Scaling Checkup: Is Your Leadership Fit for the Future?
04/02/25 • 25 min
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: [email protected]
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/
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: [email protected]
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/
Previous Episode
The Hidden Growth Killer: A Stagnant Team
When your leadership team can’t evolve with your business, scaling challenges become even harder to navigate. How do you know when it’s time to make tough decisions about key positions in your organization?
In this episode, Maartje van Krieken talks about the uncomfortable reality that the leaders who helped you get to where you are may not be the ones who can take you further. As businesses grow, the need for leadership change becomes more evident. So, how do you spot the signs like decision bottlenecks or a shift from proactive to reactive thinking before they derail your progress?
Maartje shares insights on how to approach leadership transitions strategically, with a focus on redefining roles before filling them and knowing when to seek external help. She challenges leaders to take emotion out of tough decisions and be proactive about putting the right leadership in place to drive long-term success.
Episode Breakdown:
00:00 The Challenge: Evolving Teams for Growth
02:10 Leadership Gaps: A Universal Problem
04:52 Recognizing the Signs of Leadership Issues
08:29 Taking Action: How to Navigate Change
09:56 Business First: Making Hard Decisions
12:14 Moving Fast but Smart
14:26 Delegation and Interim Solutions
18:00 The Value of External Perspective
22:02 The Importance of Clear Expectations
24:46 Act Quickly and Strategically
26:02 Invitation to Strategize and Seek Help
Links
Connect with Maartje van Krieken:
https://www.thechaosgamesconsulting.com/
https://www.linkedin.com/in/maartje/
Next Episode
The Danger of Drifting: Why Businesses Fail in Volatile Times
Waiting out the chaos might feel safe, but in business, standing still during a storm is often the fastest way to lose your course entirely.
When a crisis hits, why do so many leaders freeze? What makes waiting feel safer than steering, even when we know the storm won’t pass anytime soon?
In this episode, Maartje van Krieken digs into what happens when leadership inertia during uncertainty takes hold and how it quietly erodes momentum, clarity, and confidence. Drawing from her experience as a skipper, she shows how business leaders often hope for conditions to improve on their own. But storms don’t wait, and neither should you.
You’ll hear a grounded, relatable take on business decision-making in crisis, with ideas for taking action even when the path ahead isn’t clear. From building a culture of timely decisions to creating space for real cross-functional collaboration, Maartje offers a toolkit for navigating business volatility without drifting off course.
If your team feels stuck or overloaded, this episode will help you reset your approach and remind you that steering through uncertainty starts with the courage to move.
Episode Breakdown:
00:00 Why Inaction in Crisis Puts Your Business at Risk
03:01 Leadership Inertia During Uncertainty
05:09 The Hidden Costs of Waiting
09:18 Business Decision-Making in Crisis
11:50 Navigating Business Volatility with Situational Awareness
20:27 When to Call in Outside Support
Links
Connect with Maartje van Krieken:
https://www.thechaosgamesconsulting.com/
https://www.linkedin.com/in/maartje/
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