Should I Take on a Leadership Role Again? (I Failed Last Time)

EntreLeadership

Ramsey Network

Business, Management, Entrepreneurship

4.7 • 4.4K Ratings

🗓️ 4 February 2026

⏱️ 50 minutes

🔗️ Recording | iTunes | RSS

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Summary

Today, we’ll hear about: · A leader questioning if he should take a promotion · A son weighing if he should leave his successful business to help save his father’s failing company · Dave’s advice on how to deliver difficult feedback to a team · A business owner considering leaving his business in the hands of his team so he can move to another country Next Steps: · 📞 Have a question for the show? Call 844-944-1070 or send us a message: https://ter.li/ask-us · 📚 Learn about the EntreLeadership System™: https://ter.li/system-p · 💻 Get EntreLeadership Elite™ for your business: https://ter.li/elite-p · ✉️ Sign up to receive tactical tools, advice and resources in your inbox every week: https://ter.li/enl · 🏢 Attend EntreLeadership Summit: https://ter.li/summit · 🎤 Attend EntreLeadership Master Series: https://ter.li/masterseries · 📖 Order Dave’s new book, Build a Business You Love: https://ter.li/b4kru2 · 🔎 Explore business coaching options: https://ter.li/wveycm · 📄 Get the Strategic Planning Template today: https://ter.li/7z7qu6 · 🚢 Set Sail with Dave Ramsey! Book your cabin today: https://ter.li/s8xnyo Connect With Our Sponsors: · 💼 Go to Belay Solutions or text ENTRE to 55123 for their free resource! · 💻 Visit NetSuite today to learn more. · 📈 Grab Sales Gravy's free resource to help you hire and lead better. Listen to More From Ramsey Network: 🪑 Front Row Seat with Ken Coleman 🎙️ The Ramsey Show 💸 The Ramsey Show Highlights 🧠 The Dr. John Delony Show 🍸 Smart Money Happy Hour 💡 The Rachel Cruze Show💰 George Kamel Ramsey Solutions Privacy Policy Learn more about your ad choices. Visit megaphone.fm/adchoices

Transcript

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0:00.0	From the headquarters of Ramsey Solutions, this is Andre Leadership, where I take calls from leaders like you about what it takes to win at any stage of business and leadership.
0:20.5	I'm Dave Ramsey, your host with over 30 years of experience leading in the trenches
0:24.3	right alongside you.
0:26.1	If you got a question you want to ask on the show, fill out the form at entreleadership.com
0:30.9	slash ask or call and leave us a number, and we'll get to you and put you on.
0:36.0	The phone number here is 844-944-1070.
0:40.6	That's 844-9-44-1070.
0:45.4	Tyler is in Naples, Florida.
0:48.0	Hi, Tyler.
0:48.6	How are you?
0:51.1	Dave, I'm doing well.
0:52.1	Thanks for taking my call.
0:53.0	How are you?
0:53.5	Better than I deserve. What's up?
0:56.8	So I was hoping to get some advice from you. I am entertaining a new position at my company,
1:05.9	and it would be a leadership position in the company. And specifically, one of the person that would be
1:16.3	on my team is older than I am. And I had an experience earlier in my tenure at the same company
1:23.4	in a leadership role, was leading a guy that was older than me as well, and it didn't
1:29.9	go so well.
1:31.9	I was very, very challenging to build trust and in relationships with the guy that was on my
1:37.7	team and just wanted to see if you had any advice for me on what I could do differently
1:43.8	this go-round.
	...

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