5 Conversations Siblings in Business Must Have - Before Time, Tension, or Transition Forces Them
When you go into business with your siblings, you assume it’ll just work.
After all — you’ve got trust, history, and maybe a similar work ethic.
But something most family businesses don’t plan for is divergence:
Different stages of life. Different values. Different dreams.
I know this first hand.
I’m one of three brothers in a commercial property business we’ve owned for years. It’s a great business. It provides us with secondary income. It’s solid. But recently, I’ve noticed something shift.
I’m still driven to grow.
My older brother is thinking about retiring and stepping back.
My younger brother has a young family and other priorities.
We’re at three very different stages — and unless we talk about that, we risk misalignment that can quietly unravel something we’ve spent years building.
So here are 5 conversations I believe every sibling-run business should have — before time, tension, or transition forces your hand.
1. What does this business mean to each of us — now?
When we started, it was about opportunity. Now? For one of us, it’s income. For another, legacy. For the third, maybe it’s just admin.
If we don’t ask this question honestly, we make assumptions — and that’s where tension begins.
Ask each other:
“What role does this business play in your life right now — and what do you want it to look like over the next 5 years?”
2. What does “enough” look like for each of us?
Financial goals change. One brother might want to grow the portfolio. Another just wants stable dividends. A third might be wondering if it’s time to cash out.
This conversation matters more than spreadsheets — it speaks to values, risk appetite, and life stage.
Ask:
“Do you want more growth, more freedom, or more simplicity — and what does that mean for our future decisions?”
3. Are we willing to evolve our roles — without resentment?
As we age, our time, energy, and capacity shift. But often, our expectations of each other don’t.
Resentment builds when one person pulls harder while another quietly steps back.
Ask:
“What do we each want to be responsible for moving forward — and what needs to shift so we stay in sync?”
4. How will we handle succession, exit, or scale?
Most sibling-run businesses avoid this one. Until someone gets sick. Or moves. Or burns out.
Whether someone wants to sell, hand off to the next generation, or do something totally different — it’s better to talk now than under pressure later.
Ask:
“If one of us wanted to step away or cash out — how would we handle it, financially and relationally?”
5. What’s the legacy we want to leave — together or individually?
We started this journey together. But that doesn’t mean we’ll finish it the same way.
And that’s okay — if we can talk about it with respect, clarity, and alignment.
Ask:
“What do we want to look back on in 10 years — and be proud of?”
Final Thoughts
Being in business with your siblings is a rare privilege. But it requires intention. These aren’t easy conversations — but they are necessary.
Because blood might make you family —
But conversation builds the future.
Ready to realign your family business?
Explore The Alignment Code Scorecard — our tool for understanding alignment to help in realigning family, relationship, and business goals.
About the Author:
Mike O. is one of three brothers in business, a coach and strategist for couples and families in business, and co-creator of The Alignment Code. He helps real people navigate real conversations — to build better businesses and even better relationships.
