500 Times in a Spiral Notebook: Lessons in Listening with Linda Rutherford (Part 1)

What does it take to go from an entry-level employee to the Chief Administration Officer of one of America's most beloved companies?

In Part 1 of my conversation with Linda Rutherford, we explore Linda's remarkable career journey from the newspaper industry to the executive leadership team at Southwest Airlines.

After losing her newspaper job when her employer closed, Linda found an opportunity at Southwest and spent decades growing into one of the airline's most influential leaders. Along the way, she discovered that one of the most important leadership skills isn't speaking—it's listening.

Linda shares how a fifth-grade teacher changed the course of her life by making her write the "Wise Old Owl" poem 500 times in a spiral notebook, a lesson that would later shape her leadership philosophy, influence her writing on listening, and guide her contributions to books on leadership and organizational change.

In this episode, we discuss:

• Making career pivots after unexpected setbacks
 • Growing from an entry-level role into executive leadership
 • Why listening is one of the most underrated leadership skills
 • The leadership lessons behind her published work on listening and change management
 • How childhood experiences can shape a lifetime of leadership

If you've ever faced a career detour, wondered how leaders build trust, or wanted to understand the difference between hearing and truly listening, this conversation is for you.

Thanks for Answering the Call.

🎙️ Caller ID Podcast: where life, career, and identity meet.

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Transcript

SPEAKER_04 0:00

So David reached out and asked us to look at the different differentiators. And when I saw the one around listening and leadership, I felt drawn to it just because of a lesson that I learned many, many years ago that I continued to try and apply. I think we called it listen before you leave, but it went all the way back to an experience I had in fifth grade where my my sweet fifth grade teacher, Mrs. Farrell, used to send home notes on the progress report that said, you know, great in academics, but excessive talking.

SPEAKER_00 0:32

You and me both, Linda.

SPEAKER_04 0:34

And then she just had enough of me and uh I was punished basically, and I had to write a poem called The Wise Old Owl and had to write it 500 times in a viral notebook. And I've never forgotten it. I've never forgotten the poem to this day. David asked me to sort of recount that story and then how I've taken that from my childhood into my professional life. And I think one of the things that we all of us in business can do more of is just hit the pause button, take time to listen and to reflect, and then to make sure we truly understand what's going on or who we're talking to before we are so quick to sort of jump in or interject with our own point of view or with a solution that someone might not even be looking for. I I honestly have to get up every single day and remind myself to stop and listen. Um, and that you know, that applies to my personal life and the things that I do professionally. And so I and I think that you know, we're all eager to learn and contribute and participate. That I think sometimes it's well-meaning, but sometimes we forget to listen.

SPEAKER_01 1:50

Hey everybody, this is Caller ID. We're calling about your identity, your direction, and what you're doing with your life.

SPEAKER_02 2:04

There's a question I keep coming back to when I think about careers, especially longer ones and ones that stay at one place for a long time within that career. How did your career shape your identity? And how did your identity kind of, you know, how is it kind of how did it kind of shape your career? So those things kind of go hand in hand. And also I'm always curious when I talk to somebody that has stayed somewhere for a long time, because that's always been a challenge for me and a lot of my generation as well. Most of us don't draw a straight line from who we were at 18 to who we become. We take turns, we say yes to things we didn't expect, we grow into rooms that we never knew existed. Well, my guest today spent decades at one of the most recognizable companies in the United States and really globally, Southwest Airlines, building a culture, helping lead through crisis, and eventually earning the title of Chief Administration Officer. Also the winner of the 2025 Betsy Plank Award for her work with young professionals and a contributor on a new book, The Heartwork of Modern Leadership: Six Differentiators of Exceptional Leaders by David Grossman, and I can't wait to ask her about that as well. Welcome into Caller ID, Linda Rutherford.

SPEAKER_04 3:15

Thank you so much for having me.

SPEAKER_02 3:17

My dad worked with you uh as a partner with with in PR. And when I said, hey, I'm looking for guests, I'm looking for folks that might be able to share some things. You were the first person that came to his mind as somebody that not only was really good at their job, but also was kind. And so I thank you for coming on. He really sends his greetings to you as well.

