Rising Millennial Leaders: Insider Tips, Insights & Issues

August 7, 2022



Rising Millennial Leaders: Insider Tips, Insights & Issues

Rising Millennial Leaders: Insider Tips, Insights & Issues

Jenn DeWall is a leadership development strategist, workshop facilitator, and coach working mostly with and on behalf of her Millennial peers. She also hosts The Leadership Habit podcast. Focused on supporting rising Millennial leaders’ progress, Jenn shares her own experiences—successes and struggles—that have shaped her perspectives and approach to leadership development in the new era of work. She explains the goals, mindsets, and concerns of many Millennials and suggests productive, sustainable ways for us all to advance and grow.


[02:49] After college, Jenn’s initial enthusiasm about leadership soon wanes.

[03:30] Despite good results, Jenn gets an unexpected, negative review.

[04:34] Jenn is devastated. “Why didn’t somebody tell me?”

[06:21] Jenn loses confidence and gets conflicting direction about how to act at work.

[08:33] After some struggles, Jenn is asked to start training and mentoring her peers.

[10:20] Organizations need diversity across many dimensions, allowing people to show up as themselves.

[12:04] How Millennials were not prepared at college for the rules of work or to know their value.

[13:40] Jenn interviewed senior leaders to find out where Millennials are getting it wrong at work.

[14:55] Issue 1: Millennials want to have fun at work.

[15:42] Issue 2: Millennials yearn to develop and understand the big picture.

[16:49] Issue 3: Millennials desire for flexibility and work/life integration.

[18:46] Initial confidence about their potential and future is dulled for those not falling into line.

[20:12] As Millennials become leaders, how are they fulfilling their needs for external validation?

[22:01] Lacking conditioning for internal validation to know “I am enough” “I have the skills I need to succeed.”

[23:20] Maslow’s Hierarchy of Needs: Our fundamental need to be connected.

[23:58] Millennials ask themselves “What is my life really worth?”

[25:02] The working environment has affected Millennials – such as 9/11 and the Great Recession.

[25:49] How technology has expanded Millennials’ worldview, footprint, and decisions.

[26:53] Jenn discusses how her peers think through “What do I want work to feel like?”

[28:42] Resignations often happen when employees assume/fear their employer will not be open to making accommodations.

[29:25] How the need for external validation affects workplace confidence and behaviors.

[31:59] Jenn shares Millennials’ confusion: Why can’t I have fun at work? And why can’t I also work hard?

[33:31] As such a large generation, Millennials are not afraid to stay and be the voice of change.

[34:52] How rising leaders benefit from being intentional about soft skills and behaviors they promote.

[38:25] Jenn advises leading with curiosity and empathy and assuming positive intent.

[41:20] You can’t hang your hat on stereotypes as everyone’s lived experience is different.

[42:46] Non-linear career paths are now the norm, requiring different consideration and allowing different possibilities.

[44:55] Reacting to “What is my life worth?” leads to disruption with new work configurations.

[47:12] IMMEDIATE ACTION TIP: Find the common ground. We all carry an invisible suitcase that is the collective experience of our hopes, dreams, fears, and pains, and there is commonality within. Be intentional and find that commonality so we can work better together.


“Through hardship comes great outcomes.”

“If we want a homogenous workforce where we are more alike, what does that do for innovation?”

“I never wanted millennials to feel less than, I just want them to feel empowered. You deserve to be recognized and seen for who you are.”

“This is where the helicopter parenting didn't set us up well because you need to have confidence at a foundational level to influence, to make a decision. And Millennials were very much conditioned for external validation.”