Building a Sticky Business Culture Using Five Key Checkpoints

Most business owners recognize the importance of a strong business culture. Few know how to keep it strong once they've built it.

The culture at one of my companies earned a Best Places to Work award three years in a row, and the reason it held up was simple: the values were everywhere.

They came up in hiring, in reviews, in the weekly meeting, in who got recognized and why. Nobody had to remember to think about them, because the business kept putting them in front of people from a different angle every week. That's what made them stick.

The way we did that was using these five checkpoints:

1. Establish core values

Core values are the foundation. They should be clear, memorable, and actionable. Three to five of them. Too many and they dilute. Too few and they miss the essentials.

They need to be visible and constantly reinforced. When they're strong, they become "leader-sourced and crowd-enforced." Leadership drives them. Everyone in the company upholds them.

2. The leadership message

This is your 30,000-foot view of the culture and the vision. Where the business is heading, and how the core values get you there. It's your job to repeat it until it stays top of mind for everyone.

It can be a "What It Means to Work Here" document. A speech. A series of emails. The form matters less than the consistency.

3. Hire against the values

Every interview and onboarding session should emphasize the values. Run a dedicated culture interview if you have to. During onboarding, share the leadership message, talk about the values in behavioral terms, and build them into the expectations from day one.

4. Review against the values

Performance reviews should evaluate how well people embody the values. Self-ratings, peer feedback, manager evaluation.

Treat repeated failure to live the values as seriously as a performance issue. A quarterly core value development plan works the same way a performance improvement plan does.

5. The culture infusion cycle

This is how the values reach every level of the business. A consistent cadence that demonstrates, reminds, and reinforces.

✔Daily: make the values visible. Call out specific examples in meetings.

✔Weekly: team members nominate each other for living the values. Share the recognitions.

✔Monthly: roll the weekly recognitions into a report and share it in the monthly meeting.

✔Quarterly: vote for an MVP based on the recognitions. Reward it with something your people will actually appreciate.

✔Annually: host a core values awards event. Build a culture book from the year's recognitions and stories.

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Do this consistently and you move from stating your values to making them a tangible part of your operations.

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Set expectations. Be consistent. Keep the values top of mind. If you don't, the culture will erode. Every time.

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I walked through all five in an episode of The Business Owner's Journey, and here's a one-page version you can download and use with your team.

tBOJ: #10 of 37

Sponsor Scout and Founders Live just released their Rising Entrepreneurship Podcasts index, and The Business Owner's Journey came in at #10 of 37.

What I like about this one: it's ranked on momentum and increasing sponsorship value, not just audience size (which is vanity AF...)

It's a great measure of where the show is headed, and that's on you. Thank you for listening, sharing, and showing up.

🙏🏻🫡

The Shiny Object Filter

Most founders don't want to miss out on an opportunity, and we’re all fighting to resist shiny objects.

But how do you know which ones are actually worth your time?

Here's a filter created from 20+ years of sorting shiny objects from the real deal. So you can make a good decision in a matter of minutes.

1. Start with the strategic plan

Use your quarterly strategy and marketing plan as guardrails. If the opportunity isn't already in the plan, the default is "no" unless the plan changes.

2. Check current goals and target audience

Does this move you toward the audience and outcomes you set for this quarter? If not, you already have your answer.

3. Assess resource trade-offs

Get specific about the time, money, and energy this will actually cost you. Then name what you'll pause or drop to make room for it. If you can't name the trade-off, you don't have a green light.

4. Match the calendar and bandwidth

Look at your real-world constraints. Family, health, travel, the work only you can do. If the ask steals from any of that, it's a pass.

5. Side-eye exceptions

Leave space for rare, high-leverage opportunities. But only after the first four criteria are met.

6. Use your truthtellers

Seek out people who'll challenge your read. Your leadership team, advisors, peer groups. Either they sharpen what you're already seeing, or they catch the bias you couldn't. When your gut whispers "You can make this work," you need someone asking, "But should you?"

Run every shiny object through this filter. Most are out in the first few steps.

The few that make it to six? Those are the ones you bet on.

Steps one and two only work if your goals are clear enough to filter against. If yours aren't, start with my guide for becoming a goal-setter and a goal-getter 🎯.

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Build the business you envision,

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