This episode of our podcast is titled “Becoming A Learning Leader.” It features a discussion with Doug Wiles, president of Herbie Wiles Insurance and former minority leader in the Florida state House of Representatives. We talk about the importance of listening, planning leadership succession, the signs of a healthy work culture, and more — have a listen!
Podcast: Play in new window | Download
Podcast Episode 10: Becoming A Learning Leader — Doug Wiles Interview
Robert Mixon:
Welcome everyone to the Level 5 podcast series as we continue our journey today. We’re privileged to have as our guest for our interview today Mr. Doug Wiles, President of Hervey Wiles Insurance, and the former Democratic leader of the Florida House of Representatives.
I’ve had the privilege of knowing Doug for about four decades now, give or take, and he has been a leader in both the military, both in the active Army and in the Florida National Guard.
He’s been an active leader in the business community, with a very successful insurance company there in headquartered in St. Augustine, and he’s been someone that I’ve admired and respected as a leader and a friend.
So Doug, thanks for joining us today as we talk about the topic, an easy one here, on becoming a learning leader.
Welcome to you, Doug.
Doug Wiles:
Well, good to be here with you, Robert, always.
Robert Mixon:
So we have some questions that I want to put forward and then obviously you can take it however you want to go, Doug.
I want to talk about your journey as a leader and some of the lessons you have learned, and I think the first question that I had in mind here was to ask you: what’s the most important aspect of being a learning leader that you have observed throughout your journey?
Doug Wiles:
Hmm, that’s a tough one… because I don’t think leadership can be put into nice, neat little containers and set aside, and you pick a little one here when you need it and others.
It’s a package, but you know, when you look at what I admire most and I think is most important is the ability to listen.
To reach out, to understand those that are working with you and for you and essentially those that you work for — to try to understand what they understand, and what they’re experiencing.
In fact, I really kind of like to work in the trench, as much as I like to work, for lack of better words, in the executive suite.
I think it gives me a perspective that is unique, and it allows me to hopefully make some good decisions, you know, in the future as well. Robert, when I was the minority leader in the House, Florida House, I worked with a very, very diverse group of members from all over the state of Florida.
Just like in Congress or in any political body today, everybody’s got their own idea, and they come to that based on where they’re from. And once you can understand a little bit better where they’re from and what sort of gave them their perspective, you begin to understand them a little better.
So one of my objectives when I first was elected to the House, goodness, now it’s 24, 25 years ago, I traveled around the state of Florida just to meet these folks, to get them to introduce me to their neighborhoods and their friends and sit around and visit with them for a little bit. I mean, heck, a lot of them, I didn’t agree with their positions… but the point was at least I could appreciate their position and understand. And with that came the ability to lead more effectively.
It was just as simple as asking or not asking somebody to do something when I knew it would be offensive to them, or perhaps not in keeping with their own set of values. You know, clearly something that’s missing in today’s political environment, but it certainly was valuable to me with a group of folks that had their own agendas and were sort of ‘type A’ personalities in the House anyhow.
I think that’s no different than really operating a business, but on a much lesser scale.
So, listening and understanding where those that work for you come from, I think has to be on the top of my list.
Robert Mixon:
Okay, thanks, Doug. You know, the Stephen Covey quote about, you know, “most people do not listen with the intent to understand, they listen with the intent to reply.”
I think that’s a powerful statement that you kind of echoed here, the importance of listening with the intent to understand.
Doug Wiles:
Absolutely.
Robert Mixon:
So as far as the Big Six goes, that’s a home run hit in my book, and good for you.
What’s the biggest mistake, perhaps, that you made as a leader when you could have learned through self-examination, or you observed someone else who didn’t learn through self-examination?
Can you share that with us?
Doug Wiles:
Yeah, another one that’s hard to pick. Robert, we could start with probably my first major mistake was not getting my armored platoon out the back gate one Sunday morning for a training exercise because of a complete failure of all of us — me, most importantly — of not properly conducting maintenance on our vehicles!
But setting that one aside, which I still vividly remember today, and that kind of serves as an example of sort of being prepared.
There’s a few years ago, well, more than a few years ago, in my business, we really relied on a very good and a very effective manager, an operations vice president, as a matter of fact, who was well liked and did a great job.
And suddenly, through no fault of anybody, she left.
Doesn’t make any difference why, really, except that it wasn’t adverse. But suddenly, we were left holding the bag, and our staff really felt that.
I’ve got today about 26 people that work for me or with me. It was about the same back then, maybe a few more.
But boy, what a void. And as I began to think about that, wow, as a leader, I really let everybody down… because I really failed to plan for that possibility.
