The conversation business owners often avoid
May 26, 2026 •

Sometimes, the hardest part of planning an exit from your business isn’t the valuation, or even finding a buyer.
Sometimes, it’s just sitting down with your family and talking about what comes next.
I work with a lot of family-owned businesses. Husband and wife built the company together, and maybe a couple of the kids are in the business, maybe a couple aren’t.
What can happen is, everybody has assumptions, but nobody has had the actual conversation.
The spouse assumes the business is worth a certain number. The kid who’s been running crews assumes they’re taking over. The one who went off into another career assumes they’re getting bought out fairly.
And the owner? The owner assumes that when the time comes, everyone will just figure it out.
I get it. You don’t want to jinx it by talking about it too early, or you don’t want to create conflict in the family when everything is running fine right now.
Or maybe you just don’t know where to start.
So, when I sit down with a business owner and their family, we’re really talking about three things:
1) The business itself
2) The money within it, and
3) The purpose behind it
Because after three to six months of golf and vacations, you and your spouse are probably going to need a new routine.
That’s why I always tell business owners that you don’t have to have all the answers today. But you do have to start the conversation.
Even if the exit is five years away. Even if you’re not sure what the business is worth yet. Even if you think everything will just work itself out.
In my experience I’ve found that families who start having these conversations before they become urgent, tend to be happier.
That’s what a coordinated plan looks like. Not one advisor in a silo giving you advice, but all of your advisors rowing in the same direction, with your family at the center of it.
The satisfaction of seeing that come together is why I do this work.
If you haven’t had that conversation yet, now might be the right time to start.
Let me know if we can help by replying to this email.
— Michael
Book a JobWalk with me and we can start the conversation.
Interested in other Rungs? Check out:
- The full Ladder here or the audio edition here

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HFM Investment Advisors, LLC is a registered investment adviser. All statements and opinions expressed are based upon information considered reliable although it should not be relied upon as such. Any statements or opinions are subject to change without notice. Information presented is for educational purposes only and does not intend to make an offer or solicitation for the sale or purchase of any specific securities, investments, or investment strategies. All investments involve risk and are not guaranteed. Information expressed does not take into account your specific situation or objectives and is not intended as a recommendation appropriate for any individual. Listeners are encouraged to seek advice from a qualified tax, legal, or investment advisor to determine whether any information presented may be suitable for their specific situation. Past performance is not indicative of future performance.




