Bridging Data & Leadership: Advice for Midmarket CEOs

In this Expert Insights Series interview, Jon Thompson hosted Karen Posey, Founder of KP Strategies, whom he affectionately introduces as “CEO Whisperer”.

Karen's key advice to CEOs? "Focus on what only you can do.”

Founded in 2016, KP Strategies is a Denver-based CEO consultancy where Karen works hand-in-hand with CEOs to navigate challenges, leverage opportunities, and sculpt success stories. In short, she helps CEOs focus on the things that only they can do. KP Strategies offers a 6-month CEO Accelerator cohort, a program that gives CEOs the best practices and tools they need to execute their strategic plans.

Prior to KP Strategies, Karen held leadership roles in sales, management consulting, and IT companies as well as a $10B healthcare payer and a MedTech startup. Each role provided her with experience in strategic planning, organizational alignment, and customer experience, paving the way for the founding of her own company.

She is the current Forum Chair for Women’s Business Enterprise Council West and an Executive in Residence at both Rev1 Ventures and The Entrepreneurs Center.

Listen to/watch the full episode, or jump to a section below for key takeaways from the interview:

Loneliness and Other Challenges of the Midmarket CEO
The Role of Data in Strategic Planning
How to Use Strategic Planning for Bold Execution

Loneliness and Other Challenges of the Midmarket CEO

“Being a CEO is a lonely job. It's a very lonely job.” - Karen Posey

Leadership is a path laden with challenges, and Karen referenced a recent statistic that over 61% of CEOs are lonely, and their job performance struggles because of it. For that reason, she recommends leaders seek out a group of peers they can go to for support and perspective, which is why she structures her 6-month CEO Accelerator program into cohorts.

While traditional cohorts might involve lengthy on-site meetings and guest speakers, Karen finds that modern CEOs prefer a more streamlined approach – virtual platforms that allow them to engage, learn, and collaborate without the time demands of physical meetings.

Beyond providing a peer group and brain trust, KP Strategies' cohorts help CEOs navigating the following challenges:

Mediocre Company Growth

According to Karen, “Over 65% of CEOs don't have the confidence [or the insight] they need to make bold moves,” and it’s hurting their ability to grow their companies.

Rapid Company Growth

On the opposite end of the spectrum, when companies grow rapidly, Karen often sees operations – billing, cash flow, and IT infrastructure – struggling to keep up.

Lack of Organizational Alignment

Karen calls organizational misalignment the “silent killer” of organizations because culture inevitably suffers, and talent starts to leave when leadership is out sync. She describes misalignment as feeling as if “everybody’s rowing in a different direction.”

Prioritization

Karen cautions CEOs from using their time and energy for tasks that other people can do. A CEO must protect their time to lead well, so surrounding themselves with a high-performance leadership team is critical to their success.

The Role of Data in Strategic Planning

“I've got a company right now. They are $60M and running on Excel spreadsheets... it’s a classic example of operations not keeping up with growth.” - Karen Posey

Too often, leaders don’t have access to the data they need to successfully run the business, satisfy the board, and align the leadership team. Having experienced this himself, Jon highlights the dilemma leaders face: "If they're stretched thin, the last thing [leaders] want to do is aggregate numbers and build reports for the board... ‘Do you want me to produce, or do you want me to give you reports?’"

Similarly, Karen often sees her CEOs struggle with a lack of data transparency. They're often using a manual, time-consuming process to get the data insights they need to feed their decision-making, strategic planning, and budgets. To address this common frustration, Karen advocates for consolidating all company data sources into a data lake to facilitate automated companywide reporting and dashboards, so that leaders have the data visibility they need to confidently oversee and lead the business.

Focus on Strategic Planning for Bold Execution

“92% of executives struggle overall with execution. That's a big stat. And I think there's a couple of reasons for that. But overall, where I help them first and foremost is looking at: Where are they going? What's their vision clarity? Let's reframe what winning really means for their organization... In today's world, you've got to be bold.” - Karen Posey

Using the example of Reed Hastings of Netflix, Karen highlights the importance of looking 20 years out into the future and being bold when setting a company vision but more analytical and methodical in near-term strategic plans.

As Karen puts it, “If you really want to get out there and drive sustainable, predictable growth, you need insight from your customers, your employees, your key stakeholders, and some market intelligence. That's what gives CEOs the confidence to make the bold moves.”

To that end, 3-year strategic plans must be closely aligned to overall financials and built on these foundational insights to ensure bold decisions aren't based solely on intuition. In the same way, yearly operations plans should be closely aligned to budgets, so that the entire leadership team has a shared understanding of the key opportunities for growth and alignment on budget allocation.

Connect with Karen Posey

If you’d like to connect directly with Karen to learn more about KP Strategies and their 6-month CEO Accelerator, connect with her on LinkedIn, send her an email at kposey@kpstrategies.net, or visit her website here.

About Blue Margin

Blue Margin partners with midmarket companies to provide a fractional team of data and analytics experts. Through our subscription Managed Data Service, we build and manage data platforms, advise on data strategy and initiatives, and build Power BI reports that evolve as your company grows.

Learn more about our approach and philosophy through our book and podcast, "The Dashboard Effect". Download your copy here and subscribe to our podcast for weekly insights.