There was really nobody in line to step up and take her position. And it was an awful lot of hard work with those of us who had other duties and responsibilities to really step in.
So, from that point on, we’ve tried not to be unprepared for most potential things that could happen.
And I mean, frankly, we’re all put on this earth for a given period of time. And we could be taken for any reason… automobile accidents, stepping in front of a train. If that happens to a key leader in the world, what do you do?
And beyond that, I think, in Florida, at least, we have lots of other contingencies like hurricanes, and other nasty things that could happen. And if we’re not really prepared for that, you know, it could be a disaster. The irony of it is, we were pretty good at preparing for natural storms and hurricanes.
We were terrible back then at really lining up our leadership.
So I think the failure to plan was really one of the most painful things for me, other than failing to get out of the back gate in 1975!
Robert Mixon:
Well, that’s an excellent point, Doug. You know, “who’s the next you?” is an important question, I think we all need to ask ourselves when we’re in position of leadership. “Who’s the next you?”
And have that ‘next you’ identified, and do something about getting him or her ready to assume the role — before they have to step into it, I think is where you’re going.
Doug Wiles:
Well, exactly. And I think when it comes to personally, you know, that’s probably the hardest thing for most leaders to do. I mean, we’re enjoying ourselves, life is good. No plans for retirement. You know, why do I need to plan that way?
But I’ll tell you, from what I’ve seen, the most effective leaders are those that have a plan after them, a succession plan.
And I think it does more than just give you some level of comfort. It means that you’re really preparing your subordinates, those that work for you for that next opportunity. Those that understand will deeply appreciate that.
And now you’ve got a much more competent, much more educated, much more prepared staff. But, you know, beyond that, it’s the right thing to do. Bottom line. I’m surprised at how many of us really don’t do that.
Robert Mixon:
Excellent point.
Next question I want to ask is we’re talking about the journey here, you know, is how do you identify which managers, and I think by managers, we’re talking about those who steward resources, right? How do you identify managers that could become leaders who could be responsible for others, in addition to allocating and controlling resources?
Because some never make that transition very well. And we, you know, we’ve made the mistake, I certainly have, of putting some managers in leadership positions who weren’t who weren’t ready for that, or didn’t have the ‘DNA’ to do it. What’s your thoughts?
Doug Wiles:
Goodness, I think we’ve all, you know, even in our best guess, or best analysis, have always not found the right person.
You know, it’s an interesting question, especially given what we just talked about.
You know, the irony of that story is that the person who is the vice president of operations for my business today was the person in 2007 that reached out to me that stepped up and said, “Wiles, I know you got a problem. If there’s anything in the world I can do to help with the departure of this manager, I’m here, let me know.”
The other irony of that is that they were one of the most junior members of my staff.
In other words, the folks that I would have expected to jump into the breach and help me with the fire, they were there… I think they did what they thought they could do.
But the person who really made the difference was someone who’d been with us about four months. And so we gave her that chance and gave her that opportunity.
And the rest is history. And today, she’s literally number two in the office.
So, I mean, that goes to show you what anyone can do if they’re ready and are prepared to accept leadership.
But beyond that, I think what you asked is, well, how do you identify those folks? … I don’t think there’s a single set of criteria that we look at. But I’ll tell you a little bit of what I think.
One, it’s looking for people who step up for the tough jobs when nobody else does. I think that shows teamwork. I think it shows commitment.
I believe it shows that you care… not only about what it is you’re doing, but those that you work with. And it could be just something as simple as, you know, “I’ll lock up the office tonight.”
“Or yeah, it’s a mess in the bathroom. I’ll clean that up for everybody else.”
Or, as I find sometimes when somebody is on vacation who has a kitchen duty, we call it, that is: making sure the dishes are clean. Somebody will go in there every night, even though the person responsible happens to be out of the office, and they’ll clean it up for us.
So somebody that steps up.
I think the second thing I like to see and I look for is: somebody that’s got bigger ears than they have a mouth! Somebody that, it’s funny, but the person that stands in the crowd or on the edge of the crowd in the team, and they’re listening and observing, so that they can understand what’s going on.
I think it’s a lot better than the person in the of that crowd who’s beaten on their chest all day long. I think that shows maturity and a sense of reserve that many of us look for in leaders.
I think the third thing is, especially if you’re looking within your own group, you know, who is it that gets the respect of others?
And I think you got to give respect in order to get it. And we want respectful leaders, those that understand, you know, how the buttons are pushed, but also who are caring enough not to ask their subordinates to do something that they wouldn’t do either. And I think I see that in our team, and our work with those who really get a little more attention, a little more respect.
“Oh, give it to Joe. He can handle that.”
