Difficult Conversations Build Stronger Teams | Colonel DeDe Halfhill

TRANSCRIPT Difficult Conversations Build Stronger Teams - Colonel DeDe Halfhill

 [Host: Roger Kastner]

Have you ever wanted to say something to a colleague or in a meeting but didn't? Me too. Many leaders stay silent when it's time to just say the thing that needs to be said.

They avoid speaking their truth or naming what's going on because it feels uncomfortable, irrelevant, or a distraction from the real work. But retired U.S. Air Force Colonel Dede Halfhill learned something different firsthand while serving and leading in the most challenging environments. And that is, when leaders ignore what people are feeling and what's going on in the room, teams get weaker and results suffer.

[Guest: DeDe Halfhill]

The most successful leaders I saw in the military are doing the exact same thing I see the most successful leaders outside of the military doing, which is seeing people, seeing the experience their teams emotionally are having and being able to sit in the uncertainty and messiness of that in a way that brings people together.

[Roger]

Welcome to What Do You Know To Be True. I'm your host, Roger Kastner. These conversations are an invitation to explore becoming more of our possible selves through the experience of others who've been right where we are.

In today's conversation, we're talking about how leaders can attune to their people, how to be courageous enough to address the emotional needs of the team, and when they need to say the thing that needs to be said. I'm glad you're here. Let's dive in.

Hey, DeDe, it's truly an honor and a pleasure to be in this conversation with you today. Thank you for joining me.

[DeDe]

Thank you. I'm super excited. Like you said, we've been we've been connected on LinkedIn for a while, and we've had some great conversations back and forth.

So to get to do it like face-to-face is so much fun.

[Roger]

I'm excited to learn more about your superpower of telling the truth to power in a way that disarms and not harms. But before we get too far, what's important for us to know about you?

[DeDe]

I think when I like I've spent a lot of time wondering why do I do the work I'm doing? And when it comes down to it, I think the most important thing to know about me is that I share the message I share because I want leaders to feel less alone, and I want to feel the responsibility of leadership to be I want it to feel a little easier to carry, a little lighter. I mean, it's going to be heavy, but it doesn't have to be as heavy as it is.

Going through all the things you have to go through when you leave a career of 25 years, I spent 25 years in the United States Air Force. Moving into something new, what inspires me every day is the ability to help leaders navigate the big challenges they're facing. So I think that's the most important thing that I do this because I want leading to be fun, and I want more people to want to do it.

[Roger]

Was there a time where you learned that lesson when you learned that truth that you wanted to help other leaders be better at what they do and ultimately have fun? Doing it, that it can be fun, that it can be rewarding?

[DeDe]

Is that a surprise? Actually, I've seen it be both miserable and fun. And yes, there's a very distinct moment.

I was deployed to Iraq in 2010. I was a squadron commander over there. So I had a team of about probably about 70 or so military people, but about 1300 contractors.

So it was a pretty big operation. We were taking care of a base of about 25,000. It was hard.

And I was struggling. And every day, I felt like a failure. And every day, I was watching myself show up in a way that was different than I had imagined I would be showing up.

I watched myself behave in a way that was definitely not building trust, if not, in some ways, destroying trust. I mean, destroy is a big word. I can't think of a less egregious word right now.

But like, I wasn't behaving how I thought I would. And I had this moment where it all kind of, it kind of all came together. And I realized like, I am not living up to who I wanted to be.

I'm not leading the way I want to lead. And I'm definitely not as good as this. I'm not as good at it as I thought I would naturally be, right?

Because you really don't know until you step up to lead, are you going to be able to do it or not. I went into my trailer. And I was pretty upset because I had always envisioned I would be so much better at this.

And I was really grappling with the realization that I wasn't. I called a friend of mine and I was quite upset. And I was crying because it was a hard moment for me.

And he picks up the phone and all he hears is me crying. And remember, I'm in Iraq, he's not. And he picks up the phone to hear me crying.

And he immediately thinks something's wrong. Oh my gosh, what's wrong? What happened?

Are you okay? And I'm, I'm having such a hard time that I'm not even really able to communicate at that point, right? I'm doing the whole, this is horrible.

You know, he finally calms me down and he asks me what's going on. I tell him and he kind of laughs, which at first pissed me off, but he, he kind of laughs and he goes, “DeeDee, we all feel like we're failing.” Like we all have moments where we realize, man, this isn't working out like I thought it would, or man, that's not a skill I naturally possess.

And I thought I did. And, and man, I might be worse at this than I'd ever told myself I might be, you know, and he says, we all feel like we're failing. We all feel like we're not measuring up.

And I remember hearing that. And the very first thing I said is, well, why doesn't anybody ever say that? Like, it would be so much easier to process on my own.