SPEAKER_04 3:37

Uh well, please give him my best. Um, he was a joy to work with.

SPEAKER_02 3:40

You know, he said that Southwest Airlines was one of his favorite clients, if not his favorite client, although he said sometimes it's like your children, it's hard to pick a favorite. But he said one of the reasons was the culture. And I want to ask you about that before we dive into your career about Southwest, and no company or or corporation or organization is perfect, but they really did seem to live by the golden rule that was apparently on the wall by the cafeteria. Is that is that what you found there too?

SPEAKER_04 4:08

Absolutely. In in my 30 plus years um with the airline, you know, there's there's a lot of growth. Um, there were a lot of exciting things that happened. There were a lot of sad and scary things that happened along the way. But one of the things, one of the things that really stayed constant was that jovial workplace. I mean, we we we worked hard, but we played hard, we respected one another in times of crisis, both personally and professionally, we took care of one another. And, you know, I I spent a lot of time there. So I really don't have a lot to compare it to in terms of other workplaces, but I believe that even through all of that change, it's a very special place. And I think that is because of the kind of people that we search for and recruit to come to Southwest who are wired to serve others. And when you come from that kind of uh value system and upbringing and orientation, I think it creates a really special place to work.

SPEAKER_02 5:11

Do you think that's why you stayed there for basically your entire adult career?

SPEAKER_04 5:15

It's one of the reasons, certainly. I mean, it's a workplace that allows you to bring your full self to work. It takes the work seriously, but we don't have to take ourselves too seriously. Um, I was fortunate enough to work with and for leaders who allowed me to spread spread my wings and grow. Even when I started to get those seven-year itches, like I might need to go somewhere else. I was asked, what do you what do you need? Like, what do you what do you need to do in order to continue to learn and grow? And Southwest and my leadership provided that. So it was definitely one of the reasons uh why it just continued to be a great place to work. You know, I know that for the thousands of people that work there, and I knew it to be true for me.

SPEAKER_02 5:57

So you're retired now officially, although that doesn't mean you're not doing anything, you're you're doing a lot of work on the side. What are you up to nowadays in retirement? And how is that? This is kind of a twofold question, how has that affected your identity and kind of like how you view yourself? Because I think we all sort of identify at some point with our job and the work that we do. But when you retire or you shift jobs, or maybe you're somebody's laid off or or they're not sure, like how have you approached that?

SPEAKER_04 6:25

So in April of 2025, I retired from my executive duties. Uh, I do still serve the airline as an advisor. So on a consulting basis, most of that work is in leadership, coaching, and mentoring uh these days, because that's really how I spent the last four years or so of my career at Southwest. I would say, in terms of how I describe myself now, I've actually been pleasantly surprised. I thought that when I retired, so much of my identity was tied up in Southwest Airlines that I wouldn't really be getting a lot of phone calls, emails, asks to do to do things. And I've actually been blown away by the activity post-Southwest. And so I and I guess I really thought about it, but I assumed it was sort of the brand and the notoriety of the company that I worked for. Um what I've come to realize is it was, you know, more about, you know, talk about the the lessons that you've learned during your career and your experience uh and things that you you know did while out south at Southwest. And so um I've been doing some teaching uh at the collegiate level. I've been contributing to some books that colleagues are writing, and I'm actually co-authoring a book right now on change management with a colleague who just retired from Notre Dame. Those are some things professionally that keep me fulfilled, and then personally, my husband and I have been definitely working our way through our travel bucket list.

SPEAKER_02 7:52

The the writing, and and you know, you're but you're part of the the book from uh David Grossman. You wrote a chapter um about learning to listen, I think. And in how like I've always talked about how hard that is for me as an external processor, as somebody who's an extrovert that has had to work really hard at listening to people, regardless of whether it's in a leadership position or just in my house. Um, you know, what makes that so important in the workplace? What why was that the chapter that you were like, or that David reached out to you, or that you said, I want to write that?

