Episode 37
Scaling Checkup: Is Your Leadership Fit for the Future?
Most CEOs don’t plan their own exit. What happens when the person who built the company isn’t the right one to scale it?
Scott Calderwood joins Maartje van Krieken to talk about CEO transition strategies, scaling leadership challenges, and executive hiring mistakes. When a company reaches a breaking point—whether at Series C funding, IPO, or another growth stage—how do leaders know if they’re still the right fit? And more importantly, what happens when they aren’t?
Scott shares hard-earned insights from decades in executive search, and reveals why cultural fit matters as much as technical skill in leadership hires. He introduces the “bad hire calculator,” a tool that puts real numbers behind the cost of hiring the wrong person. With firsthand stories of leadership transitions gone right (and wrong), this episode is a must-listen for leaders going through the realities of executive growth and change.
Episode Breakdown:
00:00 Leadership Challenges in Modern Business
01:24 CEO Replacement Dynamics
03:45 Recognizing the Need for Leadership Change
05:10 Cultural Fit in Leadership Roles
09:46 Challenges in Leadership Transition
12:44 The Cost of a Bad Hire
16:10 Interim Solutions for Leadership Gaps
18:10 Trust and Cultural Fit in Teams
20:29 Entrepreneurial Spirit in Small to Mid-Sized Companies
Links
Connect with Scott Calderwood:
Website: https://calderwoodsearch.com/
E-mail: scott@calderwoodsearch.com
Scott Calderwood, President and CEO of Calderwood Search Partners Inc., is a seasoned executive recruiter and sales expert with 30 years of experience in corporate and entrepreneurial roles. He specializes in mid-to-senior-level placements in technical sales and marketing, managing executive, director, and managerial searches.
Known for his professionalism and client-focused approach, Scott builds long-term relationships by delivering tailored solutions and exceptional service. Under his leadership, Calderwood Search Partners has become a trusted talent partner across the U.S. and Canada, aligning top talent with company culture and business needs.
Connect with Maartje van Krieken:
https://www.thechaosgamesconsulting.com/
https://www.linkedin.com/in/maartje/
https://maartjeturnschaosaround.substack.com/