It would be so much easier to process if I had a normalization of the fact that we all feel it. If I knew I wasn't alone in that feeling, if I knew that this was an experience that most people will feel when they are being stretched in a leadership position. And when he said that to me and I suddenly felt less alone, that was the moment where I realized I will do everything I can to share the truth of that and normalize the truth of that, that it is a fleeting experience, that it does happen.

It comes and goes. I will do everything I can so that every leader that I can communicate with will know that that is a normal part of leading and growing as a leader is you will feel like you absolutely suck and nothing you are doing is, is how you thought you would, or it's getting the results you thought you would. And that is completely normal.

How about you? I mean, like what was your, when did you realize kind of what, how you wanted to help?

[Roger]

I remember early in my career when I was managing people, I was managing a group of project managers at AOL, the place that sent all those CDs to you. You're welcome. Hopefully you made great art with it in the backyard to scare away the birds.

What I realized that we would build a new version of the product and leaders would say, you know, we don't need everything to be a hit. We just need 3% of these features or products to be a hit. And then people will continue to subscribe.

That made me think about the 97% of the effort that we were putting into that version was deemed throwaway, non-valuable. And I thought about these people showing up 40, 50, 60 hours a week to work and they could be working on something that was a complete crap shoot. And when it turned out to be more crap than, than, than gold, like, okay, nine months of your life and the sacrifices you made to work on this product nights and weekends that yeah, it doesn't matter.

Like we tried. Oh, well. And that's easy for a leader to say it's really hard for someone who's done that work to just let that go.

And what, what made sense for me is around that time, I was reading Marcus Buckingham's first break, all the rules to get better at being a manager and a leader. And in that book, Buckingham talks about some research from Gallup where it came from that said that people only, you know, only 20% of people get to use their strength, that combination of what they're good at. And they're passionate about only 20% of people get to use that in any one given day.

And I thought, okay, wait a minute. Like as humans, our basic needs of wanting to be seen, heard and recognized for the value we bring. And we all have a sense, an innate sense of what our purpose is.

Only 20% of us get to feel that on a given day and maybe not ever. So sad. That number's way too low.

And I've seen that number recently from Gallup. It's up to 34%. So we're doing better, but still two thirds of people out there don't get to experience their strengths in any one given day.

That is sad. You know, in this day and age, there's really no excuse why we shouldn't be able to do the thing that gives us meaning and have impact on others that we want. And so that's what, what inspires me to continue to do what I do and why it shows up in my day job as when I'm doing, you know, organizational development work, working with leaders and teams to drive clarity into the work.

That's why it shows up in the coaching I do with individuals, help them learn how to get in touch with their own self-leadership. And it's really the reason why this podcast exists because I want to have conversations with people who have been where the audience is and found out how to lean into and tap into that superpower, live in alignment with values and purpose to inspire other people to do that. And I think you and I have that in common.

[DeDe]

What came to mind as you were saying that is we're in the military, you got assigned to a position. You didn't get to choose the work you got assigned to, and you got assigned to a career field. You know, I was a junior in college and I was told you're going to be a public affairs officer.

And I was for 25 years. I didn't really get to choose that. I got to put it in my wishlist, but fortunately for me, it was the right path.

But finding a way to navigate the work you have to do to make a living in a way that you can do it, that still brings who you are and what you care about and the gifts you have, like that is the magic is finding a way to do the work that sustains you in a way that fulfills you.

[Roger]

And I think there's a reason why people choose the careers they do, why they choose the companies that they do, that there's that potential. And yet something happens along the way where that spark just gets turned down gradually. And then suddenly it's gone.

And I don't think we necessarily have to change careers. I don't think we necessarily have to change jobs to let our superpower show up, to let our purpose be lived into, but sometimes it does. You've advised the chairman of the Joint Chiefs of Staff.

You've led teams in Iraq during combat operations. And most of your career has been in the military and in very challenging situations. Most people would assume, people on the outside would assume that the military runs on hierarchy and command and control, but you said the most capable leaders lead with something else, which was surprising.

What did you learn from being a leader in the most challenging of situations that most people would never expect?

[DeDe]

You know, sometimes people think the military is this environment that is so unique. And what I tell people all the time, like what you do may be unique. You might work at Starbucks.

I might've been in the Air Force, but what you do may be unique, but your humanity is not. Like we are still people coming to work every day, whether that's in combat boots or a sports jacket. Right.

And so I think what I'm going to tell you, it probably won't surprise you, is that the most successful leaders I saw in the military are doing the exact same thing I see the most successful leaders outside of the military doing, which is seeing people, seeing the experience their teams emotionally are having, seeing where they are struggling and being able to sit in the uncertainty and messiness of that in a way that brings people together. So I think the leaders who are the most successful, regardless of institution, regardless of profession, are those who can connect person to person.