And then finally, and I think obvious, I think you need to have somebody that’s smart.
And I don’t mean that necessarily as book smart. I think just smart when it comes to, you know, they’re working with others and understanding, you know, what makes the world go around. And that’s an intuitive sort of smart.
I think more importantly, in being smart is to understand how dumb you are, so that you don’t make the same mistake, and perhaps you’re calling on somebody else to give you a hand.
So, that’s sort of my summary of what we’ve looked for in the past. And, you know, sometimes it works, and sometimes it doesn’t.
Folks have a tendency of, I won’t say fooling you, but you know, you may misunderstand a few… you have a pretty complete package, you know, if you look at somebody who steps up, who listens, who’s respected, and who’s fairly street smart.
Robert Mixon:
Yeah, good point. I think those are four excellent components of leadership, as far as ingredients of being able to be responsible for others, as opposed to simply stewarding the resource, which could be, you know, finite resources and not necessarily people.
Given that, you know, being able to have someone you identify who steps up, that seems to be an essential ingredient of a healthy culture.
What else do you think is symptomatic, or indicative of having a world-class culture?
Dave Wiles:
Well, you know, that’s hard to, it’s hard to sometimes put that into a nice, neat little package, just as it is to identify.
You know, I’d like to think that we’ve got a pretty good culture in my agency. And I see other places that do pretty well, as well.
I think that… I know in one of your books I recently read, “Doing the right thing, even when nobody is looking”… is a clear indication of a commitment to others that you just don’t find all the time.
I kind of look at people that go out of their way to do the right thing as part of a culture that encourages that… not the culture, but at least the person sometimes.
I think a level of trust among members of the team, fellow employees, knowing that they have your back, if you’re called out of the office or you get busy, or frankly, you raise your hand and you need a little help about something, somebody’s going to step up and say, “yeah, I can give you a hand with that.”
And knowing that it’s going to be done right, or, you know, perhaps when the boss has to leave a little early, intentionally or otherwise, that he can do that, or she can do that, without a whole lot of trouble … or a lot of worry. So trust, I think, is in there.
I think, along with doing the right thing is empowering folks to do the right thing.
In my business, we’re all about trying to provide peace of mind and protection for families and businesses across, you know, North Florida. And that means more than just writing a policy.
It means a lot of other things. And I think we empower, try to empower our folks to do the full job, so that when the customer calls and asks a question, the response is not, “well, that sounds like it’s a pretty good idea. Let me go ask my supervisor.”
Boy, that’s a no-no in my business.
You take responsibility for that accountability. If it’s a reasonable and fair thing to do, we’ll figure out a way to do it in the back office.
And so we really try to encourage people to make good decisions. And by the way, I think that helps them become good leaders, because they have a piece of this action now. They’ve got to sell it to me!
We’ll figure out how to do it. But we’re going to ask the person who made the commitment first, how do we fix, or how do we change, or how do we meet that expectation? I think communication is critical.
Man, and boy, is that tough today. Fortunately, most of our staff is in the office during this Coronavirus pandemic, but we’ve got six people who work outside the office as permanent telecommuters. And so when this thing hit, having Zoom conferences and videos and conference calls were not unusual to us.
And we had the hardware and the technology in order to do that, Robert.
So it turned out well, but it’s more than that. It’s having the right number of meetings, even if it’s only for 10 or 15 minutes, to kind of bring us together.
You know, I’m dressed up today in a tropical shirt, because it’s ‘Tropical Thursday’ at my office. It’s kind of a fun thing to do, which I’m going to tell you about in a minute.
But, in order to make that happen, we gathered together this morning for eight minutes, I think it was, total, so that everybody at home could show off their tropical shirts as well.
And some of them had some pretty interesting combinations there! And that brings me to the last point, I think, and part of a culture is, you know, we got to have fun. I mean, this has got to be a good place to go to.
Somebody’s got to wake up in the morning, get through the morning routine with an expectation that they’re going to enjoy what they do during the day. And as I encourage my folks, ‘hey, if you’re not having fun, let’s figure out how we can fix that… Or maybe there’s another place for you that I can help you be, if you’re really not enjoying yourself here’.
So I think those key elements, to me, seem to have worked pretty good for us and other places that I’ve been. Robert … that is a long answer to a short question, but I hope that helps.
Robert Mixon:
Yeah, it’s very thoughtful, Doug.
You know, the ecosystem that we call a culture has some certain qualities.
As you know, it’s been one of my passions over recent years is to identify what those qualities are.
But I certainly think you’ve given us some great insights in that regard.
