountability, or expectations were unclear
Then we diagnose, rather than judge.
Once teams see why their plans didn’t stick, the discouragement lifts. The disappointment had a cause — and causes can be corrected.
And this is where confidence starts to return
When a Builder finally understands,
“It’s not that we can’t plan — it’s that we weren’t set up to succeed,”
planning stops feeling like failure and starts feeling like possibility again.
Early wins matter at this stage.
Small successes rebuild belief in the system.
Rhythm replaces doubt.
We don’t tell Builders to do more — we help them do less, better:
Fewer priorities
More clarity
Right conditions around the work
A cadence that keeps the plan alive
Progress becomes visible again.
When planning becomes achievable instead of exhausting
Once the load is right-sized and the conditions match the ambition, planning finally works the way it was intended — not as “another thing to maintain,” but as the structure that keeps everyone moving together.
For many leadership teams, that’s the moment the fear lifts. Planning stops feeling like a reminder of all the times it slipped away, and starts feeling like alignment, clarity, and traction.
Curious whether you’re truly in the Builder stage (or further along)?
We created a short Annual Planning Quiz to help leadership teams quickly see whether they’re operating as a Pathfinder, Builder, Optimizer, or Strategist.
Most Builder-stage leaders discover that their struggles weren’t a lack of discipline, but a mismatch between expectations and capacity — and there’s real relief in seeing that clearly.
If you’d like to know which planning stage you’re actually in, the quiz is a good place to start.