And they focus on that just as much as they focus on all of the other metrics we're meant to be tracking, whether that be production timelines, revenue, you know, P&L, all the things, the systems you track. Leaders who can track the human system just the same are successful everywhere in the military, outside of the military.

[Roger]

When you're speaking with leaders in the corporate world, do they ever push back and say, well, no, you can do this in the military because of rank, because of that sense of hierarchy. We don't have that same ability to do that here within the corporate world. Do you run into that type of resistance?

[DeDe]

I'm curious, and I have an answer, but I'm curious. From someone on the civilian side, what is it about the military that you think might make that easier?

[Roger]

In the corporate world, we talk about bring your true self, your authentic self to the workplace. You can be you. You control your own career.

There's this idea of you have all this agency, and then you get in there and you find out like, oh, no, there are some limits to the, you know, this isn't free range. My understanding is there is a little bit of a, is it rigidity or is it more of a, you know, more structure living on base or being deployed? You're spending a lot more time with people.

Whereas what I'm seeing in the corporate world with reorgs, with changing strategies, with new leaders come in, there's an expectation of you're getting deployed immediately and you did not have, you know, six months of basic training. You did not have all this time of building, you know, repetition and camaraderie. You're just, boom, placed in into the arena with the expectation of, hey, the clock's on.

These are the metrics. Go.

[DeDe]

It is a responsibility of leaders to be able to navigate this space effectively. And when I'm out talking to leaders about emotion and I share very real stories about where emotion showed up and where our inability to process it got in our way, they often will say to me, well, it makes sense that in the military you would talk about emotion because you are experiencing very emotional things, right? Like you deployed to war, you have lost loved ones, you are doing really hard things is the perception that's out there.

And because you're doing these really hard things, it makes sense that you would talk about emotion. So my civilian audiences sometimes dismiss it. Like I can see why that would work in the military.

Then I go to a military organization. And this happened a lot when Dare to Lead came out, the chief of staff of the Air Force, I think put it on the reading list, which meant it was one of the books recommended by the chief of staff of the Air Force for the entire force to read. And a lot of people, I would hear them talking about it and they would say, well, that's great, but that doesn't work here because we do really hard things.

And when you do really hard things, you don't have time for emotion. And I just find it so fascinating that outside of the military, they say you do hard things. So it makes sense that you talk about emotion.

And then in the military, they say, we do hard things. We don't have time to talk about emotion. And I laugh because I'm like, both audiences are dismissing it because of the discomfort.

Yeah, that's for those people over there. That's for those people over there who have time to talk about feelings. And I have evidence now that proves, especially inside the military, that that is a false belief because the men who fought the most horrific war, who were the bravest among us, men from World War II, actually talked about the responsibility leaders have to understand emotion.

And very specific emotion. They talked about shame. They talked about grief.

They talked about fear. And so this idea that it's not meant for me is a complete lie. As leaders, it's meant for all of us to understand our own, to understand others.

So it's just, I always laugh at that because I get it from both sides. Like, that won't work here. We don't do that.

And I'm like, where will it work?

[Roger]

Yeah, and the inability to see that there is, you know, emotions in both arenas, and that those emotions are impacting performance, relationships, results. And there are examples of leaders in both arenas that are doing it really well.

[DeDe]

Do you have an example of a leader you've seen who has done it really well?

[Roger]

I was working with a leader recently who, you know, came into a new position, was promoted into a pretty big position within a corporate environment. What we were working on was this idea of he has always held on to this principle of being warm and demanding. You know, underneath that, you don't have to dig very far, is that there's a certain level of accountability that he will hold himself and others to, but he wants to do it in a way that recognizes the humanity in the room.

And so we were talking about, you know, what does that look like? What does it look like to be warm and demanding? And why is it different when, you know, you went from your title being this long to now just being a couple letters?

And so we would talk about scenarios that would come up and time was always a factor, like less time, more demand, bigger problems. And like, okay, is it really less time than before? Are these really bigger problems than before?

We found out there's a lot of assumptions going on that there was less time than before, than that, you know, the bigger impact. Like, no, those things weren't true. There were presumptions that he had, that it was harder, that he thought that the man side, you know, he would need to be more demanding and he would not be as warm.

And it turned out that was a choice.

[DeDe]

I actually have a theory about leaders specifically, you know, I spent my whole career around mostly men. I was often the only woman in the leadership team or on the staff. And so I've had 25 years of observing leaders, mostly men, right?

And I have a theory about the leaders I've encountered who are really, really good at tapping into their empathy and tapping into another person's struggle and being able to sit with another person in that struggle. My experience was the people who I saw who were exceptional at this, because I'm sure there are people who can tap into it, right? But the leaders I saw who were exceptional, like where they really stood out.

