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David Mills
By David Mills on November 13, 2025

Family Business: How to tell if you are in a Going Deeper Moment

If you want to go bigger, you always have to go deeper. That means recognizing the "going bigger" moments in your business when it's time to pay attention to more than tactics and the latest urgent task.

 

There are moments in a business when the right step is to be intentional about going deeper to work on something that might feel a little bit less tangible.

Here are some ways to tell if you are at a going deeper moment:

  • You've noticed that your team (or your family) isn't getting along in front of the kids (i.e. customers, employees, or vendors)
  • You're getting ready to make a big investment to scale or expand, or increase your digital presence
  • You're tired of fighting to find and keep employees and know that to win, you're going to have to find a path to employee retention
  • You're thinking about passing on your business to your children, or handing it off to managers

The key thing to do when you're at a going deeper moment is to ask yourself what kind of foundation will be needed to support the direction you want your business to go. Whenever you work to go farther or bigger, you've got to a more substantial right foundation in place. You've got to go deeper.

Going further or bigger may include financing, equipment, real estate, and technology, but it also has to include a deeper look at shared values, what makes your team more effective, how you stand out against competitors, and a bigger purpose that keeps good team members on board.

Those things might not feel as tangible as a written contract or a new website, but they will have a long-term impact on how far you actually can travel forward as a business.

The actual win might not just be in making a big business move, but in:

  • Tending to the humans who will take you down the road and connecting around values and purpose to help them engage more deeply
  • Understanding how well your team is actually working together, and learning about their unique profile as a group
  • Courageously asking, how well your business is standing out against the competition, and making adjustments to messaging and sales before you start marketing
  • Getting everyone on the same page around shared and deeply held values to help you retain employees and customers

It's pretty easy to run down the checklist of the things you'll need for your next big step. But if you're at one of those going deeper moments, it's the foundation that you build that counts. 

 

Published by David Mills November 13, 2025
David Mills