What happens when a great employee gets promoted into leadership, but no one has prepared them to lead?

In this episode of the Serving Second Podcast, Dr. Toussaint Williams sits down with Rich Ashton, author of Growing Your Own: Common Sense Advice for Developing Leaders Within a Small Business, to talk about one of the biggest leadership gaps in small businesses and organizations: developing leaders from within.

Rich shares lessons from more than 45 years in leadership and ownership of eight businesses. He explains why hiring from the outside can threaten culture, why loyal employees still need leadership training, and why some people are more effective and fulfilled as strong number twos rather than chasing the top seat.

Keywords

second-chair leadership, leadership development, small business leadership, growing leaders from within, Rich Ashton, Growing Your Own, Serving Second Podcast, leadership training, number two leader, executive leadership, internal leadership development, organizational culture, developing employees, relational leadership, leadership podcast

Key Topics Covered

How small businesses hit a leadership ceiling as they grow

Why great employees are not automatically ready to lead

The risk of bringing in outside leaders who do not understand the culture

Why leaders should develop people to be themselves, not copies of the founder

The importance of being a strong number two

How transparency helps leaders have difficult conversations

Why trust is built before the hard conversation happens

How intellectual curiosity helps second-chair leaders keep growing

Best Quotes and Takeaways

“Just because someone is a good employee and loyal to you does not mean they can take the next step.”

“If I couldn’t be the best number one, I could be the best number two.”

“The number one role can be isolating and lonely.”

“Trust is built through transparency.”

“If you are not pursuing intellectual curiosity, get on board with one.”

Why This Matters for Second-Chair Leaders

Second-chair leaders do not have to spend their whole career trying to become a copy of the person in the first chair. Rich makes it clear that leadership growth starts with self-awareness, integrity, and the willingness to develop your own leadership voice.

For some leaders, the goal is not always the top seat. Sometimes the greatest influence comes from becoming the trusted, capable, and grounded leader who helps the organization move forward from the second chair.

Guest Information

Guest: Rich Ashton
Book: Growing Your Own: Common Sense Advice for Developing Leaders Within a Small Business
Website: growingyourown.net
Email: [email protected]

Chapters

00:00 Welcome to the Serving Second Podcast
01:12 Why growing businesses need more leaders
02:54 The leadership ceiling in small businesses
04:01 How Rich’s book started as leadership blogs
08:10 Developing leaders, not copies of yourself
09:54 Learning from mentors and relationships
12:42 The power of being the best number two
15:21 Growing your own leadership team
17:35 Integrity and relational leadership
20:03 Handling difficult leadership conversations
22:39 Trust, transparency, and decision-making
26:09 Intellectual curiosity as a leadership habit
28:28 How to connect with Rich Ashton