I worked for several leaders who could tap into it in such a way that they would bring a room to tears. They were the leaders who to this day, if I even hint about that leader on LinkedIn, and I do sometimes, because he was very inspiring and was one of, I mean, I consider him almost like a second dad. He was so good at it that it has inspired such a devotion and such a admiration, maybe admiration is a better word, and his ability to inspire.

And I've seen a couple leaders like that who just have it, and almost to a leader, it happened after going through, they changed how they showed up after going through something really hard. And it was almost this hard thing, and sometimes I say trauma, but I'll give you two examples. One of the leaders who I know who has such a gift at doing this was in Cobar Towers bombing, and that I often say broke him open in a way.

And then the other gentleman I was just talking about, I talk about him all the time, so people know this story, but I worked for him when he was a colonel and I was a captain, and he was a good leader. I loved working for him. I had a lot of fun.

He was fair. He was brilliant. He was very good at the job.

No complaints. I worked for him several times over the years because I just really enjoyed him, and he took good care of me. And then I worked for him again when he was a four-star.

Like I said, I worked for him several times, but by the time I worked for him when he was a four-star, he had been deployed to Iraq. And while in Iraq, he was the base commander of the base that the primary hospital in Iraq was located, it was Bilad Air Base. And it was the hospital where we could get you there within an hour of your injury, you had a 95% chance of surviving.

And he would go to that hospital every couple days and talk to the men and women who were wounded. He would call their parents and talk to their parents and reassure them that we were doing everything we can to take care of their child or their loved one or their spouse. And I think the rawness of being exposed or being exposed to the rawness of that, to the humanity of that, shifts a comfort level to the point where the humanity of others was no longer uncomfortable because he had so many reps in it.

And I always say, I'm so grateful that that was the outcome, but we shouldn't have to wait for leaders to go through something hard to build that skill. We should be able to build that skill as part of how we are developing leaders, period. We shouldn't wait for trauma to create the leaders we need.

What's been your experience and the leaders you've seen who've done this really well?

[Roger]

Yeah, it's a fascinating point of, do we have to go through a traumatic event to be more convicted or compelled to lean into empathy, to see the power of empathy and showing up as a more empathetic leader? In every conversation that I've had in this forum where we're talking about people's superpowers, there is either an explicit story or implicit story of the unmet need. Something happened in someone's life that, yeah, that unmet need was sitting inside of them until they found an action that attended to that need.

And so they start doing that thing over and over and over again because it creates understanding, because it could be healing. Whatever the motivation is, they keep doing that thing over and over again until it becomes a talent. And then I talk about it becoming a superpower once that talent is used in service of other people.

And so people go on that journey. And so I think there is something about whether that unmet need comes from early in development or it happens later on in life. I think there is that spark.

And oftentimes there is a traumatic event there, something that was too much for the system, too fast, and it was stored. And then the discovery of an action that responds to that. Does it have to happen or can we train it in?

I don't know. I think it's probably both. I think there's so much optionality until our path is lit up and our path is revealed.

I think it is those moments, whether it's traumatic or just insightful, that is the spark that people need.

[DeDe]

And I think you said something so important there. Up until we go through a moment that shifts us, it's kind of optional, especially if we've been successful. If what got you here has been very operational and you've been very good at the operational side, you think that's going to continue.

That's going to be what continues to propel you, to continue for you to advance. And I'm on this mission because I was heavily involved, heavily influenced by Brene Brown's work, started following her in 2010, ended up getting my coaching certification in 2014, marrying the skill with the knowledge. I'm so fascinated by what does it look like as a leader when you have that skill, when you have the ability to do that, to sit in that space, to identify emotion, to sit with emotion, to lead with an understanding of emotion.

And when you said the word optionality, I think it's so important because I think so many leaders believe that, sure, that might be for them, but that's not for me. And I do think a lot of leaders believe that it's always been that way, right? We're hearing this whole conversation of, we need to be more human.

We need to bring our humanity to work. We need to lead human first, human centered leadership. It's everywhere.

And when I encounter leaders and I ask them, what do you think about when you hear that? A lot of people say one of two things. Well, actually one of three things.

One, what does that even look like? Sure, that sounds great, but I don't even know what that looks like. Two, we don't have time for that here.

And then the third one is usually probably the people who are following those leaders that are either one or two and they're going, yeah, and I wish more leaders got it. And I'm on this mission right now to kind of show people that that whole human first movement is actually not new. It's not a new age style leadership.

It's actually taking us right back to what the men in 1948 World War II tried to tell us. It's actually something we had and we lost. We had, and it was removed.

And so we're kind of just now going back to what wisdom, real wisdom leading in the hardest of spaces tried to share with us. It was taken out. And so we're just kind of going back to what we knew, what we learned the hard way.