SPEAKER_04 8:26

So David reached out and asked us to look at the different, you know, differentiators. Um, and when I saw the one around um, you know, listening and leadership, I felt drawn to it just because of a lesson that I learned many, many years ago that I've continued to try and apply. Um, I think we called it listen before you leave, but it went all the way back to an experience I had in fifth grade where my my sweet fifth grade teacher, Mrs. Farrell, uh used to send home notes on the progress report that said, you know, great in academics, but excessive talking. Um you and me both, Linda. And I I was uh I was punished basically, and I had to write um a poem um called The Wise Old Owl, and had to write it 500 times in a spiral notebook. Um, and I've never forgotten it. I've never forgotten the poem to this day. Um, and so uh David asked me to sort of recount that story and then how I've taken that from my childhood into my professional life. And I think one of the things um that we we all of us in business can do more of is just you know hit the pause button, take time to listen and to reflect, and then to make sure we truly understand uh what's going on or who we're talking to before we are so quick to sort of jump in or interject um with our own point of view or with a solution that someone might not even be looking for. So I I honestly have to get up every single day and remind myself to stop and listen. Um, and that you know, that applies to my personal life and the things that I do professionally. And so I and I think that you know, we're all eager to learn and contribute and participate that I think sometimes it's well-meaning, but sometimes we forget to listen. So David reached out and asked us to look at the different differentiators. And when I saw the one around listening and leadership, I felt drawn to it just because of a lesson that I learned many, many years ago that I've continued to try and apply. I think we called it listen before you leave, but it went all the way back to an experience I had in fifth grade where my my sweet fifth grade teacher, Mrs. Farrell, uh, used to send home notes on the progress report that said, you know, great in academics, but excessive talking.

SPEAKER_00 10:50

You and me both, Linda.

SPEAKER_04 10:53

And then she just had enough of me and uh I was punished basically, and I had to write a poem called The Wise Old Owl and had to write it 500 times in a spiral notebook. And I've never forgotten it. I've never forgotten the poem to this day. David asked me to sort of recount that story and then how I've taken that from my childhood into my professional life. And I think one of the things that we we all of us in business can do more of is just hit the pause button, take time to listen and to reflect, and then to make sure we truly understand what's going on or who we're talking to before we are so quick to sort of jump in or interject with our own point of view or with a solution that someone might not even be looking for. I I honestly have to get up every single day and remind myself to stop and listen. Um, and that you know, that applies to my personal life and the things that I do professionally. And so I and I think that you know, we're all eager to learn and contribute and participate. That I think sometimes it's well meaning, but sometimes we forget to listen.

SPEAKER_02 12:00

Tell me about the new book. Um, I mean, I know we're not we're talking books and we're gonna get in, you know, this is part of your career arc, but I'm also fascinated as somebody who is married to a writer. Um, my father was a writer. Um, you know, tell me about the new book and what what's going on there.

SPEAKER_04 12:17

So my background is actually in newspaper and magazine journalism. So before I went into a career in public relations communications, um, I too have a love of writing. And uh as I was retiring from my executive duties, I had a colleague at Notre Dame ask if I would be interested in co-authoring a book with him. Basically, it is a book uh that is told in case study form. So we're talking to 12 big brands who have been through massive transformational change, and we talk about the role that change management takes in making sure that that transformation is successful. So, in other words, chief communications officers are often called upon to, you know, create communication strategies, and more and more, the complexity of that change, the speed of that change, and the technology disruption of that change have communications professionals having to lean into change management to help their organization get change to stick. I always joke that you know, with with how complex things are today, you can't just call the all hands meeting and write the memo and say, poof, we've changed.

SPEAKER_02 13:26

Right. Wow. Well, I'm I when is that book due out?

SPEAKER_04 13:30

So we hope to get it finished um early summer, and then hopefully by late summer 2026, um, we'll have a a completed book that that'll be um out and available to readers. Um right now we're calling it Pivot.

SPEAKER_02 13:43

When you think back to when you were 18 looking at college, is this what you thought your career would look like? Is there is there any way you could have looked forward and said, I want to do these things? What were you thinking at 18?

SPEAKER_04 13:56

Well, if I could back up one more step from there, in the age of 12, I knew I wanted to be a newspaper reporter. And it was because I fell in love with a TV show that was on years ago called Lou Grant. Oh, yeah. And uh it had Ed Asner as this sort of grumpy newspaper editor and then a newsroom full of personalities. And I was obsessed with that show and knew right then I wanted to be a journalist. And I wrote for my high school paper, I uh studied journalism in college, I wrote for my university paper. When I got out of school, I worked for Newsweek magazine, and then I worked for a number of newspaper chains, and um last was at the Dallas Times Herald, which was then the other uh competing Metropolitan Daily Newspaper.

