Does Gender Change How We Lead? with retired colonel DeDe Halfhill | A Bit of Optimism Podcast
Here are the top 10 key takeaways from Simon Sinek's conversation with retired Air Force Colonel DeDe Halfhill about how gender shapes leadership approaches and what truly makes an effective leader in today's changing world.
1. Leadership is leadership, regardless of gender
DeDe Halfhill initially believed leadership qualities were gender-neutral. Before taking command in Iraq, she asked a female leader she respected what she needed to know as a woman in command. The response was simple: "nothing, leadership is leadership." This seemingly straightforward answer suggested that good leadership principles transcend gender.
However, Halfhill soon discovered reality was more complex. During her command, she encountered situations where her leadership style was perceived differently than her male counterparts'. She experienced being dismissed by subordinates and received feedback that she was "flirting to get her way." These experiences highlighted that while leadership principles might be universal, how they're perceived and received can differ based on gender.
2. Different standards for the same behaviors
Gender expectations create double standards in leadership environments. In Iraq, Halfhill observed that three female commanders, including herself, were investigated for allegedly mistreating airmen. The investigating officer noted these women weren't doing anything different from what men did daily, but when women exhibited the same behaviors, they were perceived as more toxic.
A specific example involved swearing. When male leaders swore, it was often seen as decisive and authoritative. When female leaders used the same language, they faced formal complaints and investigations. This double standard created additional challenges for women in leadership positions, forcing them to navigate complex social expectations while still maintaining command authority.
The existence of these different standards doesn't mean leadership itself is gendered, but rather that societal expectations and perceptions of appropriate behavior differ between men and women leaders. These expectations create "lanes" of acceptable behavior that change over time but still impact how leaders are perceived and evaluated.
3. Emotional labor as an unseen burden
One of the most significant challenges Halfhill faced as a female leader was the emotional labor required. People from various units would seek her out for advice or to discuss their problems because she created a space where they felt comfortable sharing their concerns. While this demonstrated trust in her leadership, it also created a hidden workload that took time away from other responsibilities.
This emotional labor represented a quantifiable disadvantage. The time Halfhill spent supporting others emotionally was time not spent on administrative tasks, visiting units, or handling emails. This created an imbalance where her capacity to be the kind of empathetic leader she wanted to be consumed resources her male peers didn't have to expend.
The concept of emotional labor highlights an often overlooked aspect of leadership differences. While not exclusively a female burden, societal conditioning often means women are more practiced at and expected to provide this type of support, creating an additional workload that isn't recognized in traditional leadership metrics.
4. Vulnerability as a leadership strength
The podcast reveals that accepting vulnerability transformed Halfhill's leadership approach. During her deployment in Iraq, she initially tried to prove herself by being tough and focusing on performance metrics. After months of struggling and feeling like a failure, she shifted her focus to ensuring her team members felt valued and understood that their work mattered.
This shift from performance-focused to people-focused leadership dramatically improved both morale and results. When Halfhill accepted her own vulnerability and limitations, she created space for authentic connection with her team. This led to reduced stress levels throughout the organization, increased laughter, more innovative ideas, and ultimately better performance outcomes.
The power of vulnerability is further illustrated in Halfhill's story about confronting a difficult subordinate. Instead of maintaining a rigid authoritarian stance, she admitted the relationship wasn't working and asked for input on how to improve it. This vulnerability created an opening for the subordinate to share his own struggles, transforming a combative relationship into a workable one.
5. Loneliness is often disguised as exhaustion
A profound insight from the conversation is that loneliness in workplaces is often masked as exhaustion. Halfhill describes asking her squadron who felt tired, and three-quarters raised their hands. When she later asked who felt lonely, the same proportion responded affirmatively. This revealed that people were experiencing loneliness but using the more socially acceptable language of exhaustion to express it.
This misidentification leads to ineffective solutions. When someone reports exhaustion, leaders typically offer time off, which may actually increase isolation rather than address the underlying loneliness. The military's ongoing struggle with rising suicide rates despite various interventions suggests they may have been treating symptoms rather than root causes.
Halfhill realized that discussing loneliness openly was essential, despite the discomfort it caused among military leaders. She began intentionally using the word "lonely" to normalize conversations about connection and belonging. This approach represented a significant shift in how emotional wellbeing was addressed in her command.
