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The CEO Check-In: A Mirror, Not a Scorecard


CEO Check-in
Photo by Michelle Silva, Overgrown Garden

By Michelle Silva | The Savvy Business Woman – Where Smart Women Grow Together


A few weeks ago, I found myself staring at my garden—neglected, overgrown, and thirsty.

Between client work, podcast recordings, and trying to remember what I last ate (was it lunch or a protein bar at my desk?), the weeds had started to creep in. Not just in the soil, but in my schedule, my energy, my business.


That garden—once a place of intention and growth—suddenly felt like a metaphor.


Because business is a lot like gardening, isn’t it?


We start with clear goals and fresh energy. We map out the seasons. We plant what we want to grow. But if we’re not checking in regularly—if we’re not tending to what matters—we risk growing a whole lot of something we didn’t actually want.


The same is true of our businesses. And more specifically—our leadership.


The CEO Role Isn’t Just a Title


Most women I work with wear the “CEO” hat in theory, but not in practice.


They’re stuck in delivery. Overwhelmed by marketing. Unsure where the next growth lever is. Their calendar is full, but their goals feel fuzzy.


They’ve built something meaningful—but haven’t had time to check if it’s still aligned. They’ve been hustling—but haven’t asked themselves if it's sustainable.They’ve been showing up—but not always as the leader they want to be.


I call this the “Busy But Drifting” stage. And every powerful, smart, heart-led businesswoman hits it at some point.


That’s why I created the CEO Check-In.


Your CEO Check-In: 10 Questions to Reclaim Your Role


Not to guilt you. Not to measure your worth.But to give you a mirror.

This is your pause. Your check-in. Your chance to course-correct or recommit.


Ask yourself:

  1. Clarity – Do I know what matters most in my business right now?

  2. Cash Flow – Do I have visibility on my income and expenses for the next 30 days?

  3. Conversion – Is my offer aligned with my people—and priced accordingly?

  4. Capacity – Am I working in my business more than on it?

  5. Connection – Am I nurturing relationships that truly matter to me and my mission?

  6. Consistency – Am I showing up in the ways I promised myself I would?

  7. Content – Am I sharing my wisdom and positioning myself as a leader?

  8. Confidence – Where am I playing small or hesitating—and why?

  9. Care – How am I taking care of myself right now?

  10. Celebration – Have I acknowledged a recent win, no matter how small?


No shame. No shoulds. Just honest reflection.


Your Invitation:


Choose just one of the ten questions and answer it for yourself this week.


Better yet—share your answer inside The Savvy Business Woman community. Let’s normalize real reflection and brave leadership in a space that’s not about hustle culture—but heart-centered growth.

You don’t need to “fix” anything right now. But you do need to see clearly. And that starts with the check-in.


Inside The Savvy Business Woman, you’ll find:

  • Meaningful conversations (not just content)—with women who lead, build, and support bold businesses

  • Supportive peer circles—whether you’re the CEO or the strategic right-hand

  • Monthly inspiration + strategy drops—including exclusive prompts, checklists, and growth tools

  • No ads, no distractions, no spam—just a calm, curated space to grow alongside other smart, generous women

  • Opportunities to share your expertise—through guest teaching, podcast features, or collaborative offerings


If you’re craving depth, clarity, and momentum without the noise of social media—this space was made for you.


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I work with small and midsize businesses, nonprofits, and entrepreneurs committed to equity and impact. I support LGBTQIA+ rights, social and environmental justice, civil rights, and mental health advocacy. I believe in dismantling systems of oppression—patriarchy, white supremacy, and diet culture—and stand with Black Lives Matter and communities of color. As a Compassionate Warrior, I create inclusive spaces grounded in Diversity, Equity, Inclusion, Wellness, and Belonging (DEIWB).

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