Jenny Olson left Microsoft twice, built a state government office from scratch with no background in the field, and now leads the advancement team at Concordia College. Her grandma asked why she’d forsake a bird in the hand for two in the bush, and she walked away from the sure thing anyway. Six leaps in, she sat down with Max Kringen to talk about authentic leadership, managing your emotions at work, and why she still calls a mentor she hasn’t seen in years before she decides. 🎯 This one is for anyone staring down a change they don’t feel ready for.

Before you listen, ask yourself:

• Whose career are you watching to figure out your own next move?
• When you weigh a big risk, who do you actually call?
• Are you dampening your personality down to fit a room?
• When you walked away from a sure thing, what did the fear sound like?
• Who refills your bucket, and are you keeping that thread alive?

By the end, you’ll know how to:

• Pick your next move by watching where leaders you admire spend their energy
• Call a mentor you’ve lost touch with and keep that relationship alive
• Set up a hard conversation by putting all your cards on the table first
• Coach your team from what works for you, offered as a perspective and not a playbook
• Bring your full personality to work instead of filing it down to fit in
• Refill an empty tank by turning outward, the way a runner at mile 10 thanks the volunteers and gets the energy back
• Walk away from a golden-handcuffs job when the calling in your gut won’t quiet down

Key quote highlights:

“I’ve always followed good leaders in my career. I fundamentally believe in the principle you are what you surround yourself and what you will become.”

“I did not know you could be inspired in your work, actually feel the feeling and the emotion of being inspired literally five days a week.”

About Jenny Olson: Jenny Olson grew up in Cokato, Minnesota, graduated from Concordia College in 2001, and built her career in the Fargo-Moorhead region. She spent years at Microsoft and Great Plains Software, then left to launch Recovery Reinvented, North Dakota’s initiative to eliminate the stigma of addiction, before returning to Microsoft to lead the Fargo campus. Today she leads the advancement team at Concordia College, her alma mater, where she describes herself as a confetti cannon in a sector known for moving slowly. Learn more at [CONCORDIA URL]

⏱ Timestamps
00:00 Who the heck is Jenny
05:00 The gutsy leaps and the golden handcuffs
09:10 What it looks like to follow a good leader
14:35 Emotions at work, and why self-awareness is the job
19:53 Recovery Reinvented and the heroes in her backyard
26:39 How every road led to Concordia
34:46 Showing up when the energy is hard to bring
43:40 One good thing: everybody wants to help

📌 Resources Mentioned

• Concordia College: [CONCORDIA URL]
• Recovery Reinvented: https://www.recoveryreinvented.com
• The Go-Giver by Bob Burg and John David Mann

🔔 Stay Connected
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Website: https://wetellwell.com
Tellwell on LinkedIn: https://www.linkedin.com/company/wetellwell/
Max on LinkedIn: https://www.linkedin.com/in/maxkringen

📣 About Tellwell: The Podcast
Tellwell: The Podcast is a weekly conversation with nonprofit leaders, fundraisers, and mission-driven storytellers about building trust and belonging. Host Max Kringen, Chief Storyteller and founder of Tellwell Story Co. in Fargo, North Dakota, talks with the people doing the work about what worked, what didn’t, and what they learned along the way.

#followinggoodleaders #nonprofitleadership #authenticleadership #sayingyes #concordiacollege #tellwellpodcast