6. The importance of going first as a leader
True leadership involves demonstrating the behaviors you want to see in others. Sinek emphasizes that a leader isn't called "leader" because they're in charge or have rank, but because they "go first." This means being the first to show vulnerability, the first to admit mistakes, and the first to model desired behaviors.
Halfhill demonstrates this principle in her story about confronting an underperforming team member. Instead of maintaining an authoritarian stance, she opened up about her own frustrations and desires to improve their working relationship. This vulnerability created space for the team member to share his own struggles, transforming their interaction from confrontational to collaborative.
Going first requires courage—perhaps more courage than speaking truth to power. It means stepping outside comfort zones and risking rejection or criticism. However, this willingness to be authentic creates psychological safety for others to do the same, ultimately building stronger teams and more effective organizations.
7. Changing expectations of leadership styles
Leadership expectations are evolving rapidly across all sectors, including the military. Halfhill notes that the command-and-control leadership style that was once standard is increasingly less tolerated, even in traditionally hierarchical environments. Younger generations expect more collaborative, empathetic leadership approaches.
This shift presents challenges for leaders trained in older models who have not seen alternative approaches modeled. Many feel lost as they try to adapt to new expectations without clear examples to follow. The leadership qualities once celebrated—decisiveness without consideration, unwavering certainty, emotional detachment—are now often seen as liabilities rather than strengths.
These changing expectations suggest a broader cultural shift toward valuing traditionally feminine leadership traits in all leaders, regardless of gender. As Halfhill notes, "We don't actually need more female leaders. What we need is more leaders who act like females. And women just happen to be better at that." This represents a fundamental reframing of effective leadership qualities.
8. The importance of mental fitness over mental health
Sinek proposes reframing "mental health" as "mental fitness" to better capture the ongoing nature of emotional wellbeing. He argues that "mental health" sounds like a destination to achieve rather than a continuous practice, setting up unrealistic expectations of permanent resolution.
The concept of mental fitness aligns psychological wellbeing with physical fitness—something that requires constant attention and varies naturally over time. Sometimes mental fitness is strong, sometimes it needs more work, and this fluctuation is normal rather than a failure. This framing reduces stigma by removing the achievement orientation of "mental health."
Halfhill embraced this perspective through practicing shame resilience—identifying negative self-talk, reality-checking these thoughts with trusted others, and rewriting harmful narratives. She describes this as "the regular weightlifting of my mental fitness," highlighting the ongoing, practical nature of maintaining emotional wellbeing.
9. Responding to vulnerability with empathy, not solutions
When someone shares vulnerability, the natural response for many—especially those in leadership positions—is to offer solutions. Sinek demonstrates this tendency during the podcast when Halfhill explains shame resilience. He immediately tries to analyze and fix the hypothetical problem rather than responding with empathy and curiosity.
This "fixer" mentality often stems from discomfort with others' difficult emotions. Halfhill explains that fixers want to solve problems quickly not just to help the other person but to alleviate their own discomfort with emotional vulnerability. This approach, while well-intentioned, can shut down genuine connection and prevent deeper understanding.
The more effective response to vulnerability is empathy and curiosity. Instead of saying "here's why you're wrong" or "here's how to fix it," leaders should acknowledge the difficulty of what's being shared and ask questions to better understand the experience. This creates space for authentic connection and often leads to more sustainable solutions.
10. Courage as the essential leadership quality
Beyond all other leadership traits discussed, courage emerges as the essential quality for effective leadership. While conventional wisdom often emphasizes vision, charisma, or decisiveness, Sinek and Halfhill agree that courage underpins all effective leadership, regardless of style or personality.
This courage manifests in various ways: the courage to be vulnerable when it would be easier to maintain distance, the courage to admit mistakes, the courage to ask for help, and the courage to go first in modeling desired behaviors. It's not just about making bold decisions but about having the personal bravery to connect authentically with others despite the risks.
The most effective leaders, according to Sinek, are "weirdly open about their shortcomings." They normalize imperfection and humanity in leadership positions. This openness requires significant courage but creates environments where innovation, trust, and genuine connection can flourish. In the end, it is this courage—more than any technical skill or charismatic quality—that defines truly transformative leadership.