Six questions leaders should ask themselves 

NASHVILLE, TN – Leaders who want to level up need to ask themselves these six questions. 

Ryan Leak, CEO of a leadership firm and bestselling author of Chasing Failure, Leveling Up, and How to Work with Complicated People, told SEPC Southern Innovations attendees September 10, 2026 that leaders can always improve. 

He has dedicated his life to this for himself, and he trains more than 30,000 leaders how to become more effective leaders. 

Leak said these six questions, when answered honestly, can make leaders the kind who take their organizations to unknown success and have followers who find it hard to leave them. 

1. What’s it like to be on the other side of me? 

2. How can I be intentional? 

3. What’s my part to play? 

4. Who can I pave the way for? 

5. Am I enjoying it? 

6. What would I do if I knew I couldn’t fail? 

He said many leaders either lead the way they were taught or lead the way they want to be led. But the most effective leader leads everyone the way they need to be led. 

Doing that means moving slowly enough to get to know them and really find out what they need. 

Leak said with so many things, especially in the produce industry, out of our control, the most important things to control is our own attitudes and enjoyment. 

“Enjoyment is a choice,” he said. “Gratitude determines enjoyment.” 

Regarding failure, it’s important to assess what the parameters are, and be willing to take risks and even fail.  

“Start something and keep improving it,” Leak said. “If you can’t beat the fear, do it scared.”