Episode 32
Growing Pains: The Leadership Shift from Doing to Delegating
Scaling a business comes with big decisions, tough conversations, and the challenge of building a team that can grow with you. How do you know when it’s time to shift roles, implement structure, or step back so others can take the lead?
Maartje van Krieken sits down with Jennifer Cresswell, a growth strategist and the founder of Thoughtgro, to break down the realities of scaling in entrepreneurship. They dig into the people dynamics that make or break a growing business. When the team that got you here isn’t the team that will get you there, how do you navigate that transition with clarity and respect? Jennifer shares why removing emotion from role decisions can help leaders make choices that serve both the company and the employees.
The episode also tackles a common misconception about process. Many entrepreneurs see structure as a creativity killer, but Jennifer argues the opposite. She explains how the right processes reduce stress, create efficiency, and free up leaders to focus on innovation instead of getting caught in daily operations.
From recognizing the warning signs of stalled growth to handling difficult leadership transitions, this episode provides insights for anyone going through the next phase of their business. Jennifer leaves listeners with a key takeaway: growth isn’t just about adding more, but also about building smarter.
Episode Breakdown:
00:00 Introduction
00:33 Leadership in Uncertainty
01:06 Overlapping Challenges in Different Business Sizes
01:38 People Dynamics in Growing Businesses
03:13 Removing Emotion from Role Assessment
05:29 Process Management in Scaling
07:02 Efficiency Through Process
08:20 Leadership Transition and Delegation
13:06 Fractional Leadership and Finding the Right Fit
15:57 Symptoms of Growing Pains
18:46 Bottlenecks and Decision-Making Overload
21:14 Addressing Feedback and Disgruntledness
22:39 Closing
Links
Connect with Jennifer Cresswell:
https://www.linkedin.com/in/jennifer-cresswell-2a39892b/
Jennifer Cresswell is the Founder & Principal of Thoughtgro, helping business owners build lasting legacies through sustained growth and succession planning.
With 20+ years in leadership, operations, strategy, and communications, she strengthens businesses using her four foundational pillars—structure, team, process, and culture. A problem-solver at heart, she has quadrupled sales, integrated diverse business models, and boosted both morale and revenue. Whether preparing a company for acquisition or securing long-term stability, she helps owners achieve their vision.
Jennifer holds a Bachelor of Science in Engineering from Cornell University. Outside of work, she enjoys time with her husband and daughter, tennis, cooking, baking, crafting, and continuous learning.
Connect with Maartje van Krieken:
https://www.thechaosgamesconsulting.com/
https://www.linkedin.com/in/maartje/
https://maartjeturnschaosaround.substack.com/