[Roger]

This 1948 Air Force Leadership Manual that you introduced to Brene Brown and Brene writes about, and then you're now researching it. I love this arc of we knew it then, but it took that global traumatic event of World War II. Fast forward 75 plus years, we're now coming out of a global traumatic event where leading up to it, we had epidemic levels of loneliness, isolation, depression, anxiety.

And then we have the pandemic, which was an existential threat, which created separation. There's an element of an aftermath of that. Now we're hearing about AI.

AI is going to come for all of our jobs or AI is going to be another tool that is going to do the transactional part of our jobs. And what's left is the more human skills. So it seems like there's an opportunity for us to lean into that humanity.

And maybe we've had the traumatic experience that we've all shared that we don't need to go looking for a new traumatic event. We just had it. We need to recognize it for what it is.

[Roger]

Inspiration added on to epidemic levels of mental health crises and now, you know, this idea of how we're going to deal with this game-changing technology. Maybe the moment is now. Maybe we've had it, a shared experience, and there'll be more of an agreement and awareness and willingness to lean into being more of an empathetic leader.

[DeDe]

As I'm writing the book and I'm digging into this military manual and how differently the military manual talked about the inner experience, both of leading and being led. They talked about this inner experience so much more. And I'm digging into why did the manual change?

How did it change? When did it change? And what I'm finding in the research is that the manual is really a reflection of also how society changed.

And what you just said is what is actually like what the research is showing is that during the time of the manual, the 1948, like 1940s, right after World War II, the entire manual was written about how, what is the responsibility you have to the team? What is the responsibility you have to understand their inner experience, their inner world? And over time, we really shifted it to the leader's inner experience and inner world.

And that's kind of where we've stayed in the whole self-help era, right? We've stayed in this space of how do I understand how I'm showing up? How do I understand my emotions, where I feel vulnerability, where I feel courage so that I can lead?

But that is distinctly different from how the men in the manual talked about leading. They did talk about the leader's inner experience, but I would say they talked more about the team's inner experience and understanding it. It's fascinating how much it's shifted and why.

[Roger]

I can't remember the gentleman's name, U.S. Navy SEAL, who was talking to Michael Gervais on Finding Mastery, who was talking about team resilience. And they were kind of riffing on this idea that there's so much literature and so many speeches, thought leadership out there about leadership and what it means to be a leader, to your point, the inner experience of being a leader. And there's a dearth of what it takes to be a good teammate.

And yet leaders don't accomplish anything by themselves, right? And team members don't accomplish anything by themselves. It's in relationship with each other that wins and losses happen.

I'm curious about, could you tell us a story of where you experienced, where you started seeing this difference between the leader who was focused inward to a leader who then became team focused and the impact it had on the team?

[DeDe]

I can tell you more where I saw that it didn't happen. And maybe we start there because I think understanding, I saw a clip from Ed Sheeran yesterday, of all people, but he was talking about how we really don't learn a lot from success. We learn so much more from failure.

And yet we want to talk about success. We want to talk about where it worked, but we don't really want to talk about where it didn't. And I think that's my whole, like my whole keynote is where it didn't, you know, because I think if we can see where it didn't, and then we understand the cost, that's actually what motivates us to then try and practice so that we can make up for that, so that we can have those successes.

But if we don't understand the cost first, then I think we lose the motivation to really make the change we need to make. And so one of the stories that's in, in this book I have coming out is about COVID. And I was in the Pentagon at the start of COVID.

And I was working for the Chairman of the Joint Chiefs. I was his communication advisor. So most of the Pentagon was shutting down, a very small percentage of the building was still coming to work every day.

And because I was working for the Chairman, my team and the rest of the Chairman's staff were coming to work every day. And I was watching kind of all of this really odd behavior. And I was seeing things like people were making fun of people who were masking up, people were really frustrated about having to come into the building.

I was seeing a lot of people push back about having to come into the building. I was, I had members of my own staff who were upset that they couldn't wear yoga pants to the Pentagon. Because well, when people get to work from home, they get to wear yoga pants.

And I was just like, what is happening? Why are people acting so, so weird? I hate to use the word weird, but it was so different than I had seen.

And I had this moment where I was so frustrated. And I thought, what is going on? We've been to war.

I myself had deployed twice to Iraq. Almost everyone I was around had deployed numerous times to either Iraq or Afghanistan. We'd gone into these hard places.

We'd gone into places where there was a ton of uncertainty, and we didn't know what was going to happen. And I remember saying to myself, what is going on? We've been at war for 20 years.

We all have deployed, and I haven't seen people acting like this. And then it kind of hit me. And I thought, oh, when I deployed to Iraq, I was putting myself in harm's way.

When I come into the building every day, I'm putting those I love in harm's way. Because I had people who had parents who were navigating cancer. I had people on my team whose spouses were immunocompromised.