What advice would you give aspiring leaders to become learners, to be receptive to the idea that things aren’t going to go well sometimes? You know, we need to learn and grow from it.
Doug Wiles:
Well, I think reading is a pretty important part. You’ve published some great books, by the way. I’ve enjoyed reading each one, and I enjoy your blogs, especially the one today, Robert.
But I think leadership and organization… is not something that you can teach, but I think you can identify some traits within yourself if you just know kind of what to look for.
Most people are just not going to be able to effectively articulate what a good leader is to the average person that works for them. So I think getting a good idea, and there’s a ton of folks out there, including you, that write about leadership and what makes organizations good.
I think overall, that not only makes you a better person, but it also makes you a better team member.
I think the second thing is, if you can, is identify a mentor. Pick somebody that you think is a pretty sharp person and look up to him or her for advice and counsel.
They don’t necessarily need to know that you’re a mentor, although that might not be a bad thing to communicate. But find somebody that you can emulate, that you trust, that you feel does a good job, and that you want to be like. Maybe not all the traits, but most of them.
And watch them!
And I think every business that’s worth its weight in gold has got more than a few of those running around.
And they may not even be leaders.
They may be aspiring leaders, folks that understand what’s happening.
And then what somebody, anybody can always do is watch. Watch what’s going on.
Identify things that maybe aren’t going right, and why. Maybe traits in people that are not good. And why is it not good?
Or things that people do that, ‘hey, I’d like to do that one day.’
And watching people is a clear way of doing that. And if nothing else, just watching folks on the news.
You know, there are leaders that stand out, both good and bad, in every nightly newscast that I’ve seen. And they’re pretty quick to identify whether somebody’s doing it right, or whether they may need a little improvement.
So from a national level, right down to your own office, perhaps in your own family, there are opportunities to watch, to find a mentor.
And then certainly to read about leadership and what it takes are three things that I think folks could use and might, especially younger, might really take advantage of.
Robert Mixon:
Okay, thanks. Thanks, Doug. So if there’s one big idea, and we’ve talked about several here, that you’d recommend to our listeners to take away from the podcast today, what would be that big idea?
Doug Wiles:
Well, if I could say two, Robert… I’ll focus on one. I’ll focus on one.
But I really believe that I’ve gotten more by being a listener than just about anything else I’ve done. And a listener and an observer.
And then, you know, finding both good and bad that you can listen to and observe and then create your own opinion.
So, you know, I think we need more good listeners in the world than we need good speakers. So being a listener is key.
But, you know, even more importantly to that is that when your time comes to be a leader, you’re only as effective as you are prepared.
And, you know, by being prepared, I mean, doing the right things where you are in the sandbox today, so that when that opportunity arises, you’re better prepared, you know, to meet the crisis.
In my office is an example… she kept her head down for two or three months.
That opportunity unexpectedly arose when we lost a manager. And all she did was say, “let me help.” And that was a door that opened a crack, and became much wider as time went along.
And obviously, she had prepared herself to, in her own way, to really take over. And frankly, together, we had a lot of mistakes along the way. I mean, we’re all human.
We’re not going to be the best in the world. But the fact that you intuitively are prepared for that next level, for that next job, for that next duty, for that next leadership opportunity, is what I think separates those who are successful initially — and those who fail.
Robert Mixon:
That’s great insight, Doug. Thanks a lot. I think as we reflect on what you’ve given us today in terms of some nuggets of experience and wisdom here, there’s a lot of takeaways that I think our audience can put in their toolbox, whether it’s self-awareness, self-examination, preparedness, and listening.
I think all of those tools are going to resonate with a lot of the leaders that are out there. And I want to say thanks again, my friend, for taking the time to share your thoughts with us and give us some insights. You know, this is ‘a journey with no summit.’
And we’re privileged to have had people like you come on the podcast. And now we have created and are creating a ‘library’ of information that people can listen to and then go back and refer to. And I think that’s outstanding.
So, appreciate all you are doing and have done for our leaders and create a world-class culture up there at Herbie Wiles Insurance and throughout North Florida and what you’re doing. But it’s great being with you, Doug, and I encourage our listeners to tune in next time for our next podcast in the series as we’ll continue to explore the Big Six principles and how the journeys of people who have been successful, like you, have learned from their mistakes, but still been willing to make mistakes and learn from them, and grow other leaders who have that same belief.
Doug Wiles:
Thank you, Robert. It’s been an honor to be with you, and I mean that sincerely.
Don’t forget! Subscribe to our podcast to get our latest episodes right away, as well as have access to our past episodes.
Did you find this podcast beneficial? If so, please consider sharing it with your audience. It’ll just take a second, but could improve someone’s work habits for a long time to come.
