In this Expert Insights Series interview, Jon Thompson sits down with Karen Posey, Founder of KP Strategies—whom he affectionately introduces as a “CEO Whisperer.”
Karen’s core advice to CEOs is simple, but difficult to execute: “Focus on what only you can do.”
Founded in 2016, KP Strategies is a Denver-based CEO consultancy where Karen works closely with founders and executives to navigate complexity, align leadership teams, and drive meaningful growth. Central to her work is the belief that CEOs must protect their time and attention for the decisions only they are equipped to make.
KP Strategies offers a six-month CEO Accelerator cohort that equips leaders with proven frameworks, peer support, and practical tools to turn strategy into execution.
Prior to founding KP Strategies, Karen held leadership roles across sales, management consulting, IT services, a $10B healthcare payer, and a MedTech startup. These experiences shaped her expertise in strategic planning, organizational alignment, and customer experience.
She currently serves as Forum Chair for the Women’s Business Enterprise Council West and as an Executive in Residence at both Rev1 Ventures and The Entrepreneurs Center.
Listen to or watch the full episode below, or jump to a section for key takeaways:
- Loneliness and the Challenges of the Midmarket CEO
- The Role of Data in Strategic Planning
- Using Strategic Planning for Bold Execution
Loneliness and the Challenges of the Midmarket CEO
“Being a CEO is a lonely job. It’s a very lonely job.” – Karen Posey
Karen points to research showing that more than 60% of CEOs experience loneliness—and that it directly impacts performance. For that reason, she strongly encourages leaders to build a trusted peer network where they can share challenges openly and gain perspective.
This philosophy is why KP Strategies structures its Accelerator program as a cohort. Rather than traditional, time-intensive offsites, Karen finds modern CEOs prefer streamlined, virtual environments that allow them to learn and collaborate without pulling them away from the business.
Beyond peer support, Karen regularly helps CEOs address four recurring challenges:
Mediocre Company Growth
According to Karen, “Over 65% of CEOs don’t have the confidence or clarity to make bold moves,” which often results in stalled growth and incremental decision-making.
Rapid Company Growth
On the other end of the spectrum, rapid growth can overwhelm internal operations. Karen frequently sees billing, cash flow, and IT infrastructure lag behind, creating risk just as opportunity accelerates.
Lack of Organizational Alignment
Karen refers to misalignment as the “silent killer” of organizations. When leadership teams aren’t aligned, culture erodes and talent disengages. As she puts it, it feels like “everyone is rowing in a different direction.”
Poor Prioritization
CEOs often spend too much time on tasks others could handle. Karen emphasizes that protecting a CEO’s time—and surrounding them with a high-performing leadership team—is essential for sustainable success.
The Role of Data in Strategic Planning
“I’ve got a company right now—$60 million in revenue—still running on Excel spreadsheets. It’s a classic example of operations not keeping up with growth.” – Karen Posey
Too often, CEOs lack timely, trustworthy data to run the business, align leadership, and satisfy board expectations. Jon echoes this reality, highlighting the tension leaders face: “Do you want me producing, or do you want me building reports?”
Karen regularly sees executives relying on manual, time-consuming reporting processes that delay insight and weaken decision-making. Her recommendation is clear: consolidate data sources into a centralized data platform that supports automated reporting and real-time dashboards.
With consistent, company-wide data visibility, leaders gain the clarity they need to plan confidently, allocate resources effectively, and focus on strategy rather than spreadsheet management.
Strategic Planning for Bold Execution
“Ninety-two percent of executives struggle with execution. Where I start is helping them clarify where they’re going—and what winning actually means. In today’s world, you have to be bold.” – Karen Posey
Karen points to leaders like Reed Hastings as examples of bold, long-term vision paired with disciplined short-term execution. The most effective CEOs think decades ahead, while remaining analytical and methodical in near-term planning.
“If you want sustainable, predictable growth, you need insight—from customers, employees, key stakeholders, and the market. That’s what gives CEOs confidence to make bold moves.”
Three-year strategic plans, Karen argues, must be grounded in data and aligned with financial realities—not intuition alone. Annual operating plans should tie directly to budgets, ensuring leadership teams share a clear understanding of priorities, trade-offs, and growth opportunities.
Connect with Karen Posey
To learn more about KP Strategies or the six-month CEO Accelerator, connect with Karen on LinkedIn, email her at kposey@kpstrategies.net, or visit kpstrategies.net.
About Blue Margin
Blue Margin partners with midmarket companies as a fractional data and analytics team. Through our subscription Managed Data Service, we build and manage modern data platforms, advise on data strategy, and deliver Power BI reporting that evolves as your business grows.
Learn more about our philosophy through our book and podcast, The Dashboard Effect. Download your copy and subscribe to the podcast for weekly insights.