I had people on my team whose kids, whose child had asthma. I mean, they were going home to really uncertain about what their coming into the building was going to do to those they loved. And we had never experienced that before.

When we deploy and we go off to Iraq or Afghanistan, we are accepting the risk we are taking. But we are certainly not putting those we love in that same risk, right? We're not putting them at the same risk.

The chairman wanted to send a letter out to the entire joint staff, which would basically go out to everybody at the Pentagon, right? And I was talking to another senior leader on his team, kind of the individual that was corralling all of us advisors. You know, we had the congressional advisor.

I was his media and public communication advisor. You had his internal joint staff director advisor, like, how is the internal team going to take this? And I said to this individual, we need to talk about how afraid people are.

Like, when we're in this letter, we need to talk about the fear people are experiencing. And he looked at me and like, immediately had this moment of disgust. And he goes, Oh, so effeminate.

And I was like, effeminate. And it kind of threw me back for a second where I was like, effeminate. Are you in the militaries?

I was like, Are you effing kidding me? You know, I didn't say that. But that's what was going through my mind.

And so we didn't he wouldn't do it. He wouldn't put it in the letter. Like it was a done.

There was no discussion to be had. And I spent a lot of time sitting with that moment. And today, when I look back on that moment, I think like that is the problem we have is that we think understanding the inner experience, especially if it's an emotion we're uncomfortable with.

If it's an emotion we don't talk about a lot, it can feel really soft. And looking back on it now, I think about that letter. And I think there's nothing effeminate or soft about saying something like, Hey, listen, we're dealing with a ton of uncertainty.

And I know this is different than uncertainty we have dealt with in the past. I know that when we have done hard things, we are doing hard things. And now we're faced with a situation where we don't know how this is transmitted from one person to another.

Remember, this is the very beginning. We don't know what this is going to mean for those we love. But here's what I do know.

I do know that anytime we take risk, we go into it with our eyes wide open together. I know that anytime we are navigating uncertainty, we do it together. And I know that anytime we are navigating something that is hard, we do it together.

And we will do it the same way we have always done it by taking care of one another, by talking to one another, by being honest about what it is we're wrestling with. And I thought there's nothing effeminate about that. Because here's the problem.

When we didn't do that, when we didn't just be honest about the human experience that was happening, that behavior continued. There continued to be this distrust. There continued to be frustration.

There continued to be energy spent on conversations that did not need to happen. Like, I didn't need to be talking about yoga pants. Like, I had real things I was trying to manage.

But without acknowledging the humanity, that's actually what it looks like. It looks like this messiness that leaders end up going, I shouldn't have to deal with this. And you're right, you shouldn't.

If you can deal with the humanity first. Like, if you can deal with the humanity, a lot of that goes away. And we missed that opportunity.

When you ask about leaders who have done it well, I think we see fewer of those. I would say they're more the exception rather than rule. The reality is we see more of what I saw.

We see more where it's just uncomfortable and we avoid it.

[Roger]

And I think for leaders right now who've never been equipped to identify and to better connect with people, we need it more than ever. Whether it's everything that's going on in the news, politics, the environment, the economy. We're telling people, bring your full authentic self to the workplace.

And leaders don't know how to handle authentic, people being authentic in the workplace. And so we've really put leaders in a very difficult place right now, circumstantial as well as by duty. And by not equipping them and not reinforcing to deal with the humans in front of them, we're doing them a disservice.

[DeDe]

Yeah. I spent a lot of time thinking about this, which is, are women inherently better at this emotional space? And I think a few years ago I would have told you yes.

I would have said, oh yeah, women are inherently better. And then I met my partner and he is one of the most empathetic people I have ever met. What being around that every day really taught me, because he is so empathetic.

The second I talk about any type of frustration or something that has bothered me, he is just... I've never seen anyone who has such a skill at naming the emotion under the emotion you're expressing. He's just so good at it.

And what I realized is that I don't know if I believe any longer that women are inherently better. I think empathy, emotional recognition, understanding the human experience, I think it's a human trait equally available in men and women. I think the difference is women have been given permission to practice it in society more.

We've been given permission to wrestle with it, to stumble through it our whole lives in a way most men haven't. And so I don't think it's... I think of emotional recognition and understanding empathy and humanity is quite like a muscle.

And I think women have just had the opportunity to get more reps.

[Roger]

And I love the conversation you had with Simon Sinek recently, where you talked about the subject about male versus female leaders and male and female traits. And I love the idea that maybe part of the problem with the conversation is that we're labeling them as feminine or masculine. When you used another word that I love, permission.

We all have the ability to access those traits. Just culturally, females have had the permission and males have not. Well, is that a permission slip we can write for ourselves?

[DeDe]

Yeah, right. When we first started dating, I met him right before COVID. So COVID changed a lot in my life.

