The Power of the Quarterly Check-In: How’s Your Business Really Doing?

As small business owners and professionals, we’re always sprinting—chasing leads, closing deals, managing client relationships, and putting out daily fires. I get it; it’s the nature of entrepreneurship. But amidst the hustle, how often do we hit pause and ask ourselves, “How’s my business actually doing?”

This is where the power of a quarterly check-in comes in. It’s not just a meeting or a self-assessment; it’s a habit that can transform how you lead and grow your business.

Why Every Business Needs a Quarterly Check-In

A quarterly check-in gives you the chance to zoom out and view the bigger picture. It’s easy to get lost in the weeds when you’re running your business day-to-day. However, by stepping back every 90 days, you gain valuable perspective on what’s working, what’s not, and where adjustments are needed.

Several of our clients and Network In Action (NIA) members here in Denver use frameworks like EOS (Entrepreneurial Operating System) or “The 12 Week Year” to structure their quarterly planning. Both are fantastic tools that emphasize the power of breaking the year into bite-sized, 12-week chunks, creating a cadence of accountability and momentum. I’ve seen firsthand how this approach helps business owners stay laser-focused and results-driven.

What Should You Be Asking During a Quarterly Check-In?

Here are a few questions I recommend every business owner sit with each quarter:

• Are we hitting the goals we set three months ago?

• What’s been our biggest win this quarter? What contributed to it?

• What challenges slowed us down or caught us off guard?

• How is my team performing? Are they motivated and aligned?

• How am I, as the leader, feeling about the business? Burned out or energized?

It’s also a good time to look at key metrics like revenue growth, customer acquisition, client retention, and referral activity. (I always stress the importance of tracking referrals—your network is often your most underleveraged asset.)

The Emotional Check-In

And don’t forget, this isn’t just about numbers. The quarterly check-in is a chance to check on yourself as well. How’s your work-life balance? Are you showing up as the leader you want to be? Are you still passionate about the mission you set out to accomplish? These questions matter just as much as your bottom line.

Make It a Non-Negotiable Appointment

I often recommend putting the quarterly check-in on your calendar like you would a client meeting. Better yet, get someone to hold you accountable—whether that’s a coach, a peer in your network, or a fellow business owner.

For example, in the Denver NIA groups I facilitate, many of our members find value in pairing up with an accountability partner. They’ll do quarterly reviews together and exchange honest feedback. Not only does this strengthen professional relationships, but it also creates a space for fresh ideas and new perspectives.

Moving Forward with Intention

As a Certified Value Builder and Exit Planning Advisor, I can tell you that businesses don’t stumble into long-term success—they plan for it, quarter by quarter.

Whether you’re running your own version of EOS, implementing “The 12 Week Year,” or just taking a simple, thoughtful approach to your quarterly review, the goal is the same: run your business with clarity and intention.

So, how about it? When’s your next quarterly check-in scheduled?