SPEAKER_02 14:40

Yeah, you see, you see kids out there listening. There used to be multiple newspapers in pretty much every city. Now you're lucky if you have one.

SPEAKER_04 14:47

Yeah, we're lucky if you have one now. Um, and so you know that was my background. So I I honestly knew I knew what I wanted to major on when I went to school, I knew what I wanted to be. That career lasted about four years after college when I was working at the Dallas Times Herald and the Dallas Morning News bought the Dallas Times Herald and shut it down. And so I think I was around 24, 25 years old and was kind of like, huh. Um, you know, I had to pivot and decide what I might want to do differently. And honestly, I was afraid to go to work for another newspaper because of what had just happened, you know, to my workplace. And so um I had been covering airlines at the time uh for the Dallas Times Herald and was lucky enough to, you know, have Southwest Airlines say, Hey, would you be, you know, would you be interested uh in something called a public relations coordinator? And so I remember having to ask, well, what exactly is that? So, you know, they told me they wanted me to do media relations and help uh pitch stories to the media. And the reason they thought that I would be great at that job is because I was a member of the news media and knew what a good story looked like. I started work with Southwest June 1st, 1992, and my first job was to go to Dallas Fort Worth uh airport and get on a Delta flight at the time and fly to Columbus, Ohio, because Southwest was starting service there, and our then CEO Kirk Kelleher was giving a chamber speech. And so I was going there to help support that event.

SPEAKER_02 16:16

You know, I think so many of us have started out in something, you know. For me, I I studied journalism as well in college, and I studied on the broadcast side, and so many of us have started out in one thing and ended up in something either adjacent, right? Which is sort of what ended up with you, and you know, or something completely different. That happens too. I don't know if you know this, but my dad's story is a little bit similar in very I don't know if you guys have had that conversation, but yeah, working for the Cleveland Press, they shut down, he had to figure out what was next, and it took him a few more years before he got onto the PR side. What was it that you did? You must have done something right when you were covering airlines and particularly with Southwest, what was it that you think attracted them to you, other than your skill? Because skill will only get you so far. Was it relationships? Had you developed those with folks? Um, you know, how did that transpire?

SPEAKER_04 17:07

Yeah, I had some great relationships. Um, obviously at many airlines, then Continental, which was based in Houston, American, which was based in Fort Worth, uh Delta, which at the time had a big presence at DFW Airport, as well as my friends uh at Southwest Airlines. And so beat reporters developed those relationships with their sources. And so, yeah, they knew me. And I think they sensed that I had a personality that would thrive, you know, at the airline and fit in well culturally, certainly writing skill, experience at media, you know, knowing what the news media was hungry for, and honestly, a mutual admiration society. I mean, I always found that when I arrived on the Southwest campus to cover a story or to interview an executive, I had a hard time being objective, to be honest. And I knew that was my reporter's duty, but there was really something special about that place. And I thought, you know, if I ever had uh the chance to work somewhere like that, I would I would jump at it. So I was very fortunate to get the entry-level role that I did in in 1992.

SPEAKER_02 18:09

How did you work your way up from an entry-level PR coordinator role to basically the head of all communications, right? I mean, you you worked yourself up in one company, you know, and and clearly you liked Southwest, but what was that process like? Were there any twists and turns? Was there anything that you're like, oh yeah, this was this was a pivotal moment? Or, you know, how did that work?

