Executive Roundtable
The decisions that define your organization shouldn't be made in isolation. Join a curated community of senior executives and business owners in Medford and Southern Oregon who sharpen each other's thinking, challenge each other's assumptions and accelerate each other's results.
Limited to 10 members. Q1 2026 cohort now accepting applications.
Leadership Doesn't Have to Be Lonely
You've earned your seat at the top. But no one warned you about the isolation that comes with it.
Your team looks to you for answers—even when you're still finding your footing. Your board expects confidence. Your family sees the stress but can't fully understand the stakes. And the colleagues you once confided in? They either report to you now or have their own agendas that complicate candor.
The result is a kind of leadership solitary confinement: surrounded by people, but alone with the decisions that matter most.
The cost of this isolation is measurable:
- Slower decisions. Without trusted peers to pressure-test your thinking, you second-guess yourself—or worse, move forward with blind spots intact.
- Repeated mistakes. Problems you're facing for the first time? Another leader solved them last year. But without access to their experience, you pay full tuition on lessons someone else has already learned.
- Strategic drift. When you're caught in daily operations, it's difficult to hold yourself accountable to the bigger vision. The urgent consumes the important.
- Diminished resilience. Leadership is a long game. Without a community that understands the weight, burnout becomes a matter of when—not if.
Research consistently shows that executives with peer advisory support make better decisions, grow their businesses faster, and report higher satisfaction in their roles. The question isn't whether peer community has value. The question is whether you have access to the right one.
What Changes When You Have the Right Room
Imagine walking into a room where:
- Everyone understands what it means to be responsible for an organization's future
- No one is trying to sell you anything or position themselves politically
- The conversation goes deeper than surface-level advice because trust has been earned
- You can say "I don't know" without it undermining your authority
- The collective experience in the room exceeds what any consultant could offer
This is what peer community provides at its best. Not networking. Not another meeting on your calendar. A genuine thinking partnership with leaders who make you sharper.
The Executive Roundtable is designed to be that room—a premier peer advisory group for accomplished leaders in Southern Oregon who are ready to think bigger, decide more confidently, and lead with renewed clarity.
We bring together 10 senior leaders from non-competing organizations for monthly facilitated sessions in Medford. No sales pitches. No networking performances. Just honest conversation with peers navigating similar complexity—and a skilled facilitator who ensures every session delivers real value.
One decision improved. One mistake avoided. One insight you couldn't have reached alone. That's what the right room provides.
How It Works
We meet for 2.5 hours each month. Every session combines structured problem-solving with open strategic dialogue, designed so every member receives focused attention on their challenges while contributing to others' breakthroughs.
A typical session includes strategic check-ins on what's demanding your attention, deep-dive problem-solving on one or two members' pressing challenges, accountability review on commitments from previous sessions, and dedicated time to capture insights before we adjourn. You'll leave with clarity—not just conversation.
The value of any peer group depends entirely on who's in the room. That's why membership is by application only. Each prospective member goes through a structured process to assess mutual fit: leadership level, willingness to contribute as generously as you receive, openness to challenge, and commitment to confidentiality. We also screen for competitive conflicts—you won't be sitting across from a direct competitor.
This selectivity isn't exclusivity for its own sake. It's protection for your experience. Every member should raise the room.
What's shared in the Roundtable stays in the Roundtable. Every member signs a participation agreement committing to confidentiality. This isn't a formality—it's the foundation that makes honest conversation possible. You can discuss sensitive personnel decisions, financial challenges, strategic vulnerabilities, and personal struggles knowing the room is sealed. Trust isn't optional here. It's structural.
Who Belongs Here
The Executive Roundtable is designed for leaders who are accomplished enough to contribute and humble enough to learn.
You've led through complexity. You've made hard calls. You have wisdom earned the hard way—and when another member presents a challenge, you have perspective worth offering. At the same time, you know what you don't know. You're not looking for affirmation; you're looking for insight. You're willing to be challenged, to have your assumptions questioned, and to change your mind when the evidence warrants it.
This room works for business owners leading companies through growth or transition, CEOs and senior executives responsible for organizational outcomes, leaders new to the C-suite seeking trusted peer perspective, and entrepreneurs scaling beyond founder-led operations.
It's not the right fit if you're primarily looking for leads and referrals, unable to commit to monthly in-person attendance, early in your leadership journey, or resistant to honest feedback. We'd rather have the right ten members than fill seats with the wrong ones.
What Membership Includes
Monthly facilitated sessions with your peer cohort, structured for insight and action. A curated community of 10 accomplished leaders who become your confidential sounding board and accountability partners. Strategic thinking frameworks and practical tools drawn from two decades of executive coaching. Priority access to AdvantEdge Leadership programs before they open to the public. And a $500 credit toward any individual coaching program - our investment in your continued growth.
The Investment
$500 per month | $6,000 annually
Membership is an annual commitment because meaningful peer relationships don't develop in a quarter. The leaders who benefit most from this experience commit to the long game.
Consider what one better decision is worth to your organization. One avoided mistake. One strategic insight you wouldn't have reached alone. The annual investment is a fraction of what most leaders spend on consultants who disappear after the engagement ends. Here, you're building a lasting asset—a community of trusted advisors that compounds in value the longer you're part of it.
Common Questions
How is this different from other peer groups? Three things: curation (we're selective about who joins), facilitation (every session is professionally guided), and depth (we're optimizing for 10 meaningful relationships, not 100 superficial ones). This isn't networking. It's strategic peer partnership.
How are members selected? Every applicant completes a brief application and has a personal conversation with me. I'm evaluating fit in both directions—whether you'll benefit from the group and whether you'll contribute to others' growth. Not everyone is accepted.
What's the time commitment? One 2.5-hour session per month in Medford, plus brief preparation when applicable. The annual commitment is structured because trust takes time and relationships deepen significantly after the first several months.
Is there a virtual option? No. The depth of conversation we're cultivating requires physical presence. If monthly in-person attendance isn't realistic, this isn't the right fit—but individual coaching may be.
Where do you meet? At a dedicated venue in Medford. The specific address is provided upon enrollment.
What industries are represented? We intentionally curate across industries to maximize diversity of perspective. You'll sit alongside leaders from different sectors who've solved problems you're facing in completely different contexts.
When does the next cohort launch? Q1 2026. We're currently accepting applications. Space is limited to 10 members.
What happens after I apply? I'll reach out within one week to schedule a brief conversation—not a sales call, just a mutual exploration of fit. If we both agree the Roundtable is right for you, I'll share next steps for enrollment.
Ready to Lead in Community?
If you've read this far, something resonated. Maybe it's the weight of decisions made alone. Maybe it's the hunger for peers who truly understand. Maybe it's the recognition that your next level of growth requires more than you can access by yourself.
The application takes about 10 minutes. Once submitted, I'll reach out to schedule a conversation—an honest discussion about where you are in your leadership journey and whether this community is the right fit.
The right room changes everything.
Questions first? Email me directly at info@annabarnhill.com