As I was writing this, I found myself smiling, because this past Wednesday’s experience was not something I could have predicted even a few years ago.

I was on my way to Krispy Kreme, picking up donuts for the team. Not exactly a strategic planning moment… but it turned into one.

We’re setting up two new office spaces for two new team members starting next week.

My wife was in the office coordinating furniture installations.

My son Zach, without being asked, worked until midnight the night before to hit a client deadline.

My nephew Ben, fresh out of college, has been stepping up and supporting new clients like a seasoned pro.

And Nick, who was the ring bearer in my wedding 30 years ago, is still right there with me, helping drive the success of 40 Accounting.

Somewhere between the donuts and the drive, it hit me:

I’ve taken this for granted.

The loyalty.
The work ethic.
The willingness to do whatever it takes.

And honestly… the fact that they’re not just supporting the business, they’re supporting me.

I’m incredibly grateful.

This Was Never the Plan

If I’m being honest, I actually tried to avoid having a family business.

Why?

Because at some point, you have to make hard decisions to grow. And those decisions don’t care about last names.

Sometimes growth requires changing people.

That’s a lot harder when you’re sitting across from someone at Thanksgiving dinner.

And yet… over the years, I’ve found something interesting:

I love working with family businesses.

We’ve worked with:

• Husband-and-wife leadership teams

• Sibling partnerships

• Multi-generational companies with kids in different roles

• Entire family ecosystems, cousins, uncles, nephews… you name it

When they work, they really work.

When they don’t… Thanksgiving gets awkward.

A Look Back (and a Lesson Learned)

Earlier in my career, I worked at a company I really respected.

We had a key employee who clearly wasn’t meeting expectations. Everyone knew it.

The CEO said to me:

“I can’t let him go… he’s like a son to me.”

I understood the emotion.

But I also knew the business couldn’t sustain that decision.

I took a recruiting call shortly after, and left within three months.

And I made a promise to myself:

If I ever led a business like that… I’d lead differently.

What Actually Works

After working with dozens of family-run businesses, here are five things that separate the ones that succeed from the ones that struggle:

1. Communicate Like Adults (Not Like Family)

Family members know how to push each other’s buttons, sometimes better than anyone else.

That’s the problem.

The key is learning to communicate in a way the other person can actually hear, not just how you want to say it.

Simple concept. Hard execution.

2. Profits Still Matter

It sounds obvious. It’s not.

In The Goal, the premise is clear:
The purpose of a business is to generate profit.

Not comfort. Not harmony. Not avoiding difficult conversations.

Profit.

Because without it:

• There’s no cash flow

• No reinvestment

• No long-term sustainability

Family businesses sometimes blur this line, making decisions based on relationships instead of results.

That works… until it doesn’t.

And by the way, it also makes Thanksgiving more stressful, not less.

3. Be Willing to Make the Tough Calls

At some point, every leader faces this reality:

Someone can’t perform at the level they used to.

It could be:

• Health

• Life circumstances

• Or just changing capacity

We will all exit at some point. The question is when and how.

Great family businesses handle these transitions with:

• Dignity

• Respect

• And clarity

But they still make the decision.

4. Build a Culture of Accountability

This is where most family businesses struggle.

Why?

Because accountability creates uncomfortable conversations.

So instead… they avoid them.

The fix:

• Clear expectations

• Defined incentives

• Minimum performance standards

When everyone knows what “success” looks like, it removes emotion from the equation.

And replaces it with clarity.

5. Bring in Outside Perspective

This one is a game changer.

Family businesses often need someone from the outside to say what everyone inside is thinking but won’t say.

That’s where external advisors, coaches, and structured accountability come in.

For us, we use 40 Week Sprints to drive this.

Why it works:

• Consistent cadence

• Clear accountability

• No place for bad ideas to hide

Sometimes the most valuable voice in a family business… is the one that isn’t family.

Final Thought

Family businesses are one of the most powerful forces in the economy.

They’re built on trust, loyalty, and long-term thinking.

But those same strengths, if unmanaged, can become weaknesses.

If you get it right?

You build something special.

If you get it wrong?

Well… let’s just say the holidays get interesting.

Run your business like a business…
So your family can still be a family.