Once you finally have the space to think — whenever that is for your business — you need a clear starting point.
That starting point isn’t a goal-setting worksheet or a long planning retreat.
It’s Lessons Learned.
Not complicated.
Not formal.
Just a structured way to understand what actually happened so you can stop repeating the same frustrations and start making better decisions.
This step is deceptively simple, but it’s where strategic thinking either gets grounded in reality or drifts into wishful thinking.
Lessons Learned: The Easiest Strategic Tool You Aren’t Using Enough
Most businesses only do this once a year, if at all — and that’s exactly why they feel like they’re always behind.
A strong Lessons Learned session should happen:
- after a major initiative
- at the end of a busy season
- at minimum quarterly
It is a tool that is hard to overuse. Your business may benefit from doing Lessons Learned after specific initiatives and doing a general Lessons Learned quarterly.
Waiting until the end of the year guarantees that details are fuzzy and patterns are harder to see.
Everyone involved should contribute — not just leadership.
Your team sees things you don’t.
They experience friction you’re insulated from.
They hear customer complaints long before those complaints reach you.
Group conversations work best because one person’s observation often unlocks clarity for someone else.
Use the same four questions every time.
- What should we definitely do again?
This surfaces what actually worked — not what you hoped would work.
Examples:
- Staffing the store an hour earlier during peak season so shelves were stocked before customers arrived
- Starting trade-show prep a month earlier, which reduced stress and improved execution
- What didn’t go well and needs to change?
This highlights breakdowns and bottlenecks.
Examples:
- Bringing in seasonal help too late to train them properly
- Always being short-staffed on Mondays
- What should we discontinue?
This question is often the most uncomfortable — and the most valuable.
Examples:
- Letting bookkeeping slide and scrambling at year end
- Opening on days where customer traffic doesn’t justify the effort
- What should we start doing?
This reveals opportunities hiding in plain sight.
Examples:
- Spotlighting one product per month to improve customer education
- Setting clear execution benchmarks so people know what “done well” actually looks like
An Important Distinction: Not Everything Becomes Strategy
It is important to shift to strategic thinking when you shift from gathering data to analyzing it. Your job is to look at all the input from an owner’s altitude and decide what actually moves the business forward.
Some feedback is simple, low-risk, and immediately actionable.
Examples:
- Restock earlier → do it.
- Everyone is confused by the form → fix it.
- Customers can’t find pricing → improve the signage.
You do not need analysis for these.
The purpose of Lessons Learned is to surface patterns, not to create a long to-do list disguised as strategy.
Patterns are what belong in strategic planning.
Analyzing the Data: Where Strategy Actually Begins
Once you’ve gathered insights, the next step is to make sense of them.
This is where there can be a natural tendency to treat all feedback as equally important.
Your team experiences the business at the ground level.
They see symptoms.
They feel friction.
They notice what’s annoying, confusing, or inefficient.
What they don’t see is the full picture.
They don’t see:
- financial implications
- seasonality
- workload distribution across the year
- long-term positioning
- strategic tradeoffs
That doesn’t make their input wrong.
It means it needs interpretation.
A Simple Example
Your team says:
“Mondays are slow — we should close.”
From their vantage point, that makes sense.
From the owner’s perspective, Mondays may be essential for:
- stocking and inventory
- bookkeeping and admin work
- resetting for the week
The correct response isn’t automatically yes or no.
The correct response is:
What problem is actually being described?
That’s the heart of analysis.
Your Role in This Step
As the owner, your job isn’t to react to preferences.
It’s to look for patterns and implications.
Ask yourself four owner-level questions:
- What actually worked this year?
Not what you planned — what actually moved the business forward?
- What didn’t work, and why?
Operational stress almost always points to a deeper structural issue.
- What do we want to be different next year?
If your answers are mostly small tweaks, you’re still in the weeds.
Strategic thinking lives at the category level:
- revenue growth
- product or service development
- marketing direction
- hiring and capacity planning
Each category shapes dozens of downstream decisions.
- What information do we need before deciding?
Strategy is investigation, not guessing.
Examples:
- Before hiring → understand real workload patterns
- Before changing pricing → know true delivery costs
- Before buying equipment → evaluate expected revenue impact
- Before expanding → review financial trajectory with your CPA
This step is where clarity forms.
Without it, planning stays reactive.
What’s Coming Next: Turning Insight Into Direction
Lessons Learned gives you raw information.
Analysis turns that information into understanding.
But understanding alone doesn’t move a business forward.
In Part 3, we’ll focus on the two steps that actually create traction:
- setting true owner-level priorities (not vague goals or wish lists)
- organizing the work so those priorities actually get executed
This is where strategy stops being theoretical and starts shaping real decisions — whether you’re running a solo business, a tiny team, or a growing organization.