I had come home from work one day and I was talking to my mom on FaceTime. And my mom is a cashier at a grocery store in my hometown of Dubuque, Iowa. And she was telling me about being at work and this woman coming through her line and this woman saying, oh my gosh, I have all these kids back in the house.

I've got to cook three meals a day again. She's got a cart full of groceries. And she says, and sometimes it's just so overwhelming.

And I'm like, and as she did that, remember, this is the start of COVID. As she did that, spit flew out and landed on my mom. And that's where I get my sailor traits from.

My mom is a sailor through and through. And so she immediately started cussing this woman out. You can imagine, my mom's five foot two.

You can imagine this little woman just cussing you out. And so she's telling me about this. Now, I come from a background in the military.

I'm a fixer. I always joke around and say vanilla ice. You got a problem?

Yo, I'll solve it. I jump in to make things happen. And so I immediately start asking her, mom, her manager and I went to high school together.

And so I was like, mom, have you talked to Mike about getting the plexiglass? Are you wearing your mask? Are you wearing sleeves?

Has Mike gotten the plexiglass? Do I need to call Mike? I will call Mike.

And my mom's like, I do not need you to call Mike, like chillax. So I start like scolding her on all these things she needs to do to protect herself. And she does what she always does when I was in Colonel mode, which is, okay, okay.

And she's kind of like, you can tell, right? She's starting to shut me down. She's not really listening.

She's appeasing me at this moment, this moment. And Stefan starts to come downstairs and I get super excited because I'd been single my whole life. So it was always one V one me versus my mom and her trying to, me trying to convince her I'm right.

And I suddenly now think, Oh, I got backup. Cause you know, she really likes Stefan. She trusts him.

And so I now have reinforcements. And so Stefan comes down the stairs and I say, mom, tell Stefan what happened. And so Stefan comes and he sits down and my mom starts telling him the whole story and Stefan's listening.

And when she finishes, he goes, Oh, that must've been so hard. And I watched my mom just melt. And she goes, it was.

And I was like, are you kidding me? You were supposed to be my backup and you're agreeing with her. And so, you know, she of course like loves him and like two weeks go by.

And I say something to her, I said, Hey, I have some bad news. And she says right away, you didn't break up with Stefan. Did you?

And I'm like, no, Stefan is still here. Don't worry. I mean, we're together now.

So he, he made it through, but, um, but I just watched it was, it was like that moment where I realized two things, like one, it is who he is. And while he has had practice to build it, it is who he is. It's in there.

And he just had to do the work to bring it out. And two, that empathy, we talk so much about empathy with leaders. They think it's this deep enmeshment into another person's emotion and all.

And I think they really wrestle with empathy versus accountability. And he showed me that that's not it at all. It was as simple as saying, Oh, that must've been hard.

And he saw her, he saw that moment. And so it was such a, it was such a shift for me on how easy empathy can be and how, and what it looks like to practice it and how we can build it. It was, it was kind of like, I still give him a hard time about that moment.

Cause I'm pretty sure she said, I love you before I did. Like she's.

[Roger]

So DeeDee in this moment, what do you know to be true about your superpower of telling truth to power in a way that's disarming and not harming?

[DeDe]

What I know to be true is that the things we are most afraid to say are actually probably the things everybody actually wants to hear that being the one to say it again, with kindness in a way that is not an attack in a way that sees the person who's receiving it's humanity, right? If you can deliver the thing that needs to be said that probably everyone wants to hear it as a gift. Sometimes I work with leaders and they'll say, well, I really don't want them.

I don't want them to feel like I don't care. I don't want them to feel like we haven't taken this into consideration. And then I'll say, well, why don't you just say that?

Why don't you just say it? Like, just say it. We spend so much time in our heads thinking through, like, I don't want this.

I want this. I don't want that as we're trying to manage relationships when most often what we need to do is just be kind and honest. And so I'd say, just do it.

Like, that's what I know to be true. You have to just do it.

[Roger]

You're reminding me of a manager that, I was a consultant at a tech company here in Seattle, and in this 800 person organization of all the leaders in the organization, the one leader that had the highest engagement scores was a line manager. And so my client said, hey, go have a conversation with the manager and find out what do they do? Yeah.

What's the bright spot? So I went and talked with the person. I set it up just like I just said of, like, hey, you have the highest scores than any other manager.

And the first thing he says is, oh, that's funny. No one's told me that. I'm like, okay.

Like, note to self to talk to the leader about that. I asked him, so what is it that you do that's different than anyone else? Can you articulate that?

And he's like, yes. I make sure my people know I give a shit about them. Oh, yeah.

You know, that's verbatim. I've never forgotten it. And I tell the story over and over again, because there's something so visceral about that.

You know, when someone gives a shit about you and being a leader, like, how do you do that? What are the actions? What are the things you say?

