Imagine this scene: a remote air base in Iraq, the constant hum of aircraft and generators punctuating the dry desert air. A young officer, recently promoted and given her first command, sits alone in her trailer after another grueling day where nothing seems to be working. Six months into a year-long deployment, she’s crying herself to sleep night after night, questioning every decision, regretting her career choice, and feeling like an absolute failure.
This was DeDe Halfhill’s reality during what would become the most defining leadership experience of her career.
DeDe spent 25 years in the Air Force, rising to the rank of colonel in a profession dominated by men. As a public affairs officer, she served as a strategic advisor to some of the military’s most senior leaders, including Chiefs of Staff and the Chairman of the Joint Chiefs during critical moments of the War in Iraq. After retiring from the military, DeDe has become a highly sought-after leadership consultant, helping organizations navigate the same challenges she faced throughout her military career.
This week, DeDe sat down with Simon in the latest episode of A Bit of Optimism (which you can view in full here or click to listen here).
As DeDe shared with Simon, she faced a perfect storm of leadership challenges. She had been:
- Promoted early (about four years of experience behind her peers)
- Given her first command (while her peers were on their second)
- Deployed to Iraq for 365 days
- Put in charge of a squadron with operations she had no experience in
- Made responsible for “feeding, fitness, and fun” for an entire air base
“Everything I had envisioned about who I would be as a leader did not show up in that experience,” DeDe said.
For six long months, she battled against what felt like inevitable failure. Nothing worked. Her inner critic ran at “max volume,” constantly telling her she was “the absolute worst thing that has ever happened to leadership.”
Then came the breakthrough that would change everything.
The Unexpected Power of Acceptance
One night, after another discouraging day, DeDe had what she calls her “mini breakdown” followed by a moment of clarity.
“If I have failed—and maybe I have, maybe I’m not meant to be a commander—what impact do I really want to have? What do I want these people, who I have been entrusted to care for, to know?”
The answer came to her with surprising simplicity: “I want them to know they matter. I want them to know what they’re doing here is not in vain.”
With this shift in thinking, everything changed. Instead of continuing to fight against her perceived failure, she accepted it and moved her focus entirely to making her people feel valued.
At first, the results were subtle. DeDe felt better, which meant she wasn’t as stressed or “barking as much.” She wasn’t tied to outcomes anymore because she was more concerned about the people. Then something magical began to happen.
“You could see a tangible shift in the way they laughed with one another,” DeDe said. “The way they came to me with opportunities and new ideas. I could see the way my own officers took a breath.”
The stress level of the entire organization dropped noticeably. And almost as a side effect, performance improved. The command that DeDe thought she had failed to turn around began to thrive.
By the end of her deployment, she had built a team that would “willingly follow her anywhere.” What had started as her greatest professional disappointment became her proudest achievement.
When We Make People Feel Like They Matter, Everything Else Follows
Our conventional thinking often gets this backward. We focus on metrics, targets, and performance, hoping that achievement will make people feel valued. But as DeDe discovered in the crucible of combat leadership, the path actually runs in the opposite direction.
This isn’t just a “feel-good” philosophy—it’s practical leadership wisdom born from one of the most challenging leadership environments imaginable.
Bringing This Insight to Your Leadership
Here’s how you can apply DeDe’s transformative insight in your own leadership context:
- The Morning Intention:
Start each day by asking: “How will I show my team they matter today?” This simple question reorients your focus before getting caught in the whirlwind of tasks and targets. - Create “Recognition Rituals:”
Develop consistent ways to recognize not just what people achieve, but who they are. DeDe’s team members were constantly “taking the brunt of everyone else’s stress.” Your recognition can be the counterweight to the difficulties they face. - Practice the Pause:
When you feel yourself becoming overly focused on metrics or disappointed by performance, pause and ask: “What would change if I accepted where we are right now and focused solely on making my people feel valued?” - Make Space for Stories:
Create opportunities for team members to share their experiences and challenges. As DeDe learned, when people feel seen and heard, their entire relationship with work deepens.
The Ultimate Leadership Paradox
What makes DeDe’s story so powerful is that it was only when she stopped trying to be an exceptional leader that she became one.
By accepting what she perceived as failure and shifting her focus to making her people feel they mattered, she achieved everything she had originally set out to do—and more.
As Simon reflected after hearing DeDe’s story: “If you take care of them in the good times, they will take care of you in the hard times. That’s how leadership works.”
Ready to show your team they matter, but not sure where to start? Simon and Zach Mercurio developed a course that teaches the essential leadership skills you need to inspire trust, empower others, and become a leader others believe in. Check it out here.