SPEAKER_04 18:33

Two things I would say is that it has all been an on-the-job training. Uh, so kudos to Southwest for investing and pouring into me so that I could be capable in each of the roles that I had. And secondly, you know, as it as the roles turned into executive level roles, I always like to say I was the accidental executive. I didn't mean to. It wasn't like I set out and said, I want to have this role. What I found was when my previous leader was promoted, I saw an org chart one day and it had an empty box in it. And it showed itself as, you know, kind of then being the leader over a team of people. And I was, I kind of looked at it and went, well, now suddenly I'm interested. Like, could my name be in that box? And I'd never really given it a lot of thought. And so I remember talking to my leader who'd just been promoted and said, Well, who are you thinking about for that role? And she said, Well, I don't know. I actually need to give a recommendation to HR or why are you interested? And I said, Well, I think I am. And so it was literally just one of those aha moments where, you know, I wanted to take the skills that I'd learned and add to them in a way that wasn't necessarily about, you know, the capabilities tied to communication, but the capabilities tied to leadership and how to be a good leader. And so that kind of opened a whole new set of doors that once I was leading communications again over the years, had different responsibilities come to me. So the I was, you know, a VP in the communications area and then became the chief communications officer. And then when the new CEO came into his role, I took on additional responsibilities for people and leadership development or what people call HR. And then I was given responsibility for technology and AI and data transformation. I had internal audit reporting to me, communications, DEI, and then culture and engagement. And really, as I said, the last four years or so of my career, I had a number, as chief administration officer, I had a number of those functional areas reporting to me, basically everything that was non-operating, um, except for you know the commercial area, finance, and legal. And what my CEO said to me is look, I don't need you to be an expert in technology or internal audit. What I need you to do is be an expert in leadership to get those functional leaders ready to take their next step. And so that was a lot of fun, honestly, to get our, you know, our head of technology ready to be a very strong CIO and to get our head of people ready to be a chief human resources officer, and to get what was then a VP of you know culture and communications ready to be the chief communications officer. And so it was really exciting to kind of then lean into the leadership experience and lessons that I've learned along the way and apply them to toward getting the next generation of leadership ready.

SPEAKER_02 21:28

It explains your penchant for teaching, right? And your you're like it sort of fleshes out like, oh, I bet you would have been a good professor all along or a good teacher. Like you clearly have that skill, but you also, I'm sure, uh, developed it over that time. Was there ever a time where you're at Southwest where you had opportunities to leave or you thought about leaving? Because I know for my dad who worked for uh Dixon Eaton for a long time. He had some opportunities to go and had to weigh the pros and cons. I'm sure you had opportunities or people approached you. How did you weigh staying where you were versus other opportunities?

SPEAKER_04 22:02

First of all, yes. You know, in that span of time, you certainly think about whether it's a call from an executive recruiter or a call or you know, just some thinking around should I actually leave and get some diverse experience to then bring potentially bring back to, you know, to a place like Southwest. You know, did I need to go somewhere else in order to be considered then for a you know a higher leadership role? All those things cross your mind.

SPEAKER_02 22:26

Yeah, it reminds me, sorry to interrupt, but it reminds me of when you're an assistant coach, and a lot of times people will say, you need to go be a head coach at a smaller school, at a smaller thing, in order to then maybe come back to the place that you love, right? So I didn't mean to interrupt you, but go ahead. Yeah.

SPEAKER_04 22:40

No, you're exactly right. So those all those thoughts are going through your mind. I think the two reasons that I um didn't pursue those opportunities. One is I was always very fortunate in terms of an immediate leader and then the CEO leadership, just to have people who continue to see my value, continue to ask me what it would take to stay. So had the stay conversations, which I really appreciated. And then I have a wonderful mentor who used to be a chief communications officer and and is now in the in teaching at the College of Charleston by the name of Tom Martin. And I've had several conversations with Tom about you know career pivots and and whether or not I should consider a different opportunity. And he always turned back and said, Lynn, I want you to think about where you work right now. And let's he said, in my view, you're in one of the top five places to do communications on the entire planet. Wow. He said, is the place you're considering to go right now one, two, three, or four? And you know, I had to be honest with myself and say, No. And so, you know, that would often, you know, sort of uh solve that uh in my head for me. But a great help, obviously, to have a mentor like that um to really challenge my thinking. But I those are the two reasons why I ultimately stayed and chose to build and then and then finish out my you know leadership career at Southwest.

SPEAKER_01 23:59

This was part one of the two-part conversation with Linda Rutherford, retired from Southwest Airlines. Come on back next week, check out the episode. Don't forget to subscribe, like, and share with all of your friends. Peace thanks for listening to the call on ID. Don't forget, don't forget, don't forget, don't forget, so we can get a lot of things.