Episode 141

full
Published on:

28th Aug 2025

126. Think Like A CEO - Your Business Keeps Breaking Because It's Ready to Grow with Ashley Connell

Ever wonder why some CEOs seem to have the magical ability to grow their businesses while maintaining sanity and work-life balance? The secret isn't superhuman productivity. It's finding the right operations partner.

Ashley Connell, founder and CEO of Prowess Project, reveals the transformative power of the CEO-operations partner relationship in this eye-opening conversation. Drawing from her experience as a "matchmaker" for visionaries and integrators, Ashley unpacks why most business owners hit painful growth ceilings and how the right second-in-command can change everything.

"Most services businesses hire an operator too late," Ashley explains, painting a picture many entrepreneurs will recognize: the visionary CEO drowning in spreadsheets, systems, and operations that drain their energy and creativity. This mismatch of talents creates the perfect storm where businesses stall despite having plenty of demand.

Discover the predictable revenue benchmarks where businesses typically "break" ($250K, $500K, $750K, and $1M) and what each threshold requires from you as a leader. Ashley's insights into the psychology of delegation reveal why many CEOs struggle to let go and how to overcome that hurdle by defining what "safety" means to you personally.

The conversation takes a refreshing turn when Ashley gives listeners permission to be content with their current business size rather than constantly chasing growth. "Being able to give yourself permission, especially in different stages and seasons, I think is really powerful and, quite frankly, responsible," she notes, challenging the perpetual growth mindset that dominates entrepreneurial culture.

Whether you're struggling with burnout from doing everything yourself or preparing for your next growth phase, this episode offers actionable wisdom on finding, trusting, and collaborating with the operations partner who'll help you build the business you've always envisioned. As Ashley puts it, this partnership creates "space, freedom, and relief that things are getting done while you focus on your zone of genius."

Ready to stop being the bottleneck in your own business? Visit prowessproject.com to download Ashley's guide to the top 15 responsibilities you can delegate to your operations partner. 

In this podcast you will learn how:

• Prowess Project acts as a matchmaking service connecting CEOs with compatible operations partners

• The visionary (CEO) and integrator (operations partner) form a crucial yin-yang leadership dynamic

• Most businesses break at predictable revenue benchmarks: $250K, $500K, $750K, and $1M

• CEOs must identify what "safety" means to them personally before they can truly delegate

• Effective delegation requires clear communication, gradual transition, and compatible working styles

• Finding your ideal operations partner allows you to focus on your zone of genius instead of struggling with systems

• Growth requires rebuilding systems and processes as your business scales

Highlights:

0:00

Introduction to Think Like a CEO

1:36

Ashley Connell and Prowess Project

5:27

Journey to CEO Mindset

9:50

Visionary vs. Integrator Roles

15:40

Safe Delegation and Common CEO Mistakes

21:29

Revenue Benchmarks Where Businesses Break

26:58

Permission to Run Your Business Right

28:33

Final Thoughts and Resources

Interested in 1:1 Coaching?

Kristin partners with high-performing financial advisors, leaders, and business owners who are ready to lead with more clarity, focus, and intention.

Clients often come to her with a strong vision, but they aren’t sure how to close the gap between where they are now and where they want to go. Many are navigating a season of growth, stepping into expanded leadership, or realizing they’ve outgrown their current systems and ways of working.

They know they’re capable of more and want a strategic thought partner to help them get there, someone who will ask the tough questions, create space to think deeply, and offer a proven process for turning ambition into meaningful progress.

If this sounds like the kind of partnership you’ve been craving, email meet@kristinburke.com to learn more and connect.

Connect with Kristin

LinkedIn

Instagram

Website

Goal Setting Success Course

Breakout Plan

Connect with Ashley

Website

LinkedIn

Top 15 Big Responsibilities

Next Episode All Episodes Previous Episode

Listen for free

Show artwork for Elite Achievement

About the Podcast

Elite Achievement
A leadership and execution podcast for financial advisors and firm leaders
Elite Achievement with Kristin Burke

You’re a financial advisor. Your calendar is booked with back-to-back client meetings. You have a vision to grow your firm. You’re not sure if you have the right team in place. You’re holding on to work you know you should be delegating. You want to spend more time doing complex planning and working with your best clients, but you’re still trying to deliver for every client in your book.

At the end of the day, you’re still the one driving the revenue.

Or…

You’re leading a team of financial advisors or a firm. You’re responsible for growth, but don’t produce the results yourself. They come through the people you recruit, develop, and retain. And many of them aren’t traditional employees, which means you’re leading as much through influence as you are through expectations and accountability.

Your calendar is full, but your time doesn’t always feel well spent. You start the day with a plan, and it quickly shifts as people come to you with questions, challenges, and decisions that need your input.

You’re constantly balancing competing priorities. Attracting and bringing in new talent. Launching and developing new financial advisors. Supporting career advisors as they continue to grow. Having difficult conversations when someone isn’t performing. Protecting the culture and keeping everyone aligned to the vision.

At the end of the day, you’re still accountable for the results.

Different roles. Same challenges.

How do you create clarity around your vision and get others aligned to it?

How do you focus on the right priorities when everything feels important?

How do you develop people and hold a high standard of performance?

How do you lead effectively while still driving results?

This is the work of Elite Achievement.

A leadership and execution podcast for financial advisors and firm leaders who are building and scaling a firm and being challenged to lead at a higher level as success becomes less about your individual effort and more about how you lead.

Kristin Burke brings over 20 years of industry experience and works closely with financial advisors and firm leaders as they build firms, develop people, and navigate the challenges that come with growth.

Elite Achievement is about setting a bold vision, executing consistently, and becoming the kind of leader capable of building a legacy.