And I think it is saying the damn thing.

[DeDe]

It reminds me of the story about the chairman. And when you say, the chairman's staff, the chairman's team, when you say they knew I gave a shit about them, what would it have said to the people in that building if we could have sent out a letter that said, I know what you're navigating. I know you're struggling with the fact that you have to be here and you go home to loved ones.

And I know that we don't know everything we would like to know about this virus just yet. What would it have said about our ability to show the people that they were cared for? Because you're acknowledging their reality.

And I want to be very clear, like, this wasn't the chairman. It was like the chairman's staff. We were having the debate.

But it was the letter. It was the chairman's letter that was going out. And what would it have done for the people on that team if they would have gotten a letter that said, we see you and we care.

And that was a missed opportunity. And I probably should have fought harder with the chairman to tell him that we had that opportunity. That was my mistake that I didn't go in and say, hey, this is what we're thinking about doing.

But I think it's a really great point. Like, people know you care through almost everything you're doing. You have the opportunity to communicate, whether you do or not.

Deedee, what did you believe early on about your superpower that you've come to learn is not true?

[DeDe]

What I believe now is that we need more of it. Whereas before, I believed what's not true now is that no one wants to hear it. Like when I was a junior officer, I really kept quiet.

And I believe now, especially having led junior officers, being a senior leader, having led junior leaders, man, how much I want to hear what they think. Even if it's like, that's never going to work. Okay, good.

Tell me what gives you that? What helps you form that opinion? What is the background you're using?

What are you seeing that makes you believe that? Now I'm like, tell me everything. Speak truth to power.

Don't be afraid to share with me, even though I'm in a position that you think is senior, like there's so much we miss. And I think a lot of leaders know that, but I think that's it now. Like I would say what's not true is that it's not needed.

It is needed.

[Roger]

So what's next for you and your superpower?

[DeDe]

Well, I have a coauthored book coming out in July where I talk a little bit about the historical leadership manual and what it tried to tell us specifically to women. So this book is called Luminaries, Women Leaders Who Light the Way. And so it's taking a look at what the men in 1948, what they shared and how that applies to us as female leaders.

Really kind of telling us like, get in there and just do it. And then I'm also working on a longer book, which you and I have talked about before. I'm working on a longer book about really digging into the wisdom that was there that we've lost and why did we lose it?

And what is the cost we're paying because we've lost it? So I'm furiously typing away.

[Roger]

Yeah, no, I'm very excited to see that. Came up in our first conversation, this idea of that manual that talked about a love for your colleagues, a love for the people that you lead. And I think again, it's in line with what that manager told me about giving, making sure your people know you give a shit about them.

[DeDe]

And often a lot of what I'm reading is they would say, people were showing up having no training in the aircraft that they were about to employ. They were learning everything on the go. And there's a quote and it says, the more powerful the technology, the more your people need to know you see them and not just the system.

And it's like, that is so perfect for today. The more powerful AI becomes and the more we lean into it, the more our people are going to need to know that we see them.

[Roger]

If an audience member wanted to follow you or ask you a question, where do you want to point them to?

[DeDe]

I'm on all the socials, LinkedIn, Instagram, and then of course my website DeDe Halfhill.com. I'm on, I don't have YouTube videos, but I have YouTube shorts. So DeDe Halfhill is a pretty unique name.

I think there might be one other out there in the world that is, we've kind of reached out to one another because it's such an odd name. And so if you just Google Dede Halfhill, I'll show up, I'll show up somewhere, I'm sure.

[Roger]

Dede, thank you so much. This conversation was everything that I was looking forward to. Your experiences and your wisdom are just so compelling that I feel truly honored to be able to be in conversation with you and be able to ask you the questions about your background and your superpower.

And I am so looking forward to the work that you're doing about understanding what leaders knew in 1948, and we've lost touch of, because I do believe wholeheartedly that that's what's going to help us rise to the moment and help establish better leaders, better teams, and bring more humanity into the workplace. So thank you for the work that you're doing. It's really important.

And thank you for taking the time to share in with me.

[DeDe]

Thank you. It was, feeling is mutual. I really enjoyed our conversation, so thank you.

[Roger]

Okay, until next time. Take care. Bye-bye.

[DeDe]

Bye-bye.

[Roger]

Thank you all for being here, and thank you, Dede, for sharing your superpower of telling truth to power in ways that disarm and not harm. What do you know to be true is a 3 Blue Pens production, and I'm your host, Roger Kastner. We are recording on the ancestral lands of the Duwamish and Suquamish people.

If you enjoyed this conversation, you'll love this one with Carrie Lynn Stanton Downs on how a leader can increase their relational capacity. And also check out this conversation with David Hutchins on how to create deeper emotional connections and transformation through storytelling. Okay, be well, my friends, and as always, love you, mean it.