Chris KobyleckiTwo woodcutters walk into a forest...
There's an old parable about two woodcutters competing in the forest.
The first works relentlessly. No breaks. All effort. From sunrise to sunset, the sound of his axe never stops.
The second disappears for an hour every day. Yet somehow, he always cuts more trees.
Finally, the first woodcutter asks: "I don't understand. You disappear for an hour each day, and still you cut more trees than me. How?"
The second woodcutter smiles: "It's simple. Every day I take a break to sharpen my axe."
Most co-founders are the first woodcutter. Constantly chopping. Never sharpening.
The result? Diverging visions. Unspoken tensions. Strategic drift that looks like execution problems.
How we sharpen our axe?
Once a year, Grzegorz and I sit down to make sure we're still heading in the same direction.
Not a planning session. Not a retreat. A focused conversation about alignment. We break it into two sessions each for 2 hours.
Four hours total. Six areas. Twenty Five questions.
This isn't soft skills work. This is preventive maintenance for the engine that runs your business.
Below is the complete framework we use. Questions inspired by Lockett Coaching
The Framework: Six Areas of Co-Founder Alignment
1. Vision
Our north star. Where are we going and where we want to be?
- What's the best case scenario for our business in 5 years?
- What's ideal scenario for you personally in 5 years?
- What must be true in 1 year for our business to thrive?
- What must be true in 1 year for you to be as engaged as possible in this work? (Giving your 100%)
- What's your dream for our partnership? (Best case scenario)
- What's your nightmare? (Worst case scenario)
2. Values
Who you need to be to get where you're going. How do we need to behave.
- When were we operating at our best this year? How were we showing up?
- When were we at our worst this year? How were we showing up?
- Who do we have to be to achieve our vision?
- How do we want to commit to being with one another?
3. Roles & Responsibilities
Are you each in the right seat? Are you using your strengths?
- To what extent are we operating in our strengths?
- Which parts of our roles give us energy?
- Which parts of our roles deplete our energy?
- Are we each in the seat that's best for the company now? To what extent do we need to evolve our roles?
- What support do we need to evolve into what the business needs next?
- What talent and systems gaps do we have? How might we fill them?
4. Collaboration
What's working? What's not? What are you avoiding saying?
- What's working well about our partnership?
- What have we not talked about and should have this year? (What's an inconvenient truth? )
- How are we making decisions together? How are we working through disagreements?
- What's a story we're holding onto about one another? ("I have a story that...")
- If we were one another's most valuable coach, how would we be operating differently than we are today?
5. Commitments
What you're committing to. How you'll know if you're on track.
- What does success look like for us this next year?
- How will we know when we've achieved it?
- What changes do we want to make to how we work together?
- What systems, structures, meetings, etc. might we put in place to support these changes?
- What will we each commit to?
6. Gratitude
Don't skip this one!
- What are you grateful for?
Why this works
Conversation beats documents. You're not creating a 20-page alignment deck. You're having the conversation you've been avoiding.
Once a year is enough. More frequent and it becomes performative. Less frequent and drift accumulates.
The questions force honesty. "What have we not talked about and should have this year?" surfaces tensions before they become crises.
It's preventive, not reactive. You sharpen the axe before it gets dull. You align before you diverge.
How to run your own Annual Alignment
Timing: End of year or early Q1. Block two blocks of two uninterrupted hours.
Setting: Somewhere neutral. Not your office. Definitely not Slack!
Ground rules:
- Both founders come prepared to be honest
- No phones, no laptops (except for physical notes)
- What's said stays between you
Process:
- Each person answers each question independently (15 minutes)
- Share answers one section at a time (60 minutes)
- Identify misalignments and commit to addressing them (30 minutes)
- Document commitments & decisions (15 minutes)
Follow-up: Review your commitments quarterly. Not to judge, but to course-correct.
The question that matters most
Of all sixteen questions, this one cuts deepest:
"What must be true in 1 year for you to be as engaged as possible in this work?"
If you and your co-founder answer this differently, you have a problem.
If you can't answer it honestly, you have a bigger problem.
If you've never asked it, start here.
Your turn
When was the last time you sharpened your axe with your co-founder?
If the answer is "never" or "I can't remember," this is your signal.
Block four hours. Print these questions. Have the conversation.
Your team can't be aligned if you and your co-founder aren't.
Framework inspired by Lockett Coaching. Tested in the field at Leave a Mark.
Getting this wrong is expensive - misaligned cofounders waste months in coordination overhead, frustration, and missed opportunities.
Chris Kobylecki
Cofounder of Leave a Mark
Chris builds magical experiences that help people to excel.
He focuses on strategy and team development. Applying his decade long experience of Venture Capital & Private Equity Firms